DHA-clozapine

DHA-clozapine (tentative trade name Clozaprexin)[1] 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.[2]

DHA-clozapine

Clinical data
Trade names	Clozaprexin
Other names	Docosahexaenoyl clozapine
ATC code	none
Legal status
Legal status	US: Investigational New Drug
Identifiers
IUPAC name (4Z,7Z,10Z,13Z,16Z,19Z)-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
CAS Number	225916-82-5^N
PubChem CID	9852332
ChemSpider	8028044^N
Chemical and physical data
Formula	C40H49ClN4O
Molar mass	637.31 g·mol^−1
3D model (JSmol)	Interactive image
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
InChI InChI=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-^N Key:RPSJOJIGGSRDMO-JDPCYWKWSA-N^N
^NY (what is this?)  (verify)

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.[3]

Protarga was purchased by Luitpold Pharmaceuticals in 2003 and development was discontinued in 2007.[1]

References

1. "DHA-clozapine". AdisInsight. Retrieved 17 March 2017.
2. Rosack, Jim (4 May 2001). "Targaceuticals Point Way To Developing Safer Drugs". Psychiatric News. doi:10.1176/pn.36.9.0036.
3. Baldessarini RJ, Campbell A, Webb NL, Swindell CS, Flood JG, Shashoua VE, et al. (January 2001). "Fatty acid derivatives of clozapine: prolonged antidopaminergic activity of docosahexaenoylclozapine in the rat". Neuropsychopharmacology. 24 (1): 55–65. doi:10.1016/S0893-133X(00)00173-1. PMID 11106876.