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Details

Stereochemistry ACHIRAL
Molecular Formula C18H27N3O
Molecular Weight 301.4265
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENTAQUINE

SMILES

COC1=CC(NCCCCCNC(C)C)=C2N=CC=CC2=C1

InChI

InChIKey=VKXQZROIIKPELG-UHFFFAOYSA-N
InChI=1S/C18H27N3O/c1-14(2)19-9-5-4-6-10-20-17-13-16(22-3)12-15-8-7-11-21-18(15)17/h7-8,11-14,19-20H,4-6,9-10H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C18H27N3O
Molecular Weight 301.4265
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Pentaquine is an 8-aminoquinoline that was used in the 1950s to treat malaria and trypanosomiasis. Pentaquine showed no significant sporontocidal activity against P. gallinaceum in Aedes aegypti. In the experimental animals, the antimalarial effect of pentaquine, its pharmacology and toxicology have been investigated (1, 2). Activity, 80 to 128 times that of quinine and two to eight times that of pamaquin in avian malaria. It has adverse effects very similar to those of primaquine. In mammals it is rapidly absorbed from the gastro-intestinal tract. In acute, and in short term chronic toxicity studies, pentaquine was from one-fourth to one-half as toxic as pamaquin. In the dog, pamaquin in large doses produces severe anorexia, emaciation and ocular paralysis due to central impairment of the sympathetic innervation of the eye. In high dosages pamaquin produces leukopenia, neutropenia, anemia, methemoglobinemia, emaciation, depression, and liver damage in the monkey, effects which are not produced with pentaquine in this species.

Approval Year

PubMed

PubMed

TitleDatePubMed
Tafenoquine and primaquine do not exhibit clinical neurologic signs associated with central nervous system lesions in the same manner as earlier 8-aminoquinolines.
2018-11-06
Mutagenic activity and mutational specificity of antiprotozoal drugs with and without nitrite treatment.
2002
8-aminoquinolines as anticoccidials - Part III.
1999-08-16
8-Aminoquinolines as anticoccidials--II.
1998-06-16
Mutagenic evaluation of primaquine, pentaquine and pamaquine in the Salmonella/mammalian microsome assay.
1994-09
Specific inhibition of cyclic AMP-dependent protein kinase by the antimalarial halofantrine and by related phenanthrenes.
1994-08
Antimalarial quinones: redox potential dependence of methemoglobin formation and heme release in erythrocytes.
1994-01
A study of the effect of 8-aminoquinolines (primaquine, pamaquine, pentaquine) on the guinea-pig isolated ileum.
1985-06
Pharmacology of 8-aminoquinolines.
1981
Assessment of causal prophylactic activity in Plasmodium berghei yoelii and its value for the development of new antimalarial drugs.
1974
Phospholipid metabolism, osmotic stability and reducing potential of human red cells exposed to pentaquine and hydroxy derivatives.
1971-08
The binding of primaquine, pentaquine, pamaquine, and plasmocid to deoxyribonucleic acid.
1968-11
Metabolism of pentaquine in the rhesus monkey.
1956-01
Pentaquine and quinine in the treatment of Korean vivax malaria; a controlled study in 101 patients.
1955-04

Sample Use Guides

60 mg of base (or less) daily
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:31:37 GMT 2025
Edited
by admin
on Mon Mar 31 19:31:37 GMT 2025
Record UNII
NH99Y5GNF7
Record Status Validated (UNII)
Record Version
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Name Type Language
PENTAQUINE
INN  
INN  
Official Name English
pentaquine [INN]
Preferred Name English
8-(5-ISOPROPYLAMINOAMYLAMINO)-6-METHOXY QUINOLINE
Systematic Name English
Code System Code Type Description
FDA UNII
NH99Y5GNF7
Created by admin on Mon Mar 31 19:31:37 GMT 2025 , Edited by admin on Mon Mar 31 19:31:37 GMT 2025
PRIMARY
NCI_THESAURUS
C174758
Created by admin on Mon Mar 31 19:31:37 GMT 2025 , Edited by admin on Mon Mar 31 19:31:37 GMT 2025
PRIMARY
SMS_ID
100000082510
Created by admin on Mon Mar 31 19:31:37 GMT 2025 , Edited by admin on Mon Mar 31 19:31:37 GMT 2025
PRIMARY
EVMPD
SUB09687MIG
Created by admin on Mon Mar 31 19:31:37 GMT 2025 , Edited by admin on Mon Mar 31 19:31:37 GMT 2025
PRIMARY
MESH
C016038
Created by admin on Mon Mar 31 19:31:37 GMT 2025 , Edited by admin on Mon Mar 31 19:31:37 GMT 2025
PRIMARY
PUBCHEM
21558
Created by admin on Mon Mar 31 19:31:37 GMT 2025 , Edited by admin on Mon Mar 31 19:31:37 GMT 2025
PRIMARY
EPA CompTox
DTXSID40235339
Created by admin on Mon Mar 31 19:31:37 GMT 2025 , Edited by admin on Mon Mar 31 19:31:37 GMT 2025
PRIMARY
CAS
86-78-2
Created by admin on Mon Mar 31 19:31:37 GMT 2025 , Edited by admin on Mon Mar 31 19:31:37 GMT 2025
PRIMARY
ChEMBL
CHEMBL35802
Created by admin on Mon Mar 31 19:31:37 GMT 2025 , Edited by admin on Mon Mar 31 19:31:37 GMT 2025
PRIMARY
INN
409
Created by admin on Mon Mar 31 19:31:37 GMT 2025 , Edited by admin on Mon Mar 31 19:31:37 GMT 2025
PRIMARY
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SALT/SOLVATE -> PARENT
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ACTIVE MOIETY