Details of the Drug

General Information of Drug (ID: DMUF0BJ)

Drug Name
CYTISINE
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]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 190.24
Logarithm of the Partition Coefficient (xlogp) 0.2
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Clearance
The renal clearance of drug is 43 mL/min []
Half-life
The concentration or amount of drug in body reduced by one-half in 4.8 hours [2]
Vd
The volume of distribution (Vd) of drug is 6.2 L/kg []
Chemical Identifiers
Formula
C11H14N2O
IUPAC Name
(1R,9S)-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one
Canonical SMILES
C1[C@H]2CNC[C@@H]1C3=CC=CC(=O)N3C2
InChI
InChI=1S/C11H14N2O/c14-11-3-1-2-10-9-4-8(5-12-6-9)7-13(10)11/h1-3,8-9,12H,4-7H2/t8-,9+/m0/s1
InChIKey
ANJTVLIZGCUXLD-DTWKUNHWSA-N
Cross-matching ID
PubChem CID
10235
ChEBI ID
CHEBI:4055
CAS Number
485-35-8
UNII
53S5U404NU
DrugBank ID
DB09028
TTD ID
D08XPW
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Neuronal acetylcholine receptor alpha-2 (CHRNA2) TTF4E0J ACHA2_HUMAN Inhibitor [3]
Neuronal acetylcholine receptor alpha-4 (CHRNA4) TT4H1MQ ACHA4_HUMAN Inhibitor [4]
Neuronal acetylcholine receptor alpha-7 (CHRNA7) TTLA931 ACHA7_HUMAN Inhibitor [5]
Neuronal acetylcholine receptor beta-2 (CHRNB2) TT5KPZR ACHB2_HUMAN Inhibitor [4]
Neuronal acetylcholine receptor beta-4 (CHRNB4) TTTVAFQ ACHB4_HUMAN Inhibitor [6]
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 [7]
Neuronal acetylcholine receptor subunit beta-2 (CHRNB2) OTNAT2M5 ACHB2_HUMAN Protein Interaction/Cellular Processes [7]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Tobacco dependence
ICD Disease Classification 6C4A.2
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Neuronal acetylcholine receptor beta-4 (CHRNB4) DTT CHRNB4 8.30E-01 9.66E-03 0.06
Neuronal acetylcholine receptor beta-2 (CHRNB2) DTT CHRNB2 7.10E-08 -0.15 -0.85
Neuronal acetylcholine receptor alpha-4 (CHRNA4) DTT CHRNA4 3.51E-10 -0.15 -0.61
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
2 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
3 Synthesis and pharmacological evaluation of novel 9- and 10-substituted cytisine derivatives. Nicotinic ligands of enhanced subtype selectivity. J Med Chem. 2006 May 4;49(9):2673-6.
4 Epibatidine isomers and analogues: structure-activity relationships. Bioorg Med Chem Lett. 2006 Nov 1;16(21):5493-7.
5 3,5-Bicyclic aryl piperidines: a novel class of alpha4beta2 neuronal nicotinic receptor partial agonists for smoking cessation. Bioorg Med Chem Lett. 2005 Nov 15;15(22):4889-97.
6 Deconstructing cytisine: The syntheses of (+/-)-cyfusine and (+/-)-cyclopropylcyfusine, fused ring analogs of cytisine. Bioorg Med Chem Lett. 2008 Apr 1;18(7):2316-9.
7 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.