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
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)
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
Title | Date | PubMed |
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Specific inhibition of cyclic AMP-dependent protein kinase by the antimalarial halofantrine and by related phenanthrenes. | 1994 Aug |
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Mutagenic activity and mutational specificity of antiprotozoal drugs with and without nitrite treatment. | 2002 |
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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
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18860176
60 mg of base (or less) daily
Route of Administration:
Oral
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5428-64-8
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13280
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21557
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9B8SN90ODH
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CHEMBL35802
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DTXSID70969317
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ACTIVE MOIETY
SUBSTANCE RECORD