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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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed

Sample Use Guides

In Vivo Use Guide
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
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.
Name Type Language
NOCLOPROST
INN   MART.  
INN  
Official Name English
(Z)-7-((1R,2R,3R,5R)-5-CHLORO-3-HYDROXY-2-((E)-(3R)-3-HYDROXY-4,4-DIMETHYL-1-OCTENYL)CYCLOPENTYL)-5-HEPTENOIC ACID
Systematic Name English
NOCLOPROST [MART.]
Common Name English
nocloprost [INN]
Common Name English
Code System Code Type Description
FDA UNII
7POM2OXT4Q
Created by admin on Sat Dec 16 15:51:09 UTC 2023 , Edited by admin on Sat Dec 16 15:51:09 UTC 2023
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PUBCHEM
6917718
Created by admin on Sat Dec 16 15:51:09 UTC 2023 , Edited by admin on Sat Dec 16 15:51:09 UTC 2023
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NCI_THESAURUS
C167040
Created by admin on Sat Dec 16 15:51:09 UTC 2023 , Edited by admin on Sat Dec 16 15:51:09 UTC 2023
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ChEMBL
CHEMBL2106816
Created by admin on Sat Dec 16 15:51:09 UTC 2023 , Edited by admin on Sat Dec 16 15:51:09 UTC 2023
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EPA CompTox
DTXSID101021624
Created by admin on Sat Dec 16 15:51:09 UTC 2023 , Edited by admin on Sat Dec 16 15:51:09 UTC 2023
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SMS_ID
100000083583
Created by admin on Sat Dec 16 15:51:09 UTC 2023 , Edited by admin on Sat Dec 16 15:51:09 UTC 2023
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CAS
79360-43-3
Created by admin on Sat Dec 16 15:51:09 UTC 2023 , Edited by admin on Sat Dec 16 15:51:09 UTC 2023
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MESH
C048895
Created by admin on Sat Dec 16 15:51:09 UTC 2023 , Edited by admin on Sat Dec 16 15:51:09 UTC 2023
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INN
5525
Created by admin on Sat Dec 16 15:51:09 UTC 2023 , Edited by admin on Sat Dec 16 15:51:09 UTC 2023
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EVMPD
SUB09338MIG
Created by admin on Sat Dec 16 15:51:09 UTC 2023 , Edited by admin on Sat Dec 16 15:51:09 UTC 2023
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