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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
PubMed

PubMed

TitleDatePubMed
Recent progress in the development of subtype selective nicotinic acetylcholine receptor ligands.
2002 Aug
Influence of cytisine on catecholamine release in isolated perfused rat adrenal glands.
2002 Dec
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
Nicotinic ACh receptor subtypes on gastrointestinally projecting neurones in the dorsal motor vagal nucleus of the rat.
2002 Dec 15
Nicotinic receptors regulate the release of glycine onto lamina X neurones of the rat spinal cord.
2002 Nov
Nicotinic receptor gene cluster on rat chromosome 8 in nociceptive and blood pressure hyperresponsiveness.
2002 Oct 29
Differential physiologic responses of alpha7 nicotinic acetylcholine receptors to beta-amyloid1-40 and beta-amyloid1-42.
2003 Apr
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
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
Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells.
2003 Jun 12
Localization of [3H]nicotine, [3H]cytisine, [3H]epibatidine, and [125I]alpha-bungarotoxin binding sites in the brain of Macaca mulatta.
2003 Jun 16
Nitrogen substitution modifies the activity of cytisine on neuronal nicotinic receptor subtypes.
2003 Jun 20
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
Spontaneously hypertensive rats: further evaluation of age-related memory performance and cholinergic marker expression.
2003 May
Potentiation of evoked calcitonin gene-related peptide release from oral mucosa: a potential basis for the pro-inflammatory effects of nicotine.
2003 Nov
A structural model of agonist binding to the alpha3beta4 neuronal nicotinic receptor.
2003 Nov
Beta-amyloid peptide activates non-alpha7 nicotinic acetylcholine receptors in rat basal forebrain neurons.
2003 Nov
Characterization of neuronal nicotinic acetylcholine receptors in the membrane of unmyelinated human C-fiber axons by in vitro studies.
2003 Nov
Pharmacological characterization of dopamine, norepinephrine and serotonin release in the rat prefrontal cortex by neuronal nicotinic acetylcholine receptor agonists.
2003 Nov 14
Rigidified acetylcholine mimics: conformational requirements for binding to neuronal nicotinic receptors.
2003 Nov 3
The effects of beta3 subunit incorporation on the pharmacology and single channel properties of oocyte-expressed human alpha3beta4 neuronal nicotinic receptors.
2003 Nov 7
Quinolizidine alkaloid profiles of two taxa of Teline maderensis.
2003 Nov-Dec
Recent developments in the synthesis of nicotinic acetylcholine receptor ligands.
2004
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
Evaluation of (+)-sparteine-like diamines for asymmetric synthesis.
2004 Aug 20
Nicotinic acetylcholine receptors in mouse and rat optic nerves.
2004 Feb
Expression and function of neuronal nicotinic ACh receptors in rat microvascular endothelial cells.
2004 Feb
Characterization of nicotinic receptors inducing noradrenaline release and absence of nicotinic autoreceptors in human neocortex.
2004 Feb 1
Total enantioselective synthesis of (-)-cytisine.
2004 Feb 19
Binding and functional activity of nicotinic cholinergic receptors in selected rat brain regions are increased following long-term but not short-term nicotine treatment.
2004 Jul
A short synthesis of (+/-)-cytisine.
2004 Jul 7
[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
Prenatal nicotine exposure alters the response to nicotine administration in adolescence: effects on cholinergic systems during exposure and withdrawal.
2004 May
Studies toward labeling cytisine with [11C]phosgene: rapid synthesis of a delta-lactam involving a new chemoselective lithiation-annulation method.
2004 May 28
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
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
TARGET->PARTIAL AGONIST
PARENT -> CONSTITUENT ALWAYS PRESENT
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ACTIVE MOIETY