cyamemazine

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 444653764

| IUPAC_name = 10-(3-dimethylamino-2-methyl-propyl)phenothiazine-2-carbonitrile

| image = Cyamemazine.svg

| tradename = Tercian

| Drugs.com = {{drugs.com|international|cyamemazine}}

| pregnancy_category =

| legal_status = Rx-Only

| routes_of_administration = Oral, IM, IV

| bioavailability = 10-70%

| protein_bound =

| metabolism = Hepatic

| elimination_half-life = 10 hours

| excretion = Urine

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 3546-03-0

| ATC_prefix = N05

| ATC_suffix = AA06

| PubChem = 62865

| IUPHAR_ligand = 84

| DrugBank_Ref = {{drugbankcite|changed|drugbank}}

| DrugBank = DB09000

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2104153

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 56597

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = A2JGV5CNU4

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07307

| C=19 | H=21 | N=3 | S=1

| smiles = N#Cc2cc1N(c3c(Sc1cc2)cccc3)CC(C)CN(C)C

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = SLFGIOIONGJGRT-UHFFFAOYSA-N

}}

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.{{cite book | url = https://books.google.com/books?id=5GpcTQD_L2oC&q=cyamemazine%20tercian&pg=PA280 | title = Index Nominum, International Drug | publisher = Taylor & Francis | isbn = 978-3-88763-075-1 | year = 2000 }}{{cite book | vauthors = Triggle DJ | title = Dictionary of Pharmacological Agents | publisher = Chapman & Hall/CRC | location = Boca Raton | year = 1996 | page = 534 | isbn = 0-412-46630-9 | url = https://books.google.com/books?id=DeX7jgInYFMC&pg=RA1-PA534}}{{cite book | url = https://books.google.com/books?id=X2EyLsG4bcUC&q=cyamemazine%20introduced&pg=PA397 | title = Pharmaceutical manufacturing ... - Google Books | isbn = 9780815511441 | vauthors = Sittig M | date = January 1988 | publisher = Noyes Publications }}{{cite journal | vauthors = Bret P, Bret MC, Queuille E | title = [Prescribing patterns of antipsychotics in 13 French psychiatric hospitals] | language = fr | journal = L'Encephale | volume = 35 | issue = 2 | pages = 129–138 | date = April 2009 | pmid = 19393381 | doi = 10.1016/j.encep.2008.03.007 | url = http://www.masson.fr/masson/S0013-7006(08)00103-6 | url-status = dead | archive-url = https://archive.today/20130213173522/http://www.masson.fr/masson/S0013-7006(08)00103-6 | archive-date = 2013-02-13 }}

Medical use

It is used for the treatment of schizophrenia and, especially, for psychosis-associated anxiety, due to its unique anxiolytic efficacy.{{cite book | chapter-url = http://stahlonline.cambridge.org/prescribers_drug.jsf?page=0521683505c20_p115-120.html.therapeutics&name=Cyamemazine | chapter = Cyamemazine | title = Stahl's Essential Psychopharmacology | publisher = Cambridge University Press }}{{cite journal | vauthors = Bourin M, Claude Colombel M, Dib M, Hascoët M | title = Cyamemazine as an anxiolytic drug on the elevated plus maze and light/dark paradigm in mice | journal = Behavioural Brain Research | volume = 124 | issue = 1 | pages = 87–95 | date = September 2001 | pmid = 11423169 | doi = 10.1016/S0166-4328(01)00238-8 | s2cid = 43312295 }}

It is also used to reduce anxiety associated with benzodiazepine withdrawal syndrome and anxiety in depression with suicidal tendency.{{cite journal | vauthors = Benyamina A, Naassila M, Bourin M | title = Potential role of cortical 5-HT(2A) receptors in the anxiolytic action of cyamemazine in benzodiazepine withdrawal | journal = Psychiatry Research | volume = 198 | issue = 2 | pages = 307–312 | date = July 2012 | pmid = 22421069 | doi = 10.1016/j.psychres.2012.01.009 | publisher = Elsevier BV | s2cid = 34830082 }}

Side effects

Here are some of the most common side effects and related incidence:{{cite journal | vauthors = Bourin M, Dailly E, Hascöet M | title = Preclinical and clinical pharmacology of cyamemazine: anxiolytic effects and prevention of alcohol and benzodiazepine withdrawal syndrome | journal = CNS Drug Reviews | volume = 10 | issue = 3 | pages = 219–229 | date = 2006-06-07 | pmid = 15492772 | pmc = 6741725 | doi = 10.1111/j.1527-3458.2004.tb00023.x | publisher = Wiley }}

Sedation (20%)
Vertigo (7.9%)
Constipation (4%)
Dyskinesia (4.4%)
Dryness of mouth (5.9%)
Hypotension (7.4%)
Tachycardia (3.2%)

Mechanism

Cyamemazine differs from other phenothiazine neuroleptics in that aside from the usual profile of dopamine, α₁-adrenergic, H₁, and mACh receptor antagonism,{{cite journal | vauthors = Hameg A, Bayle F, Nuss P, Dupuis P, Garay RP, Dib M | title = Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes | journal = Biochemical Pharmacology | volume = 65 | issue = 3 | pages = 435–440 | date = February 2003 | pmid = 12527336 | doi = 10.1016/S0006-2952(02)01515-0 }} it additionally produces potent blockade of several serotonin receptors, including 5-HT_2A, 5-HT_2C, and 5-HT₇.{{cite journal | vauthors = Alvarez-Guerra M, d'Alché-Birée F, Wolf WA, Vargas F, Dib M, Garay RP | title = 5-HT3- and 5-HT2C-antagonist properties of cyamemazine: significance for its clinical anxiolytic activity | journal = Psychopharmacology | volume = 147 | issue = 4 | pages = 412–417 | date = January 2000 | pmid = 10672635 | doi = 10.1007/s002130050010 | url = http://link.springer.de/link/service/journals/00213/bibs/0147004/01470412.htm | access-date = 2010-02-11 | url-status = dead | s2cid = 25162849 | archive-url = https://web.archive.org/web/20020112021448/http://link.springer.de/link/service/journals/00213/bibs/0147004/01470412.htm | archive-date = 2002-01-12 }}{{cite journal | vauthors = Alvarez-Guerra M, Hameg A, Bayle F, Dib M, Garay RP | title = 5-HT2A receptor antagonist properties of cyamemazine in rat and guinea pig smooth muscle | journal = European Journal of Pharmacology | volume = 454 | issue = 2–3 | pages = 235–239 | date = November 2002 | pmid = 12421652 | doi = 10.1016/S0014-2999(02)02489-5 }}{{cite journal | vauthors = Benyamina A, Arbus C, Nuss P, Garay RP, Neliat G, Hameg A | title = Affinity of cyamemazine metabolites for serotonin, histamine and dopamine receptor subtypes | journal = European Journal of Pharmacology | volume = 578 | issue = 2–3 | pages = 142–147 | date = January 2008 | pmid = 17936750 | doi = 10.1016/j.ejphar.2007.09.025 }} These actions have been implicated in cyamemazine's anxiolytic effects (5-HT_2C) and lack of extrapyramidal side effects (5-HT_2A), and despite being classified as a typical antipsychotic, it actually behaves like an atypical antipsychotic.{{cite journal | vauthors = Peinado J, Hameg A, Garay RP, Bayle F, Nuss P, Dib M | title = Reduction of extracellular dopamine and metabolite concentrations in rat striatum by low doses of acute cyamemazine | journal = Naunyn-Schmiedeberg's Archives of Pharmacology | volume = 367 | issue = 2 | pages = 134–139 | date = February 2003 | pmid = 12595954 | doi = 10.1007/s00210-002-0665-4 | s2cid = 682064 }}

class="wikitable sortable floatright" style="font-size:small;"

!Site

!K_i (nM)

!Species

!Ref

H₁

|9.3

|Guinea pig

|{{cite journal | vauthors = Hameg A, Bayle F, Nuss P, Dupuis P, Garay RP, Dib M | title = Affinity of cyamemazine, an anxiolytic antipsychotic drug, for human recombinant dopamine vs. serotonin receptor subtypes | journal = Biochemical Pharmacology | volume = 65 | issue = 3 | pages = 435–440 | date = February 2003 | pmid = 12527336 | doi = 10.1016/s0006-2952(02)01515-0 }}

H₂

|351

|Guinea pig

H₃

|10000+

|Rat

M₁

|13

|Human

M₂

|42

|Human