Identification

Name
Nicotine
Accession Number
DB00184  (APRD00200, EXPT02315, DB09463, DB11303)
Type
Small Molecule
Groups
Approved
Description

Nicotine is highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke.

Structure
Thumb
Synonyms
  • (−)-nicotine
  • (S)-(−)-nicotine
  • (S)-3-(1-methylpyrrolidin-2-yl)pyridine
  • (S)-3-(N-methylpyrrolidin-2-yl)pyridine
  • (S)-Nicotine
  • 3-(2-(N-methylpyrrolidinyl))pyridine
  • 3-(N-methylpyrollidino)pyridine
  • L(−)-nicotine
  • Nicotine betadex
  • Nicotine polacrilex
Product Ingredients
IngredientUNIICASInChI Key
Nicotine bitartrate7892ZN5G4165-31-6RFEJUZJILGIRHQ-OMDKHLBYSA-N
Nicotine bitartrate dihydrateR7M676M8YV6019-06-3LDMPZNTVIGIREC-ZGPNLCEMSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nicorette InvisipatchPatch25 mgTransdermalMcneil Consumer Healthcare Division Of Johnson & Johnson IncNot applicableNot applicableCanada
NicotrolInhalant4 mg/1Respiratory (inhalation)Physicians Total Care, Inc.2004-08-04Not applicableUs
NicotrolInhalant4 mg/1Respiratory (inhalation)Pharmacia & Upjohn Inc1997-05-02Not applicableUs
NicotrolSpray, metered10 mg/mLNasalPharmacia & Upjohn Inc1996-05-22Not applicableUs
Nicotrol (Professional Sample)Inhalant4 mg/1Respiratory (inhalation)US Pharmaceuticals1997-05-02Not applicableUs
Nicotrol (Professional Sample)Inhalant4 mg/1Respiratory (inhalation)U.S. Pharmaceuticals1997-05-02Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
American Fare Nicotine Transdermal SystemPatch, extended release14 mg/1TransdermalNovartis2012-01-022017-03-07Us
Basic Care NicotineGum, chewing4 mg/1OralL. Perrigo Company2017-08-08Not applicableUs
Basic Care NicotineGum, chewing2 mg/1OralL. Perrigo Company2017-08-23Not applicableUs
Basic Care nicotineGum, chewing2 mg/1OralL. Perrigo Company2017-08-08Not applicableUs
Basic Care NicotineGum, chewing4 mg/1OralL. Perrigo Company2017-08-23Not applicableUs
Berkley and Jensen NicotineGum, chewing4 mg/1OralBJWC2007-05-31Not applicableUs
Berkley and Jensen NicotineGum, chewing2 mg/1OralBJWC2006-01-19Not applicableUs
Berkley and Jensen nicotineGum, chewing2 mg/1OralBJWC2008-09-21Not applicableUs
Berkley and Jensen NICOTINEGum, chewing2 mg/1OralBJWC2017-02-28Not applicableUs
Berkley and Jensen NicotineGum, chewing4 mg/1OralBJWC2006-01-18Not applicableUs
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
NicotineGum, chewing4 mg/1OralSam's West, Inc.2017-10-16Not applicableUs
NicotineGum, chewing2 mg/1OralSam's West, Inc.2017-10-16Not applicableUs
Nicotine Coated Fruit FlavorGum, chewing2 mg/1OralSam's West, Inc.2017-10-16Not applicableUs
Nicotine Coated Fruit FlavorGum, chewing4 mg/1OralSam's West, Inc.2017-10-16Not applicableUs
Nicotine COATED ice mintGum, chewing2 mg/1OralSam's West, Inc.2017-10-16Not applicableUs
Nicotine COATED ice mintGum, chewing4 mg/1OralSam's West, Inc.2017-10-16Not applicableUs
Nicotine PolacrilexGum, chewing4 mg/1BuccalWalgreen2016-03-01Not applicableUs
Nicotine PolacrilexGum, chewing4 mg/1BuccalWalmart Stores2016-10-01Not applicableUs
Nicotine TartratePowder1 kg/kgOralNicobrand Ltd.1997-07-11Not applicableUs
Nicotine UN1654Liquid1 L/LOralNicobrand Ltd.1997-07-11Not applicableUs
International/Other Brands
Habitrol / Nicoderm
Categories
UNII
6M3C89ZY6R
CAS number
54-11-5
Weight
Average: 162.2316
Monoisotopic: 162.115698458
Chemical Formula
C10H14N2
InChI Key
SNICXCGAKADSCV-JTQLQIEISA-N
InChI
InChI=1S/C10H14N2/c1-12-7-3-5-10(12)9-4-2-6-11-8-9/h2,4,6,8,10H,3,5,7H2,1H3/t10-/m0/s1
IUPAC Name
3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
SMILES
CN1CCC[[email protected]]1C1=CN=CC=C1

Pharmacology

Indication

For the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.

Structured Indications
Pharmacodynamics

Nicotine, the primary alkaloid in tobacco products binds stereo-selectively to nicotinic-cholinergic receptors on autonomic ganglia, the adrenal medulla, neuromuscular junctions and in the brain. Nicotine exerts two effects, a stimulant effect exerted at the locus ceruleus and a reward effect in the limbic system. Itranvenous administration of nicotine causes release of acetylcholine, norepinephrine, dopamine, serotonine, vasopressin, beta-endorphin and ACTH. Nicotine is a highly addictive substance. Nicotine also induces peripheral vasoconstriction, tachycardia and elevated blood pressure. Nicotine inhalers and patches are used to treat smoking withdrawl syndrome. Nicotine is classified as a stimulant of autonomic ganglia.

Mechanism of action

Nicotine is a stimulant drug that acts as an agonist at nicotinic acetylcholine receptors. These are ionotropic receptors composed up of five homomeric or heteromeric subunits. In the brain, nicotine binds to nicotinic acetylcholine receptors on dopaminergic neurons in the cortico-limbic pathways. This causes the channel to open and allow conductance of multiple cations including sodium, calcium, and potassium. This leads to depolarization, which activates voltage-gated calcium channels and allows more calcium to enter the axon terminal. Calcium stimulates vesicle trafficking towards the plasma membrane and the release of dopamine into the synapse. Dopamine binding to its receptors is responsible the euphoric and addictive properties of nicotine. Nicotine also binds to nicotinic acetylcholine receptors on the chromaffin cells in the adrenal medulla. Binding opens the ion channel allowing influx of sodium, causing depolarization of the cell, which activates voltage-gated calcium channels. Calcium triggers the release of epinephrine from intracellular vesicles into the bloodstream, which causes vasoconstriction, increased blood pressure, increased heart rate, and increased blood sugar.

TargetActionsOrganism
ANeuronal acetylcholine receptor subunit alpha-4
agonist
Human
ANeuronal acetylcholine receptor subunit alpha-7
agonist
Human
ANeuronal acetylcholine receptor subunit beta-2
agonist
Human
UNeuronal acetylcholine receptor subunit alpha-2
agonist
Human
UNeuronal acetylcholine receptor subunit alpha-3
agonist
Human
UNeuronal acetylcholine receptor subunit alpha-5
agonist
Human
UNeuronal acetylcholine receptor subunit alpha-6
agonist
Human
UNeuronal acetylcholine receptor subunit alpha-9
agonist
Human
UNeuronal acetylcholine receptor subunit alpha-10
agonist
Human
UNeuronal acetylcholine receptor subunit beta-3
agonist
Human
UNeuronal acetylcholine receptor subunit beta-4
agonist
Human
UCytochrome P450 19A1Not AvailableHuman
UCholine O-acetyltransferaseNot AvailableHuman
Absorption

Absorption of nicotine through the buccal mucosa is relatively slow and the high and rapid rise followed by the decline in nicotine arterial plasma concentrations seen with cigarette smoking are not achieved with the inhaler. About 10% of absorbed nicotine is excreted unchanged in urine.

Volume of distribution
  • 2 to 3 L/kg
Protein binding

Less than 5%

Metabolism

Primarily hepatic, cotinine is the primary metabolite.

Route of elimination

About 10% of the nicotine absorbed is excreted unchanged in the urine.

Half life

Cotinine has a half life of 15-20 hours, while nicotine has a half life of 1-3 hours

Clearance
  • 1.2 L/min [healthy adult smoker]
Toxicity

Symptoms of overdose include nausea, abdominal pain, vomiting, diarrhea, diaphoresis, flushing, dizziness, disturbed hearing and vision, confusion, weakness, palpitations, altered respiration and hypotension. LD50= 24 mg/kg (orally in mice).

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Nicotine Action PathwayDrug action
Nicotine Metabolism PathwayDrug metabolism
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
1,10-PhenanthrolineThe risk or severity of adverse effects can be increased when 1,10-Phenanthroline is combined with Nicotine.Experimental
AbirateroneThe serum concentration of Nicotine can be increased when it is combined with Abiraterone.Approved
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Nicotine.Approved
AcetaminophenThe metabolism of Acetaminophen can be decreased when combined with Nicotine.Approved
AdenosineNicotine may increase the atrioventricular blocking (AV block) activities of Adenosine.Approved, Investigational
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Nicotine.Approved, Investigational
AlprenololThe risk or severity of adverse effects can be increased when Alprenolol is combined with Nicotine.Approved, Withdrawn
AmbenoniumThe risk or severity of adverse effects can be increased when Ambenonium is combined with Nicotine.Approved
AminophyllineThe metabolism of Aminophylline can be decreased when combined with Nicotine.Approved
AmiodaroneThe metabolism of Nicotine can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe metabolism of Amitriptyline can be decreased when combined with Nicotine.Approved
AnilineThe metabolism of Aniline can be decreased when combined with Nicotine.Experimental
AntipyrineThe metabolism of Antipyrine can be decreased when combined with Nicotine.Approved
AprepitantThe serum concentration of Nicotine can be increased when it is combined with Aprepitant.Approved, Investigational
ArformoterolThe metabolism of Arformoterol can be decreased when combined with Nicotine.Approved, Investigational
ArmodafinilThe metabolism of Nicotine can be decreased when combined with Armodafinil.Approved, Investigational
ArotinololThe risk or severity of adverse effects can be increased when Arotinolol is combined with Nicotine.Approved, Investigational
ArtemetherThe metabolism of Nicotine can be decreased when combined with Artemether.Approved
ArtesunateThe serum concentration of the active metabolites of Artesunate can be reduced when Artesunate is used in combination with Nicotine resulting in a loss in efficacy.Approved, Investigational
AtazanavirThe metabolism of Nicotine can be decreased when combined with Atazanavir.Approved, Investigational
AtenololThe risk or severity of adverse effects can be increased when Atenolol is combined with Nicotine.Approved
AtomoxetineThe metabolism of Nicotine can be decreased when combined with Atomoxetine.Approved
AzithromycinThe metabolism of Nicotine can be decreased when combined with Azithromycin.Approved
BefunololThe risk or severity of adverse effects can be increased when Befunolol is combined with Nicotine.Experimental
Benzyl alcoholThe metabolism of Benzyl alcohol can be decreased when combined with Nicotine.Approved
BetaxololThe metabolism of Nicotine can be decreased when combined with Betaxolol.Approved
BevantololThe risk or severity of adverse effects can be increased when Bevantolol is combined with Nicotine.Approved
BisoprololThe risk or severity of adverse effects can be increased when Bisoprolol is combined with Nicotine.Approved
BoceprevirThe metabolism of Nicotine can be decreased when combined with Boceprevir.Approved, Withdrawn
BopindololThe risk or severity of adverse effects can be increased when Bopindolol is combined with Nicotine.Approved
BortezomibThe metabolism of Nicotine can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Nicotine can be decreased when it is combined with Bosentan.Approved, Investigational
BrompheniramineThe metabolism of Brompheniramine can be decreased when combined with Nicotine.Approved
BucindololThe risk or severity of adverse effects can be increased when Bucindolol is combined with Nicotine.Investigational
BufuralolThe risk or severity of adverse effects can be increased when Bufuralol is combined with Nicotine.Experimental, Investigational
BupranololThe risk or severity of adverse effects can be increased when Bupranolol is combined with Nicotine.Approved
BupropionThe metabolism of Nicotine can be decreased when combined with Bupropion.Approved
CaffeineThe metabolism of Nicotine can be decreased when combined with Caffeine.Approved
CapecitabineThe metabolism of Nicotine can be decreased when combined with Capecitabine.Approved, Investigational
CapsaicinThe metabolism of Capsaicin can be decreased when combined with Nicotine.Approved
CarbamazepineThe metabolism of Nicotine can be increased when combined with Carbamazepine.Approved, Investigational
CarbinoxamineThe metabolism of Carbinoxamine can be decreased when combined with Nicotine.Approved
CarteololThe risk or severity of adverse effects can be increased when Carteolol is combined with Nicotine.Approved
CarvedilolThe metabolism of Carvedilol can be decreased when combined with Nicotine.Approved, Investigational
CelecoxibThe metabolism of Nicotine can be decreased when combined with Celecoxib.Approved, Investigational
CeliprololThe risk or severity of adverse effects can be increased when Celiprolol is combined with Nicotine.Approved, Investigational
CeritinibThe serum concentration of Nicotine can be increased when it is combined with Ceritinib.Approved
ChloramphenicolThe metabolism of Nicotine can be decreased when combined with Chloramphenicol.Approved, Vet Approved
ChloroquineThe metabolism of Nicotine can be decreased when combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe metabolism of Nicotine can be decreased when combined with Chlorpromazine.Approved, Vet Approved
ChlorzoxazoneThe metabolism of Chlorzoxazone can be decreased when combined with Nicotine.Approved
CholecalciferolThe metabolism of Nicotine can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CimetidineThe serum concentration of Nicotine can be increased when it is combined with Cimetidine.Approved
CimetropiumNicotine may decrease the anticholinergic activities of Cimetropium.Experimental, Investigational
CinacalcetThe metabolism of Nicotine can be decreased when combined with Cinacalcet.Approved
CinnarizineThe metabolism of Cinnarizine can be decreased when combined with Nicotine.Approved, Investigational
CisaprideThe metabolism of Cisapride can be decreased when combined with Nicotine.Approved, Investigational, Withdrawn
CitalopramThe metabolism of Nicotine can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Nicotine can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Nicotine can be decreased when combined with Clemastine.Approved
ClevidipineThe metabolism of Clevidipine can be decreased when combined with Nicotine.Approved
ClobazamThe metabolism of Nicotine can be decreased when combined with Clobazam.Approved, Illicit
clomethiazoleThe metabolism of clomethiazole can be decreased when combined with Nicotine.Investigational
ClomipramineThe metabolism of Nicotine can be decreased when combined with Clomipramine.Approved, Vet Approved
ClopidogrelThe metabolism of Nicotine can be decreased when combined with Clopidogrel.Approved, Nutraceutical
CloranololThe risk or severity of adverse effects can be increased when Cloranolol is combined with Nicotine.Experimental
ClotrimazoleThe metabolism of Nicotine can be decreased when combined with Clotrimazole.Approved, Vet Approved
ClozapineThe metabolism of Nicotine can be decreased when combined with Clozapine.Approved
CobicistatThe serum concentration of Nicotine can be increased when it is combined with Cobicistat.Approved
CocaineThe metabolism of Nicotine can be decreased when combined with Cocaine.Approved, Illicit
ConivaptanThe serum concentration of Nicotine can be increased when it is combined with Conivaptan.Approved, Investigational
CoumaphosThe risk or severity of adverse effects can be increased when Coumaphos is combined with Nicotine.Vet Approved
CrisaboroleThe metabolism of Nicotine can be decreased when combined with Crisaborole.Approved
CrizotinibThe metabolism of Nicotine can be decreased when combined with Crizotinib.Approved
CyclophosphamideThe metabolism of Cyclophosphamide can be decreased when combined with Nicotine.Approved, Investigational
CyclosporineThe metabolism of Nicotine can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
Cyproterone acetateThe serum concentration of Nicotine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DabrafenibThe serum concentration of Nicotine can be decreased when it is combined with Dabrafenib.Approved
DacarbazineThe metabolism of Dacarbazine can be decreased when combined with Nicotine.Approved, Investigational
DalfampridineThe metabolism of Dalfampridine can be decreased when combined with Nicotine.Approved
DapagliflozinThe metabolism of Dapagliflozin can be decreased when combined with Nicotine.Approved
DapsoneThe metabolism of Dapsone can be decreased when combined with Nicotine.Approved, Investigational
DarifenacinThe metabolism of Nicotine can be decreased when combined with Darifenacin.Approved, Investigational
DarunavirThe serum concentration of Nicotine can be increased when it is combined with Darunavir.Approved
DasatinibThe serum concentration of Nicotine can be increased when it is combined with Dasatinib.Approved, Investigational
DecamethoniumThe risk or severity of adverse effects can be increased when Decamethonium is combined with Nicotine.Approved
DeferasiroxThe serum concentration of Nicotine can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Nicotine can be decreased when combined with Delavirdine.Approved
DemecariumThe risk or severity of adverse effects can be increased when Demecarium is combined with Nicotine.Approved
DesipramineThe metabolism of Nicotine can be decreased when combined with Desipramine.Approved
DexmedetomidineThe metabolism of Dexmedetomidine can be decreased when combined with Nicotine.Approved, Vet Approved
DextromethorphanThe metabolism of Dextromethorphan can be decreased when combined with Nicotine.Approved
DichlorvosThe risk or severity of adverse effects can be increased when Dichlorvos is combined with Nicotine.Vet Approved
DihydroergotamineThe metabolism of Nicotine can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Nicotine can be decreased when combined with Diltiazem.Approved
DiphenhydramineThe metabolism of Nicotine can be decreased when combined with Diphenhydramine.Approved
DistigmineThe risk or severity of adverse effects can be increased when Distigmine is combined with Nicotine.Experimental
DonepezilThe risk or severity of adverse effects can be increased when Donepezil is combined with Nicotine.Approved
DosulepinThe metabolism of Nicotine can be decreased when combined with Dosulepin.Approved
DoxorubicinThe metabolism of Nicotine can be decreased when combined with Doxorubicin.Approved, Investigational
DoxycyclineThe metabolism of Nicotine can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronabinolThe metabolism of Dronabinol can be decreased when combined with Nicotine.Approved, Illicit
DronedaroneThe metabolism of Nicotine can be decreased when combined with Dronedarone.Approved
DuloxetineThe metabolism of Nicotine can be decreased when combined with Duloxetine.Approved
EchothiophateThe risk or severity of adverse effects can be increased when Echothiophate is combined with Nicotine.Approved
EdrophoniumThe risk or severity of adverse effects can be increased when Edrophonium is combined with Nicotine.Approved
EfavirenzThe metabolism of Nicotine can be decreased when combined with Efavirenz.Approved, Investigational
EliglustatThe metabolism of Nicotine can be decreased when combined with Eliglustat.Approved
EnfluraneThe metabolism of Enflurane can be decreased when combined with Nicotine.Approved, Investigational, Vet Approved
EnfuvirtideThe metabolism of Enfuvirtide can be decreased when combined with Nicotine.Approved, Investigational
EnzalutamideThe serum concentration of Nicotine can be decreased when it is combined with Enzalutamide.Approved
EpanololThe risk or severity of adverse effects can be increased when Epanolol is combined with Nicotine.Experimental
ErythromycinThe metabolism of Nicotine can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe metabolism of Nicotine can be decreased when combined with Eslicarbazepine acetate.Approved
EsmololThe risk or severity of adverse effects can be increased when Esmolol is combined with Nicotine.Approved
EsomeprazoleThe metabolism of Nicotine can be decreased when combined with Esomeprazole.Approved, Investigational
EstroneThe metabolism of Estrone can be decreased when combined with Nicotine.Approved
EthanolThe metabolism of Ethanol can be decreased when combined with Nicotine.Approved
Ethanolamine OleateThe metabolism of Ethanolamine Oleate can be decreased when combined with Nicotine.Approved
EthosuximideThe metabolism of Ethosuximide can be decreased when combined with Nicotine.Approved
EtoposideThe metabolism of Etoposide can be decreased when combined with Nicotine.Approved
EtravirineThe metabolism of Nicotine can be decreased when combined with Etravirine.Approved
FelbamateThe metabolism of Felbamate can be decreased when combined with Nicotine.Approved
FelodipineThe metabolism of Nicotine can be decreased when combined with Felodipine.Approved, Investigational
FenthionThe risk or severity of adverse effects can be increased when Fenthion is combined with Nicotine.Vet Approved
FingolimodThe metabolism of Fingolimod can be decreased when combined with Nicotine.Approved, Investigational
FloxuridineThe metabolism of Nicotine can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Nicotine can be decreased when combined with Fluconazole.Approved
FlunarizineThe metabolism of Flunarizine can be decreased when combined with Nicotine.Approved
FlunitrazepamThe metabolism of Flunitrazepam can be decreased when combined with Nicotine.Approved, Illicit
FluorouracilThe metabolism of Nicotine can be decreased when combined with Fluorouracil.Approved
FluoxetineThe metabolism of Nicotine can be decreased when combined with Fluoxetine.Approved, Vet Approved
FlurazepamThe metabolism of Flurazepam can be decreased when combined with Nicotine.Approved, Illicit
FluvastatinThe metabolism of Nicotine can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Nicotine can be decreased when combined with Fluvoxamine.Approved, Investigational
Folic AcidThe metabolism of Folic Acid can be decreased when combined with Nicotine.Approved, Nutraceutical, Vet Approved
FormoterolThe metabolism of Formoterol can be decreased when combined with Nicotine.Approved, Investigational
FosamprenavirThe metabolism of Nicotine can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Nicotine can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Nicotine can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Nicotine can be increased when it is combined with Fusidic Acid.Approved
GalantamineThe risk or severity of adverse effects can be increased when Galantamine is combined with Nicotine.Approved
Gallamine TriethiodideThe risk or severity of adverse effects can be increased when Gallamine Triethiodide is combined with Nicotine.Approved
GemfibrozilThe metabolism of Nicotine can be decreased when combined with Gemfibrozil.Approved
GlucosamineThe metabolism of Glucosamine can be decreased when combined with Nicotine.Approved
HaloperidolThe metabolism of Nicotine can be decreased when combined with Haloperidol.Approved
HalothaneThe metabolism of Halothane can be decreased when combined with Nicotine.Approved, Vet Approved
Huperzine AThe risk or severity of adverse effects can be increased when Huperzine A is combined with Nicotine.Investigational
IdelalisibThe serum concentration of Nicotine can be increased when it is combined with Idelalisib.Approved
IfosfamideThe metabolism of Ifosfamide can be decreased when combined with Nicotine.Approved
IloperidoneThe metabolism of Iloperidone can be decreased when combined with Nicotine.Approved
ImatinibThe metabolism of Nicotine can be decreased when combined with Imatinib.Approved
ImipramineThe metabolism of Nicotine can be decreased when combined with Imipramine.Approved
IndenololThe risk or severity of adverse effects can be increased when Indenolol is combined with Nicotine.Withdrawn
IndinavirThe metabolism of Nicotine can be decreased when combined with Indinavir.Approved
IpidacrineThe risk or severity of adverse effects can be increased when Ipidacrine is combined with Nicotine.Experimental
IrbesartanThe metabolism of Nicotine can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Nicotine can be decreased when combined with Isavuconazonium.Approved, Investigational
IsofluraneThe metabolism of Isoflurane can be decreased when combined with Nicotine.Approved, Vet Approved
IsoflurophateThe risk or severity of adverse effects can be increased when Isoflurophate is combined with Nicotine.Approved, Investigational, Withdrawn
IsoniazidThe metabolism of Nicotine can be decreased when combined with Isoniazid.Approved
IsradipineThe metabolism of Nicotine can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Nicotine can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Nicotine can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Nicotine can be decreased when combined with Ketoconazole.Approved, Investigational
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Nicotine.Approved
LandiololThe risk or severity of adverse effects can be increased when Landiolol is combined with Nicotine.Investigational
LapatinibThe metabolism of Nicotine can be decreased when combined with Lapatinib.Approved, Investigational
LeflunomideThe metabolism of Nicotine can be decreased when combined with Leflunomide.Approved, Investigational
LetrozoleThe metabolism of Letrozole can be decreased when combined with Nicotine.Approved, Investigational
LevobunololThe risk or severity of adverse effects can be increased when Levobunolol is combined with Nicotine.Approved
LidocaineThe metabolism of Nicotine can be decreased when combined with Lidocaine.Approved, Vet Approved
LobeglitazoneThe metabolism of Nicotine can be decreased when combined with Lobeglitazone.Approved, Investigational
LopinavirThe metabolism of Nicotine can be decreased when combined with Lopinavir.Approved
LorcaserinThe metabolism of Nicotine can be decreased when combined with Lorcaserin.Approved
LosartanThe metabolism of Nicotine can be decreased when combined with Losartan.Approved
LovastatinThe metabolism of Nicotine can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Nicotine can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Nicotine can be increased when it is combined with Lumacaftor.Approved
LumefantrineThe metabolism of Nicotine can be decreased when combined with Lumefantrine.Approved
MalathionThe risk or severity of adverse effects can be increased when Malathion is combined with Nicotine.Approved, Investigational
ManidipineThe metabolism of Nicotine can be decreased when combined with Manidipine.Approved, Investigational
MefloquineThe risk or severity of adverse effects can be increased when Mefloquine is combined with Nicotine.Approved
MemantineThe risk or severity of adverse effects can be increased when Memantine is combined with Nicotine.Approved, Investigational
MenadioneThe metabolism of Menadione can be decreased when combined with Nicotine.Approved, Nutraceutical
MepindololThe risk or severity of adverse effects can be increased when Mepindolol is combined with Nicotine.Experimental
MeprobamateThe metabolism of Meprobamate can be decreased when combined with Nicotine.Approved, Illicit
MethadoneThe metabolism of Nicotine can be decreased when combined with Methadone.Approved
Methanesulfonyl FluorideThe risk or severity of adverse effects can be increased when Methanesulfonyl Fluoride is combined with Nicotine.Investigational
MethotrimeprazineThe metabolism of Nicotine can be decreased when combined with Methotrimeprazine.Approved
MethoxsalenThe metabolism of Methoxsalen can be decreased when combined with Nicotine.Approved
MethoxyfluraneThe metabolism of Methoxyflurane can be decreased when combined with Nicotine.Approved, Investigational, Vet Approved
MetipranololThe risk or severity of adverse effects can be increased when Metipranolol is combined with Nicotine.Approved
MetoclopramideThe risk or severity of adverse effects can be increased when Metoclopramide is combined with Nicotine.Approved, Investigational
MetoprololThe metabolism of Nicotine can be decreased when combined with Metoprolol.Approved, Investigational
MexiletineThe metabolism of Nicotine can be decreased when combined with Mexiletine.Approved
MidostaurinThe metabolism of Nicotine can be decreased when combined with Midostaurin.Approved
MifepristoneThe serum concentration of Nicotine can be increased when it is combined with Mifepristone.Approved, Investigational
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Nicotine.Approved
MirabegronThe metabolism of Nicotine can be decreased when combined with Mirabegron.Approved
MitotaneThe serum concentration of Nicotine can be decreased when it is combined with Mitotane.Approved
MitoxantroneThe metabolism of Mitoxantrone can be decreased when combined with Nicotine.Approved, Investigational
MoclobemideThe metabolism of Nicotine can be decreased when combined with Moclobemide.Approved
ModafinilThe metabolism of Nicotine can be decreased when combined with Modafinil.Approved, Investigational
MontelukastThe metabolism of Montelukast can be decreased when combined with Nicotine.Approved
NadololThe risk or severity of adverse effects can be increased when Nadolol is combined with Nicotine.Approved
NebivololThe risk or severity of adverse effects can be increased when Nebivolol is combined with Nicotine.Approved, Investigational
NefazodoneThe metabolism of Nicotine can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Nicotine can be decreased when combined with Nelfinavir.Approved
NeostigmineThe risk or severity of adverse effects can be increased when Neostigmine is combined with Nicotine.Approved, Vet Approved
NetupitantThe serum concentration of Nicotine can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Nicotine can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Nicotine can be decreased when combined with Nicardipine.Approved
NifedipineThe metabolism of Nifedipine can be decreased when combined with Nicotine.Approved
NilotinibThe metabolism of Nicotine can be decreased when combined with Nilotinib.Approved, Investigational
NilvadipineThe metabolism of Nilvadipine can be decreased when combined with Nicotine.Approved, Investigational
OlaparibThe metabolism of Nicotine can be decreased when combined with Olaparib.Approved
OmeprazoleThe metabolism of Nicotine can be decreased when combined with Omeprazole.Approved, Investigational, Vet Approved
OndansetronThe metabolism of Ondansetron can be decreased when combined with Nicotine.Approved
OsimertinibThe serum concentration of Nicotine can be increased when it is combined with Osimertinib.Approved
OxaliplatinThe metabolism of Oxaliplatin can be decreased when combined with Nicotine.Approved, Investigational
OxprenololThe risk or severity of adverse effects can be increased when Oxprenolol is combined with Nicotine.Approved
PalbociclibThe serum concentration of Nicotine can be increased when it is combined with Palbociclib.Approved
PanobinostatThe serum concentration of Nicotine can be increased when it is combined with Panobinostat.Approved, Investigational
PantoprazoleThe metabolism of Nicotine can be decreased when combined with Pantoprazole.Approved
ParamethadioneThe metabolism of Paramethadione can be decreased when combined with Nicotine.Approved
ParaoxonThe risk or severity of adverse effects can be increased when Paraoxon is combined with Nicotine.Experimental
ParoxetineThe metabolism of Nicotine can be decreased when combined with Paroxetine.Approved, Investigational
Peginterferon alfa-2bThe serum concentration of Nicotine can be decreased when it is combined with Peginterferon alfa-2b.Approved
PenbutololThe risk or severity of adverse effects can be increased when Penbutolol is combined with Nicotine.Approved, Investigational
PentobarbitalThe metabolism of Nicotine can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenacetinThe metabolism of Phenacetin can be decreased when combined with Nicotine.Withdrawn
PhenobarbitalThe metabolism of Nicotine can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Nicotine can be increased when combined with Phenytoin.Approved, Vet Approved
PhysostigmineThe risk or severity of adverse effects can be increased when Physostigmine is combined with Nicotine.Approved
PilocarpineThe metabolism of Pilocarpine can be decreased when combined with Nicotine.Approved
PindololThe risk or severity of adverse effects can be increased when Pindolol is combined with Nicotine.Approved
PioglitazoneThe metabolism of Nicotine can be decreased when combined with Pioglitazone.Approved, Investigational
Platelet Activating FactorThe risk or severity of adverse effects can be increased when Platelet Activating Factor is combined with Nicotine.Experimental
PosaconazoleThe metabolism of Nicotine can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PractololThe risk or severity of adverse effects can be increased when Practolol is combined with Nicotine.Approved
PrimidoneThe metabolism of Nicotine can be increased when combined with Primidone.Approved, Vet Approved
ProgesteroneThe metabolism of Progesterone can be decreased when combined with Nicotine.Approved, Vet Approved
ProguanilThe metabolism of Proguanil can be decreased when combined with Nicotine.Approved
PromazineThe metabolism of Nicotine can be decreased when combined with Promazine.Approved, Vet Approved
PropofolThe metabolism of Propofol can be decreased when combined with Nicotine.Approved, Investigational, Vet Approved
PropranololThe risk or severity of adverse effects can be increased when Propranolol is combined with Nicotine.Approved, Investigational
PyridostigmineThe risk or severity of adverse effects can be increased when Pyridostigmine is combined with Nicotine.Approved
PyrimethamineThe metabolism of Nicotine can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuazepamThe serum concentration of Nicotine can be increased when it is combined with Quazepam.Approved, Illicit
QuinidineThe metabolism of Nicotine can be decreased when combined with Quinidine.Approved
QuinineThe metabolism of Nicotine can be decreased when combined with Quinine.Approved
RabeprazoleThe metabolism of Nicotine can be decreased when combined with Rabeprazole.Approved, Investigational
RanolazineThe metabolism of Nicotine can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Nicotine can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Nicotine can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Nicotine can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Nicotine can be decreased when combined with Ritonavir.Approved, Investigational
RivastigmineThe risk or severity of adverse effects can be increased when Rivastigmine is combined with Nicotine.Approved, Investigational
RolapitantThe metabolism of Nicotine can be decreased when combined with Rolapitant.Approved
RopiniroleThe metabolism of Nicotine can be decreased when combined with Ropinirole.Approved, Investigational
RosiglitazoneThe metabolism of Nicotine can be decreased when combined with Rosiglitazone.Approved, Investigational
SaquinavirThe metabolism of Nicotine can be decreased when combined with Saquinavir.Approved, Investigational
SecobarbitalThe metabolism of Nicotine can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineThe metabolism of Selegiline can be decreased when combined with Nicotine.Approved, Investigational, Vet Approved
SertralineThe metabolism of Nicotine can be decreased when combined with Sertraline.Approved
SevofluraneThe metabolism of Sevoflurane can be decreased when combined with Nicotine.Approved, Vet Approved
SildenafilThe metabolism of Nicotine can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Nicotine can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Nicotine can be increased when it is combined with Simeprevir.Approved
SorafenibThe metabolism of Nicotine can be decreased when combined with Sorafenib.Approved, Investigational
SotalolThe risk or severity of adverse effects can be increased when Sotalol is combined with Nicotine.Approved
St. John's WortThe serum concentration of Nicotine can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Nicotine can be increased when it is combined with Stiripentol.Approved
SulfadiazineThe metabolism of Nicotine can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Nicotine can be decreased when combined with Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Nicotine can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TacrineThe risk or severity of adverse effects can be increased when Tacrine is combined with Nicotine.Investigational, Withdrawn
TalinololThe risk or severity of adverse effects can be increased when Talinolol is combined with Nicotine.Investigational
TamoxifenThe metabolism of Nicotine can be decreased when combined with Tamoxifen.Approved
TegafurThe serum concentration of the active metabolites of Tegafur can be reduced when Tegafur is used in combination with Nicotine resulting in a loss in efficacy.Approved
TelaprevirThe metabolism of Nicotine can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Nicotine can be decreased when combined with Telithromycin.Approved
Tenofovir disoproxilThe metabolism of Nicotine can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TerbinafineThe metabolism of Nicotine can be decreased when combined with Terbinafine.Approved, Investigational, Vet Approved
TeriflunomideThe serum concentration of Nicotine can be decreased when it is combined with Teriflunomide.Approved
TertatololThe risk or severity of adverse effects can be increased when Tertatolol is combined with Nicotine.Experimental
ThalidomideThe metabolism of Thalidomide can be decreased when combined with Nicotine.Approved, Investigational, Withdrawn
TheobromineThe metabolism of Theobromine can be decreased when combined with Nicotine.Approved, Investigational
TheophyllineThe metabolism of Nicotine can be decreased when combined with Theophylline.Approved
ThioridazineThe metabolism of Nicotine can be decreased when combined with Thioridazine.Approved, Withdrawn
ThiotepaThe metabolism of Nicotine can be decreased when combined with Thiotepa.Approved
TicagrelorThe metabolism of Nicotine can be decreased when combined with Ticagrelor.Approved
TiclopidineThe metabolism of Nicotine can be decreased when combined with Ticlopidine.Approved
TimololThe risk or severity of adverse effects can be increased when Timolol is combined with Nicotine.Approved
TipranavirThe metabolism of Nicotine can be decreased when combined with Tipranavir.Approved, Investigational
TirapazamineThe metabolism of Tirapazamine can be decreased when combined with Nicotine.Investigational
TocilizumabThe serum concentration of Nicotine can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Nicotine can be decreased when combined with Tolbutamide.Approved
TopiramateThe metabolism of Nicotine can be decreased when combined with Topiramate.Approved
TopiroxostatThe metabolism of Nicotine can be decreased when combined with Topiroxostat.Approved, Investigational
TrabectedinThe metabolism of Trabectedin can be decreased when combined with Nicotine.Approved, Investigational
TranylcypromineThe metabolism of Nicotine can be decreased when combined with Tranylcypromine.Approved
TretinoinThe metabolism of Tretinoin can be decreased when combined with Nicotine.Approved, Investigational, Nutraceutical
TrichlorfonThe risk or severity of adverse effects can be increased when Trichlorfon is combined with Nicotine.Vet Approved
TrimethadioneThe metabolism of Trimethadione can be decreased when combined with Nicotine.Approved
TrimethoprimThe metabolism of Nicotine can be decreased when combined with Trimethoprim.Approved, Vet Approved
TubocurarineThe risk or severity of adverse effects can be increased when Tubocurarine is combined with Nicotine.Approved
Valproic AcidThe metabolism of Nicotine can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Nicotine can be decreased when combined with Valsartan.Approved, Investigational
VareniclineThe risk or severity of adverse effects can be increased when Varenicline is combined with Nicotine.Approved, Investigational
VemurafenibThe serum concentration of Nicotine can be increased when it is combined with Vemurafenib.Approved
VenlafaxineThe metabolism of Nicotine can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Nicotine can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Nicotine can be decreased when combined with Voriconazole.Approved, Investigational
VortioxetineThe metabolism of Vortioxetine can be decreased when combined with Nicotine.Approved
ZafirlukastThe metabolism of Nicotine can be decreased when combined with Zafirlukast.Approved, Investigational
ZidovudineThe metabolism of Zidovudine can be decreased when combined with Nicotine.Approved
ZiprasidoneThe metabolism of Nicotine can be decreased when combined with Ziprasidone.Approved
ZopicloneThe metabolism of Zopiclone can be decreased when combined with Nicotine.Approved
ZucapsaicinThe metabolism of Nicotine can be decreased when combined with Zucapsaicin.Approved
Food Interactions
Not Available

References

Synthesis Reference

Charles G. Chavdarian, Edward B. Sanders, "Process for the preparation of optically active nicotine analogs." U.S. Patent US4321387, issued September, 1959.

US4321387
General References
  1. Nolley EP, Kelley BM: Adolescent reward system perseveration due to nicotine: studies with methylphenidate. Neurotoxicol Teratol. 2007 Jan-Feb;29(1):47-56. Epub 2006 Oct 4. [PubMed:17129706]
  2. de Leon J, Tracy J, McCann E, McGrory A, Diaz FJ: Schizophrenia and tobacco smoking: a replication study in another US psychiatric hospital. Schizophr Res. 2002 Jul 1;56(1-2):55-65. [PubMed:12084420]
  3. de Leon J, Dadvand M, Canuso C, White AO, Stanilla JK, Simpson GM: Schizophrenia and smoking: an epidemiological survey in a state hospital. Am J Psychiatry. 1995 Mar;152(3):453-5. [PubMed:7864277]
  4. Aguilar MC, Gurpegui M, Diaz FJ, de Leon J: Nicotine dependence and symptoms in schizophrenia: naturalistic study of complex interactions. Br J Psychiatry. 2005 Mar;186:215-21. [PubMed:15738502]
External Links
Human Metabolome Database
HMDB01934
KEGG Drug
D03365
KEGG Compound
C00745
PubChem Compound
89594
PubChem Substance
46506924
ChemSpider
80863
BindingDB
82070
ChEBI
17688
ChEMBL
CHEMBL3
Therapeutic Targets Database
DAP000175
PharmGKB
PA450626
HET
NCT
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Nicotine
ATC Codes
N07BA01 — Nicotine
AHFS Codes
  • 12:92.00 — Miscellaneous Autonomic Drugs
PDB Entries
1p2y / 1p7r / 1uw6 / 2yk1 / 4ejg / 4ejj / 5kxi
FDA label
Download (11.2 MB)
MSDS
Download (77.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedNot AvailableAlcohol Consumption / Tobacco Use1
0CompletedNot AvailableTobacco Dependence1
0CompletedTreatmentStress Disorders, Posttraumatic / Tobacco Use Disorders1
0CompletedTreatmentTobacco Use Disorders1
0Not Yet RecruitingHealth Services ResearchNicotine Dependence1
0Not Yet RecruitingPreventionCessation, Smoking1
0Not Yet RecruitingSupportive CareCessation, Smoking1
0RecruitingBasic ScienceNicotine1
0RecruitingTreatmentNicotine Addiction / Panic Attacks1
0TerminatedTreatmentCessation, Smoking1
1Active Not RecruitingBasic ScienceHealthy Volunteers1
1CompletedNot AvailableHealthy Smokers2
1CompletedNot AvailableNicotine Use Disorder1
1CompletedNot AvailableSmoking1
1CompletedBasic ScienceCigarette Smoking Behavior1
1CompletedBasic ScienceHealthy Volunteers1
1CompletedBasic ScienceTobacco Dependence1
1CompletedHealth Services ResearchNicotine Dependence1
1CompletedHealth Services ResearchSmoking1
1CompletedOtherDrug Dependence / Nicotine Dependence1
1CompletedOtherNicotine Dependence, Cigarettes / Nicotine Dependence, Other Tobacco Product1
1CompletedScreeningCessation, Smoking5
1CompletedScreeningSubstance-related Discorder1
1CompletedTreatmentAnxiety Disorders / Depression Disorders / Smoking1
1CompletedTreatmentAnxiety Disorders / Smoking1
1CompletedTreatmentCessation, Smoking3
1CompletedTreatmentHealthy Volunteer Smokers2
1CompletedTreatmentNicotine Dependence / Substance Related Disorders1
1CompletedTreatmentNicotine Pharmacokinetic Study1
1CompletedTreatmentSmoking1
1CompletedTreatmentSmoking / Tobacco Withdrawal1
1CompletedTreatmentTobacco Use Disorders1
1Not Yet RecruitingBasic ScienceSmoking, Cigarette1
1RecruitingBasic ScienceDepressive Disorders1
1RecruitingOtherArterial Stiffness1
1RecruitingTreatmentAggressive Behavior / Autism Spectrum Conditions/Disorders / Irritability1
1RecruitingTreatmentNicotine Dependence1
1Unknown StatusTreatmentAge-Related Memory Disorders1
1, 2CompletedBasic ScienceHealthy Volunteers / Smokers1
1, 2CompletedTreatmentCancer Prevention / Tobacco Use Cessation1
1, 2CompletedTreatmentParkinson's Disease (PD)1
1, 2CompletedTreatmentTobacco Dependence1
1, 2Not Yet RecruitingBasic ScienceDepressive Symptoms / Smoking1
1, 2RecruitingTreatmentCessation, Smoking1
1, 2RecruitingTreatmentDown Syndrome (DS) / Mild Cognitive Impairment (MCI)1
1, 2RecruitingTreatmentSarcoidosis1
1, 2Unknown StatusTreatmentDrug Use / Smoking, Cigarette1
2Active Not RecruitingPreventionParkinson's Disease (PD)1
2CompletedBasic ScienceSchizophrenia and Disorders With Psychotic Features / Schizophrenic Disorders / Tobacco Use Disorders1
2CompletedHealth Services ResearchNicotine Dependence1
2CompletedTreatmentAlcohol Drinking1
2CompletedTreatmentBehavior, Addictive / BMI >30 kg/m2 / Psychotic Disorder NOS1
2CompletedTreatmentCannabis Dependence / Nicotine Dependence1
2CompletedTreatmentCardiovascular Disease (CVD) / Tobacco Use Disorders1
2CompletedTreatmentCessation, Smoking6
2CompletedTreatmentCessation, Smoking / Tobacco Use Disorders2
2CompletedTreatmentIdiopathic Parkinson's Disease1
2CompletedTreatmentNicotine Dependence3
2CompletedTreatmentSarcomas1
2CompletedTreatmentSchizophrenic Disorders / Tobacco Use Cessation / Tobacco Use Disorders1
2CompletedTreatmentSmokers1
2CompletedTreatmentSmoking4
2CompletedTreatmentSmoking, Cigarette2
2CompletedTreatmentSmoking / Smoking Dependence1
2CompletedTreatmentTobacco Dependence1
2CompletedTreatmentTobacco Use Disorders4
2Not Yet RecruitingTreatmentNicotine Dependence2
2RecruitingTreatmentCancer, Breast / Chemo Brain / Chemo Fog / Chemobrain / Chemotherapy-related Cognitive Impairment1
2RecruitingTreatmentCessation, Smoking1
2RecruitingTreatmentMild Cognitive Impairment (MCI)1
2RecruitingTreatmentNicotine Dependence2
2TerminatedPreventionProphylaxis against postoperative nausea and vomiting1
2TerminatedTreatmentCessation, Smoking / Nicotine Dependence1
2TerminatedTreatmentTobacco Use Disorders1
2Unknown StatusTreatmentSmoking, Cigarette1
2, 3Active Not RecruitingPreventionCessation, Smoking / Habits / Smoking1
2, 3Active Not RecruitingTreatmentSmoking / Stress Disorders, Post-Traumatic1
2, 3CompletedTreatmentNicotine Dependence1
2, 3CompletedTreatmentSmokeless Tobacco Use1
2, 3CompletedTreatmentTobacco Dependence1
2, 3RecruitingTreatmentNicotine Dependence / Tobacco Use Disorders1
2, 3TerminatedTreatmentNicotine Dependence / Smoking, Cigarette1
3Active Not RecruitingTreatmentCessation, Smoking / Human Immunodeficiency Virus (HIV)1
3CompletedNot AvailableSmoking, Cigarette1
3CompletedPreventionLung Cancers1
3CompletedTreatmentCessation, Smoking7
3CompletedTreatmentNicotine Addiction1
3CompletedTreatmentNicotine Dependence2
3CompletedTreatmentSmoking3
3CompletedTreatmentSmoking, Cigarette1
3CompletedTreatmentTobacco Dependence2
3CompletedTreatmentTobacco Use Disorders2
3Not Yet RecruitingTreatmentNicotine Dependence / Tobacco Use Disorders1
3RecruitingTreatmentCessation, Smoking2
3TerminatedPreventionLung Cancers1
3TerminatedTreatmentTobacco Dependence1
3Unknown StatusTreatmentSmoking1
3WithdrawnTreatmentCessation, Smoking1
4Active Not RecruitingTreatmentCessation, Smoking2
4Active Not RecruitingTreatmentCessation, Smoking / Nicotine Dependence1
4Active Not RecruitingTreatmentCessation, Smoking / Nicotine Dependence / Smoking1
4CompletedNot AvailableCessation, Smoking1
4CompletedNot AvailableDental Pellicle1
4CompletedBasic ScienceMarijuana Dependence1
4CompletedBasic ScienceNicotine Dependence1
4CompletedBasic ScienceSmoking1
4CompletedHealth Services ResearchSmoking1
4CompletedPreventionCessation, Smoking / Psychiatric Illness1
4CompletedPreventionCoronary Heart Disease (CHD)1
4CompletedTreatmentAlcoholism / Smoking2
4CompletedTreatmentAlzheimer's Disease (AD)1
4CompletedTreatmentBladder Cancers / Cervical Cancers / Esophageal Cancers / Head and Neck Carcinoma / Leukemias / Liver Cancer / Lung Cancers / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach / Renal Cancers / Tobacco Use Disorders1
4CompletedTreatmentCessation, Smoking4
4CompletedTreatmentCessation, Smoking / Motivation / Nicotine Dependence / Smoking1
4CompletedTreatmentCessation, Smoking / Schizophrenic Disorders1
4CompletedTreatmentCessation, Smoking / Smoking1
4CompletedTreatmentDelirium / Nicotine Replacement Therapy / Psychomotor Agitation / Substance Withdrawal Syndrome1
4CompletedTreatmentDental Crowding1
4CompletedTreatmentMajor Depressive Disorder (MDD)1
4CompletedTreatmentNicotine Dependence2
4CompletedTreatmentNicotine Dependence / Psychiatric Disorder NOS / Smoking1
4CompletedTreatmentNicotine Dependence / Substance Withdrawal Syndrome1
4CompletedTreatmentPain1
4CompletedTreatmentPelvic Pain1
4CompletedTreatmentPostoperative pain1
4CompletedTreatmentSchizoaffective Disorders / Schizophrenic Disorders2
4CompletedTreatmentSleep disorders and disturbances / Tobacco Use Cessation1
4CompletedTreatmentSmoking3
4CompletedTreatmentTobacco Dependence2
4Enrolling by InvitationPreventionTobacco Use Cessation1
4Not Yet RecruitingTreatmentAlcohol Drinking / Cessation, Smoking1
4Not Yet RecruitingTreatmentCessation, Smoking / Electronic Cigarette1
4Not Yet RecruitingTreatmentTobacco Dependence1
4RecruitingHealth Services ResearchNicotine Dependence1
4RecruitingPreventionTobacco Use Cessation1
4RecruitingTreatmentCessation, Smoking4
4RecruitingTreatmentGeneral Surgery / Nicotine Addiction / Smoking1
4RecruitingTreatmentNicotine Dependence1
4RecruitingTreatmentTobacco Use Cessation1
4SuspendedTreatmentSarcoidosis, Pulmonary1
4TerminatedSupportive CareCessation, Smoking / Nicotine Addiction1
4TerminatedTreatmentPost-Operative Ileus (POI)1
4TerminatedTreatmentPregnancy / Smoking1
4TerminatedTreatmentTobacco Use Disorders1
4Unknown StatusPreventionCessation, Smoking1
4Unknown StatusSupportive CareIntensive Care / Smoking / Ventilations, Mechanical1
4Unknown StatusTreatmentMajor Depressive Disorder (MDD) / Nicotine Dependence1
4Unknown StatusTreatmentParkinson's Disease (PD)1
Not AvailableActive Not RecruitingDiagnosticNicotine Addiction / Smoking, Cigarette1
Not AvailableActive Not RecruitingHealth Services ResearchTobacco Dependence1
Not AvailableActive Not RecruitingOtherDependence, Cocaine1
Not AvailableActive Not RecruitingPreventionSecondhand Smoke1
Not AvailableActive Not RecruitingSupportive CareCancer, Breast / Chemotherapeutic Agent Toxicity / Palmar-plantar Erythrodysesthesia (PPE)1
Not AvailableActive Not RecruitingSupportive CarePsychosocial Problem1
Not AvailableActive Not RecruitingSupportive CareTobacco Use Cessation1
Not AvailableActive Not RecruitingTreatmentCessation, Smoking1
Not AvailableActive Not RecruitingTreatmentCessation, Smoking / Human Immunodeficiency Virus (HIV)1
Not AvailableActive Not RecruitingTreatmentHomelessness / Tobacco Use Disorders1
Not AvailableActive Not RecruitingTreatmentNicotine Addiction1
Not AvailableActive Not RecruitingTreatmentSmoking1
Not AvailableCompletedNot AvailableBladder Cancers / Cancer, Breast / Colorectal Cancers / Head and Neck Carcinoma / Lung Cancers / Malignant Lymphomas / Prostate Cancer / Testicular germ cell tumour / Tobacco Use Disorders / Unspecified Adult Solid Tumor, Protocol Specific1
Not AvailableCompletedNot AvailableCessation, Smoking1
Not AvailableCompletedNot AvailableDrug Dependence1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableNicotine Dependence2
Not AvailableCompletedNot AvailableSmoking1
Not AvailableCompletedNot AvailableTobacco Dependence1
Not AvailableCompletedBasic ScienceAdhd1
Not AvailableCompletedBasic ScienceBasic Science Study of the Mechanisms of Attentional Enhancement by Compounds Acting on the Nicotinic Receptor1
Not AvailableCompletedBasic ScienceCessation, Smoking / Drug Dependence1
Not AvailableCompletedBasic ScienceCognition / Magnetic Resonance Imaging (MRI) / Mecamylamine / Nicotine1
Not AvailableCompletedBasic ScienceFocus: Effects of Nicotine and Alcohol on Brain Circuits1
Not AvailableCompletedBasic ScienceMental and Behavioral Disorders / Withdrawal State1
Not AvailableCompletedBasic ScienceNicotine Addiction1
Not AvailableCompletedBasic ScienceNicotine Dependence / Psychosis / Schizoaffective Disorders / Schizophrenic Disorders / Schizophreniform Disorders / Smoking1
Not AvailableCompletedBasic ScienceSchizophrenic Disorders1
Not AvailableCompletedBasic ScienceSmoking, Cigarette1
Not AvailableCompletedBasic ScienceTobacco Dependence3
Not AvailableCompletedBasic ScienceWound Healing1
Not AvailableCompletedDiagnosticCigarette Smokers1
Not AvailableCompletedHealth Services ResearchCessation, Smoking1
Not AvailableCompletedOtherNicotine Dependence1
Not AvailableCompletedPreventionBladder Cancers / Cervical Cancers / Esophageal Cancers / Head and Neck Carcinoma / Leukemias / Liver Cancer / Lung Cancers / Malignant Neoplasm of Pancreas / Malignant Neoplasm of Stomach / Renal Cancers / Tobacco Use Disorders1
Not AvailableCompletedPreventionEsophageal Cancers / Head and Neck Carcinoma / Lung Cancers1
Not AvailableCompletedPreventionLung Cancers1
Not AvailableCompletedPreventionSecondhand Smoke1
Not AvailableCompletedPreventionSmoking / Tobacco Use Cessation1
Not AvailableCompletedPreventionTobacco Use Cessation1
Not AvailableCompletedPreventionTobacco Use Disorders1
Not AvailableCompletedTreatmentAcute Coronary Syndromes (ACS) / Cessation, Smoking1
Not AvailableCompletedTreatmentAneurysmal Subarachnoid Hemorrhage1
Not AvailableCompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD) / Nicotine Dependence1
Not AvailableCompletedTreatmentBMI >27 kg/m2 / BMI >30 kg/m2 / Cessation, Smoking1
Not AvailableCompletedTreatmentCessation, Smoking9
Not AvailableCompletedTreatmentCessation, Smoking / Nicotine Dependence / Smoking1
Not AvailableCompletedTreatmentCessation, Smoking / Smoking1
Not AvailableCompletedTreatmentCessation, Smoking / Tobacco Use Disorders1
Not AvailableCompletedTreatmentCigarette Addiction1
Not AvailableCompletedTreatmentNicotine Dependence4
Not AvailableCompletedTreatmentPeriodontitis1
Not AvailableCompletedTreatmentSchizophrenic Disorders1
Not AvailableCompletedTreatmentSmoking3
Not AvailableCompletedTreatmentSmoking, Cigarette2
Not AvailableCompletedTreatmentTobacco Dependence7
Not AvailableCompletedTreatmentTobacco Use1
Not AvailableCompletedTreatmentTobacco Use Cessation1
Not AvailableCompletedTreatmentTobacco Use Disorders3
Not AvailableEnrolling by InvitationTreatmentCessation, Smoking1
Not AvailableEnrolling by InvitationTreatmentSmoking / Veterans1
Not AvailableNot Yet RecruitingPreventionCessation, Smoking1
Not AvailableNot Yet RecruitingPreventionTobacco Smoking1
Not AvailableNot Yet RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Tobacco Use Disorders1
Not AvailableNot Yet RecruitingTreatmentNicotine Dependence / Smokeless Tobacco1
Not AvailableRecruitingBasic ScienceSmoking, Cigarette2
Not AvailableRecruitingDevice FeasibilityNicotine Addiction / Serious Mental Illness1
Not AvailableRecruitingHealth Services ResearchTobacco Dependence1
Not AvailableRecruitingPreventionCancer Prevention / Tobacco Use Cessation1
Not AvailableRecruitingSupportive CareCervical Cancers / Cessation, Smoking / Tobacco Use1
Not AvailableRecruitingTreatmentAcute Coronary Syndromes (ACS) / Recurrences / Smoking1
Not AvailableRecruitingTreatmentCessation, Smoking3
Not AvailableRecruitingTreatmentCessation, Smoking / Posttraumatic Stress Disorders / PTSD / Smoking1
Not AvailableRecruitingTreatmentMarijuana Abuse / Smoking, Cigarette1
Not AvailableRecruitingTreatmentNicotine Dependence2
Not AvailableRecruitingTreatmentNicotine Dependence / Second Hand Tobacco Smoke1
Not AvailableRecruitingTreatmentSmoking1
Not AvailableSuspendedNot AvailableNicotine Dependence3
Not AvailableSuspendedTreatmentCessation, Smoking1
Not AvailableTerminatedNot AvailableNicotine Dependence1
Not AvailableTerminatedNot AvailableSmoking1
Not AvailableTerminatedBasic ScienceSchizophrenic Disorders1
Not AvailableUnknown StatusNot AvailableCancer, Breast / Colorectal Cancers / Lung Cancers / Prostate Cancer / Tobacco Use Disorders1
Not AvailableUnknown StatusDiagnosticCessation, Smoking1
Not AvailableUnknown StatusDiagnosticNicotine Dependence / Nicotine Use Disorder / Smoking / Tobacco Use Disorders1
Not AvailableUnknown StatusPreventionPostoperative pain1
Not AvailableUnknown StatusTreatmentCessation, Smoking1
Not AvailableWithdrawnNot AvailableSmokeless Tobacco1
Not AvailableWithdrawnPreventionProphylaxis against postoperative nausea and vomiting1
Not AvailableWithdrawnPreventionTobacco Use Cessation1
Not AvailableWithdrawnSupportive CareAnorexic / Constipation, Impaction, and Bowel Obstruction / Pain / Psychosocial Effects of Cancer and Its Treatment / Unspecified Adult Solid Tumor, Protocol Specific1
Not AvailableWithdrawnTreatmentTobacco Use Disorders1

Pharmacoeconomics

Manufacturers
  • Novartis consumer health inc
  • Sanofi aventis us llc
  • Aveva drug delivery systems inc
  • Mcneil consumer healthcare
  • Pharmacia and upjohn co
  • Pfizer inc
  • Glaxosmithkline
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Perrigo co
  • Perrigo r and d co
  • Watson laboratories inc
  • Glaxosmithkline consumer healthcare
Packagers
Dosage forms
FormRouteStrength
Patch, extended releaseTransdermal14 mg/1
Patch, extended releaseTransdermal21 mg/1
Patch, extended releaseTransdermal7 mg/1
Patch, extended releaseTransdermal21 mg/24h
Patch, extended releaseTransdermal14 mg/24h
Patch, extended releaseTransdermal7 mg/24h
LozengeOral4 mg/1
Patch, extended releaseTopical21 mg/1
Patch, extended releaseTopical7 mg/1
PatchTransdermal114 mg
PatchTransdermal36 mg
PatchTransdermal78 mg
Gum, chewingOral2 mg
PatchTransdermal25 mg
Gum, chewingOral4 mg
Gum, chewingOral2 mg/1
Gum, chewingOral4 mg/1
PatchTransdermal14 mg/24h
PatchTransdermal21 mg/24h
PatchTransdermal7 mg/24h
LozengeOral2 mg/1
Gum, chewingBuccal4 mg/1
PowderOral1 kg/kg
KitTransdermal
Kit
LiquidOral1 L/L
InhalantRespiratory (inhalation)4 mg/1
Spray, meteredNasal10 mg/mL
Gum, chewingBuccal2 mg/1
Patch, extended releaseTopical21 mg/24h
Patch, extended releaseTopical14 mg/24h
Patch, extended releaseTopical7 mg/24h
Prices
Unit descriptionCostUnit
Nicotrol 168 10 mg Inhalant Inhaler223.5USD inhaler
Nicotine 30 21 mg/24hr Patches Box206.52USD box
Nicotine 30 14 mg/24hr Patches Box196.27USD box
Nicotrol NS 10 mg/ml Solution 10ml Bottle55.88USD bottle
Nicotine polacrilex powder11.25USD g
Nicotrol ns 10 mg/ml spray5.37USD ml
Nicoderm cq 21 mg/24hr patch4.08USD patch
Nicoderm cq 14 mg/24hr patch3.52USD patch
Nicoderm cq 7 mg/24hr patch3.52USD patch
Nicotine 11 mg/24hr patch3.14USD patch
Nicotine 22 mg/24hr patch3.14USD patch
Nicotine transdermal system1.83USD each
Nicotrol cartridge inhaler1.28USD each
Commit 2 mg lozenge0.55USD lozenge
Commit 4 mg lozenge0.55USD lozenge
Nicorette 4 mg chewing gum0.52USD each
Nicorette 2 mg chewing gum0.45USD each
Thrive nicotine 2 mg gum0.42USD each
Thrive nicotine 4 mg gum0.42USD each
CVS Pharmacy nicotine 4 mg chewing gum0.38USD each
CVS Pharmacy nicotine 2 mg chewing gum0.34USD each
Nicotine 4 mg chewing gum0.3USD each
Nicotine 2 mg chewing gum0.25USD each
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5656255No1994-08-122014-08-12Us
US5501236No1993-06-082010-06-08Us
CA1333051No1994-11-152011-11-15Canada
US8323683No2008-04-302028-04-30Us
US8999379No2000-02-132020-02-13Us
US9205059No1999-12-152019-12-15Us
US8075911No2001-05-222021-05-22Us
US8663680No2000-02-132020-02-13Us
US8501164No2009-06-142029-06-14Us
US8940772No2009-04-302029-04-30Us

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)-79 °CPhysProp
boiling point (°C)247 °CPhysProp
water solubility1E+006 mg/LSEIDELL,A (1941)
logP1.17HANSCH,C ET AL. (1995)
logS0.79ADME Research, USCD
Caco2 permeability-4.71ADME Research, USCD
pKa8.5http://www.surgeongeneral.gov/library/reports/50-years-of-progress/sgr50-chap-5.pdf
Predicted Properties
PropertyValueSource
Water Solubility93.3 mg/mLALOGPS
logP0.87ALOGPS
logP1.16ChemAxon
logS-0.24ALOGPS
pKa (Strongest Basic)8.86ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.66 m3·mol-1ChemAxon
Polarizability18.59 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9748
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.8998
P-glycoprotein inhibitor IINon-inhibitor0.9368
Renal organic cation transporterInhibitor0.6868
CYP450 2C9 substrateNon-substrate0.7998
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.6347
CYP450 2C9 inhibitorNon-inhibitor0.8433
CYP450 2D6 inhibitorNon-inhibitor0.8838
CYP450 2C19 inhibitorNon-inhibitor0.8543
CYP450 3A4 inhibitorNon-inhibitor0.8308
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7589
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.9626
BiodegradationNot ready biodegradable0.9478
Rat acute toxicity3.4798 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8851
hERG inhibition (predictor II)Non-inhibitor0.7978
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (2.96 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-9500000000-f2d4835c504301f9410e
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-01q9-7900000000-1e2c38b5e4e7aae10d37
GC-MS Spectrum - EI-BGC-MSsplash10-001i-9800000000-fe889308f7088d47c31d
GC-MS Spectrum - GC-MSGC-MSsplash10-001i-9500000000-f2d4835c504301f9410e
Mass Spectrum (Electron Ionization)MSsplash10-001i-9400000000-47a036aa305825218fa2
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00di-0900000000-3e7377f36ca2547f4885
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-001i-2900000000-a505fff3a4028a6f0d52
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00lr-7900000000-b91a12a16d7688e8679d
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-01q9-7900000000-10d401d7ffa1c2cdbd9f
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-03di-0900000000-440798524836a27b78b4
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-01q9-0900000000-926940dd7f4851dbd73b
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-00lr-0900000000-6bccc06d40ab273cf972
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-0159-2900000000-f7512c405bb662e040a6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-7900000000-f1781566be5aee88f6ef
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-001i-0900000000-09e9b29571abf3a52e44
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-16cdb5f23105be4a892b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-03di-0900000000-720fe01876c739a30be0
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-85a813588b57acf531fe
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-0900000000-93a3dae1577f4f2dda53
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-001i-1900000000-cb6f8cec40dd9ed35d00
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00lr-1900000000-1443b1cf22d2de281898
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-0900000000-440798524836a27b78b4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01q9-0900000000-926940dd7f4851dbd73b
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00lr-0900000000-6bccc06d40ab273cf972
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0159-2900000000-1e50e1cd59e45e211535
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-7900000000-f1781566be5aee88f6ef
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-09e9b29571abf3a52e44
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyrrolidinylpyridines. These are compounds containing a pyrrolidinylpyridine ring system, which consists of a pyrrolidine ring linked to a pyridine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Pyrrolidinylpyridines
Direct Parent
Pyrrolidinylpyridines
Alternative Parents
Alkaloids and derivatives / Aralkylamines / N-alkylpyrrolidines / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Pyrrolidinylpyridine / Alkaloid or derivatives / Aralkylamine / N-alkylpyrrolidine / Heteroaromatic compound / Pyrrolidine / Tertiary aliphatic amine / Tertiary amine / Azacycle / Organic nitrogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
nicotine (CHEBI:17688) / Pesticides, Pyridine alkaloids, Alkaloids (C00745)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Espeseth T, Endestad T, Rootwelt H, Reinvang I: Nicotine receptor gene CHRNA4 modulates early event-related potentials in auditory and visual oddball target detection tasks. Neuroscience. 2007 Jul 29;147(4):974-85. Epub 2007 Jun 27. [PubMed:17590520]
  2. Winterer G, Musso F, Konrad A, Vucurevic G, Stoeter P, Sander T, Gallinat J: Association of attentional network function with exon 5 variations of the CHRNA4 gene. Hum Mol Genet. 2007 Sep 15;16(18):2165-74. Epub 2007 Jul 5. [PubMed:17613539]
  3. Ehringer MA, Clegg HV, Collins AC, Corley RP, Crowley T, Hewitt JK, Hopfer CJ, Krauter K, Lessem J, Rhee SH, Schlaepfer I, Smolen A, Stallings MC, Young SE, Zeiger JS: Association of the neuronal nicotinic receptor beta2 subunit gene (CHRNB2) with subjective responses to alcohol and nicotine. Am J Med Genet B Neuropsychiatr Genet. 2007 Jul 5;144B(5):596-604. [PubMed:17226798]
  4. Klaassen A, Glykys J, Maguire J, Labarca C, Mody I, Boulter J: Seizures and enhanced cortical GABAergic inhibition in two mouse models of human autosomal dominant nocturnal frontal lobe epilepsy. Proc Natl Acad Sci U S A. 2006 Dec 12;103(50):19152-7. Epub 2006 Dec 4. [PubMed:17146052]
  5. De Luca V, Voineskos S, Wong G, Kennedy JL: Genetic interaction between alpha4 and beta2 subunits of high affinity nicotinic receptor: analysis in schizophrenia. Exp Brain Res. 2006 Sep;174(2):292-6. Epub 2006 Apr 25. [PubMed:16636791]
  6. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [PubMed:19560048]
  7. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [PubMed:11006350]
  8. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [PubMed:20400469]
  9. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [PubMed:20081230]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Toxic substance binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
Gene Name
CHRNA7
Uniprot ID
P36544
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-7
Molecular Weight
56448.925 Da
References
  1. Mexal S, Jenkins PM, Lautner MA, Iacob E, Crouch EL, Stitzel JA: alpha7 nicotinic receptor gene promoter polymorphisms in inbred mice affect expression in a cell type-specific fashion. J Biol Chem. 2007 May 4;282(18):13220-7. Epub 2007 Mar 14. [PubMed:17360707]
  2. Olincy A, Harris JG, Johnson LL, Pender V, Kongs S, Allensworth D, Ellis J, Zerbe GO, Leonard S, Stevens KE, Stevens JO, Martin L, Adler LE, Soti F, Kem WR, Freedman R: Proof-of-concept trial of an alpha7 nicotinic agonist in schizophrenia. Arch Gen Psychiatry. 2006 Jun;63(6):630-8. [PubMed:16754836]
  3. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [PubMed:19560048]
  4. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [PubMed:11006350]
  5. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [PubMed:20400469]
  6. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [PubMed:20081230]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNB2
Uniprot ID
P17787
Uniprot Name
Neuronal acetylcholine receptor subunit beta-2
Molecular Weight
57018.575 Da
References
  1. Ehringer MA, Clegg HV, Collins AC, Corley RP, Crowley T, Hewitt JK, Hopfer CJ, Krauter K, Lessem J, Rhee SH, Schlaepfer I, Smolen A, Stallings MC, Young SE, Zeiger JS: Association of the neuronal nicotinic receptor beta2 subunit gene (CHRNB2) with subjective responses to alcohol and nicotine. Am J Med Genet B Neuropsychiatr Genet. 2007 Jul 5;144B(5):596-604. [PubMed:17226798]
  2. De Luca V, Voineskos S, Wong G, Kennedy JL: Genetic interaction between alpha4 and beta2 subunits of high affinity nicotinic receptor: analysis in schizophrenia. Exp Brain Res. 2006 Sep;174(2):292-6. Epub 2006 Apr 25. [PubMed:16636791]
  3. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [PubMed:19560048]
  4. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [PubMed:11006350]
  5. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [PubMed:20400469]
  6. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [PubMed:20081230]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Drug binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA2
Uniprot ID
Q15822
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-2
Molecular Weight
59764.82 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [PubMed:19560048]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [PubMed:11006350]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [PubMed:20400469]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [PubMed:20081230]
  5. Sullivan PF, Neale BM, van den Oord E, Miles MF, Neale MC, Bulik CM, Joyce PR, Straub RE, Kendler KS: Candidate genes for nicotine dependence via linkage, epistasis, and bioinformatics. Am J Med Genet B Neuropsychiatr Genet. 2004 Apr 1;126B(1):23-36. [PubMed:15048644]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA3
Uniprot ID
P32297
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-3
Molecular Weight
57479.54 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [PubMed:19560048]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [PubMed:11006350]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [PubMed:20400469]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [PubMed:20081230]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA5
Uniprot ID
P30532
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-5
Molecular Weight
53053.965 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [PubMed:19560048]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [PubMed:11006350]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [PubMed:20400469]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [PubMed:20081230]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Acetylcholine-activated cation-selective channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNA6
Uniprot ID
Q15825
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-6
Molecular Weight
56897.745 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [PubMed:19560048]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [PubMed:11006350]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [PubMed:20400469]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [PubMed:20081230]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Calcium channel activity
Specific Function
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding induces a conformation change that leads to the opening of an ion-conducting channel across the plasm...
Gene Name
CHRNA9
Uniprot ID
Q9UGM1
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-9
Molecular Weight
54806.63 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [PubMed:19560048]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [PubMed:11006350]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [PubMed:20400469]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [PubMed:20081230]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Receptor binding
Specific Function
Ionotropic receptor with a probable role in the modulation of auditory stimuli. Agonist binding may induce an extensive change in conformation that affects all subunits and leads to opening of an i...
Gene Name
CHRNA10
Uniprot ID
Q9GZZ6
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-10
Molecular Weight
49704.295 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [PubMed:19560048]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [PubMed:11006350]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [PubMed:20400469]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [PubMed:20081230]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Drug binding
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNB3
Uniprot ID
Q05901
Uniprot Name
Neuronal acetylcholine receptor subunit beta-3
Molecular Weight
52728.215 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [PubMed:19560048]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [PubMed:11006350]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [PubMed:20400469]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [PubMed:20081230]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
Gene Name
CHRNB4
Uniprot ID
P30926
Uniprot Name
Neuronal acetylcholine receptor subunit beta-4
Molecular Weight
56378.985 Da
References
  1. Mansvelder HD, Mertz M, Role LW: Nicotinic modulation of synaptic transmission and plasticity in cortico-limbic circuits. Semin Cell Dev Biol. 2009 Jun;20(4):432-40. doi: 10.1016/j.semcdb.2009.01.007. Epub 2009 Jan 22. [PubMed:19560048]
  2. Narahashi T, Fenster CP, Quick MW, Lester RA, Marszalec W, Aistrup GL, Sattelle DB, Martin BR, Levin ED: Symposium overview: mechanism of action of nicotine on neuronal acetylcholine receptors, from molecule to behavior. Toxicol Sci. 2000 Oct;57(2):193-202. [PubMed:11006350]
  3. Jackson KJ, Marks MJ, Vann RE, Chen X, Gamage TF, Warner JA, Damaj MI: Role of alpha5 nicotinic acetylcholine receptors in pharmacological and behavioral effects of nicotine in mice. J Pharmacol Exp Ther. 2010 Jul;334(1):137-46. doi: 10.1124/jpet.110.165738. Epub 2010 Apr 16. [PubMed:20400469]
  4. Zaniewska M, Przegalinski E, Filip M: Nicotine dependence - human and animal studies, current pharmacotherapies and future perspectives. Pharmacol Rep. 2009 Nov-Dec;61(6):957-65. [PubMed:20081230]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Barbieri RL, Gochberg J, Ryan KJ: Nicotine, cotinine, and anabasine inhibit aromatase in human trophoblast in vitro. J Clin Invest. 1986 Jun;77(6):1727-33. [PubMed:3711333]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Choline o-acetyltransferase activity
Specific Function
Catalyzes the reversible synthesis of acetylcholine (ACh) from acetyl CoA and choline at cholinergic synapses.
Gene Name
CHAT
Uniprot ID
P28329
Uniprot Name
Choline O-acetyltransferase
Molecular Weight
82535.025 Da
References
  1. FAHMY AR, RYMAN BE, WALSH EO: The inhibition of choline acetylase by nicotine. J Pharm Pharmacol. 1954 Sep;6(9):607-9. [PubMed:13192619]

Enzymes

Details
1. Cytochrome P450 2A6
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Const...
Gene Name
CYP2A6
Uniprot ID
P11509
Uniprot Name
Cytochrome P450 2A6
Molecular Weight
56501.005 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Exhibits a coumarin 7-hydroxylase activity. Active in the metabolic activation of hexamethylphosphoramide, N,N-dimethylaniline, 2'-methoxyacetophenone, N-nitrosomethylphenylamine, and the tobacco-s...
Gene Name
CYP2A13
Uniprot ID
Q16696
Uniprot Name
Cytochrome P450 2A13
Molecular Weight
56687.095 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Details
6. Cytochrome P450 1A2
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Serotonin binding
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. Lewis AJ, Truman P, Hosking MR, Miller JH: Monoamine oxidase inhibitory activity in tobacco smoke varies with tobacco type. Tob Control. 2012 Jan;21(1):39-43. doi: 10.1136/tc.2010.040287. Epub 2011 Jun 2. [PubMed:21636610]
  2. Leroy C, Bragulat V, Berlin I, Gregoire MC, Bottlaender M, Roumenov D, Dolle F, Bourgeois S, Penttila J, Artiges E, Martinot JL, Trichard C: Cerebral monoamine oxidase A inhibition in tobacco smokers confirmed with PET and [11C]befloxatone. J Clin Psychopharmacol. 2009 Feb;29(1):86-8. doi: 10.1097/JCP.0b013e31819e98f. [PubMed:19142115]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Lewis AJ, Truman P, Hosking MR, Miller JH: Monoamine oxidase inhibitory activity in tobacco smoke varies with tobacco type. Tob Control. 2012 Jan;21(1):39-43. doi: 10.1136/tc.2010.040287. Epub 2011 Jun 2. [PubMed:21636610]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Urakami Y, Akazawa M, Saito H, Okuda M, Inui K: cDNA cloning, functional characterization, and tissue distribution of an alternatively spliced variant of organic cation transporter hOCT2 predominantly expressed in the human kidney. J Am Soc Nephrol. 2002 Jul;13(7):1703-10. [PubMed:12089365]
  2. Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [PubMed:9808712]
  3. Okuda M, Urakami Y, Saito H, Inui K: Molecular mechanisms of organic cation transport in OCT2-expressing Xenopus oocytes. Biochim Biophys Acta. 1999 Mar 4;1417(2):224-31. [PubMed:10082798]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Secondary active organic cation transmembrane transporter activity
Specific Function
Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
Gene Name
SLC22A1
Uniprot ID
O15245
Uniprot Name
Solute carrier family 22 member 1
Molecular Weight
61153.345 Da
References
  1. Bednarczyk D, Ekins S, Wikel JH, Wright SH: Influence of molecular structure on substrate binding to the human organic cation transporter, hOCT1. Mol Pharmacol. 2003 Mar;63(3):489-98. [PubMed:12606755]
  2. Zhang L, Schaner ME, Giacomini KM: Functional characterization of an organic cation transporter (hOCT1) in a transiently transfected human cell line (HeLa). J Pharmacol Exp Ther. 1998 Jul;286(1):354-61. [PubMed:9655880]
  3. Urakami Y, Okuda M, Masuda S, Saito H, Inui KI: Functional characteristics and membrane localization of rat multispecific organic cation transporters, OCT1 and OCT2, mediating tubular secretion of cationic drugs. J Pharmacol Exp Ther. 1998 Nov;287(2):800-5. [PubMed:9808712]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Toxin transporter activity
Specific Function
Mediates potential-dependent transport of a variety of organic cations. May play a significant role in the disposition of cationic neurotoxins and neurotransmitters in the brain.
Gene Name
SLC22A3
Uniprot ID
O75751
Uniprot Name
Solute carrier family 22 member 3
Molecular Weight
61279.485 Da
References
  1. Kekuda R, Prasad PD, Wu X, Wang H, Fei YJ, Leibach FH, Ganapathy V: Cloning and functional characterization of a potential-sensitive, polyspecific organic cation transporter (OCT3) most abundantly expressed in placenta. J Biol Chem. 1998 Jun 26;273(26):15971-9. [PubMed:9632645]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Wu X, Prasad PD, Leibach FH, Ganapathy V: cDNA sequence, transport function, and genomic organization of human OCTN2, a new member of the organic cation transporter family. Biochem Biophys Res Commun. 1998 May 29;246(3):589-95. [PubMed:9618255]
  2. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. [PubMed:10525100]
  3. Wu X, Huang W, Prasad PD, Seth P, Rajan DP, Leibach FH, Chen J, Conway SJ, Ganapathy V: Functional characteristics and tissue distribution pattern of organic cation transporter 2 (OCTN2), an organic cation/carnitine transporter. J Pharmacol Exp Ther. 1999 Sep;290(3):1482-92. [PubMed:10454528]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, low affinity carnitine transporter. Probably transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without...
Gene Name
SLC22A4
Uniprot ID
Q9H015
Uniprot Name
Solute carrier family 22 member 4
Molecular Weight
62154.48 Da
References
  1. Yabuuchi H, Tamai I, Nezu J, Sakamoto K, Oku A, Shimane M, Sai Y, Tsuji A: Novel membrane transporter OCTN1 mediates multispecific, bidirectional, and pH-dependent transport of organic cations. J Pharmacol Exp Ther. 1999 May;289(2):768-73. [PubMed:10215651]
  2. Wu X, George RL, Huang W, Wang H, Conway SJ, Leibach FH, Ganapathy V: Structural and functional characteristics and tissue distribution pattern of rat OCTN1, an organic cation transporter, cloned from placenta. Biochim Biophys Acta. 2000 Jun 1;1466(1-2):315-27. [PubMed:10825452]

Drug created on June 13, 2005 07:24 / Updated on November 19, 2017 20:33