Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C26H35NO4 |
Molecular Weight | 425.5604 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 3 / 3 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC2=C1C=C(CCCCC(O)=O)N2C3=CC=CC=C3
InChI
InChIKey=CZIIGGQJILPHEU-HCHVXQBBSA-N
InChI=1S/C26H35NO4/c1-2-3-5-13-21(28)15-16-22-23-17-20(12-8-9-14-26(30)31)27(24(23)18-25(22)29)19-10-6-4-7-11-19/h4,6-7,10-11,15-17,21-22,25,28-29H,2-3,5,8-9,12-14,18H2,1H3,(H,30,31)/b16-15+/t21-,22+,25+/m0/s1
Piriprost (U-60, 257) is a structural analog of prostaglandin I2 (PGI2) with low IP receptor-mediated activity. It inhibits 5-LO (5-lipoxygenase). Piriprost inhibits the release of histamine and leukotrienes, implicating its role in inflammation and allergic responses. However, it was shown, that piriprost did not influence the airway responses after allergen in asthma. Nevertheless, even more, the drug was irritant to the respiratory tract than was placebo.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P09917 Gene ID: 240.0 Gene Symbol: ALOX5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1775638 |
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Target ID: GO:0019370 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2936098 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Sources: https://www.ncbi.nlm.nih.gov/pubmed/3538476 |
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Piriprost: a selective inhibitor of leukotriene synthesis. | 1985 |
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Effect of inhaled piriprost (U-60, 257) a novel leukotriene inhibitor, on allergen and exercise induced bronchoconstriction in asthma. | 1986 Oct |
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Examination of the effects of piriprost (U-60,257B) on alkaline phosphatase activity of rat endometrial stromal cells in vitro. | 1991 Aug |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3538476
On separate study days subjects inhaled either piriprost 1 mg or vehicle placebo, followed 15 minutes later by the PS25 allergen or exercise. The FEV1 was measured at regular intervals before and after challenge up to 60 minutes
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1775638
It was discovered, that the effects piriprost on possible in vitro decidualization may be due to inhibition of 5-lipoxygenase. Piriprost (100 microM) was found to decrease 5-hydroxyeicosatetraenoic acid (a 5-lipoxygenase product) by 53% after 72 hr which provided evidence that 5-lipoxygenase was being inhibited by piriprost. Three microM PGE2 or 20 microM carba-prostacyclin (CP), an analogue of PGI2, maximally increased (p less than 0.01) ALP activity at 72 hr and the further addition of 100 microM piriprost to PGE2 or CP caused an additional, additive increase in ALP activity. This indicated that the mechanism of action of piriprost was probably different from that of PGE2 or PGI2. The possibility that piriprost was shunting arachidonic acid into PG production was examined. The effects of the combination of 100 microM piriprost and 10 microM IM were statistically additive, suggesting that the effects of piriprost were not due to an increase in PG production.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C78568
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NCI_THESAURUS |
C1322
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C66425
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T-99
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79672-88-1
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R802O5NILK
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SUB09917MIG
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100000081650
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6437373
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C035296
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5546
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CHEMBL2105239
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)