View source for DHA-clozapine

{{short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 462084620
| IUPAC_name = (4''Z'',7''Z'',10''Z'',13''Z'',16''Z'',19''Z'')-1-[3-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzodiazepin-11-yl]docosa-4,7,10,13,16,19-hexaen-1-one
| image = Docosahexaenoyl-clozapine.svg
| alt = 
| caption =

<!--Clinical data-->
| tradename = Clozaprexin
| Drugs.com = 
| MedlinePlus = 
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category= 
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled-->
| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM -->
| legal_US = Investigational New Drug<!-- OTC / Rx-only / Schedule I, II, III, IV, V -->
| legal_status = 
| routes_of_administration =

<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion = 
| synonyms = Docosahexaenoyl clozapine

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = 225916-82-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Q5Q5VSN8DL
| ATCvet = 
| ATC_prefix = none
| ATC_suffix = 
| PubChem = 9852332
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 8028044
| smiles = Clc1ccc2N(C(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC)c4ccccc4C(=N/c2c1)\N3CCN(C)CC3
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C40H49ClN4O/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-26-39(46)45-37-25-23-22-24-35(37)40(44-31-29-43(2)30-32-44)42-36-33-34(41)27-28-38(36)45/h4-5,7-8,10-11,13-14,16-17,19-20,22-25,27-28,33H,3,6,9,12,15,18,21,26,29-32H2,1-2H3/b5-4-,8-7-,11-10-,14-13-,17-16-,20-19-
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = RPSJOJIGGSRDMO-JDPCYWKWSA-N
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =

<!--Chemical data-->
| C=40 | H=49 | Cl=1 | N=4 | O=1
}}

'''DHA-clozapine''' (tentative trade name '''Clozaprexin''')<ref name=Adis>{{cite news|title=DHA-clozapine|url=http://adisinsight.springer.com/drugs/800014710|access-date=17 March 2017|work=AdisInsight|language=en}}</ref> is an atypical [[antipsychotic]] drug candidate that was created and originally tested by chemists at Protarga, a small pharmaceutical in Pennsylvania, and scientists at Harvard University.<ref>{{cite journal|last1=Rosack|first1=Jim|title=Targaceuticals Point Way To Developing Safer Drugs|journal=Psychiatric News|date=4 May 2001|volume=36 |issue=9 |pages=36–37 |language=en|doi=10.1176/pn.36.9.0036}}</ref>   

It is a [[prodrug]] of  [[clozapine]]; the fatty acid [[docosahexaenoic acid]] (DHA) was added to clozapine in order to increase penetration of the [[blood–brain barrier]].<ref name=NPP>{{cite journal | vauthors = Baldessarini RJ, Campbell A, Webb NL, Swindell CS, Flood JG, Shashoua VE, Kula NS, Hemamalini S, Bradley MO | display-authors = 6 | title = Fatty acid derivatives of clozapine: prolonged antidopaminergic activity of docosahexaenoylclozapine in the rat | journal = Neuropsychopharmacology | volume = 24 | issue = 1 | pages = 55–65 | date = January 2001 | pmid = 11106876 | doi = 10.1016/S0893-133X(00)00173-1 | doi-access = free }}</ref> 

Protarga was purchased by Luitpold Pharmaceuticals in 2003 and development was discontinued in 2007.<ref name=Adis/>

==References==
{{Reflist}}

{{Antipsychotics}}
{{Adrenergic receptor modulators}}
{{Dopamine receptor modulators}}
{{Histamine receptor modulators}}
{{Muscarinic acetylcholine receptor modulators}}
{{Serotonin receptor modulators}}
{{Piperazines}}
{{Tricyclics}}

[[Category:4-Methylpiperazin-1-yl compounds]]
[[Category:Abandoned drugs]]
[[Category:Atypical antipsychotics]]
[[Category:Chloroarenes]]
[[Category:Dibenzodiazepines]]
[[Category:Dopamine antagonists]]
[[Category:M1 receptor antagonists]]
[[Category:M2 receptor antagonists]]
[[Category:M3 receptor antagonists]]
[[Category:M4 receptor agonists]]
[[Category:M5 receptor antagonists]]
[[Category:Prodrugs]]
[[Category:Serotonin receptor antagonists]]

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