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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H14N2O
Molecular Weight 190.2421
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYTISINICLINE

SMILES

c1cc2[C@]3([H])C[C@@]([H])(CNC3)Cn2c(=O)c1

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 190.2421
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
PubMed

PubMed

TitleDatePubMed
Genetic and pharmacological strategies identify a behavioral function of neuronal nicotinic receptors.
2000 Aug
Prenatal nicotine exposure is associated with an increase in [125I]epibatidine binding in discrete cortical regions in rats.
2000 Oct
Nicotine-induced alterations in the expression of nicotinic receptors in primary cultures from human prenatal brain.
2001
Characterization of human alpha4beta2 neuronal nicotinic receptors stably expressed in SH-EP1 cells.
2001 Jun
Indolizidine and quinolizidine alkaloids.
2001 Oct
Differential effect of nicotinic agonists on the [3H]norepinephrine release from rat hippocampal slices.
2001 Sep
Activity of cytisine and its brominated isosteres on recombinant human alpha7, alpha4beta2 and alpha4beta4 nicotinic acetylcholine receptors.
2001 Sep
Characterization of epibatidine binding to medial habenula: potential role in analgesia.
2002 Aug
Acetylcholine receptors and thresholds for convulsions from flurothyl and 1,2-dichlorohexafluorocyclobutane.
2002 Dec
(+)-2,3-dehydro-10-oxo-alpha-isosparteine in Uresiphita reversalis larvae fed on Cytisus monspessulanus leaves.
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
Autonomic function in mice lacking alpha5 neuronal nicotinic acetylcholine receptor subunit.
2002 Jul 15
Fast synaptic transmission mediated by alpha-bungarotoxin-sensitive nicotinic acetylcholine receptors in lamina X neurones of neonatal rat spinal cord.
2002 Nov 1
Differential regulation of nicotinic receptor-mediated neurotransmitter release following chronic (-)-nicotine administration.
2002 Oct
Pharmacological properties of nicotinic acetylcholine receptors expressed by guinea pig small intestinal myenteric neurons.
2002 Sep
Study of the calcium dynamics of the human alpha4beta2, alpha3beta4 and alpha1beta1gammadelta nicotinic acetylcholine receptors.
2002 Sep
Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells.
2003 Dec
Subtype-selective up-regulation by chronic nicotine of high-affinity nicotinic receptors in rat brain demonstrated by receptor autoradiography.
2003 Dec
Functional role of nicotinic acetylcholine receptors in apoptosis in HL-60 cell line.
2003 Dec 15
Blockade of nicotine-induced locomotor sensitization by a novel neurotensin analog in rats.
2003 Jan 1
Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells.
2003 Jun 12
Nitrogen substitution modifies the activity of cytisine on neuronal nicotinic receptor subtypes.
2003 Jun 20
Cytisine derivatives as ligands for neuronal nicotine receptors and with various pharmacological activities.
2003 Mar
Characterization of neuronal nicotinic acetylcholine receptors in the membrane of unmyelinated human C-fiber axons by in vitro studies.
2003 Nov
Rigidified acetylcholine mimics: conformational requirements for binding to neuronal nicotinic receptors.
2003 Nov 3
Quinolizidine alkaloid profiles of two taxa of Teline maderensis.
2003 Nov-Dec
Maternal exposure to nicotine and chlorpyrifos, alone and in combination, leads to persistently elevated expression of glial fibrillary acidic protein in the cerebellum of the offspring in late puberty.
2004 Aug
[Application of bisalkaloid derivatives of dicarboxylic acids based on lupinine, anabasine and cytisine as cholinesterase inhibitors of various origin].
2004 Jul-Aug
Subunit composition and pharmacology of two classes of striatal presynaptic nicotinic acetylcholine receptors mediating dopamine release in mice.
2004 Jun
Nicotine activation of alpha4* receptors: sufficient for reward, tolerance, and sensitization.
2004 Nov 5
Pharmacology of the neuronal nicotinic acetylcholine receptor of cultured Kenyon cells of the honeybee, Apis mellifera.
2004 Oct
A-186253, a specific antagonist of the alpha 4 beta 2 nAChRs: its properties and potential to study brain nicotinic acetylcholine receptors.
2004 Sep
ABT-089: pharmacological properties of a neuronal nicotinic acetylcholine receptor agonist for the potential treatment of cognitive disorders.
2004 Summer
High-affinity epibatidine binding of functional, human alpha7-nicotinic acetylcholine receptors stably and heterologously expressed de novo in human SH-EP1 cells.
2005 Apr
Genetic correlation between the free-choice oral consumption of nicotine and alcohol in C57BL/6JxC3H/HeJ F2 intercross mice.
2005 Feb 10
Selective deletion of the alpha5 subunit differentially affects somatic-dendritic versus axonally targeted nicotinic ACh receptors in mouse.
2005 Feb 15
Subunit composition of nicotinic receptors in monkey striatum: effect of treatments with 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine or L-DOPA.
2005 Jan
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 Sat Jun 26 16:18:55 UTC 2021
Edited
by admin
on Sat Jun 26 16:18:55 UTC 2021
Record UNII
53S5U404NU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
CYTISINE
HSDB   MART.   MI   WHO-DD  
Common Name English
6039 SOPHARMA
Code English
CYTITON
Brand Name English
BAPTITOXINE
Common Name English
CYTISINE [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 Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
207-616-0
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
INN
11015
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
RXCUI
1723152
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY RxNorm
MESH
C004712
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
WIKIPEDIA
CYTISINE
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
DRUG CENTRAL
5217
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
PUBCHEM
10235
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
HSDB
3560
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
NCI_THESAURUS
C166810
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
MERCK INDEX
M4056
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY Merck Index
FDA UNII
53S5U404NU
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
EVMPD
SUB31171
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
DRUG BANK
DB09028
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
CAS
485-35-8
Created by admin on Sat Jun 26 16:18:56 UTC 2021 , Edited by admin on Sat Jun 26 16:18:56 UTC 2021
PRIMARY
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SALT/SOLVATE -> PARENT
TARGET->PARTIAL AGONIST
PARENT -> CONSTITUENT ALWAYS PRESENT
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ACTIVE MOIETY