Details of the Drug

General Information of Drug (ID: DMCEZ1B)

Drug Name

Cotinine

Synonyms

cotinine; (-)-Cotinine; 486-56-6; Cotinina; Cotininum; (S)-(-)-Cotinine; (5S)-1-methyl-5-(pyridin-3-yl)pyrrolidin-2-one; Cotinine (-); (S)-Cotinine; UNII-K5161X06LL; (S)-1-Methyl-5-(3-pyridinyl)-2-pyrrolidinone; 2-Pyrrolidinone, 1-methyl-5-(3-pyridinyl)-, (5S)-; CHEBI:68641; (S)-1-Methyl-5-(3-pyridyl)-2-pyrrolidinone; UIKROCXWUNQSPJ-VIFPVBQESA-N; K5161X06LL; Cotinine [INN]; MFCD00077696; Cotininum [INN-Latin]; Cotinina [INN-Spanish]; S(-)-1-Methyl-5-(3-pyridyl)-2-pyrrolidone; (5S)-1-methyl-5-pyridin-3-ylpyrrolidin-2-one

Indication

Disease Entry	ICD 11	Status	REF
Insecticide	N.A.	Approved	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

176.21

Logarithm of the Partition Coefficient (xlogp)

-0.3

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [2]
Bioavailability: 97% of drug becomes completely available to its intended biological destination(s) [3]
Clearance: The drug present in the plasma can be removed from the body at the rate of 0.89 mL/min/kg [4]
Half-life: The concentration or amount of drug in body reduced by one-half in 17 hours [4]
Vd: Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.1 L/kg [4]

Chemical Identifiers

Formula: C10H12N2O
IUPAC Name: (5S)-1-methyl-5-pyridin-3-ylpyrrolidin-2-one
Canonical SMILES: CN1[C@@H](CCC1=O)C2=CN=CC=C2
InChI: 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

Cross-matching ID

PubChem CID: 854019
ChEBI ID: CHEBI:68641
CAS Number: 486-56-6
TTD ID: D0TY5N
INTEDE ID: DR2026

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Nicotinic acetylcholine receptor (nAChR)	TTJSZTB	NOUNIPROTAC	Modulator	[5]

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Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
UDP-glucuronosyltransferase 2B10 (UGT2B10)_{Main DME}	DEI8NGH	UDB10_HUMAN	Substrate	[6]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Aryl hydrocarbon receptor repressor (AHRR)	OTSJ12W6	AHRR_HUMAN	Post-Translational Modifications	[7]
Arylamine N-acetyltransferase 1 (NAT1)	OTCCNQ3H	ARY1_HUMAN	Regulation of Drug Effects	[8]
Contactin-associated protein-like 2 (CNTNAP2)	OT48T2ZP	CNTP2_HUMAN	Post-Translational Modifications	[7]
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Post-Translational Modifications	[7]
Cytochrome P450 1A2 (CYP1A2)	OTLLBX48	CP1A2_HUMAN	Gene/Protein Processing	[9]
Cytochrome P450 2A6 (CYP2A6)	OT52TWG3	CP2A6_HUMAN	Regulation of Drug Effects	[10]
Cytochrome P450 2B6 (CYP2B6)	OTOYO4S7	CP2B6_HUMAN	Biotransformations	[11]
Exostosin-1 (EXT1)	OTRPALJK	EXT1_HUMAN	Post-Translational Modifications	[7]
G1/S-specific cyclin-D1 (CCND1)	OT8HPTKJ	CCND1_HUMAN	Gene/Protein Processing	[12]
Mitogen-activated protein kinase 1 (MAPK1)	OTH85PI5	MK01_HUMAN	Post-Translational Modifications	[12]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

References

1	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
2	BDDCS predictions, self-correcting aspects of BDDCS assignments, BDDCS assignment corrections, and classification for more than 175 additional drugs
3	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
4	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
5	Functional versus chemical diversity: is biodiversity important for drug discovery. Trends Pharmacol Sci. 2002 May;23(5):225-31.
6	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.
7	450K epigenome-wide scan identifies differential DNA methylation in newborns related to maternal smoking during pregnancy. Environ Health Perspect. 2012 Oct;120(10):1425-31. doi: 10.1289/ehp.1205412. Epub 2012 Jul 31.
8	N-acetyltransferase 1 polymorphism increases cotinine levels in Caucasian children exposed to secondhand smoke: the CCAAPS birth cohort. Pharmacogenomics J. 2015 Apr;15(2):189-95. doi: 10.1038/tpj.2014.44. Epub 2014 Aug 26.
9	Predictive three-dimensional quantitative structure-activity relationship of cytochrome P450 1A2 inhibitors. J Med Chem. 2005 Jun 2;48(11):3808-15.
10	Deficient cotinine formation from nicotine is attributed to the whole deletion of the CYP2A6 gene in humans. Clin Pharmacol Ther. 2000 Jan;67(1):57-69. doi: 10.1067/mcp.2000.103957.
11	Down-regulation of hepatic nicotine metabolism and a CYP2A6-like enzyme in African green monkeys after long-term nicotine administration. Mol Pharmacol. 2003 Jan;63(1):96-104. doi: 10.1124/mol.63.1.96.
12	Cotinine, a major nicotine metabolite, induces cell proliferation on urothelium in vitro and in vivo. Toxicology. 2020 Jan 15;429:152325. doi: 10.1016/j.tox.2019.152325. Epub 2019 Nov 1.