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
Pharmacogenetics: data, concepts and tools to improve drug discovery and drug treatment.	2008 Feb	18224312
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

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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