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
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
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.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3038461 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25231024 |
5.5 µM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | tabex Approved UseApproved and marketed as an aid for the cessation of smoking, to be used in combination with a strong will. |
|||
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.1 ng/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30526213/ |
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 CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30526213/ |
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 CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30526213/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
81.9 ng × h/mL CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30526213/ |
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 CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30526213/ |
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 CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30526213/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
4.4 h CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30526213/ |
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 CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30526213/ |
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 CLINICAL TRIAL https://pubmed.ncbi.nlm.nih.gov/30526213/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
64% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20331614/ |
CYTISINE plasma | Homo sapiens |
Doses
Dose | Population | Adverse events |
---|---|---|
1.5 mg 6 times / day multiple, oral Studied dose Dose: 1.5 mg, 6 times / day Route: oral Route: multiple Dose: 1.5 mg, 6 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
Disc. AE: AEs... AEs leading to discontinuation/dose reduction: AEs (0%) Sources: |
3 mg 6 times / day multiple, oral Studied dose Dose: 3 mg, 6 times / day Route: oral Route: multiple Dose: 3 mg, 6 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M F Food Status: FASTED Sources: |
Disc. AE: AEs... AEs leading to discontinuation/dose reduction: AEs (0%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
AEs | 0% Disc. AE |
1.5 mg 6 times / day multiple, oral Studied dose Dose: 1.5 mg, 6 times / day Route: oral Route: multiple Dose: 1.5 mg, 6 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: |
AEs | 0% Disc. AE |
3 mg 6 times / day multiple, oral Studied dose Dose: 3 mg, 6 times / day Route: oral Route: multiple Dose: 3 mg, 6 times / day Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M F Food Status: FASTED Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
inconclusive [IC50 31.6228 uM] | ||||
inconclusive [IC50 31.6228 uM] | ||||
Page: 49.0 |
inconclusive | |||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
no [IC50 >10 uM] | ||||
yes [Inhibition 10 uM] | ||||
yes [Inhibition 10 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 235 | 239 |
no |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 210.0 |
PubMed
Title | Date | PubMed |
---|---|---|
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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25517706
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24244538
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
Edited
Mon Mar 31 19:53:04 GMT 2025
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Record UNII |
53S5U404NU
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Validated (UNII)
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N07BA04
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CYTISINE
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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ACTIVE MOIETY |
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