Chemistry:Cyamemazine

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Short description: Antipsychotic medication

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Cyamemazine
Cyamemazine.svg
Clinical data
Trade namesTercian
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral, IM, IV
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability10-70%
MetabolismHepatic
Elimination half-life10 hours
ExcretionUrine
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC19H21N3S
Molar mass323.46 g·mol−1
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

Cyamemazine (Tercian), also known as cyamepromazine, is a typical antipsychotic drug of the phenothiazine class which was introduced by Theraplix in France in 1972 and later in Portugal as well.[1][2][3][4]

Medical use

It is used for the treatment of schizophrenia and, especially, for psychosis-associated anxiety, due to its unique anxiolytic efficacy.[5][6]

It is also used to reduce anxiety associated with benzodiazepine withdrawal syndrome and anxiety in depression with suicidal tendency.[7]

Side effects

Here are some of the most common side effects and related incidence:[8]

Mechanism

Cyamemazine differs from other phenothiazine neuroleptics in that aside from the usual profile of dopamine, α1-adrenergic, H1, and mACh receptor antagonism,[9] it additionally produces potent blockade of several serotonin receptors, including 5-HT2A, 5-HT2C, and 5-HT7.[9][10][11][12] These actions have been implicated in cyamemazine's anxiolytic effects (5-HT2C) and lack of extrapyramidal side effects (5-HT2A),[9][10] and despite being classified as a typical antipsychotic, it actually behaves like an atypical antipsychotic.[13]

Site Ki (nM) Species Ref
H1 9.3 Guinea pig [14]
H2 351 Guinea pig [14]
H3 >10,000 Rat [14]
M1 13 Human [14]
M2 42 Human [14]
M3 32 Human [14]
M4 12 Human [14]
M5 35 Human [14]
5-HT1A 517 Human [14]
5-HT2A 1.5 Human [14]
5-HT2C 12 Human [14]
5-HT3 2,943 Human [14]
5-HT7 22 Human [14]
D1 3.8 Human [14]
D2 5.8 Human [14]
D3 2.5 Human [14]
D4 5.3 Human [14]
α1 2.3 Rat [14]
α2 1320 Rat [14]
GABAA >10,000 Rat [14]
GABAB >10,000 Rat [14]
Values are Ki (nM). The smaller the value,

the more strongly the drug binds to the site.

Synthesis

Synthesis:[15] Patent:[16]

2-Cyanophenothiazine [38642-74-9] (1) 3-Chloro-2-methylpropyl(dimethyl)amine [23349-86-2] (2)

References

  1. ↑ Index Nominum, International Drug. Taylor & Francis. 2000. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&q=cyamemazine%20tercian&pg=PA280. 
  2. ↑ Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. 1996. p. 534. ISBN 0-412-46630-9. https://books.google.com/books?id=DeX7jgInYFMC&pg=RA1-PA534. 
  3. ↑ Pharmaceutical manufacturing ... - Google Books. Noyes Publications. January 1988. ISBN 9780815511441. https://books.google.com/books?id=X2EyLsG4bcUC&q=cyamemazine%20introduced&pg=PA397. 
  4. ↑ "[Prescribing patterns of antipsychotics in 13 French psychiatric hospitals"] (in fr). L'Encephale 35 (2): 129–138. April 2009. doi:10.1016/j.encep.2008.03.007. PMID 19393381. http://www.masson.fr/masson/S0013-7006(08)00103-6. 
  5. ↑ "Cyamemazine". Stahl's Essential Psychopharmacology. Cambridge University Press. http://stahlonline.cambridge.org/prescribers_drug.jsf?page=0521683505c20_p115-120.html.therapeutics&name=Cyamemazine. 
  6. ↑ "Cyamemazine as an anxiolytic drug on the elevated plus maze and light/dark paradigm in mice". Behavioural Brain Research 124 (1): 87–95. September 2001. doi:10.1016/S0166-4328(01)00238-8. PMID 11423169. 
  7. ↑ "Potential role of cortical 5-HT(2A) receptors in the anxiolytic action of cyamemazine in benzodiazepine withdrawal". Psychiatry Research (Elsevier BV) 198 (2): 307–312. July 2012. doi:10.1016/j.psychres.2012.01.009. PMID 22421069. 
  8. ↑ "Preclinical and clinical pharmacology of cyamemazine: anxiolytic effects and prevention of alcohol and benzodiazepine withdrawal syndrome". CNS Drug Reviews (Wiley) 10 (3): 219–229. 2006-06-07. doi:10.1111/j.1527-3458.2004.tb00023.x. PMID 15492772. 
  9. ↑ 9.0 9.1 9.2 "Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes". Biochemical Pharmacology 65 (3): 435–440. February 2003. doi:10.1016/S0006-2952(02)01515-0. PMID 12527336. 
  10. ↑ 10.0 10.1 "5-HT3- and 5-HT2C-antagonist properties of cyamemazine: significance for its clinical anxiolytic activity". Psychopharmacology 147 (4): 412–417. January 2000. doi:10.1007/s002130050010. PMID 10672635. http://link.springer.de/link/service/journals/00213/bibs/0147004/01470412.htm. Retrieved 2010-02-11. 
  11. ↑ "5-HT2A receptor antagonist properties of cyamemazine in rat and guinea pig smooth muscle". European Journal of Pharmacology 454 (2–3): 235–239. November 2002. doi:10.1016/S0014-2999(02)02489-5. PMID 12421652. 
  12. ↑ "Affinity of cyamemazine metabolites for serotonin, histamine and dopamine receptor subtypes". European Journal of Pharmacology 578 (2–3): 142–147. January 2008. doi:10.1016/j.ejphar.2007.09.025. PMID 17936750. 
  13. ↑ "Reduction of extracellular dopamine and metabolite concentrations in rat striatum by low doses of acute cyamemazine". Naunyn-Schmiedeberg's Archives of Pharmacology 367 (2): 134–139. February 2003. doi:10.1007/s00210-002-0665-4. PMID 12595954. 
  14. ↑ 14.00 14.01 14.02 14.03 14.04 14.05 14.06 14.07 14.08 14.09 14.10 14.11 14.12 14.13 14.14 14.15 14.16 14.17 14.18 14.19 14.20 "Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes". Biochemical Pharmacology 65 (3): 435–440. February 2003. doi:10.1016/s0006-2952(02)01515-0. PMID 12527336. 
  15. ↑ "Synthesis of Phenothiazines. VI. Certain 2-Substituted Phenothiazines and Their 10-Aminoalkyl Derivatives". The Journal of Organic Chemistry 26 (4): 1138–1143. 1961. doi:10.1021/jo01063a040. 
  16. ↑ Jacob RM, Georges RJ gdate = 1959, US patent 2877224, assigned to Rhone Poulenc Sa



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