PAMAQUINE NAPHTHOATE

US Previously Marketed

First marketed in 1926

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 Search

SMILES

CCN(CC)CCCC(C)NC1=C2N=CC=CC2=CC(OC)=C1.OC(=O)C3=C(O)C(CC4=C5C=CC=CC5=CC(C(O)=O)=C4O)=C6C=CC=CC6=C3

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
Sources: https://www.snpedia.com/index.php/Pamaquine | DOI: 10.1016/S0165-7208(97)80043-8 | https://www.ncbi.nlm.nih.gov/pubmed/15306708 | https://www.ncbi.nlm.nih.gov/pubmed/17978087

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

Dose	Population	Adverse events
10 mg 3 times / day multiple, oral Recommended Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/	Other AEs: Haemoglobinuria... Other AEs: Haemoglobinuria (5 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/
10 mg 3 times / day multiple, oral Recommended Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/	Other AEs: Haemoglobinuria... Other AEs: Haemoglobinuria (13 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/
40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Green R. The treatment of “crescent carriers” with plasmoquine compound. Kuala Lumpur, Government Printing Office, 1929:1–20 (Bulletins Institute for Medical Research (Malaysia), Issue 3).	unhealthy Health Status: unhealthy Sex: M Sources: Green R. The treatment of “crescent carriers” with plasmoquine compound. Kuala Lumpur, Government Printing Office, 1929:1–20 (Bulletins Institute for Medical Research (Malaysia), Issue 3).	Other AEs: Abdominal pain... Other AEs: Abdominal pain (3 patients) Sources: Green R. The treatment of “crescent carriers” with plasmoquine compound. Kuala Lumpur, Government Printing Office, 1929:1–20 (Bulletins Institute for Medical Research (Malaysia), Issue 3).
60 mg 1 times / day multiple, oral Recommended Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: Green R. The treatment of quartan malaria with plasmoquine. Kuala Lumpur, Government Printing Office, 1929 (Bulletins Institute for Medical Research (Malaysia), Issue 3).	unhealthy Health Status: unhealthy Sex: M Sources: Green R. The treatment of quartan malaria with plasmoquine. Kuala Lumpur, Government Printing Office, 1929 (Bulletins Institute for Medical Research (Malaysia), Issue 3).	Other AEs: Abdominal pain, Cardiac disorder NOS... Other AEs: Abdominal pain (10%) Cardiac disorder NOS (5%) Sources: Green R. The treatment of quartan malaria with plasmoquine. Kuala Lumpur, Government Printing Office, 1929 (Bulletins Institute for Medical Research (Malaysia), Issue 3).
10 mg 3 times / day multiple, oral Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	Other AEs: Abdominal pain, Urine discoloration... Other AEs: Abdominal pain (69%) Urine discoloration (58%) Anorexia (45%) Jaundice (45%) Headache (39%) Nausea and vomiting (34%) Fever (25%) Weakness (23%) Backache (22%) Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/

AEs

AE	Significance	Dose	Population
Haemoglobinuria	5 patients	10 mg 3 times / day multiple, oral Recommended Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/
Haemoglobinuria	13 patients	10 mg 3 times / day multiple, oral Recommended Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/
Abdominal pain	3 patients	40 mg 1 times / day multiple, oral Recommended Dose: 40 mg, 1 times / day Route: oral Route: multiple Dose: 40 mg, 1 times / day Sources: Green R. The treatment of “crescent carriers” with plasmoquine compound. Kuala Lumpur, Government Printing Office, 1929:1–20 (Bulletins Institute for Medical Research (Malaysia), Issue 3).	unhealthy Health Status: unhealthy Sex: M Sources: Green R. The treatment of “crescent carriers” with plasmoquine compound. Kuala Lumpur, Government Printing Office, 1929:1–20 (Bulletins Institute for Medical Research (Malaysia), Issue 3).
Abdominal pain	10%	60 mg 1 times / day multiple, oral Recommended Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: Green R. The treatment of quartan malaria with plasmoquine. Kuala Lumpur, Government Printing Office, 1929 (Bulletins Institute for Medical Research (Malaysia), Issue 3).	unhealthy Health Status: unhealthy Sex: M Sources: Green R. The treatment of quartan malaria with plasmoquine. Kuala Lumpur, Government Printing Office, 1929 (Bulletins Institute for Medical Research (Malaysia), Issue 3).
Cardiac disorder NOS	5%	60 mg 1 times / day multiple, oral Recommended Dose: 60 mg, 1 times / day Route: oral Route: multiple Dose: 60 mg, 1 times / day Sources: Green R. The treatment of quartan malaria with plasmoquine. Kuala Lumpur, Government Printing Office, 1929 (Bulletins Institute for Medical Research (Malaysia), Issue 3).	unhealthy Health Status: unhealthy Sex: M Sources: Green R. The treatment of quartan malaria with plasmoquine. Kuala Lumpur, Government Printing Office, 1929 (Bulletins Institute for Medical Research (Malaysia), Issue 3).
Backache	22%	10 mg 3 times / day multiple, oral Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/
Weakness	23%	10 mg 3 times / day multiple, oral Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/
Fever	25%	10 mg 3 times / day multiple, oral Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/
Nausea and vomiting	34%	10 mg 3 times / day multiple, oral Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/
Headache	39%	10 mg 3 times / day multiple, oral Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/
Anorexia	45%	10 mg 3 times / day multiple, oral Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/
Jaundice	45%	10 mg 3 times / day multiple, oral Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/
Urine discoloration	58%	10 mg 3 times / day multiple, oral Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/
Abdominal pain	69%	10 mg 3 times / day multiple, oral Dose: 10 mg, 3 times / day Route: oral Route: multiple Dose: 10 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy Health Status: unhealthy Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP450 59

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP450 59	substrate 4014 Sources: https://www.ajtmh.org/view/journals/tpmd/85/6/article-p1010.xml	likely

Sourcing

Vendor/Aggregator	ID	URL
abcr GmbH	AB548833	http://www.abcr.com/shop/en/AB548833
Accela ChemBio Inc	SY248279	http://www.accelachem.com/cn/search.html?keyword=SY248279&attname=GoodsCode
Alfa Chemistry	491-92-9	https://www.alfa-chemistry.com/cas_491-92-9.htm
Ambinter	Amb16225675	http://www.ambinter.com/reference/16225675
BOC Sciences	491-92-9	https://buildingblock.bocsci.com/product/n1-n1-diethyl-n4-6-methoxy-8-quinolyl-1-cas-491-92-9-318624.html
Chemspace	CSSB00015367680	https://chem-space.com/CSSB00015367680
Finetech	FT-0775257	https://www.finetechnology-ind.com/prod/detail/pub/491-92-9.html
Smolecule	S538578	http://www.smolecule.com/products/s538578
THE BioTek	bt-278675	https://www.thebiotek.com/product/inhibitors/bt-278675
Yuhao Chemical	YH67095	http://www.chemyuhao.com/491-92-9.html

PubMed

Title	Date	PubMed
Structural modifications of quinoline-based antimalarial agents: Recent developments.	2010-04	21814435
Molecular biosensing mechanisms in the spleen for the removal of aged and damaged red cells from the blood circulation.	2010	22163593
Antimalarials and the fight against malaria in Brazil.	2009-08	19753125
Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment.	2008-02	18224312
Glucose-6-phosphate dehydrogenase deficiency and antimalarial drug development.	2007-10	17978087
How did the ancestral HIV-1 group M retrovirus get to Leopoldville from southeastern Cameroon?	2007	17448608
Mechanism and history of evolution of symbiotic HIV strains into lethal pandemic strains: the key event may have been a 1927 trial of pamaquine in Leopoldville (Kinshasa), Congo.	2007	17368749
Short report: the activity of pamaquine, an 8-aminoquinoline drug, against sporozoite-induced infections of Plasmodium vivax (New Guinea strains).	2004-08	15306708
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.	2003-09-01	14505493
Mutagenic activity and mutational specificity of antiprotozoal drugs with and without nitrite treatment.	2002	11813295

Name

Type

Language

PAMAQUINE NAPHTHOATE

Common Name

English

PAMAQUINE PAMOATE

Preferred Name

English

PAMAQUINE PAMOATE [MI]

Common Name

English

N(SUP 1),N(SUP 1)-DIETHYL-N(SUP 4)-(6-METHOXYQUINOLIN-8-YL)PENTANE-1,4-DIAMINE PAMOATE

Common Name

English

QUINOLINE, 6-METHOXY-8-(1-METHYL-4-DIETHYLAMINO)BUTYLAMINO, METHYLENE-BIS-.BETA.-HYDROXYNAPHTHOATE

Common Name

English

PAMAQUINE EMBONATE

Common Name

English

NSC-14220

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C271