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Details

Stereochemistry ACHIRAL
Molecular Formula C18H27N3O.H3O4P
Molecular Weight 399.4217
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PENTAQUINE PHOSPHATE

SMILES

OP(O)(O)=O.COC1=CC(NCCCCCNC(C)C)=C2N=CC=CC2=C1

InChI

InChIKey=MFHDWFVXLYMMKW-UHFFFAOYSA-N
InChI=1S/C18H27N3O.H3O4P/c1-14(2)19-9-5-4-6-10-20-17-13-16(22-3)12-15-8-7-11-21-18(15)17;1-5(2,3)4/h7-8,11-14,19-20H,4-6,9-10H2,1-3H3;(H3,1,2,3,4)

HIDE SMILES / InChI
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
Name Type Language
NSC-13280
Preferred Name English
PENTAQUINE PHOSPHATE
Common Name English
8-(5-ISOPROPYLAMINOAMYLAMINO)-6-METHOXY QUINOLINE PHOSPHATE
Systematic Name English
Code System Code Type Description
CAS
5428-64-8
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
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NSC
13280
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
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PUBCHEM
21557
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
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FDA UNII
9B8SN90ODH
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
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ChEMBL
CHEMBL35802
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
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EPA CompTox
DTXSID70969317
Created by admin on Mon Mar 31 17:49:05 GMT 2025 , Edited by admin on Mon Mar 31 17:49:05 GMT 2025
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