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=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

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

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 Co-administed with:: quinine(650 mg; 3/day for 2 days) mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/	unhealthy n = 10000 Health Status: unhealthy Condition: malaria Sex: M Population Size: 10000 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/	unhealthy n = 10000 Health Status: unhealthy Condition: malaria Sex: M Population Size: 10000 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 Co-administed with:: quinine(500 mg; 1/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 n = 56 Health Status: unhealthy Condition: crescents in blood Sex: M Population Size: 56 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 n = 40 Health Status: unhealthy Condition: quartan malaria Sex: M Population Size: 40 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy n = 258 Health Status: unhealthy Condition: malaria Sex: M Population Size: 258 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 Co-administed with:: quinine(650 mg; 3/day for 2 days) mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/	unhealthy n = 10000 Health Status: unhealthy Condition: malaria Sex: M Population Size: 10000 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/21019545/	unhealthy n = 10000 Health Status: unhealthy Condition: malaria Sex: M Population Size: 10000 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 Co-administed with:: quinine(500 mg; 1/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 n = 56 Health Status: unhealthy Condition: crescents in blood Sex: M Population Size: 56 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 n = 40 Health Status: unhealthy Condition: quartan malaria Sex: M Population Size: 40 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 n = 40 Health Status: unhealthy Condition: quartan malaria Sex: M Population Size: 40 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy n = 258 Health Status: unhealthy Condition: malaria Sex: M Population Size: 258 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy n = 258 Health Status: unhealthy Condition: malaria Sex: M Population Size: 258 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy n = 258 Health Status: unhealthy Condition: malaria Sex: M Population Size: 258 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy n = 258 Health Status: unhealthy Condition: malaria Sex: M Population Size: 258 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy n = 258 Health Status: unhealthy Condition: malaria Sex: M Population Size: 258 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy n = 258 Health Status: unhealthy Condition: malaria Sex: M Population Size: 258 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy n = 258 Health Status: unhealthy Condition: malaria Sex: M Population Size: 258 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy n = 258 Health Status: unhealthy Condition: malaria Sex: M Population Size: 258 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 Co-administed with:: mepacrine(100 mg; 3/day for 5 days) Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/	unhealthy n = 258 Health Status: unhealthy Condition: malaria Sex: M Population Size: 258 Sources: https://pubmed.ncbi.nlm.nih.gov/20991220/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP450 65

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP450 65	substrate 3367 Sources: https://www.ajtmh.org/view/journals/tpmd/85/6/article-p1010.xml	likely

Sourcing

Vendor/Aggregator	ID	URL
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
abcr GmbH	AB548833	http://www.abcr.com/shop/en/AB548833

PubMed

Title	Date	PubMed
Mutagenic activity and mutational specificity of antiprotozoal drugs with and without nitrite treatment.	2002	11813295
The relationship of physico-chemical properties and structure to the differential antiplasmodial activity of the cinchona alkaloids.	2003 Sep 1	14505493
Short report: the activity of pamaquine, an 8-aminoquinoline drug, against sporozoite-induced infections of Plasmodium vivax (New Guinea strains).	2004 Aug	15306708
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
Glucose-6-phosphate dehydrogenase deficiency and antimalarial drug development.	2007 Oct	17978087
Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment.	2008 Feb	18224312
Antimalarials and the fight against malaria in Brazil.	2009 Aug	19753125
Molecular biosensing mechanisms in the spleen for the removal of aged and damaged red cells from the blood circulation.	2010	22163593
Structural modifications of quinoline-based antimalarial agents: Recent developments.	2010 Apr	21814435

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:09:24 GMT 2023` Edited by `admin` on `Fri Dec 15 16:09:24 GMT 2023`
Record UNII	96Y4A9AODB
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PAMAQUINE NAPHTHOATE

Common 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

PAMAQUINE PAMOATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C271