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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H37ClO4
Molecular Weight 400.98
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of NOCLOPROST

SMILES

CCCCC(C)(C)[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H](Cl)[C@@H]1C\C=C/CCCC(O)=O

InChI

InChIKey=AIOFTOLPMOTZKD-OPVFONCOSA-N
InChI=1S/C22H37ClO4/c1-4-5-14-22(2,3)20(25)13-12-17-16(18(23)15-19(17)24)10-8-6-7-9-11-21(26)27/h6,8,12-13,16-20,24-25H,4-5,7,9-11,14-15H2,1-3H3,(H,26,27)/b8-6-,13-12+/t16-,17-,18-,19-,20-/m1/s1

HIDE SMILES / InChI

Description

Nocloprost is a stable prostaglandin E2 analog with gastroprotective and ulcer-healing properties. It shows very high gastroprotective potency, relatively weak gastric inhibitory activity, and low systemic bioavailability after oral administration. Schering AG have discontinued development of the drug, which was in phase II clinical trials for the treatment of peptic ulcer.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Nocloprost at doses of 50 and 100 ugrams was ineffective, but at a dose of 200 ugrams it reduced the response to pentagastrin significantly and that to a peptone meal by 30-50% and abolished plasma gastrin response without affecting the rate of gastric emptying. Nocloprost given at a dose of 100 ugrams three times daily 30 min before the major meals (breakfast, lunch, and dinner) did not affect intragastric pH significantly as monitored by continuous intraluminal pH-metry. Nocloprost does not affect gastric acid secretion or intraluminal pH when applied at a dose (50-100 ugrams) that is gastroprotective and that is proposed for peptic ulcer therapy. A higher dose (200 ugrams) of nocloprost causes moderate gastric acid inhibition and suppression of plasma gastrin release without affecting gastric emptying or causing any side effects.
Route of Administration: Oral
In Vitro Use Guide
Nocloprost inhibited release of endogenous norepinephrine from rat isolated trachea with the potency value (the concentration producing 35% inhibition of norepinephrine release (half-maximal effect)) of 8 nmol/L.