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Identification
NameNicotine
Accession NumberDB00184  (APRD00200, EXPT02315)
Typesmall molecule
Groupsapproved
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. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(±)-nicotineNot AvailableNot Available
(R,S)-nicotineNot AvailableNot Available
(RS)-nicotineNot AvailableNot Available
NicotinNot AvailableNot Available
NikotinNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
HabitrolNot Available
NicodermNot Available
Nicoderm CQNot Available
NicoretteNot Available
NicotrolNot Available
Brand mixturesNot Available
Categories
CAS number54-11-5
WeightAverage: 162.2316
Monoisotopic: 162.115698458
Chemical FormulaC10H14N2
InChI KeySNICXCGAKADSCV-UHFFFAOYSA-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
IUPAC Name
3-(1-methylpyrrolidin-2-yl)pyridine
SMILES
CN1CCCC1C1=CN=CC=C1
Mass Specshow(2.96 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassAlkaloids and Derivatives
ClassNot Available
SubclassNot Available
Direct parentAlkaloids and Derivatives
Alternative parentsPyrrolidinylpyridines; Pyrrolidines; Tertiary Amines; Polyamines
Substituentspyridine; pyrrolidine; tertiary amine; polyamine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
Pharmacology
IndicationFor the relief of nicotine withdrawal symptoms and as an aid to smoking cessation.
PharmacodynamicsNicotine, 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 actionNicotine 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.
AbsorptionAbsorption 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 bindingLess than 5%
Metabolism

Primarily hepatic, cotinine is the primary metabolite.

SubstrateEnzymesProduct
Nicotine
Not Available
N-MethylnicotiniumDetails
Nicotine
Nicotine imineDetails
Nicotine
Not Available
CotinineDetails
Nicotine
Not Available
NornicotineDetails
Nicotine
Nicotine glucuronideDetails
Nicotine
Not Available
NorcotinineDetails
Nicotine
Nicotine-1'-N-oxideDetails
Nicotine
Not Available
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanoneDetails
Nicotine
Not Available
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanolDetails
Nicotine imine
CotinineDetails
Cotinine
Not Available
Cotinine N-oxideDetails
Cotinine
3'-HydroxycotinineDetails
Cotinine
Not Available
NornicotineDetails
Cotinine
Nicotine-1'-N-oxideDetails
Cotinine
Cotinine glucuronideDetails
Route of eliminationAbout 10% of the nicotine absorbed is excreted unchanged in the urine.
Half lifeCotinine 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]
ToxicitySymptoms 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
PathwayCategorySMPDB ID
Nicotine Action PathwayDrug actionSMP00431
Nicotine Metabolism PathwayDrug metabolismSMP00628
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9748
Caco-2 permeable + 0.8867
P-glycoprotein substrate Substrate 0.5
P-glycoprotein inhibitor I Non-inhibitor 0.8998
P-glycoprotein inhibitor II Non-inhibitor 0.9368
Renal organic cation transporter Inhibitor 0.6868
CYP450 2C9 substrate Non-substrate 0.7998
CYP450 2D6 substrate Substrate 0.8918
CYP450 3A4 substrate Non-substrate 0.5
CYP450 1A2 substrate Non-inhibitor 0.6347
CYP450 2C9 substrate Non-inhibitor 0.8433
CYP450 2D6 substrate Non-inhibitor 0.8838
CYP450 2C19 substrate Non-inhibitor 0.8543
CYP450 3A4 substrate Non-inhibitor 0.8308
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7589
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.9626
Biodegradation Not ready biodegradable 0.9478
Rat acute toxicity 3.4798 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8851
hERG inhibition (predictor II) Non-inhibitor 0.7978
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
CapsuleOral
Capsule, extended releaseOral
DiscTransdermal
Drug delivery systemRespiratory (inhalation)
GumOral
LiquidIntramuscular
LiquidOral
PatchTransdermal
PowderOral
SolutionIntramuscular
Solution / dropsOral
TabletOral
Tablet, extended releaseOral
Prices
Unit descriptionCostUnit
Nicotrol 168 10 mg Inhalant Inhaler223.5USDinhaler
Nicotine 30 21 mg/24hr Patches Box206.52USDbox
Nicotine 30 14 mg/24hr Patches Box196.27USDbox
Nicotrol NS 10 mg/ml Solution 10ml Bottle55.88USDbottle
Nicotine polacrilex powder11.25USDg
Nicotrol ns 10 mg/ml spray5.37USDml
Nicoderm cq 21 mg/24hr patch4.08USDpatch
Nicoderm cq 14 mg/24hr patch3.52USDpatch
Nicoderm cq 7 mg/24hr patch3.52USDpatch
Nicotine 11 mg/24hr patch3.14USDpatch
Nicotine 22 mg/24hr patch3.14USDpatch
Nicotine transdermal system1.83USDeach
Nicotrol cartridge inhaler1.28USDeach
Commit 2 mg lozenge0.55USDlozenge
Commit 4 mg lozenge0.55USDlozenge
Nicorette 4 mg chewing gum0.52USDeach
Nicorette 2 mg chewing gum0.45USDeach
Thrive nicotine 2 mg gum0.42USDeach
Thrive nicotine 4 mg gum0.42USDeach
CVS Pharmacy nicotine 4 mg chewing gum0.38USDeach
CVS Pharmacy nicotine 2 mg chewing gum0.34USDeach
Nicotine 4 mg chewing gum0.3USDeach
Nicotine 2 mg chewing gum0.25USDeach
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States56562551994-08-122014-08-12
United States55012361993-06-082010-06-08
Canada13330511994-11-152011-11-15
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point-79 °CPhysProp
boiling point247 °CPhysProp
water solubility1E+006 mg/LSEIDELL,A (1941)
logP1.17HANSCH,C ET AL. (1995)
logS0.79ADME Research, USCD
Caco2 permeability-4.71ADME Research, USCD
pKa3.1TOMLIN,C (1997); pKa1
Predicted Properties
PropertyValueSource
water solubility9.33e+01 g/lALOGPS
logP0.87ALOGPS
logP1.16ChemAxon
logS-0.24ALOGPS
pKa (strongest basic)8.86ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area16.13ChemAxon
rotatable bond count1ChemAxon
refractivity49.66ChemAxon
polarizability18.62ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot 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 Reference
  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
  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
  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
  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
External Links
ResourceLink
KEGG DrugD03365
KEGG CompoundC00745
PubChem Compound942
PubChem Substance46506924
ChemSpider917
ChEBI18723
ChEMBLCHEMBL3
Therapeutic Targets DatabaseDAP000175
PharmGKBPA450626
HETNCT
Drug Product Database2241228
RxListhttp://www.rxlist.com/cgi/generic2/nicotini.htm
Drugs.comhttp://www.drugs.com/nicotine.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/nic1292.shtml
WikipediaNicotine
ATC CodesN07BA01A11HA01C04AC01C10AD02
AHFS Codes
  • 12:92.00
  • 24:06.92
  • 92:02.00*
  • 88:08.00
PDB Entries
FDA labelshow(11.2 MB)
MSDSshow(77.6 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Neuronal acetylcholine receptor subunit alpha-4

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-4 P43681 Details

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
  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
  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;144(5):596-604. Pubmed
  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
  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
  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. Epub 2009 Jan 22. Pubmed
  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
  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. Epub 2010 Apr 16. Pubmed
  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

2. Neuronal acetylcholine receptor subunit alpha-7

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-7 P36544 Details

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
  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
  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. Epub 2009 Jan 22. Pubmed
  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
  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. Epub 2010 Apr 16. Pubmed
  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

3. Neuronal acetylcholine receptor subunit beta-2

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit beta-2 P17787 Details

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;144(5):596-604. Pubmed
  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
  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. Epub 2009 Jan 22. Pubmed
  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
  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. Epub 2010 Apr 16. Pubmed
  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

4. Neuronal acetylcholine receptor subunit alpha-2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-2 Q15822 Details

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. Epub 2009 Jan 22. Pubmed
  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
  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. Epub 2010 Apr 16. Pubmed
  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
  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;126(1):23-36. Pubmed

5. Neuronal acetylcholine receptor subunit alpha-3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-3 P32297 Details

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. Epub 2009 Jan 22. Pubmed
  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
  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. Epub 2010 Apr 16. Pubmed
  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

6. Neuronal acetylcholine receptor subunit alpha-5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-5 P30532 Details

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. Epub 2009 Jan 22. Pubmed
  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
  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. Epub 2010 Apr 16. Pubmed
  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

7. Neuronal acetylcholine receptor subunit alpha-6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-6 Q15825 Details

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. Epub 2009 Jan 22. Pubmed
  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
  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. Epub 2010 Apr 16. Pubmed
  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

8. Neuronal acetylcholine receptor subunit alpha-9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-9 Q9UGM1 Details

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. Epub 2009 Jan 22. Pubmed
  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
  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. Epub 2010 Apr 16. Pubmed
  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

9. Neuronal acetylcholine receptor subunit alpha-10

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit alpha-10 Q9GZZ6 Details

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. Epub 2009 Jan 22. Pubmed
  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
  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. Epub 2010 Apr 16. Pubmed
  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

10. Neuronal acetylcholine receptor subunit beta-3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit beta-3 Q05901 Details

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. Epub 2009 Jan 22. Pubmed
  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
  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. Epub 2010 Apr 16. Pubmed
  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

11. Neuronal acetylcholine receptor subunit beta-4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Neuronal acetylcholine receptor subunit beta-4 P30926 Details

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. Epub 2009 Jan 22. Pubmed
  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
  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. Epub 2010 Apr 16. Pubmed
  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

12. Cytochrome P450 19A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Cytochrome P450 19A1 P11511 Details

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

13. Choline O-acetyltransferase

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Choline O-acetyltransferase P28329 Details

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

Enzymes

1. Cytochrome P450 2A6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2A6 P11509 Details

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. Epub 2009 Nov 24. Pubmed
  2. Lexicomp.

2. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

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. Epub 2009 Nov 24. Pubmed
  2. Lexicomp.

3. Cytochrome P450 2A13

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2A13 Q16696 Details

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. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

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. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 1A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inducer

Components

Name UniProt ID Details
Cytochrome P450 1A1 P04798 Details

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. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 1A2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inducer

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

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. Epub 2009 Nov 24. Pubmed

8. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

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. Epub 2009 Nov 24. Pubmed

9. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

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. Epub 2009 Nov 24. Pubmed

10. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

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. Epub 2009 Nov 24. Pubmed

11. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

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. Epub 2009 Nov 24. Pubmed

12. Amine oxidase [flavin-containing] A

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] A P21397 Details

References:

  1. Lewis AJ, Truman P, Hosking MR, Miller JH: Monoamine oxidase inhibitory activity in tobacco smoke varies with tobacco type. Tob Control. 2011 Jun 2. Pubmed
  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. Pubmed

13. Amine oxidase [flavin-containing] B

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Amine oxidase [flavin-containing] B P27338 Details

References:

  1. Lewis AJ, Truman P, Hosking MR, Miller JH: Monoamine oxidase inhibitory activity in tobacco smoke varies with tobacco type. Tob Control. 2011 Jun 2. Pubmed

Transporters

1. Solute carrier family 22 member 2

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 2 O15244 Details

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
  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
  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

2. Solute carrier family 22 member 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 1 O15245 Details

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
  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
  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

3. Solute carrier family 22 member 3

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 3 O75751 Details

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

4. Solute carrier family 22 member 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

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
  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
  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

5. Solute carrier family 22 member 4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 4 Q9H015 Details

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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:08