nicotine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1920 54-11-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nicotine
  • L-Nicotine
  • (S)-Nicotine
  • (-)-Nicotine
  • nicotine bitartrate anhydrous
  • nicotine polacrilex
Devices or delivery systems used to aid in ending a TOBACCO habit.
  • Molecular weight: 162.24
  • Formula: C10H14N2
  • CLOGP: 0.88
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 16.13
  • ALOGS: -0.24
  • ROTB: 1

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
30 mg Chewing gum
60 mg Inhal
30 mg N
30 mg SL
14 mg TD

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 16.70 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 3.52 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 30 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 2.60 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 18 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.95 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 7, 1991 FDA SANOFI AVENTIS US

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Nicotine dependence 650.07 37.65 83 1322 69 2356611
Drug dependence 496.90 37.65 99 1306 2946 2353734
Overdose 424.28 37.65 125 1280 19782 2336898
Incorrect product administration duration 405.90 37.65 81 1324 2414 2354266
Foetal exposure during pregnancy 335.26 37.65 79 1326 5173 2351507
Drug withdrawal syndrome neonatal 317.89 37.65 51 1354 406 2356274
Product adhesion issue 304.37 37.65 57 1348 1195 2355485
Intentional product misuse 202.65 37.65 60 1345 9429 2347251
Accidental overdose 197.75 37.65 49 1356 3923 2352757
Drug ineffective 167.43 37.65 103 1302 101521 2255159
Premature delivery 166.89 37.65 41 1364 3159 2353521
Exposure during pregnancy 165.99 37.65 66 1339 25153 2331527
Product quality issue 161.38 37.65 52 1353 10777 2345903
Application site erythema 151.45 37.65 32 1373 1248 2355432
Dependence 146.46 37.65 26 1379 395 2356285
Myocardial stunning 143.91 37.65 19 1386 25 2356655
Nausea 143.35 37.65 97 1308 112092 2244588
Application site pruritus 139.02 37.65 28 1377 858 2355822
Toxicity to various agents 127.01 37.65 59 1346 32695 2323985
Maternal exposure during pregnancy 115.60 37.65 44 1361 14819 2341861
Palpitations 97.38 37.65 40 1365 16416 2340264
Treatment noncompliance 92.26 37.65 29 1376 5505 2351175
Completed suicide 91.11 37.65 41 1364 20993 2335687
Premature baby 89.32 37.65 25 1380 3179 2353501
Maternal exposure during breast feeding 88.49 37.65 18 1387 578 2356102
Application site rash 87.81 37.65 18 1387 601 2356079
Dizziness 79.73 37.65 53 1352 58612 2298068
Malaise 77.41 37.65 51 1354 55534 2301146
Drug abuse 73.69 37.65 30 1375 11996 2344684
Low birth weight baby 71.51 37.65 16 1389 813 2355867
Drug hypersensitivity 67.81 37.65 44 1361 46599 2310081
Caesarean section 66.37 37.65 21 1384 4060 2352620
Anxiety 64.13 37.65 36 1369 29323 2327357
Dyspnoea 63.60 37.65 52 1353 78681 2277999
Maternal drugs affecting foetus 61.58 37.65 16 1389 1531 2355149
Jaundice neonatal 59.89 37.65 11 1394 203 2356477
Vomiting 59.29 37.65 48 1357 71554 2285126
Application site irritation 56.66 37.65 12 1393 470 2356210
Drug interaction 53.65 37.65 32 1373 29131 2327549
Application site reaction 48.78 37.65 10 1395 333 2356347
Hyperhidrosis 48.05 37.65 24 1381 15398 2341282
Tobacco abuse 47.32 37.65 8 1397 89 2356591
Chest pain 46.92 37.65 29 1376 28108 2328572
Application site vesicles 46.67 37.65 10 1395 414 2356266
Heart rate increased 45.92 37.65 21 1384 11084 2345596
Application site swelling 45.51 37.65 9 1396 249 2356431
Wrong technique in product usage process 45.19 37.65 25 1380 19723 2336957
Abortion induced 44.95 37.65 15 1390 3421 2353259
Hypoglycaemia 44.79 37.65 19 1386 8388 2348292
Pruritus 44.35 37.65 33 1372 43307 2313373
Feeling abnormal 43.66 37.65 26 1379 23555 2333125
Abnormal dreams 41.40 37.65 13 1392 2445 2354235
Premature separation of placenta 40.32 37.65 9 1396 451 2356229
Drug screen positive 38.96 37.65 10 1395 910 2355770
Pre-eclampsia 38.54 37.65 11 1394 1493 2355187

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug dependence 527.77 43.29 112 1099 3215 1742355
Nicotine dependence 515.00 43.29 68 1143 45 1745525
Incorrect product administration duration 382.38 43.29 71 1140 984 1744586
Foetal exposure during pregnancy 375.10 43.29 96 1115 6263 1739307
Intentional product misuse 351.63 43.29 94 1117 7264 1738306
Overdose 336.11 43.29 109 1102 16592 1728978
Accidental overdose 331.20 43.29 80 1131 4084 1741486
Drug withdrawal syndrome neonatal 311.87 43.29 56 1155 632 1744938
Toxicity to various agents 197.83 43.29 86 1125 29055 1716515
Product adhesion issue 194.27 43.29 34 1177 324 1745246
Maternal exposure during breast feeding 164.44 43.29 30 1181 368 1745202
Drug abuse 142.26 43.29 55 1156 13634 1731936
Premature baby 122.95 43.29 34 1177 2908 1742662
Dependence 118.29 43.29 22 1189 301 1745269
Alcohol abuse 116.44 43.29 24 1187 573 1744997
Low birth weight baby 106.97 43.29 24 1187 863 1744707
Drug abuser 95.12 43.29 24 1187 1433 1744137
Drug ineffective 93.47 43.29 69 1142 63732 1681838
Drug screen positive 81.99 43.29 20 1191 1037 1744533
Product quality issue 79.49 43.29 29 1182 6064 1739506
Treatment noncompliance 76.28 43.29 27 1184 5174 1740396
Application site erythema 70.15 43.29 16 1195 618 1744952
Jaundice neonatal 66.14 43.29 13 1198 241 1745329
Nausea 62.87 43.29 50 1161 51146 1694424
Substance abuse 62.85 43.29 16 1195 987 1744583
Tobacco poisoning 62.66 43.29 8 1203 2 1745568
Application site pruritus 62.52 43.29 13 1198 323 1745247
Intentional product use issue 59.16 43.29 19 1192 2700 1742870
Withdrawal syndrome 53.94 43.29 17 1194 2271 1743299
Rash 49.99 43.29 39 1172 38654 1706916
Tobacco abuse 47.22 43.29 8 1203 61 1745509
Completed suicide 46.69 43.29 27 1184 16285 1729285
Tremor neonatal 45.27 43.29 8 1203 80 1745490
Anxiety 45.23 43.29 26 1185 15501 1730069

Pharmacologic Action:

SourceCodeDescription
ATC N07BA01 NERVOUS SYSTEM
OTHER NERVOUS SYSTEM DRUGS
DRUGS USED IN ADDICTIVE DISORDERS
Drugs used in nicotine dependence
FDA EPC N0000175706 Cholinergic Nicotinic Agonist
FDA Chemical/Ingredient N0000006496 Nicotine
CHEBI has role CHEBI:59163 biomarker
CHEBI has role CHEBI:50846 immunomodulator
CHEBI has role CHEBI:49110 peripheral nervous system drug
CHEBI has role CHEBI:35471 psychotropic drug
CHEBI has role CHEBI:35474 anxiolytic drug
CHEBI has role CHEBI:47958 nicotinic acetylcholine receptor agonist
CHEBI has role CHEBI:22917 phytogenic insecticide
MeSH PA D018678 Cholinergic Agents
MeSH PA D018679 Cholinergic Agonists
MeSH PA D005731 Ganglionic Stimulants
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018722 Nicotinic Agonists
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D000077444 Smoking Cessation Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Nicotine dependence indication 56294008 DOID:0050742
Smoking cessation assistance indication 384742004
Pellagra indication 418186002 DOID:8457
Niacin deficiency indication 418279001
Nicotine Withdrawal Symptoms indication
Hyperlipidemia off-label use 55822004 DOID:1168
Hypophosphatemia contraindication 4996001
Alcoholism contraindication 7200002
Peptic ulcer contraindication 13200003 DOID:750
Esophagitis contraindication 16761005 DOID:11963
Myocardial infarction contraindication 22298006 DOID:5844
Hyperthyroidism contraindication 34486009 DOID:7998
Temporomandibular joint disorder contraindication 41888000
Low blood pressure contraindication 45007003
Diabetes mellitus type 1 contraindication 46635009 DOID:9744
Thromboangiitis obliterans contraindication 52403007 DOID:12918
Blood coagulation disorder contraindication 64779008 DOID:1247
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Prinzmetal angina contraindication 87343002
Gout contraindication 90560007 DOID:13189
Magnetic resonance imaging contraindication 113091000
Liver function tests abnormal contraindication 166603001
Angina pectoris contraindication 194828000
Arterial hemorrhage contraindication 234003006
Disease of liver contraindication 235856003 DOID:409
Raynaud's phenomenon contraindication 266261006
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Pheochromocytoma contraindication 302835009
Acute coronary syndrome contraindication 394659003
Pharyngitis contraindication 405737000 DOID:2275
Disorder of coronary artery contraindication 414024009
Myocardial infarction in recovery phase contraindication 418044006
Hypertensive urgency contraindication 443482000
Life-Threatening Cardiac Arrhythmias contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.05 Basic
pKa2 3.14 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
14MG/24HR NICODERM CQ SANOFI AVENTIS US N020165 Aug. 2, 1996 OTC FILM, EXTENDED RELEASE TRANSDERMAL 8999379 Feb. 13, 2020 A METHOD TO REDUCE WITHDRAWAL SYMPTOMS, INCLUDING NICOTINE CRAVING, ASSOCIATED WITH SMOKING CESSATION
21MG/24HR NICODERM CQ SANOFI AVENTIS US N020165 Aug. 2, 1996 OTC FILM, EXTENDED RELEASE TRANSDERMAL 8999379 Feb. 13, 2020 A METHOD TO REDUCE WITHDRAWAL SYMPTOMS, INCLUDING NICOTINE CRAVING, ASSOCIATED WITH SMOKING CESSATION
7MG/24HR NICODERM CQ SANOFI AVENTIS US N020165 Aug. 2, 1996 OTC FILM, EXTENDED RELEASE TRANSDERMAL 8999379 Feb. 13, 2020 A METHOD TO REDUCE WITHDRAWAL SYMPTOMS, INCLUDING NICOTINE CRAVING, ASSOCIATED WITH SMOKING CESSATION

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Neuronal acetylcholine receptor; alpha4/beta2 Ion channel AGONIST Ki 8.56 WOMBAT-PK CHEMBL
Acetylcholine receptor; alpha1/beta1/delta/gamma Ion channel Ki 5.83 CHEMBL
Serotonin 3 (5-HT3) receptor Ion channel Ki 4.15 CHEMBL
Acetylcholine receptor subunit alpha Ion channel IC50 4.68 CHEMBL
Neuronal acetylcholine receptor; alpha3/beta4 Ion channel Ki 5.95 WOMBAT-PK
Neuronal acetylcholine receptor; alpha3/beta2 Ion channel Ki 7.85 WOMBAT-PK
Cytochrome P450 2A6 Enzyme IC50 5.36 WOMBAT-PK
Potassium voltage-gated channel subfamily D member 3 Ion channel IC50 7.40 WOMBAT-PK
Neuronal acetylcholine receptor subunit alpha-7 Ion channel Ki 5.39 WOMBAT-PK
Transient receptor potential cation channel subfamily A member 1 Ion channel ACTIVATOR EC50 4.80 IUPHAR
Neuronal acetylcholine receptor; alpha2/beta2 Ion channel Ki 8.26 CHEMBL
Neuronal acetylcholine receptor; alpha4/beta4 Ion channel Ki 7.64 CHEMBL
Neuronal acetylcholine receptor subunit alpha-3 Ion channel IC50 7.35 CHEMBL
Neuronal acetylcholine receptor; alpha2/beta4 Ion channel Ki 7.15 CHEMBL
Neuronal acetylcholine receptor; alpha3/alpha6/beta2/beta3 Ion channel IC50 7.07 CHEMBL
Neuronal acetylcholine receptor subunit alpha-4 Ion channel Ki 9.03 CHEMBL
Neuronal acetylcholine receptor subunit alpha-4 Ion channel IC50 8.15 CHEMBL
Neuronal acetylcholine receptor Ion channel Kd 11 CHEMBL
Neuronal acetylcholine receptor subunit alpha-9 Ion channel Kd 8.30 CHEMBL
Neuronal acetylcholine receptor subunit beta-4 Ion channel Ki 7.14 CHEMBL
Neuronal acetylcholine receptor subunit alpha-2 Ion channel Ki 7.92 CHEMBL
Neuronal acetylcholine receptor; alpha3/beta2 Ion channel Ki 9 CHEMBL
Neuronal acetylcholine receptor; alpha3/beta4 Ion channel Ki 6.70 CHEMBL
Neuronal acetylcholine receptor; alpha2/beta2 Ion channel Ki 8.26 CHEMBL
Neuronal acetylcholine receptor; alpha2/beta4 Ion channel Ki 7.15 CHEMBL
Nicotinic acetylcholine receptor alpha 5 subunit Ion channel Ki 5.61 CHEMBL
Acetylcholine receptor subunit delta Ion channel Ki 9 CHEMBL
Neuronal acetylcholine receptor; alpha4/beta4 Ion channel Ki 8.26 CHEMBL
Neuronal acetylcholine receptor; alpha4/beta2 Ion channel Kd 9.40 CHEMBL
Neuronal acetylcholine receptor subunit alpha-7 Ion channel Ki 6.89 CHEMBL
Neuronal acetylcholine receptor subunit alpha-7 Ion channel Ki 6.61 CHEMBL
Acetylcholine receptor Ion channel Ki 5.20 CHEMBL
Neuronal acetylcholine receptor subunit alpha-3 Ion channel Ki 7.33 CHEMBL
Acetylcholine receptor subunit beta-like 2 Ion channel Ki 5.57 CHEMBL
Muscarinic acetylcholine receptor GPCR IC50 4.55 CHEMBL
Lycopene cyclase Enzyme IC50 5.32 CHEMBL
Acetylcholine receptor subunit alpha Ion channel IC50 4.64 CHEMBL
Soluble acetylcholine receptor Unclassified Ki 7.52 CHEMBL
Neuronal acetylcholine receptor subunit alpha-4 Ion channel Ki 8.72 CHEMBL
Acetylcholine-binding protein Unclassified Ki 7.20 CHEMBL
Potassium voltage-gated channel subfamily D member 3 Unclassified BLOCKER IC50 7.40 IUPHAR

External reference:

IDSource
4020286 VUID
N0000148163 NUI
C0028040 UMLSCUI
D03365 KEGG_DRUG
6M3C89ZY6R UNII
65-31-6 SECONDARY_CAS_RN
323283001 SNOMEDCT_US
4020286 VANDF
11529 MMSL
7407 RXNORM
68540007 SNOMEDCT_US
5173 MMSL
d00316 MMSL
001770 NDDF
89594 PUBCHEM_CID
CHEBI:17688 CHEBI
CHEMBL3 ChEMBL_ID
DB00184 DRUGBANK_ID
CHEMBL1201536 ChEMBL_ID
D009538 MESH_DESCRIPTOR_UI
D061485 MESH_DESCRIPTOR_UI
2585 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Nicotrol HUMAN PRESCRIPTION DRUG LABEL 1 0009-5400 INHALANT 4 mg RESPIRATORY (INHALATION) NDA 14 sections
Nicotrol HUMAN PRESCRIPTION DRUG LABEL 1 0009-5401 SPRAY, METERED 10 mg NASAL NDA 15 sections
Good Sense Nicotine HUMAN OTC DRUG LABEL 1 0113-0029 GUM, CHEWING 2 mg ORAL ANDA 10 sections
Good Sense Nicotine HUMAN OTC DRUG LABEL 1 0113-0053 GUM, CHEWING 4 mg ORAL ANDA 15 sections
Good Sense Nicotine HUMAN OTC DRUG LABEL 1 0113-0170 GUM, CHEWING 4 mg ORAL ANDA 10 sections
good sense nicotine HUMAN OTC DRUG LABEL 1 0113-0206 GUM, CHEWING 2 mg ORAL ANDA 10 sections
Good Sense Nicotine HUMAN OTC DRUG LABEL 1 0113-0344 LOZENGE 2 mg ORAL ANDA 10 sections
Good Sense Nicotine HUMAN OTC DRUG LABEL 1 0113-0422 GUM, CHEWING 4 mg ORAL ANDA 10 sections
Good Sense Nicotine HUMAN OTC DRUG LABEL 1 0113-0456 GUM, CHEWING 2 mg ORAL ANDA 10 sections
Good Sense Nicotine HUMAN OTC DRUG LABEL 1 0113-0532 GUM, CHEWING 4 mg ORAL ANDA 10 sections
basic care nicotine HUMAN OTC DRUG LABEL 1 0113-0704 GUM, CHEWING 2 mg ORAL ANDA 15 sections
basic care nicotine HUMAN OTC DRUG LABEL 1 0113-0713 GUM, CHEWING 4 mg ORAL ANDA 15 sections
Good Sense Nicotine HUMAN OTC DRUG LABEL 1 0113-0734 LOZENGE 2 mg ORAL ANDA 11 sections
basic care nicotine HUMAN OTC DRUG LABEL 1 0113-0749 GUM, CHEWING 4 mg ORAL ANDA 10 sections
basic care nicotine HUMAN OTC DRUG LABEL 1 0113-0761 GUM, CHEWING 2 mg ORAL ANDA 10 sections
good sense nicotine HUMAN OTC DRUG LABEL 1 0113-0873 LOZENGE 4 mg ORAL ANDA 10 sections
Good Sense Nicotine HUMAN OTC DRUG LABEL 1 0113-0957 LOZENGE 4 mg ORAL ANDA 11 sections
good sense nicotine HUMAN OTC DRUG LABEL 1 0113-1190 LOZENGE 4 mg ORAL ANDA 10 sections
good sense nicotine HUMAN OTC DRUG LABEL 1 0113-1352 GUM, CHEWING 2 mg ORAL ANDA 10 sections
basic care nicotine HUMAN OTC DRUG LABEL 1 0113-7007 LOZENGE 4 mg ORAL ANDA 14 sections
basic care nicotine HUMAN OTC DRUG LABEL 1 0113-7008 LOZENGE 2 mg ORAL ANDA 8 sections
basic care nicotine HUMAN OTC DRUG LABEL 1 0113-7029 GUM, CHEWING 2 mg ORAL ANDA 15 sections
basic care nicotine HUMAN OTC DRUG LABEL 1 0113-7124 LOZENGE 2 mg ORAL ANDA 10 sections
basic care nicotine HUMAN OTC DRUG LABEL 1 0113-7170 GUM, CHEWING 4 mg ORAL ANDA 10 sections
basic care nicotine HUMAN OTC DRUG LABEL 1 0113-7190 LOZENGE 4 mg ORAL ANDA 10 sections
Basic Care nicotine HUMAN OTC DRUG LABEL 1 0113-7201 LOZENGE 2 mg ORAL ANDA 15 sections
Basic Care nicotine HUMAN OTC DRUG LABEL 1 0113-7203 LOZENGE 4 mg ORAL ANDA 10 sections
basic care nicotine HUMAN OTC DRUG LABEL 2 0113-7300 KIT 2 mg None ANDA 15 sections
basic care nicotine HUMAN OTC DRUG LABEL 2 0113-7300 KIT 2 mg None ANDA 15 sections
basic care nicotine HUMAN OTC DRUG LABEL 1 0113-7344 LOZENGE 2 mg ORAL ANDA 10 sections