U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H14N2O
Molecular Weight 190.2417
Optical Activity ( - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYTISINICLINE

SMILES

O=C1C=CC=C2[C@H]3CNC[C@H](C3)CN12

InChI

InChIKey=ANJTVLIZGCUXLD-DTWKUNHWSA-N
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

HIDE SMILES / InChI

Molecular Formula C11H14N2O
Molecular Weight 190.2417
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Cytisine ( aka baptitoxine and sophorine) is a naturally occurring alkaloid that can be found in several plant genera, such as Laburnum and Cytisus of the family Fabaceae. It has been found to be clinically superior to nicotine replacement therapy for the cessation of smoking. It is available in Eastern Europe under the brand names Tabex and Desmoxan and in Canada under the brand name Cravv. However certain undesirable side effects exist, Cytisine can interfere with breathing and cause death (LD50 i.v., in mice, is about 2 mg/kg) and Cytisine is also teratogenic. Cytosine is an α4β2 nicotinic Acetylcholine receptor agonist. In addition to clinical use as a smoking cessation aid, It has demonstrated anti-depressant effects in mice.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
5.5 µM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
tabex

Approved Use

Approved and marketed as an aid for the cessation of smoking, to be used in combination with a strong will.
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
12.1 ng/mL
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYTISINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
27.8 ng/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYTISINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
43.1 ng/mL
4.5 mg single, oral
dose: 4.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYTISINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
81.9 ng × h/mL
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYTISINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
181.9 ng × h/mL
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYTISINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
254.5 ng × h/mL
4.5 mg single, oral
dose: 4.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYTISINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.4 h
1.5 mg single, oral
dose: 1.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYTISINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.4 h
3 mg single, oral
dose: 3 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYTISINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.9 h
4.5 mg single, oral
dose: 4.5 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
CYTISINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
64%
CYTISINE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
1.5 mg 6 times / day multiple, oral
Studied dose
healthy, ADULT
Disc. AE: AEs...
3 mg 6 times / day multiple, oral
Studied dose
healthy, ADULT
Disc. AE: AEs...
AEs

AEs

Overview

Overview

OverviewOther

Other InhibitorOther SubstrateOther Inducer






Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
inconclusive [IC50 31.6228 uM]
inconclusive [IC50 31.6228 uM]
inconclusive
no [IC50 >10 uM]
no [IC50 >10 uM]
no [IC50 >10 uM]
yes [Inhibition 10 uM]
yes [Inhibition 10 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Nicotinic agonists stimulate acetylcholine release from mouse interpeduncular nucleus: a function mediated by a different nAChR than dopamine release from striatum.
2001 Jan
Alcohol preference: association with reduced striatal nicotinic receptors.
2001 Jul-Aug
Relationship between the increased cell surface alpha7 nicotinic receptor expression and neuroprotection induced by several nicotinic receptor agonists.
2001 Nov 15
Differential nicotinic receptor expression in monkey basal ganglia: effects of nigrostriatal damage.
2002
Pharmacological evaluation of a Br-76 analog of epibatidine: a potent ligand for studying brain nicotinic acetylcholine receptors.
2002 Aug
Influence of cytisine on catecholamine release in isolated perfused rat adrenal glands.
2002 Dec
Protons enhance the gating kinetics of the alpha3/beta4 neuronal nicotinic acetylcholine receptor by increasing its apparent affinity to agonists.
2002 Feb
Distribution and pharmacology of alpha 6-containing nicotinic acetylcholine receptors analyzed with mutant mice.
2002 Feb 15
Loss of nicotinic receptors in monkey striatum after 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine treatment is due to a decline in alpha-conotoxin MII sites.
2002 Jan
[3H]Epibatidine binding to bovine adrenal medulla: evidence for alpha3beta4* nicotinic receptors.
2002 Jan 25
Cytisine derivatives as high affinity nAChR ligands: synthesis and comparative molecular field analysis.
2002 Jun
A non-alpha7 nicotinic acetylcholine receptor modulates excitatory input to hippocampal CA1 interneurons.
2002 Mar
Differential physiologic responses of alpha7 nicotinic acetylcholine receptors to beta-amyloid1-40 and beta-amyloid1-42.
2003 Apr
Modulation of inhibitory synaptic activity by a non-alpha4beta2, non-alpha7 subtype of nicotinic receptors in the substantia gelatinosa of adult rat spinal cord.
2003 Jan
Blockade of nicotine-induced locomotor sensitization by a novel neurotensin analog in rats.
2003 Jan 1
Bisalkaloid derivatives of dicarboxylic acids on the basis of lupinine, anabasine, and cytisine as reversible cholinesterase inhibitors.
2003 Jan-Feb
Localization of [3H]nicotine, [3H]cytisine, [3H]epibatidine, and [125I]alpha-bungarotoxin binding sites in the brain of Macaca mulatta.
2003 Jun 16
Deficiency of nicotinic acetylcholine receptor beta 4 subunit causes autonomic cardiac and intestinal dysfunction.
2003 Mar
Attenuation of cell adhesion in lymphocytes is regulated by CYTIP, a protein which mediates signal complex sequestration.
2003 Mar 3
Characterization of neuronal nicotinic acetylcholine receptors in the membrane of unmyelinated human C-fiber axons by in vitro studies.
2003 Nov
[Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin].
2004 Jul-Aug
Nicotine activation of alpha4* receptors: sufficient for reward, tolerance, and sensitization.
2004 Nov 5
Nicotinic AChR in subclassified capsaicin-sensitive and -insensitive nociceptors of the rat DRG.
2005 Mar
Patents

Sample Use Guides

1310 adult daily smokers who were motivated to quit received cytisine tablets (1/5 mg/tablet) for 25 days according to the manufacturers recommended protocol: days 1 through 3, one tablet every 2 hours through the waking day (up to six tablets per day); days 4 through 12, one tablet every 2.5 hours (up to five tablets per day); days 13 through 16, one tablet every 3 hours (up to four tablets per day); days 17 through 20, one tablet every 4 to 5 hours (three tablets per day); and days 21 through 25, one tablet every 6 hours (two tablets per day). When combined with brief behavioral support, cytisine was found to be superior to nicotine-replacement therapy in helping smokers quit smoking, but it was associated with a higher frequency of self-reported adverse events.
Route of Administration: Oral
The parenteral cell line tsA201 (derived from embryonic kidney HEK-293 cells) was transfected with Human α3, α4, α7, β2 and β4 nicotinic acetylcholine receptor DNA. Transfected cells stably expressing α4β2 AChRs were grown in Dulbecco's modified Eagle's medium with 10% fetal bovine serum supplemented with 2 mM glutamine and incubated at 37 deg C in a 5% CO2 atmosphere. Cells were plated in a 96-well plate and incubated for 48 hours prior to assaying against various nicotinic agonists, including Cytisine. To measure responses to various nicotinic agonists, 100 µl of a fluorescent dye which is sensitive to changes in membrane potential was added to the wells with the addition of 0.5 microM atropine to block muscarinic responses. The plates were then incubated for 1 hour at 37 deg-C. Serial dilutions of Cytisine were prepared in Hanks Balanced Salt Solution and added to the appropriate well after 20 seconds and fluorescence response monitored for 60 - 120 seconds using a FLEX Station at 25°C. The EC50 of Cytisine was found to be 5.5 micro M against α4β2 AChRs.
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:53:04 GMT 2025
Edited
by admin
on Mon Mar 31 19:53:04 GMT 2025
Record UNII
53S5U404NU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYTISINE
HSDB   MART.   MI   WHO-DD  
Preferred Name English
CYTISINICLINE
USAN   INN  
Official Name English
CYTISINE [HSDB]
Common Name English
CYTISINICLINE [USAN]
Common Name English
cytisinicline [INN]
Common Name English
(1R,5S)-1,2,3,4,5,6-HEXAHYDRO-1,5-METHANO-8H-PYRIDO-(1,2-A)(1,5)DIAZOCIN-8-ONE
Systematic Name English
1,5-METHANO-8H-PYRIDO(1,2-A)(1,5)DIAZOCIN-8-ONE, 1,2,3,4,5,6-HEXAHYDRO-, (1R,5S)-
Systematic Name English
6039 SOPHARMA
Code English
CYTITON
Brand Name English
BAPTITOXINE
Common Name English
Cytisinicline [WHO-DD]
Common Name English
NSC-407282
Code English
SOPHORINE
Common Name English
CYTISINE [MI]
Common Name English
(1R,5S)-1,2,3,4,5,6-HEXAHYDRO-8H-1,5-METHANOPYRIDO(1,2-A)(1,5)DIAZOCIN-8-ONE (CYTISINE)
Systematic Name English
ULEXINE
Common Name English
TABEX
Brand Name English
CYTISINE [MART.]
Common Name English
Classification Tree Code System Code
WHO-ATC N07BA04
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
Code System Code Type Description
ECHA (EC/EINECS)
207-616-0
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
INN
11015
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
RXCUI
1723152
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY RxNorm
MESH
C004712
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
WIKIPEDIA
CYTISINE
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
DRUG CENTRAL
5217
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
PUBCHEM
10235
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
HSDB
3560
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
NCI_THESAURUS
C166810
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
MERCK INDEX
m4056
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY Merck Index
SMS_ID
100000115739
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
FDA UNII
53S5U404NU
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
EVMPD
SUB31171
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
DRUG BANK
DB09028
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
CHEBI
4055
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
USAN
FG-48
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
DAILYMED
53S5U404NU
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
CAS
485-35-8
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
NSC
407282
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
EPA CompTox
DTXSID00883395
Created by admin on Mon Mar 31 19:53:04 GMT 2025 , Edited by admin on Mon Mar 31 19:53:04 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
TARGET->PARTIAL AGONIST
LABELED -> NON-LABELED
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
ACTIVE MOIETY