NILEPROST

Details

Stereochemistry	MIXED
Molecular Formula	C22H33NO5
Molecular Weight	391.5011
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 6
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCC(C)[C@H](O)\C=C\[C@H]1[C@H](O)C[C@@H]2O\C(C[C@H]12)=C(/CCCC(O)=O)C#N

InChI

InChIKey=OJIGXQJDLFUVFM-MBLRWRSDSA-N

InChI=1S/C22H33NO5/c1-3-4-6-14(2)18(24)10-9-16-17-11-20(28-21(17)12-19(16)25)15(13-23)7-5-8-22(26)27/h9-10,14,16-19,21,24-25H,3-8,11-12H2,1-2H3,(H,26,27)/b10-9+,20-15+/t14?,16-,17-,18-,19-,21+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C22H33NO5
Molecular Weight	391.5011
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	5 / 6
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800000602 | https://www.ncbi.nlm.nih.gov/pubmed/2285983 | https://www.ncbi.nlm.nih.gov/pubmed/2441164

Nileprost is a prostacyclin analogue stabilized by introduction of the cyano group at its 5-position. Nileprost is a mixed type PGI2/PGE2 agonist. The development of the prostaglandin analogue nileprost [ZK 34798] for use in peptic ulcers has been discontinued at phase II by Schering AG in Germany.

Approval Year

PubMed

Title	Date	PubMed
Degradation and isomerization of nileprost, 5-cyano-16-methyl-prostacyclin, in aqueous solution.	1990-09	2285983
Influence of some prostaglandins and prostaglandin analogues on PAF-induced shock in mice.	1990-06	1696744
Influence of prostaglandins and PG-analogues on the mortality of PAF-acether in mice and the TXB2 release from human granulocytes.	1988	3248104
Development of a radioimmunoassay and its application to the pharmacokinetics of the stable prostacyclin analogue, nileprost, in the rat.	1984-04	6374676

Sample Use Guides

In Vivo Use Guide

Nileprost (0.5 ug/kg/min intravenously, i.v.) protected the left ventricular myocardium of cats subjected to 5 h of coronary artery ligation from ischemic injury.

Route of Administration: Intravenous

In Vitro Use Guide

Isolated bovine coronary arteries were relaxed by Nileprost at low concentrations (less than 3 uM), whereas higher concentrations produced a marked vasoconstriction.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:48:30 GMT 2025` Edited by `admin` on `Mon Mar 31 18:48:30 GMT 2025`
Record UNII	YGD81BG4SN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NILEPROST

Official Name

English

(E)-(3AR,4R,5R,6AS)-.DELTA.-CYANO-3,3A,4,5,6,6A-HEXAHYDRO-5-HYDROXY-4-((E)-(3S,4RS)-3-HYDROXY-4-METHYL-1-OCTENYL)-2H-CYCLOPENTA(B)FURAN-.DELTA.(SUP 2,.DELTA.)-VALERIC ACID

Preferred Name

English

nileprost [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78568