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

General Information of Drug (ID: DR2026)
Drug Name
Cotinine
Synonyms
Cotinina; Cotinina [INN-Spanish]; Cotinine (-); Cotinine [INN]; Cotininum; Cotininum [INN-Latin]; K5161X06LL; UIKROCXWUNQSPJ-VIFPVBQESA-N; cotinine; (-)-Cotinine; (5S)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one; (5S)-1-methyl-5-pyridin-3-ylpyrrolidin-2-one; (S)-(-)-Cotinine; (S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone; (S)-1-Methyl-5-(3-pyridyl)-2-pyrrolidinone; (S)-Cotinine; 2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (5S)-; 486-56-6; CHEBI:68641; MFCD00077696; S(-)-1-Methyl-5-(3-pyridyl)-2-pyrrolidone; UNII-K5161X06LL
Indication Nicotine dependence [ICD11: 6C4A] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 176.21 Topological Polar Surface Area 33.2
Heavy Atom Count 13 Rotatable Bond Count 1
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
854019
PubChem SID
585010 ; 1096246 ; 9167258 ; 10321235 ; 11336036 ; 11361275 ; 11364950 ; 11367512 ; 11370074 ; 11371779 ; 11375504 ; 11378245 ; 11462247 ; 11466110 ; 11467230 ; 11485679 ; 11490516 ; 11493607 ; 11495798 ; 11537576 ; 15195099 ; 15321989 ; 17404848 ; 24278324 ; 24892255 ; 26611674 ; 26719720 ; 45842446 ; 46386857 ; 47216831 ; 47216832 ; 47440317 ; 47589047 ; 47959806 ; 48035187 ; 48110503 ; 48185048 ; 48259286 ; 48334554 ; 49681728 ; 49698332 ; 53777391 ; 53788514 ; 57408847 ; 57653976 ; 74938588 ; 81092919 ; 85165356 ; 85787848 ; 85789411
ChEBI ID
CHEBI:68641
CAS Number
486-56-6
TTD Drug ID
D0TY5N
Formula
C10H12N2O
Canonical SMILES
CN1C(CCC1=O)C2=CN=CC=C2
InChI
1S/C10H12N2O/c1-12-9(4-5-10(12)13)8-3-2-6-11-7-8/h2-3,6-7,9H,4-5H2,1H3/t9-/m0/s1
InChIKey
UIKROCXWUNQSPJ-VIFPVBQESA-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
3'-hydroxycotinine DM002181
10219774
Oxidation - Hydrolyzationn 1 [3] , [4]
Cotinine-N-glucuronide DM002178
3398121
Conjugation - Glucuronidation 1 [2]
Cotinine-N-oxide DM004915
108114
Oxidation - Oxdation 1 [6]
Norcotinine DM002186
413
Oxidation - N-demethylation 1 [2]
Trans-3'-hydroxycotinine DM004912
107963
Oxidation - Hydrolyzationn 1 [2]
Trans-3'-Hydroxycotinine-O-glucuronide DM004913
183115
Conjugation - Glucuronidation 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005300 Cotinine Trans-3'-hydroxycotinine Oxidation - Hydrolyzationn CYP2A6 ... [2]
MR005302 Cotinine 3'-hydroxycotinine Oxidation - Hydrolyzationn Cyp2a5 [3], [4]
MR005303 Cotinine Cotinine-N-glucuronide Conjugation - Glucuronidation UGT1A4 ... [2]
MR005304 Cotinine Norcotinine Oxidation - N-demethylation CYP2A6 [2]
MR005305 Cotinine Cotinine-N-oxide Oxidation - Oxdation Unclear [6]
MR005301 Trans-3'-hydroxycotinine Trans-3'-Hydroxycotinine-O-glucuronide Conjugation - Glucuronidation UGT2B7 ... [2]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2A13 (CYP2A13) DME0030 Homo sapiens
CP2AD_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A5 (Cyp2a5) DMEN247 Mus musculus
CP2A5_MOUSE
1.14.14.1
[3] , [4]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B10 (UGT2B10) DME0205 Homo sapiens
UDB10_HUMAN
2.4.1.17
[5]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
⏷ Show the Full List of 7  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
UDP-glucuronosyltransferase 2B10 (UGT2B10) DME0205 Km = 0.0278 microM
UDB10_HUMAN
[5]
References
1 National Center for Advancing Translational Science-Inxight: drug (K5161X06LL)
2 Interindividual variability in nicotine metabolism: C-oxidation and glucuronidation
3 Characterization and comparison of nicotine and cotinine metabolism in vitro and in vivo in DBA/2 and C57BL/6 mice
4 Metabolism of nicotine and cotinine by human cytochrome P450 2A13. Drug Metab Dispos. 2005 Feb;33(2):258-61.
5 Human UDP-glucuronosyltransferase (UGT) 2B10: validation of cotinine as a selective probe substrate, inhibition by UGT enzyme-selective inhibitors and antidepressant and antipsychotic drugs, and structural determinants of enzyme inhibition. Drug Metab Dispos. 2016 Mar;44(3):378-88.
6 Increased cotinine elimination and cotinine-N-oxide formation by phenobarbital induction in rat and mouse

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