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]
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) 1
Hydrogen Bond Donor Count (hbonddonor) 0
Hydrogen Bond Acceptor Count (hbondacc) 2
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
CHEMBL578211
CAS Number
486-56-6
TTD ID
D0TY5N
INTEDE ID
DR2026
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug

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]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 2B10 (UGT2B10)
Main DME 		DEI8NGH UDB10_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Aryl hydrocarbon receptor repressor (AHRR) OTSJ12W6 AHRR_HUMAN Post-Translational Modifications [7]
Contactin-associated protein-like 2 (CNTNAP2) OT48T2ZP CNTP2_HUMAN Post-Translational Modifications [7]
Exostosin-1 (EXT1) OTRPALJK EXT1_HUMAN Post-Translational Modifications [7]
Mitogen-activated protein kinase 1 (MAPK1) OTH85PI5 MK01_HUMAN Post-Translational Modifications [8]
Mitogen-activated protein kinase 3 (MAPK3) OTCYKGKO MK03_HUMAN Post-Translational Modifications [8]
Tetratricopeptide repeat protein 7B (TTC7B) OTUE51B3 TTC7B_HUMAN Post-Translational Modifications [7]
UDP-glucuronosyltransferase 1A4 OT4PU620 UD14_HUMAN Biotransformations [9]
UDP-glucuronosyltransferase 1A9 OTPCHAFX UD19_HUMAN Biotransformations [10]
Unconventional myosin-Ig (MYO1G) OTOCFS3Q MYO1G_HUMAN Post-Translational Modifications [7]
Zinc finger protein Gfi-1 (GFI1) OT9HB9H8 GFI1_HUMAN Post-Translational Modifications [7]
Molecular Interaction Atlas (MIA) 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 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.
9 N-glucuronidation of nicotine and cotinine by human liver microsomes and heterologously expressed UDP-glucuronosyltransferases. Drug Metab Dispos. 2003 Nov;31(11):1361-8. doi: 10.1124/dmd.31.11.1361.
10 Interindividual variability in nicotine metabolism: C-oxidation and glucuronidation. Drug Metab Pharmacokinet. 2005 Aug;20(4):227-35. doi: 10.2133/dmpk.20.227.