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
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
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
Title | Date | PubMed |
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Effects of nocloprost on gastric functions in man. | 1991 Nov |
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Prostanoids inhibit release of endogenous norepinephrine from rat isolated trachea. | 1992 Nov |
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Effects of nocloprost on some monooxygenases of rat and human liver. | 1993 Oct |
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Effects of PGE2 and of different synthetic PGE derivatives on the glycosylation of pig gastric mucins. | 1998 Jul |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1754849
Curator's Comment: The effects of nocloprost on gastric acid secretion and intraluminal pH and on gastric emptying and plasma gastrin levels were determined in humans.
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1443867
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.
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ACTIVE MOIETY