General Information of Drug (ID: DMUF0BJ)

Drug Name
CYTISINE Drug Info
Synonyms
CYTISINE; 485-35-8; Sophorine; Baptitoxine; (-)-Cytisine; Laburnin; Baptitoxin; Tabex; Ulexin; Cytiton; Ulexine; Tsitizin; Cytitone; Cystisine; Cytizin; Citizin; Tabax; (1R,5S)-3,4,5,6-Tetrahydro-1H-1,5-methanopyrido[1,2-a][1,5]diazocin-8(2H)-one; Baphitoxine; UNII-53S5U404NU; Cytisine (-); HSDB 3560; EINECS 207-616-0; NSC 407282; BRN 0083882; Cytisin; (1r,5s)-1,2,3,4,5,6-Hexahydro-8h-1,5-Methanopyrido[1,2-A][1,5]diazocin-8-One; CHEBI:4055; CHEMBL497939; 53S5U404NU; Cytisine, 98%
Indication
Disease Entry ICD 11 Status REF
Tobacco dependence 6C4A.2 Phase 3 [1]
Cross-matching ID
PubChem CID
10235
ChEBI ID
CHEBI:4055
CAS Number
CAS 485-35-8
TTD Drug ID
DMUF0BJ

Molecule-Related Drug Atlas

Molecule-Related Drug Atlas
Molecule Type:
DTT
DOT
Drug Status:
Approved Drug(s)
Clinical Trial Drug(s)
Investigative Drug(s)
Discontinued Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ziprasidone DMM58JY Bipolar disorder 6A60 Approved [7]
ALCURONIUM DM2U4XQ Anaesthesia 9A78.6 Approved [8]
AMG 386 DMQJXL4 Breast cancer 2C60-2C65 Phase 3 [9]
EVP-6124 DMLQO7F Alzheimer disease 8A20 Phase 3 [10]
GTS-21 DMEN5KA Parkinson disease 8A00.0 Phase 2 [11]
JNJ-39393406 DMUOEKM Depression 6A70-6A7Z Phase 2 [12]
ABT-126 DM2OS51 Alzheimer disease 8A20 Phase 2 [13]
TC-6987 DMNFP21 Asthma CA23 Phase 2 [14]
AQW-051 DMD2RFO Alzheimer disease 8A20 Phase 2 [15]
MEM-3454 DMPNDYU Schizophrenia 6A20 Phase 2 [7]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Rocuronium DMY9BMK Muscle spasm MB47.3 Approved [16]
Tubocurarine DMBZIVP Anaesthesia 9A78.6 Approved [16]
Cisatracurium DMUZPJ5 Muscle spasm MB47.3 Approved [16]
Vecuronium DMP0UK2 Spasm MB47.3 Approved [16]
Levallorphan DMCOLUP Narcotic depression 6A7Z Approved [17]
Mivacurium DM473VD Anaesthesia 9A78.6 Approved [16]
Carbachol DMX9K8F Glaucoma/ocular hypertension 9C61 Approved [17]
Pipecuronium DM5F84A Spasm MB47.3 Approved [17]
CHOLINE DM5D9YK Insomnia 7A00-7A0Z Investigative [18]
[125I]epibatidine DMZWQH3 Discovery agent N.A. Investigative [19]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Trimethaphan DMHF4IQ Aneurysm BD51.Z Approved [20]
Pentolinium DM38VYQ Hypotension BA20-BA21 Approved [21]
ABT-594 DMGMBCW N. A. N. A. Discontinued in Phase 2 [22]
ABT-418 DMNP72I Alzheimer disease 8A20 Discontinued in Phase 2 [23]
HOMOEPIBATIDINE DMHP9WV N. A. N. A. Terminated [3]
4-(4-butylpiperidin-1-yl)-1-o-tolylbutan-1-one DMM9X0G Discovery agent N.A. Investigative [24]
Barbituric acid derivative DM2I19P Discovery agent N.A. Investigative [25]
(2S,3S)-2-Phenyl-3,5,5-trimethylmorpholin-2-ol DMDUGZS Discovery agent N.A. Investigative [26]
(2S,3S)-2-(m-Tolyl)-3,5,5-trimethylmorpholin-2-ol DMDUI8R Discovery agent N.A. Investigative [26]
BOLDINE DMMVB5P Discovery agent N.A. Investigative [27]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
SIB-1553A DM7XC0U Alzheimer disease 8A20 Discontinued in Phase 2 [28]
HOMOEPIBATIDINE DMHP9WV N. A. N. A. Terminated [3]
(2S,3S)-2-Phenyl-3,5,5-trimethylmorpholin-2-ol DMDUGZS Discovery agent N.A. Investigative [26]
(2S,3S)-2-(m-Tolyl)-3,5,5-trimethylmorpholin-2-ol DMDUI8R Discovery agent N.A. Investigative [26]
GCCSNPVCHLEHSNLC* DMJ0ICN Discovery agent N.A. Investigative [29]
18-Methylaminocoronaridine DMOYC0U Discovery agent N.A. Investigative [30]
15-nor-18-Methoxycornaridine DMDKFGX Discovery agent N.A. Investigative [30]
2-Acetylaminoethyl 18-methoxycoronaridinate DM9ZOX4 Discovery agent N.A. Investigative [30]
N,N-Dimethylaminoethyl 18-methoxycoronaridinate DMWJ2PM Discovery agent N.A. Investigative [30]
2-Methoxyethyl 18-methoxycoronaridinate DM6X8GN Discovery agent N.A. Investigative [30]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [31]
Cotinine DMCEZ1B Insecticide N.A. Approved [32]
Pancuronium DMB0VY8 Anaesthesia 9A78.6 Approved [16]
Atracurium DM42HXN Anaesthesia 9A78.6 Approved [16]
Mecamylamine DMGQFYB Essential hypertension BA00 Approved [33]
Dexefaroxan DMTY4KN Parkinson disease 8A00.0 Phase 2 [7]
BMS-954561 DM7XV4R Diabetic neuropathy 8C0Z Phase 2 [34]
ASM-024 DM35S2I Asthma CA23 Phase 2 [35]
NIC-002 DMKLJMI Nicotine dependence 6C4A.2 Phase 2 [36]
TRIDMAC DMWU41P Mood disorder 6A60-6E23 Phase 2 [37]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
TC-5214 DM8AM60 Palmar hyperhidrosis EE00.00 Phase 2 [38]
SUVN-911 DMLPBVF Major depressive disorder 6A70.3 Phase 1 [1]
AZD-9684 DMHA5ME Thrombosis DB61-GB90 Discontinued in Phase 2 [39]
ABT-594 DMGMBCW N. A. N. A. Discontinued in Phase 2 [22]
ABT-418 DMNP72I Alzheimer disease 8A20 Discontinued in Phase 2 [40]
HOMOEPIBATIDINE DMHP9WV N. A. N. A. Terminated [3]
4-(4-butylpiperidin-1-yl)-1-o-tolylbutan-1-one DMM9X0G Discovery agent N.A. Investigative [24]
(2S,3S)-2-Phenyl-3,5,5-trimethylmorpholin-2-ol DMDUGZS Discovery agent N.A. Investigative [26]
(2S,3S)-2-(m-Tolyl)-3,5,5-trimethylmorpholin-2-ol DMDUI8R Discovery agent N.A. Investigative [26]
BOLDINE DMMVB5P Discovery agent N.A. Investigative [27]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Fulvestrant DM0YZC6 Breast cancer 2C60-2C65 Approved [41]
Selenium DM25CGV N. A. N. A. Approved [42]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [43]
Atropine DMEN6X7 Organophosphate poisoning NE6Z Approved [44]
Galantamine DMEO794 Alzheimer disease 8A20 Approved [44]
Rivastigmine DMG629M Alzheimer disease 8A20 Approved [44]
Rosiglitazone DMILWZR Chronic kidney disease GB61 Approved [45]
Scopolamine DMOM8AL Addictive disorder 6C50-6C5Z Approved [44]
Arsenic DMTL2Y1 N. A. N. A. Approved [46]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [47]
⏷ Show the Full List of 10 Drug(s)
Drug Name Drug ID Indication ICD 11 Highest Status REF
Ciclosporin DMAZJFX Graft-versus-host disease 4B24 Approved [48]
Valproate DMCFE9I Epilepsy 8A60-8A68 Approved [43]
Atropine DMEN6X7 Organophosphate poisoning NE6Z Approved [44]
Galantamine DMEO794 Alzheimer disease 8A20 Approved [44]
Rivastigmine DMG629M Alzheimer disease 8A20 Approved [44]
Scopolamine DMOM8AL Addictive disorder 6C50-6C5Z Approved [44]
Estradiol DMUNTE3 Acne vulgaris ED80 Approved [49]
Nicotine DMWX5CO Lung cancer 2C25.0 Approved [50]
Carbamazepine DMZOLBI Epilepsy 8A60-8A68 Approved [51]
Benzo(a)pyrene DMN7J43 N. A. N. A. Phase 1 [52]
⏷ Show the Full List of 10 Drug(s)

Molecular Interaction Atlas of This Drug

Molecular Interaction Atlas

Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Neuronal acetylcholine receptor alpha-2 (CHRNA2) TTF4E0J ACHA2_HUMAN Inhibitor [2]
Neuronal acetylcholine receptor alpha-4 (CHRNA4) TT4H1MQ ACHA4_HUMAN Inhibitor [3]
Neuronal acetylcholine receptor alpha-7 (CHRNA7) TTLA931 ACHA7_HUMAN Inhibitor [4]
Neuronal acetylcholine receptor beta-2 (CHRNB2) TT5KPZR ACHB2_HUMAN Inhibitor [3]
Neuronal acetylcholine receptor beta-4 (CHRNB4) TTTVAFQ ACHB4_HUMAN Inhibitor [5]
Nicotinic acetylcholine receptor (nAChR) TTJSZTB NOUNIPROTAC Antagonist [1]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Neuronal acetylcholine receptor subunit alpha-4 (CHRNA4) OT1H0ZXC ACHA4_HUMAN Protein Interaction/Cellular Processes [6]
Neuronal acetylcholine receptor subunit beta-2 (CHRNB2) OTNAT2M5 ACHB2_HUMAN Protein Interaction/Cellular Processes [6]

References

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5 Deconstructing cytisine: The syntheses of (+/-)-cyfusine and (+/-)-cyclopropylcyfusine, fused ring analogs of cytisine. Bioorg Med Chem Lett. 2008 Apr 1;18(7):2316-9.
6 ABT-089 [2-methyl-3-(2-(S)-pyrrolidinylmethoxy)pyridine]: I. A potent and selective cholinergic channel modulator with neuroprotective properties. J Pharmacol Exp Ther. 1997 Oct;283(1):235-46.
7 The pipeline and future of drug development in schizophrenia. Mol Psychiatry. 2007 Oct;12(10):904-22.
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10 Normalizing effects of EVP-6124, an alpha-7 nicotinic partial agonist, on event-related potentials and cognition: a proof of concept, randomized trial in patients with schizophrenia. J Psychiatr Pract. 2014 Jan;20(1):12-24.
11 The brain alpha7 nicotinic receptor may be an important therapeutic target for the treatment of Alzheimer's disease: studies with DMXBA (GTS-21). Behav Brain Res. 2000 Aug;113(1-2):169-81.
12 Allosteric alpha-7 nicotinic receptor modulation and P50 sensory gating in schizophrenia: a proof-of-mechanism study. Neuropharmacology. 2013 Jan;64:197-204.
13 A phase 2 randomized, controlled trial of the alpha7 agonist ABT-126 in mild-to-moderate Alzheimer's dementia. Alzheimer's & Dementia: Translational Research & Clinical Interventions Volume 1, Issue 1, June 2015, Pages 81-90.
14 ClinicalTrials.gov (NCT01293669) Glycemic Control, Safety and Tolerability of TC-6987 Monotherapy in Type 2 Diabetes Mellitus. U.S. National Institutes of Health.
15 AQW051, a novel and selective nicotinic acetylcholine receptor alpha7 partial agonist, reduces l-Dopa-induced dyskinesias and extends the duration of l-Dopa effects in parkinsonian monkeys. Parkinsonism Relat Disord. 2014 Nov;20(11):1119-23.
16 Pharmacological characteristics of the inhibition of nondepolarizing neuromuscular blocking agents at human adult muscle nicotinic acetylcholine receptor. Anesthesiology. 2009 Jun;110(6):1244-52.
17 Synergy between pairs of competitive antagonists at adult human muscle acetylcholine receptors. Anesth Analg. 2008 Aug;107(2):525-33.
18 Pharmacology of the agonist binding sites of rat neuronal nicotinic receptor subtypes expressed in HEK 293 cells. Bioorg Med Chem Lett. 2004 Apr 19;14(8):1845-8.
19 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Target id: 463).
20 Mechanism of long-lasting block of ganglion nicotinic receptors by mono-ammonium compounds with long aliphatic chain. J Auton Nerv Syst. 1994 Aug;48(3):231-40.
21 Nicotinic and nonnicotinic receptor-mediated actions of vinblastine. Proc Soc Exp Biol Med. 1993 Jul;203(3):372-6.
22 The nicotinic acetylcholine receptor agonist ABT-594 increases FGF-2 expression in various rat brain regions. Neuroreport. 1999 Dec 16;10(18):3909-13.
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24 Discovery of N-{1-[3-(3-oxo-2,3-dihydrobenzo[1,4]oxazin-4-yl)propyl]piperidin-4-yl}-2-phenylacetamide (Lu AE51090): an allosteric muscarinic M1 rec... J Med Chem. 2010 Sep 9;53(17):6386-97.
25 Whiting PJ: The GABAA receptor gene family: new opportunities for drug development. Curr Opin Drug Discov Devel. 2003 Sep;6(5):648-57.
26 Synthesis and characterization of in vitro and in vivo profiles of hydroxybupropion analogues: aids to smoking cessation. J Med Chem. 2010 Jun 24;53(12):4731-48.
27 Aporphine metho salts as neuronal nicotinic acetylcholine receptor blockers. Bioorg Med Chem. 2007 May 15;15(10):3368-72.
28 SIB-1553A, (+/-)-4-[[2-(1-methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride, a subtype-selective ligand for nicotinic acetylcholine receptors with putative cognitive-enhancing properties: effectson working and reference memory performances in aged rodents and nonhuman primates. J Pharmacol Exp Ther. 2001 Oct;299(1):297-306.
29 Neuronal nicotinic acetylcholine receptors: structural revelations, target identifications, and therapeutic inspirations. J Med Chem. 2005 Jul 28;48(15):4705-45.
30 Synthesis and biological evaluation of 18-methoxycoronaridine congeners. Potential antiaddiction agents. J Med Chem. 2003 Jun 19;46(13):2716-30.
31 Atypical antipsychotics as noncompetitive inhibitors of alpha4beta2 and alpha7 neuronal nicotinic receptors. Neuropharmacology. 2009 Aug;57(2):183-91.
32 Functional versus chemical diversity: is biodiversity important for drug discovery. Trends Pharmacol Sci. 2002 May;23(5):225-31.
33 Mecamylamine (Inversine): an old antihypertensive with new research directions. J Hum Hypertens. 2002 Jul;16(7):453-7.
34 EP patent application no. 2774991, Drug delivery system for use in the treatment or diagnosis of neurological disorders.
35 Effects of ASM-024, a modulator of acetylcholine receptor function, on airway responsiveness and allergen-induced responses in patients with mild asthma. Can Respir J. 2015 Jul-Aug;22(4):230-4.
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37 Novel drugs and therapeutic targets for severe mood disorders. Neuropsychopharmacology. 2008 Aug;33(9):2080-92.
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39 Blockade and activation of the human neuronal nicotinic acetylcholine receptors by atracurium and laudanosine. Anesthesiology. 2001 Apr;94(4):643-51.
40 Nicotine, brain nicotinic receptors, and neuropsychiatric disorders. Arch Med Res. 2000 Mar-Apr;31(2):131-44.
41 DNA methylome-wide alterations associated with estrogen receptor-dependent effects of bisphenols in breast cancer. Clin Epigenetics. 2019 Oct 10;11(1):138. doi: 10.1186/s13148-019-0725-y.
42 Selenium and vitamin E: cell type- and intervention-specific tissue effects in prostate cancer. J Natl Cancer Inst. 2009 Mar 4;101(5):306-20.
43 Integrative omics data analyses of repeated dose toxicity of valproic acid in vitro reveal new mechanisms of steatosis induction. Toxicology. 2018 Jan 15;393:160-170.
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45 Rosiglitazone inhibits alpha4 nicotinic acetylcholine receptor expression in human lung carcinoma cells through peroxisome proliferator-activated receptor gamma-independent signals. Mol Cancer Ther. 2009 Jan;8(1):110-8. doi: 10.1158/1535-7163.MCT-08-0719.
46 Prenatal arsenic exposure and the epigenome: identifying sites of 5-methylcytosine alterations that predict functional changes in gene expression in newborn cord blood and subsequent birth outcomes. Toxicol Sci. 2015 Jan;143(1):97-106. doi: 10.1093/toxsci/kfu210. Epub 2014 Oct 10.
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