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Details

Stereochemistry RACEMIC
Molecular Formula C23H16O6.C19H29N3O
Molecular Weight 703.8226
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PAMAQUINE NAPHTHOATE

SMILES

CCN(CC)CCCC(C)NC1=CC(OC)=CC2=C1N=CC=C2.OC(=O)C3=CC4=C(C=CC=C4)C(CC5=C6C=CC=CC6=CC(C(O)=O)=C5O)=C3O

InChI

InChIKey=IPPMKVWUPMOGFL-UHFFFAOYSA-N
InChI=1S/C23H16O6.C19H29N3O/c24-20-16(14-7-3-1-5-12(14)9-18(20)22(26)27)11-17-15-8-4-2-6-13(15)10-19(21(17)25)23(28)29;1-5-22(6-2)12-8-9-15(3)21-18-14-17(23-4)13-16-10-7-11-20-19(16)18/h1-10,24-25H,11H2,(H,26,27)(H,28,29);7,10-11,13-15,21H,5-6,8-9,12H2,1-4H3

HIDE SMILES / InChI

Description

The discovery of pamaquine, developed by replacing one of the methyl groups of methylene blue by a dialkylaminoalkyl chain, was a landmark in the design of drugs for malaria. It is closely related to primaquine. The administration of pamaquine during the incubation period delayed but did not prevent primary attacks of a New Guinea strain of Plasmodium vivax malaria. Hemolytic anemia after administration of the antimalarial drug pamaquine was reported in patients with Glucose-6-phosphate dehydrogenase (G6PD) deficiency. Pamaquine itself could not be used clinically due to high toxicity.

Approval Year

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

PubMed