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Cyamemazine

From Wikipedia, the free encyclopedia
Antipsychotic medication

Pharmaceutical compound
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
Eliminationhalf-life10 hours
ExcretionUrine
Identifiers
  • 10-(3-dimethylamino-2-methyl-propyl)phenothiazine-2-carbonitrile
CAS Number
PubChemCID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.020.541Edit this at Wikidata
Chemical and physical data
FormulaC19H21N3S
Molar mass323.46 g·mol−1
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 checkY
  • Key:SLFGIOIONGJGRT-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Cyamemazine (Tercian), also known ascyamepromazine, is atypical antipsychoticdrug of thephenothiazineclass which was introduced byTheraplix inFrance in 1972 and later inPortugal as well.[1][2][3][4]

Medical use

[edit]

It is used for the treatment ofschizophrenia and, especially, forpsychosis-associatedanxiety, due to its uniqueanxiolytic efficacy.[5][6]

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

Side effects

[edit]

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

Mechanism

[edit]

Cyamemazine differs from other phenothiazine neuroleptics in that aside from the usual profile ofdopamine,α1-adrenergic,H1, andmACh receptorantagonism,[9] it additionally produces potent blockade of severalserotonin receptors, including5-HT2A,5-HT2C, and5-HT7.[9][10][11][12] These actions have been implicated in cyamemazine's anxiolytic effects (5-HT2C) and lack ofextrapyramidalside effects (5-HT2A),[9][10] and despite being classified as atypical antipsychotic, it actually behaves like anatypical antipsychotic.[13]

SiteKi (nM)SpeciesRef
H19.3Guinea pig[14]
H2351Guinea pig[14]
H310000+Rat[14]
M113Human[14]
M242Human[14]
M332Human[14]
M412Human[14]
M535Human[14]
5-HT1A517Human[14]
5-HT2A1.5Human[14]
5-HT2C12Human[14]
5-HT32943Human[14]
5-HT722Human[14]
D13.8Human[14]
D25.8Human[14]
D32.5Human[14]
D45.3Human[14]
α12.3Rat[14]
α21320Rat[14]
GABAA10000+Rat[14]
GABAB10000+Rat[14]
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

Synthesis

[edit]
Synthesis:[15] Patent:[16]

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

References

[edit]
  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 fromthe 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. ^abcHameg 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. ^abAlvarez-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 fromthe original on 2002-01-12. Retrieved2010-02-11.
  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. ^abcdefghijklmnopqrstuHameg 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
(andprodrugs)
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
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