Welcome to DrugBank 4.0! If you prefer, you can still go back to version 3.0.
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 KeyInChIKey=SNICXCGAKADSCV-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
    N-MethylnicotiniumDetails
    Nicotine
    Nicotine imineDetails
    Nicotine
      CotinineDetails
      Nicotine
        NornicotineDetails
        Nicotine
        Nicotine glucuronideDetails
        Nicotine
          NorcotinineDetails
          Nicotine
          Nicotine-1'-N-oxideDetails
          Nicotine
            4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanoneDetails
            Nicotine
              4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanolDetails
              Nicotine imine
              CotinineDetails
              Cotinine
                Cotinine N-oxideDetails
                Cotinine
                3'-HydroxycotinineDetails
                Cotinine
                  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

                  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

                  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

                  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

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