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Atlas / Drug / Nicotine

Nicotine

drug
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Also known as HabitrolNicabateNicoderm cqNicopassNicopatchNicorette invisiNicotinell classicNicotinell supportNicotinell tts 10Nicotinell tts 20Nicotinell tts 30NicotrolNiquitinNiquitin clrNiquitin minis cherryNiquitin minis mintNiquitin minis orangeNiquitin mintNiquitin pre-quit

Summary

Nicotine (CHEMBL3) is an approved small-molecule anxiolytic drug (ATC N07BA01) targeting CHRNA3, CHRNA4, and CHRNA9; indicated across 26 conditions including nicotine dependence and heart failure.

At a glance

  • Status: Approved (max clinical phase 4)
  • Modality: Small molecule
  • ATC class: N07BA01
  • Targets: 6 (CHRNA3, CHRNA4, CHRNA9…)
  • Indications: 26 conditions
  • Clinical trials: 428
  • Chemistry: 162.23 Da · C10H14N2

Identifiers

Drug identity and classification

FieldValue
ChEMBL IDCHEMBL3
NameNicotine
TypeSmall molecule
Max phase4
FDA approvedyes
PubChem CID89594
ChEBICHEBI:17688
ATCN07BA01
Molecular formulaC10H14N2
Molecular weight162.23
InChIKeySNICXCGAKADSCV-JTQLQIEISA-N

SMILES: CN1CCC[C@H]1C2=CN=CC=C2

IUPAC name: 3-[(2S)-1-methylpyrrolidin-2-yl]pyridine

ChEBI definition: A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.

Pharmacological roles (ChEBI): phytogenic insecticide, teratogenic agent, neurotoxin, anxiolytic drug, nicotinic acetylcholine receptor agonist, biomarker, immunomodulator, mitogen, peripheral nervous system drug, psychotropic drug.

Other ChEBI roles (chemical / environmental): plant metabolite, xenobiotic.

Also known as: Habitrol, Nicabate, Nicoderm cq, Nicopass, Nicopatch, Nicorette invisi, Nicotine, Nicotinell classic, Nicotinell support, Nicotinell tts 10, Nicotinell tts 20, Nicotinell tts 30

Parent form; salt/anhydrous children: CHEMBL151515, CHEMBL225057, CHEMBL1201536, CHEMBL3137669, CHEMBL3182465, CHEMBL3989563

Patent coverage: 70,209 distinct patent families (184,969 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 184,925 (100%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

GeneTargetActionpAffinityCancer dependencyUniProt
CHRNA3nicotinic acetylcholine receptor α3 subunitAgonist5.760%P32297
CHRNA4nicotinic acetylcholine receptor α4 subunitAgonist8.660.2%P43681
CHRNA9nicotinic acetylcholine receptor α9 subunitAntagonist0.1%Q9UGM1
CHRNA10nicotinic acetylcholine receptor α10 subunitAntagonist1.3%Q9GZZ6
TRPA1TRPA1Activation4.80.1%O75762
KCND3Kv4.37.45.5%Q9UK17

Broader ChEMBL bioactivity targets: 52 (assay-derived). Sample: Transient receptor potential cation channel subfamily A member 1, Microtubule-associated protein tau, Inositol monophosphatase 1, Solute carrier family 22 member 2, Neuronal acetylcholine receptor; alpha3/beta2, Acetylcholine receptor; alpha1/beta1/delta/gamma, Neuronal acetylcholine receptor; alpha4/beta2, Neuronal acetylcholine receptor; alpha2/beta4, Neuronal acetylcholine receptor; alpha4/beta4, Neuronal acetylcholine receptor; alpha2/beta2.

Bioactivity

ChEMBL activities: 411 potent at pChembl ≥ 5 of 464 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

TargetpChemblTypeValueUnitActivity ID
P0475711Kd0.01nMCHEMBL_ACT_1189416
P0475710.66Kd0.02nMCHEMBL_ACT_1195595
CHRNB210.35Ki0.04nMCHEMBL_ACT_18424477
CHRNB29.22Ki0.6nMCHEMBL_ACT_13307190
CHRNB29.21Ki0.61nMCHEMBL_ACT_29199812
CHRNB29.21Ki0.62nMCHEMBL_ACT_29199821
P094839.08Ki0.84nMCHEMBL_ACT_1090274
P094839.03Ki0.93nMCHEMBL_ACT_1908951
P094839.03Ki0.94nMCHEMBL_ACT_1908952
P094839.03Ki0.94nMCHEMBL_ACT_201691
P094839.03Ki0.94nMCHEMBL_ACT_2272253
P094839.03Ki0.94nMCHEMBL_ACT_2296474
P094839.02Ki0.95nMCHEMBL_ACT_1482209
P094839.02Ki0.95nMCHEMBL_ACT_1507113
CHRNB29EC501nMCHEMBL_ACT_10965841
P094839Ki1nMCHEMBL_ACT_1188971
P094839Ki1nMCHEMBL_ACT_1222961
P094839Ki1nMCHEMBL_ACT_1431600
CHRNB29Ki1nMCHEMBL_ACT_22432836
P047579Ki1nMCHEMBL_ACT_574853
P047579Ki1nMCHEMBL_ACT_594206
P094839Ki1.01nMCHEMBL_ACT_653707
P027109IC501nMCHEMBL_ACT_710566
P047579Ki1nMCHEMBL_ACT_732299
P094839Ki1nMCHEMBL_ACT_749656
P047579Ki1nMCHEMBL_ACT_807137
P094839Ki1nMCHEMBL_ACT_825715
P094839Ki1nMCHEMBL_ACT_848418
CHRNB28.98Ki1.05nMCHEMBL_ACT_12479252
P094838.98Ki1.05nMCHEMBL_ACT_88888

Target pathways

Aggregated over 6 target gene(s): CHRNA3, CHRNA4, CHRNA9, CHRNA10, TRPA1, KCND3.

Top Reactome pathways

19 total, by targets touching each:

PathwayTargetsGenes
Neuronal System4CHRNA3, CHRNA4, CHRNA9, KCND3
Neurotransmitter receptors and postsynaptic signal transmission3CHRNA3, CHRNA4, CHRNA9
Transmission across Chemical Synapses3CHRNA3, CHRNA4, CHRNA9
Acetylcholine binding and downstream events3CHRNA3, CHRNA4, CHRNA9
Postsynaptic nicotinic acetylcholine receptors3CHRNA3, CHRNA4, CHRNA9
Highly calcium permeable postsynaptic nicotinic acetylcholine receptors3CHRNA3, CHRNA4, CHRNA9
Presynaptic nicotinic acetylcholine receptors2CHRNA3, CHRNA4
Highly sodium permeable postsynaptic acetylcholine nicotinic receptors2CHRNA3, CHRNA4
Highly calcium permeable nicotinic acetylcholine receptors2CHRNA3, CHRNA4
Sensory processing of sound2CHRNA10, CHRNA9
Sensory processing of sound by outer hair cells of the cochlea2CHRNA10, CHRNA9
Acetylcholine inhibits contraction of outer hair cells2CHRNA10, CHRNA9
Sensory Perception2CHRNA10, CHRNA9
Potassium Channels1KCND3
Voltage gated Potassium channels1KCND3
TRP channels1TRPA1
Muscle contraction1KCND3
Cardiac conduction1KCND3
Phase 1 - inactivation of fast Na+ channels1KCND3

Dominant GO biological processes

GO termTargets
monoatomic ion transport6
monoatomic ion transmembrane transport6
regulation of membrane potential4
membrane depolarization4
excitatory postsynaptic potential4
calcium ion transport4
chemical synaptic transmission4
synaptic transmission, cholinergic3
acetylcholine receptor signaling pathway3
regulation of postsynaptic membrane potential3
calcium ion transmembrane transport3
signal transduction2
neuromuscular synaptic transmission2
response to nicotine2
behavioral response to nicotine2

Indications & clinical

Indications

26 indications (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

IndicationTrial phaseMONDOEFO
nicotine dependence4MONDO:0008575EFO:0003768
heart failure3MONDO:0005252EFO:0003144
chronic obstructive pulmonary disease3MONDO:0005002EFO:0000341
cannabis dependence3MONDO:0005689EFO:0007191
lung neoplasm3MONDO:0021117MONDO:0008903
severe acute respiratory syndrome3MONDO:0005091EFO:0000694
injury2MONDO:0021178EFO:0000546
sarcoma2MONDO:0005089EFO:0000691
depressive disorder2MONDO:0002050MONDO:0002050
carcinoma2MONDO:0004993EFO:0000313
Parkinson disease2MONDO:0005180MONDO:0005180
attention deficit-hyperactivity disorder1MONDO:0007743EFO:0003888
cocaine dependence1MONDO:0005186EFO:0002610
sarcoidosis1MONDO:0019338MONDO:0019338
drug dependence1MONDO:0005303EFO:0003890
pulmonary sarcoidosis0MONDO:0001708DOID:13406

10 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 428.

Phase distribution

PhaseTrials
Not specified169
PHASE473
PHASE254
PHASE153
PHASE337
EARLY_PHASE125
PHASE1/PHASE29
PHASE2/PHASE38

Top trials by phase / activity

NCTPhaseStatusTitle
NCT02162849PHASE4ACTIVE_NOT_RECRUITINGReward Sensitivity and Pharmacotherapy for Smoking Cessation
NCT03315910PHASE4ACTIVE_NOT_RECRUITINGImplementing Tobacco Treatment in Low Dose CT Lung Cancer Screening Sites
NCT04604509PHASE4RECRUITINGNicotine Replacement Therapy, Counseling, Varenicline, and Bupropion for Smoking Cessation, the PISCES I Trial
NCT05206435PHASE4ACTIVE_NOT_RECRUITINGMethadone-Maintained Smokers Switching to E-Cigarettes
NCT05587361PHASE4RECRUITINGBeta-Adrenergic Modulation of Drug Cue Reactivity
NCT06474299PHASE4RECRUITINGThe Avenues Study: Dual Use Cessation
NCT06534047PHASE4RECRUITINGTranscranial Magnetic Stimulation for Nicotine Dependence: An Effectiveness-Implementation Trial
NCT06595459PHASE4RECRUITINGThe Options 2 Study
NCT07095205PHASE4RECRUITINGPET Imaging Using the Tracer [18F]VAT to Assess the Antidepressant Effect of Nicotine.
NCT07419425PHASE4NOT_YET_RECRUITINGMy Path to Quit Tobacco
NCT07503925PHASE4NOT_YET_RECRUITINGTHRIVE Study: Understanding How Oral Nicotine Pouches Affect Public Health
NCT00046813PHASE4TERMINATEDNicotine Patch for Nicotine Dependence in Individuals With Schizophrenia or Schizoaffective Disorder - 1
NCT00132821PHASE4COMPLETEDImpact of Smoking Cessation on Sleep - 5
NCT00232817PHASE4COMPLETEDAnesthesia and Postoperative Pain
NCT00235313PHASE4COMPLETEDAdjustment of DOses of NIcotine in Smoking Cessation (ADONIS)
NCT00296647PHASE4COMPLETEDSmoking Cessation Intervention: Effectiveness in Primary Care
NCT00332644PHASE4COMPLETEDSmoking Cessation Medications: Efficacy, Mechanisms and Algorithms
NCT00365508PHASE4COMPLETEDCounseling and Nicotine Replacement Therapy in Helping Adult Smokers Quit Smoking
NCT00373126PHASE4COMPLETEDThe Effects of Nicotine Withdrawal on Reward Responsivity in Schizophrenia
NCT00383747PHASE4COMPLETEDThe Effects of Nicotine on Cognition in Schizophrenia
NCT00385216PHASE4COMPLETEDNicotine as an Adjuvant Analgesic for Third Molar Surgery
NCT00440505PHASE4COMPLETEDEffect of Nicotine on Chronic Pelvic Pain
NCT00440830PHASE4COMPLETEDNicotine Patch as an Analgesic Adjuvant After Surgery
NCT00586482PHASE4COMPLETEDPilot Study: Preoperative Nicotine Lozenges
NCT00657020PHASE4COMPLETEDFunctional Magnetic Resonance Imaging (fMRI) Investigation of Nicotine Withdrawal Symptoms
NCT00749463PHASE4COMPLETEDEvaluation of the Safety Profile, Quit and Reduction Rate After Nicorette® Gum and Patch Treatment
NCT00770666PHASE4COMPLETEDCombination Medications vs. Patch Alone for Medically-Ill Smokers
NCT00959972PHASE4COMPLETEDVarenicline Versus Transdermal Nicotine Patch for Smoking Cessation in Patients With Coronary Heart Disease
NCT01047527PHASE4COMPLETEDAn Effectiveness Trial of Maintenance Therapy for Nicotine Dependence
NCT01048944PHASE4COMPLETEDNicotine Replacement Therapy (NRT) and Bupropion Mechanisms of Effectiveness in Smokers
NCT01087905PHASE4COMPLETEDImproving the Population-Wide Effectiveness of U.S. Tobacco Cessation Quitlines
NCT01104896PHASE4UNKNOWNEffect of Daily Nicotine Patch Application on Mechanical Ventilation Weaning in Smoking Patients
NCT01122238PHASE4COMPLETEDIdentifying Treatments to Motivate Smokers to Quit
NCT01216904PHASE4UNKNOWNNicotine Treatment of Impulsivity in Parkinson’s Disease
NCT01289275PHASE4COMPLETEDSmoking Cessation in Hospitalized Smokers
NCT01330043PHASE4COMPLETEDExtended Treatment for Smoking Cessation
NCT01362959PHASE4COMPLETEDNicotine Replacement Therapy in the Intensive Care Unit
NCT01400243PHASE4COMPLETEDNicotine Patch for Marijuana Withdrawal
NCT01538394PHASE4COMPLETEDClinical Trial to Evaluate the Efficacy of Smoking Cessation
NCT01553084PHASE4COMPLETEDA Comparative Effectiveness & Long Term Health Study in Wisconsin Smokers

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

187 molecules share ≥1 primary target. Top 60 by shared-target count:

MoleculeSourceStatusShared targets
ACETYLCHOLINEChEMBL + PubChemPhase 4 (approved)CHRNA10, CHRNA3, CHRNA4, CHRNA9
STILONIUM IODIDEChEMBLPhase 2CHRNA10, CHRNA3, CHRNA4, CHRNA9
PALONOSETRONChEMBL + PubChemPhase 4 (approved)CHRNA4, KCND3
SUNITINIBChEMBL + PubChemPhase 4 (approved)CHRNA4, KCND3
BUPROPIONChEMBLPhase 4 (approved)CHRNA3, CHRNA4
GRANISETRONChEMBLPhase 4 (approved)CHRNA3, CHRNA4
MECAMYLAMINEChEMBLPhase 4 (approved)CHRNA3, CHRNA4
ONDANSETRONChEMBLPhase 4 (approved)CHRNA3, CHRNA4
TROPISETRONChEMBLPhase 4 (approved)CHRNA3, CHRNA4
VARENICLINEChEMBLPhase 4 (approved)CHRNA3, CHRNA4
CYTISINICLINEChEMBL + PubChemPhase 3 (approved)CHRNA3, CHRNA4
DEXMECAMYLAMINEChEMBLPhase 3CHRNA3, CHRNA4
ALTINICLINEChEMBLPhase 2CHRNA3, CHRNA4
AZD1446ChEMBLPhase 2CHRNA3, CHRNA4
GTS-21ChEMBLPhase 2CHRNA3, CHRNA4
RADAFAXINEChEMBLPhase 2CHRNA3, CHRNA4
RIVANICLINEChEMBLPhase 2CHRNA3, CHRNA4
SOFINICLINEChEMBLPhase 2CHRNA3, CHRNA4
TEBANICLINEChEMBLPhase 2CHRNA3, CHRNA4
MoxifloxacinPubChemApprovedCHRNA4, KCND3
PemigatinibPubChemApprovedCHRNA10, CHRNA9
TadalafilPubChemApprovedCHRNA4, KCND3
CRIZOTINIBChEMBL + PubChemPhase 4 (approved)CHRNA4
DARIFENACINChEMBL + PubChemPhase 4 (approved)KCND3
DARUNAVIRChEMBL + PubChemPhase 4 (approved)KCND3
DEFERASIROXChEMBL + PubChemPhase 4 (approved)KCND3
DICLOFENACChEMBL + PubChemPhase 4 (approved)TRPA1
DISULFIRAMChEMBL + PubChemPhase 4 (approved)TRPA1
DULOXETINEChEMBL + PubChemPhase 4 (approved)KCND3
MEFENAMIC ACIDChEMBL + PubChemPhase 4 (approved)TRPA1
NEBIVOLOLChEMBL + PubChemPhase 4 (approved)KCND3
PALIPERIDONEChEMBL + PubChemPhase 4 (approved)KCND3
RIFAMPINChEMBL + PubChemPhase 4 (approved)CHRNA4
SOLIFENACINChEMBL + PubChemPhase 4 (approved)KCND3
TOLTERODINEChEMBL + PubChemPhase 4 (approved)KCND3
VARDENAFILChEMBL + PubChemPhase 4 (approved)KCND3
ANISOTROPINEChEMBLPhase 4 (approved)CHRNA4
ATRACURIUMChEMBLPhase 4 (approved)CHRNA4
AZELASTINEChEMBLPhase 4 (approved)CHRNA4
CARBAMOYLCHOLINEChEMBLPhase 4 (approved)CHRNA4
CHLOROPROCAINEChEMBLPhase 4 (approved)CHRNA4
CHLORPHENTERMINEChEMBLPhase 4 (approved)CHRNA4
DAUNORUBICINChEMBLPhase 4 (approved)CHRNA4
DIPHEMANILChEMBLPhase 4 (approved)CHRNA4
EPALRESTATChEMBLPhase 4 (approved)CHRNA4
FENTANYLChEMBLPhase 4 (approved)CHRNA4
ILOPERIDONEChEMBLPhase 4 (approved)CHRNA4
MEDAZEPAMChEMBLPhase 4 (approved)CHRNA4
MENTHOLChEMBLPhase 4 (approved)TRPA1
MOXISYLYTEChEMBLPhase 4 (approved)CHRNA4
NIMESULIDEChEMBLPhase 4 (approved)CHRNA4
NITAZOXANIDEChEMBLPhase 4 (approved)CHRNA4
OXYPERTINEChEMBLPhase 4 (approved)CHRNA4
PALBOCICLIBChEMBLPhase 4 (approved)CHRNA4
PONATINIBChEMBLPhase 4 (approved)CHRNA4
PYRVINIUMChEMBLPhase 4 (approved)CHRNA4
RIFAXIMINChEMBLPhase 4 (approved)CHRNA4
SERTINDOLEChEMBLPhase 4 (approved)CHRNA4
THIORIDAZINEChEMBLPhase 4 (approved)CHRNA4
VANDETANIBChEMBLPhase 4 (approved)CHRNA4

About this page

Generated deterministically by Sugi Atlas from primary biomedical databases via BioBTree. Every record on this page traces to a primary source.

Generated
Atlas version
v1.1.2
BioBTree
v2.0.2

Sources 30

This page pulls from 30 datasets indexed by BioBTree:

chebichembl_activitychembl_moleculechembl_targetcivic_evidenceclingen_dosageclinical_trialsdepmapefoensemblentrezgogoparentgtopdbgtopdb_interactiongtopdb_ligandhgncmeshmondomsigdbpatent_compoundpharmgkbpharmgkb_guidelinepubchempubchem_activityreactomereactomeparentrefseqtranscriptuniprot