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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

Molecular Formula C19H29N3O
Molecular Weight 315.4531
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Molecular Formula C23H16O6
Molecular Weight 388.3695
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Substance Class Chemical
Record UNII
96Y4A9AODB
Record Status Validated (UNII)
Record Version