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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
Structure of ARBAPROSTIL

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

HIDE SMILES / InChI

Description

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.

Originator

Approval Year

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
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
Unknown