Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR1148)
Drug Name
Nicotine
Synonyms
Nicoderm; Nicoderm Cq; Nicorette; Nicotina [Italian]; Nicotine polacrilex; Nicotrol; Nicotrol Inhaler; Nicotrol NS; Nikotin [German]; Nikotyna [Polish]; Destruxol orchid spray; Flux MAAG; Fumetobac; Habitrol; L-Nicotine; Micotine; NICOTINE AND SALTS; Niagara P.A. dust; Ortho N-4 dust; Ortho N-5 dust; Prostep; XL All Insecticide; nicotine; (-)-Nicotine; (S)-(-)-Nicotine; (S)-3-(1-methylpyrrolidin-2-yl)pyridine; (S)-Nicotine; 3-(N-Methylpyrollidino)pyridine; 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
Indication Nicotine dependence [ICD11: 6C4A] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 162.23 Topological Polar Surface Area 16.1
Heavy Atom Count 12 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
89594
PubChem SID
4007 ; 794580 ; 829184 ; 829311 ; 833584 ; 3137564 ; 7889325 ; 7980122 ; 8144582 ; 10223753 ; 11537938 ; 14748051 ; 15171051 ; 17389805 ; 17397514 ; 24862741 ; 24870064 ; 24897663 ; 24897737 ; 25621940 ; 26752744 ; 26752745 ; 26752746 ; 44420693 ; 46393352 ; 47515453 ; 47515454 ; 47959911 ; 48110586 ; 48414101 ; 48423841 ; 48425389 ; 49854422 ; 50105392 ; 50105393 ; 50271161 ; 53788316 ; 53801040 ; 56310810 ; 56311904 ; 56312242 ; 56312459 ; 56312463 ; 56312785 ; 56313106 ; 56313907 ; 56314421 ; 56314547 ; 56314548 ; 56314824
ChEBI ID
ChEBI:17688
CAS Number
54-11-5
TTD Drug ID
D0T8GD
Formula
C10H14N2
Canonical SMILES
CN1CCCC1C2=CN=CC=C2
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
InChIKey
SNICXCGAKADSCV-JTQLQIEISA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
(S)-Nicotine delta-1',5'-iminium ion DM002190
181139
Oxidation - Heteroring Dehydrogenation 1 [9]
2'-hydroxynicotine DM002191
23615292
Oxidation - Hydroxylation 1 [10]
4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone DM002188
47289
Unclear 1 [11]
Cotinine DM003093
854019
Unclear 1 [11]
N-Methylnicotinium DM002184
430
Unclear 1 [12]
Nicotine glucuronide metabolite DM002185
3035848
Conjugation - Glucuronidation 1 [9]
Nicotine imine DM002183
431
Unclear 1 [12]
Nicotine-1'-N-oxide DM002187
68107
Oxidation - 1'-N-Oxidation 1 [12]
NNAL DM002189
104856
Unclear 1 [11]
Norcotinine DM002186
413
Unclear 1 [11]
Nornicotine DM002180
412
Unclear 1 [11]
3'-hydroxycotinine DM002181
10219774
Oxidation - 3'-Hydroxylation 2 [9]
Cotinine DM003093
854019
Unclear 2 [11]
Cotinine N-oxide metabolite DM002182
9815514
Oxidation - N-Oxidation 2 [9]
Cotinine-N-glucuronide DM002178
3398121
Conjugation - Glucuronidation 2 [9]
Nicotine-1'-N-oxide DM002187
68107
Oxidation - 1'-N-Oxidation 2 [9]
Nornicotine DM002180
412
Unclear 2 [11]
⏷ Show the Full List of 17  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002952 Nicotine Nornicotine Unclear Unclear [11]
MR002953 Nicotine Nicotine imine Unclear CYP2B6 ... [12]
MR002954 Nicotine N-Methylnicotinium Unclear Unclear [12]
MR002955 Nicotine Nicotine glucuronide metabolite Conjugation - Glucuronidation UGT1A1 ... [9]
MR002956 Nicotine Norcotinine Unclear Unclear [11]
MR002957 Nicotine Nicotine-1'-N-oxide Oxidation - 1'-N-Oxidation FMO3 [12]
MR002958 Nicotine 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanone Unclear Unclear [11]
MR002959 Nicotine 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol Unclear Unclear [11]
MR002960 Nicotine (S)-Nicotine delta-1',5'-iminium ion Oxidation - Heteroring Dehydrogenation CYP2B6 ... [9]
MR002961 Nicotine 2'-hydroxynicotine Oxidation - Hydroxylation CYP2A6 [10]
MR002963 Nicotine Cotinine Unclear Unclear [11]
MR002964 Cotinine Cotinine glucuronide metabolite Conjugation - Glucuronidation UGT1A1 ... [9]
MR002965 Cotinine Nornicotine Unclear Unclear [11]
MR002966 Cotinine 3'-hydroxycotinine Oxidation - 3'-Hydroxylation CYP2A6 [9]
MR002967 Cotinine Cotinine N-oxide metabolite Oxidation - N-Oxidation Unclear [9]
MR002968 Cotinine Nicotine-1'-N-oxide Oxidation - 1'-N-Oxidation FMO3 [9]
MR002962 Nicotine imine Cotinine Unclear AOX1 [11]
⏷ Show the Full List of 17 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A1 (CYP1A1) DME0006 Homo sapiens
CP1A1_HUMAN
1.14.14.1
[2]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A13 (CYP2A13) DME0030 Homo sapiens
CP2AD_HUMAN
1.14.14.1
[3]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[4]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[5]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2E1 (CYP2E1) DME0013 Homo sapiens
CP2E1_HUMAN
1.14.14.1
[6]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
Nicotinate dehydrogenase (nicA) DME1069 Pseudomonas putida
NICA_PSEPK
1.17.2.1
[7]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[8]
⏷ Show the Full List of 13  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Nicotinate dehydrogenase (nicA) DME1069 Km = 0.24 microM
NICA_PSEPK
[7]
References
1 Nicotine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Roles of CYP2A6 and CYP2B6 in nicotine C-oxidation by human liver microsomes. Arch Toxicol. 1999 Mar;73(2):65-70.
3 Inactivation of CYP2A6 and CYP2A13 during nicotine metabolism. J Pharmacol Exp Ther. 2006 Jan;316(1):295-303.
4 CYP2A6- and CYP2A13-catalyzed metabolism of the nicotine delta-5'(1')iminium ion. J Pharmacol Exp Ther. 2012 Nov;343(2):307-15.
5 Nicotine and 4-(methylnitrosamino)-1-(3-pyridyl)-butanone metabolism by cytochrome P450 2B6. Drug Metab Dispos. 2005 Dec;33(12):1760-4.
6 Effects of nicotine on cytochrome P450 2A6 and 2E1 activities. Br J Clin Pharmacol. 2010 Feb;69(2):152-9.
7 Optimization of a nicotine degrading enzyme for potential use in treatment of nicotine addiction. BMC Biotechnol. 2019 Aug 2;19(1):56.
8 Liquid chromatography-tandem mass spectrometry method for measurement of nicotine N-glucuronide: a marker for human UGT2B10 inhibition. J Pharm Biomed Anal. 2011 Jul 15;55(5):964-71.
9 Pharmacogenomics knowledge for personalized medicine Clin Pharmacol Ther. 2012 Oct;92(4):414-7. doi: 10.1038/clpt.2012.96.
10 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
11 DrugBank(Pharmacology-Metabolism)Nicotine
12 U. S. FDA Label -Nicotine

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