Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H34O5 |
| Molecular Weight | 366.4917 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 2 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCC[C@@](C)(O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O
InChI
InChIKey=XSGQFHNPNWBVPT-VFXMVCAWSA-N
InChI=1S/C21H34O5/c1-3-4-9-13-21(2,26)14-12-17-16(18(22)15-19(17)23)10-7-5-6-8-11-20(24)25/h5,7,12,14,16-17,19,23,26H,3-4,6,8-11,13,15H2,1-2H3,(H,24,25)/b7-5-,14-12+/t16-,17-,19-,21-/m1/s1
Arbaprostil (15(R)-15-methylprostaglandin E2) is a prodrug, which is activated by epimerization to form the active S-epimer. It was shown, that arbaprostil markedly accelerated the healing rate of active duodenal ulcers, due to inhibition of acid secretion as well as gastric cytoprotection.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of 15(R)-15-methyl prostaglandin E2 (arbaprostil) on the healing of duodenal ulcer: a double-blind multicenter study. | 1982 Aug |
|
| Comparative studies with 15(R)-15-methylprostaglandin E2 (arbaprostil) in rat femoral arterial preparations in vivo and in vitro. | 1993 Sep |
Patents
Sample Use Guides
A multicenter study was conducted on 173 patients with active, endoscopically proven duodenal ulcers (158 men, 15 women). They were randomly assigned, in a double-blind manner, to two groups: those receiving placebo capsules (91 patients) and those receiving capsules containing 100 microgram of 15(R)-15-methyl prostaglandin E2 (arbaprostil) (82 patients). Each drug was ingested four times a day (1 h before meals and at bedtime) for 28 days.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: The vasocontractor responses to arbaprostil in isolated femoral arterial strips were significantly potentiated by removal of the endothelium and the presence of NG-monomethyl L-arginine. The result indicated that the endothelium-dependent mechanism might play an important role in the vascular response to arbaprostil, like PGE2 and ACh.
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NCI_THESAURUS |
C78568
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ACTIVE MOIETY
