General Information of Drug (ID: DMWX5CO)

Drug Name
Nicotine
Synonyms
Habitrol; Micotine; NCT; NICOTINE AND SALTS; Nicoderm Patch; Nicotina [Italian]; Nicotine Patch; Nicotine [USAN]; Nicotine replacement patch; Nicotine solution; Nictoine patch; Nikotin [German]; Nikotyna [Polish]; Transdermal Nicotine; Nicotine [UN1654] [Poison]; ENT 3,424; Habitrol (TN); Nicorette (TN); Nicotine (USP); Nicotine (compounds related to); Nicotine [BSI:ISO]; L(-)-nicotine; Beta-Pyridyl-alpha-N-methyl pyrrolidine; (-)-Nicotine solution; (2S) 3-(1-Methyl-pyrrolidin-2-yl)-pyridine; (S)-(-)-NICOTINE, 3-[(2S)-1-METHYL-2-PYRROLIDINYL] PYRIDINE; (S)-(-)-Nicotine; (S)-3-(1-methylpyrrolidin-2-yl)pyridine; (S)-3-(N-methylpyrrolidin-2-yl)pyridine; (S)-Nicotine; 3-(2-(N-methylpyrrolidinyl))pyridine; 3-(N-Methylpyrollidino)pyridine; 3-(N-Methylpyrrolidino)pyridine; 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
Indication
Disease Entry ICD 11 Status REF
Nicotine dependence 6C4A.2 Approved [1], [2]
Tobacco dependence 6C4A.2 Clinical trial [3]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 162.23
Topological Polar Surface Area (xlogp) 1.2
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 [4]
Clearance
The clearance of drug is 1.2 L/min in healthy adult smoker [5]
Elimination
16.7% of drug is excreted from urine in the unchanged form [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 15 - 20 hours [6]
Metabolism
The drug is metabolized via the hepatic [7]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 3.522 micromolar/kg/day [8]
Unbound Fraction
The unbound fraction of drug in plasma is 0.95% [6]
Vd
The volume of distribution (Vd) of drug is 2-3 L/kg [5]
Chemical Identifiers
Formula
C10H14N2
IUPAC Name
3-[(2S)-1-methylpyrrolidin-2-yl]pyridine
Canonical SMILES
CN1CCC[C@H]1C2=CN=CC=C2
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/t10-/m0/s1
InChIKey
SNICXCGAKADSCV-JTQLQIEISA-N
Cross-matching ID
PubChem CID
89594
ChEBI ID
CHEBI:17688
CAS Number
54-11-5
DrugBank ID
DB00184
TTD ID
D0T8GD
VARIDT ID
DR00679
INTEDE ID
DR1148

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Nicotinic acetylcholine receptor (nAChR) TTJSZTB NOUNIPROTAC Antagonist [9], [10]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 3A4 (CYP3A4) DE4LYSA CP3A4_HUMAN Substrate [11]
Cytochrome P450 2E1 (CYP2E1) DEVDYN7 CP2E1_HUMAN Substrate [12]
Cytochrome P450 2D6 (CYP2D6) DECB0K3 CP2D6_HUMAN Substrate [11]
Cytochrome P450 2C9 (CYP2C9) DE5IED8 CP2C9_HUMAN Substrate [11]
Cytochrome P450 1A1 (CYP1A1) DE6OQ3W CP1A1_HUMAN Substrate [11]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [13]
Mephenytoin 4-hydroxylase (CYP2C19) DEGTFWK CP2CJ_HUMAN Substrate [11]
Cytochrome P450 2A6 (CYP2A6) DEJVYAZ CP2A6_HUMAN Substrate [14]
Cytochrome P450 1A2 (CYP1A2) DEJGDUW CP1A2_HUMAN Substrate [11]
Cytochrome P450 2B6 (CYP2B6) DEPKLMQ CP2B6_HUMAN Substrate [15]
Cytochrome P450 2C8 (CYP2C8) DES5XRU CP2C8_HUMAN Substrate [11]
Cytochrome P450 2A13 (CYP2A13) DEXZA9U CP2AD_HUMAN Substrate [16]
Nicotinate dehydrogenase (nicA) DE4AMLP NICA_PSEPK Substrate [17]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Nicotine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Alpelisib DMEXMYK Moderate Increased metabolism of Nicotine caused by Alpelisib mediated induction of CYP450 enzyme. Breast cancer [2C60-2C6Y] [110]
Cenobamate DMGOVHA Moderate Increased metabolism of Nicotine caused by Cenobamate mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [111]
Fenofibrate DMFKXDY Moderate Decreased metabolism of Nicotine caused by Fenofibrate mediated inhibition of CYP450 enzyme. Hyper-lipoproteinaemia [5C80] [112]
Ceritinib DMB920Z Moderate Decreased metabolism of Nicotine caused by Ceritinib mediated inhibition of CYP450 enzyme. Lung cancer [2C25] [112]
Abametapir DM2RX0I Moderate Decreased metabolism of Nicotine caused by Abametapir mediated inhibition of CYP450 enzyme. Pediculosis [1G00] [113]
Telotristat ethyl DMDIYFZ Moderate Increased metabolism of Nicotine caused by Telotristat ethyl mediated induction of CYP450 enzyme. Small intestine developmental anomaly [DA90] [110]
⏷ Show the Full List of 6 DDI Information of This Drug

References

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