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=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)
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 |
|---|---|---|
| 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
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