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Cyamemazine

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Antipsychotic medication


Cyamemazine
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
  • 10-(3-dimethylamino-2-methyl-propyl)phenothiazine-2-carbonitrile
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.020.541 Edit this at Wikidata
Chemical and physical data
FormulaC19H21N3S
Molar mass323.46 g·mol
3D model (JSmol)
  • N#Cc2cc1N(c3c(Sc1cc2)cccc3)CC(C)CN(C)C
  • InChI=1S/C19H21N3S/c1-14(12-21(2)3)13-22-16-6-4-5-7-18(16)23-19-9-8-15(11-20)10-17(19)22/h4-10,14H,12-13H2,1-3H3
  • Key:SLFGIOIONGJGRT-UHFFFAOYSA-N
  (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.

Medical use

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

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

Side effects

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

Mechanism

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

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

the more strongly the drug binds to the site.

Synthesis

Synthesis: Patent:

2-Cyanophenothiazine (1) 3-Chloro-2-methylpropyl(dimethyl)amine (2)

References

  1. Index Nominum, International Drug. Taylor & Francis. 2000. ISBN 978-3-88763-075-1.
  2. Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 534. ISBN 0-412-46630-9.
  3. Sittig M (January 1988). Pharmaceutical manufacturing ... - Google Books. Noyes Publications. ISBN 9780815511441.
  4. Bret P, Bret MC, Queuille E (April 2009). "[Prescribing patterns of antipsychotics in 13 French psychiatric hospitals]". L'Encephale (in French). 35 (2): 129–138. doi:10.1016/j.encep.2008.03.007. PMID 19393381. Archived from the original on 2013-02-13.
  5. "Cyamemazine". Stahl's Essential Psychopharmacology. Cambridge University Press.
  6. Bourin M, Claude Colombel M, Dib M, Hascoët M (September 2001). "Cyamemazine as an anxiolytic drug on the elevated plus maze and light/dark paradigm in mice". Behavioural Brain Research. 124 (1): 87–95. doi:10.1016/S0166-4328(01)00238-8. PMID 11423169. S2CID 43312295.
  7. Benyamina A, Naassila M, Bourin M (July 2012). "Potential role of cortical 5-HT(2A) receptors in the anxiolytic action of cyamemazine in benzodiazepine withdrawal". Psychiatry Research. 198 (2). Elsevier BV: 307–312. doi:10.1016/j.psychres.2012.01.009. PMID 22421069. S2CID 34830082.
  8. Bourin M, Dailly E, Hascöet M (2006-06-07). "Preclinical and clinical pharmacology of cyamemazine: anxiolytic effects and prevention of alcohol and benzodiazepine withdrawal syndrome". CNS Drug Reviews. 10 (3). Wiley: 219–229. doi:10.1111/j.1527-3458.2004.tb00023.x. PMC 6741725. PMID 15492772.
  9. ^ Hameg A, Bayle F, Nuss P, Dupuis P, Garay RP, Dib M (February 2003). "Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes". Biochemical Pharmacology. 65 (3): 435–440. doi:10.1016/S0006-2952(02)01515-0. PMID 12527336.
  10. ^ Alvarez-Guerra M, d'Alché-Birée F, Wolf WA, Vargas F, Dib M, Garay RP (January 2000). "5-HT3- and 5-HT2C-antagonist properties of cyamemazine: significance for its clinical anxiolytic activity". Psychopharmacology. 147 (4): 412–417. doi:10.1007/s002130050010. PMID 10672635. S2CID 25162849. Archived from the original on 2002-01-12. Retrieved 2010-02-11.
  11. Alvarez-Guerra M, Hameg A, Bayle F, Dib M, Garay RP (November 2002). "5-HT2A receptor antagonist properties of cyamemazine in rat and guinea pig smooth muscle". European Journal of Pharmacology. 454 (2–3): 235–239. doi:10.1016/S0014-2999(02)02489-5. PMID 12421652.
  12. Benyamina A, Arbus C, Nuss P, Garay RP, Neliat G, Hameg A (January 2008). "Affinity of cyamemazine metabolites for serotonin, histamine and dopamine receptor subtypes". European Journal of Pharmacology. 578 (2–3): 142–147. doi:10.1016/j.ejphar.2007.09.025. PMID 17936750.
  13. Peinado J, Hameg A, Garay RP, Bayle F, Nuss P, Dib M (February 2003). "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. doi:10.1007/s00210-002-0665-4. PMID 12595954. S2CID 682064.
  14. ^ Hameg A, Bayle F, Nuss P, Dupuis P, Garay RP, Dib M (February 2003). "Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes". Biochemical Pharmacology. 65 (3): 435–440. doi:10.1016/s0006-2952(02)01515-0. PMID 12527336.
  15. Craig PN, Gordon M, Lafferty JJ, Lester BM, Saggiomo AJ, Zirkle CL (1961). "Synthesis of Phenothiazines. VI. Certain 2-Substituted Phenothiazines and Their 10-Aminoalkyl Derivatives". The Journal of Organic Chemistry. 26 (4): 1138–1143. doi:10.1021/jo01063a040.
  16. US 2877224, Jacob RM, Georges RJ gdate = 1959, assigned to Rhone Poulenc Sa 
Typical
Disputed
Atypical
Others
α1
Agonists
Antagonists
α2
Agonists
Antagonists
β
Agonists
Antagonists
D1-like
Agonists
PAMs
Antagonists
D2-like
Agonists
Antagonists
H1
Agonists
Antagonists
H2
Agonists
Antagonists
H3
Agonists
Antagonists
H4
Agonists
Antagonists
mAChRsTooltip Muscarinic acetylcholine receptors
Agonists
Antagonists
Precursors
(and prodrugs)
5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Classes
Antidepressants
(Tricyclic antidepressants (TCAs))
Antihistamines
Antipsychotics
Anticonvulsants
Anticholinergics
Others
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