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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=CC2=CC=CN=C2C(NCCCCCNC(C)C)=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
Metabolism of pentaquine in the rhesus monkey.
1956 Jan
Assessment of causal prophylactic activity in Plasmodium berghei yoelii and its value for the development of new antimalarial drugs.
1974
8-Aminoquinolines as anticoccidials--II.
1998 Jun 16
8-aminoquinolines as anticoccidials - Part III.
1999 Aug 16
Mutagenic activity and mutational specificity of antiprotozoal drugs with and without nitrite treatment.
2002
Tafenoquine and primaquine do not exhibit clinical neurologic signs associated with central nervous system lesions in the same manner as earlier 8-aminoquinolines.
2018 Nov 6

Sample Use Guides

60 mg of base (or less) daily
Route of Administration: Oral
Name Type Language
PENTAQUINE PHOSPHATE
Common Name English
8-(5-ISOPROPYLAMINOAMYLAMINO)-6-METHOXY QUINOLINE PHOSPHATE
Systematic Name English
NSC-13280
Code English
Code System Code Type Description
CAS
5428-64-8
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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NSC
13280
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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PUBCHEM
21557
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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FDA UNII
9B8SN90ODH
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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ChEMBL
CHEMBL35802
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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EPA CompTox
DTXSID70969317
Created by admin on Fri Dec 15 15:10:39 GMT 2023 , Edited by admin on Fri Dec 15 15:10:39 GMT 2023
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