Cyamemazine

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Cyamemazine
Systematic (IUPAC) name
10-(3-dimethylamino-2-methyl-propyl)phenothiazine-2-carbonitrile
Clinical data
AHFS/Drugs.com International Drug Names
Pregnancy cat.  ?
Legal status Rx-Only
Routes Oral, IM, IV
Pharmacokinetic data
Bioavailability 10-70%
Metabolism Hepatic
Half-life 10 hours
Excretion Urine
Identifiers
CAS number 3546-03-0
ATC code N05AA06
PubChem CID 62865
IUPHAR ligand 84
ChemSpider 56597 YesY
UNII A2JGV5CNU4 YesY
KEGG D07307 YesY
Chemical data
Formula C19H21N3S
Mol. mass 323.46 g/mol
 YesY (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] It is used for the treatment of schizophrenia and, especially, for psychosis-associated anxiety, due to its unique anxiolytic efficacy.[5][6]

Cyamemazine differs from other phenothiazine neuroleptics in that aside from the usual profile of dopamine, α1-adrenergic, H1, and mACh receptor antagonism,[7] it additionally produces potent blockade of several serotonin receptors, including 5-HT2A, 5-HT2C, and 5-HT7.[7][8][9][10] These actions have been implicated in cyamemazine's anxiolytic effects (5-HT2C) and lack of extrapyramidal side effects (5-HT2A),[7][8] and despite being classified as a typical, it actually behaves like an atypical antipsychotic.[11]

See also

References

  1. ^ Index nominum, international drug ... - Google Books. http://books.google.com/books?id=5GpcTQD_L2oC&lpg=PA280&dq=cyamemazine%20tercian&as_brr=3&pg=PA280#v=onepage&q=&f=false.
  2. ^ David J. Triggle (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. p. 534. ISBN 0-412-46630-9. http://books.google.com/books?id=DeX7jgInYFMC&lpg=RA1-PA534&as_brr=3&pg=RA1-PA534#v=onepage&q=&f=false.
  3. ^ Pharmaceutical manufacturing ... - Google Books. http://books.google.com/books?id=X2EyLsG4bcUC&lpg=PA397&dq=cyamemazine%20introduced&as_brr=3&pg=PA397#v=onepage&q=&f=false.
  4. ^ Bret P, Bret MC, Queuille E (April 2009). "[Prescribing patterns of antipsychotics in 13 French psychiatric hospitals"] (in French). L'Encéphale 35 (2): 129–38. doi:10.1016/j.encep.2008.03.007. PMID 19393381. http://www.masson.fr/masson/S0013-7006(08)00103-6.
  5. ^ "Stahl's Essential Psychopharmacology - Cambridge University Press". http://stahlonline.cambridge.org/prescribers_drug.jsf?page=0521683505c20_p115-120.html.therapeutics&name=Cyamemazine.
  6. ^ Bourin M, Nic Dhonnchadha BA, 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. http://linkinghub.elsevier.com/retrieve/pii/S0166432801002388.
  7. ^ a b c 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): 435–40. doi:10.1016/S0006-2952(02)01515-0. PMID 12527336. http://linkinghub.elsevier.com/retrieve/pii/S0006295202015150.
  8. ^ a b 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): 412–7. doi:10.1007/s002130050010. PMID 10672635. http://link.springer.de/link/service/journals/00213/bibs/0147004/01470412.htm.
  9. ^ 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): 235–9. doi:10.1016/S0014-2999(02)02489-5. PMID 12421652. http://linkinghub.elsevier.com/retrieve/pii/S0014299902024895.
  10. ^ 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): 142–7. doi:10.1016/j.ejphar.2007.09.025. PMID 17936750. http://linkinghub.elsevier.com/retrieve/pii/S0014-2999(07)01053-9.
  11. ^ 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): 134–9. doi:10.1007/s00210-002-0665-4. PMID 12595954.