Cyamemazine

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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
JSmol)
SMILES
  • 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 as cyamepromazine, is a

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

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 10000+ 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 2943 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 10000+ Rat [14]
GABAB 10000+ 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. ISBN 978-3-88763-075-1
    .
  2. ISBN 0-412-46630-9
    .
  3. ISBN 9780815511441
    .
  4. PMID 19393381. Archived from the original
    on 2013-02-13.
  5. ^ "Cyamemazine". Stahl's Essential Psychopharmacology. Cambridge University Press.
  6. S2CID 43312295
    .
  7. S2CID 34830082
    .
  8. PMID 15492772
    .
  9. ^
    PMID 12527336
    .
  10. ^
    S2CID 25162849. Archived from the original
    on 2002-01-12. Retrieved 2010-02-11.
  11. PMID 12421652
    .
  12. PMID 17936750
    .
  13. S2CID 682064
    .
  14. ^
    PMID 12527336
    .
  15. doi:10.1021/jo01063a040
    .
  16. ^ US 2877224, Jacob RM, Georges RJ gdate = 1959, assigned to Rhone Poulenc Sa