TAPROSTENE SODIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H29O5.Na
Molecular Weight	420.4738
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].[H][C@]12C[C@@H](O)[C@H](\C=C\[C@@H](O)C3CCCCC3)[C@@]1([H])C\C(O2)=C\C4=CC=CC(=C4)C([O-])=O

InChI

InChIKey=KPQVOJYDUCZQEQ-REHYUDDHSA-M

InChI=1S/C24H30O5.Na/c25-21(16-6-2-1-3-7-16)10-9-19-20-13-18(29-23(20)14-22(19)26)12-15-5-4-8-17(11-15)24(27)28;/h4-5,8-12,16,19-23,25-26H,1-3,6-7,13-14H2,(H,27,28);/q;+1/p-1/b10-9+,18-12-;/t19-,20-,21-,22-,23+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C24H29O5
Molecular Weight	397.4841
Charge	-1
Count

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

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21427652 | https://www.ncbi.nlm.nih.gov/pubmed/8404943 | https://www.ncbi.nlm.nih.gov/pubmed/2508112 | https://adisinsight.springer.com/drugs/800000164

Taprostene (also known as CG 4203), a stable prostacyclin (PGI2) analog was developed by Gruenenthal as a selective agonist of the prostanoid receptor IP1. Taprostene was studied in a clinical trial in patients with acute myocardial infarction, where it was shown that the drug could be a useful adjuvant to thrombolytic agents in acute myocardial infarction. In addition, taprostene participated in a clinical trial for the treatment of critical limb ischemia, where the drug was safe and effective. Besides taprostene was studied in patients with advanced peripheral arterial disease. However, further development of the drug was discontinued.

Approval Year

PubMed

Title	Date	PubMed
Role of renin release in the hemodynamic, renal and dipsogenic actions of the prostacyclin analogue CG 4203 in conscious rats.	1983 Aug	6353423
Relaxant actions of nonprostanoid prostacyclin mimetics on human pulmonary artery.	1997 Apr	9156364
The Scottish-Finnish-Swedish PARTNER study of taprostene versus placebo treatment in patients with critical limb ischemia.	2011 Apr	21427652
Binding and activity of the prostacyclin receptor (IP) agonists, treprostinil and iloprost, at human prostanoid receptors: treprostinil is a potent DP1 and EP2 agonist.	2012 Jul 1	22480736

Sample Use Guides

In Vivo Use Guide

Three doses of taprostene were used: 6.25; 12.5; or 25.0 ng.kg-1 x min-1.

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Sat Dec 16 10:05:23 GMT 2023` Edited by `admin` on `Sat Dec 16 10:05:23 GMT 2023`
Record UNII	3M078713KZ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TAPROSTENE SODIUM

Common Name

English

TAPROSTENE SODIUM SALT

Common Name

English

CG-4203

Code

English

SE-63

Code

English

BENZOIC ACID, 3-((Z)-((3AR,4R,5R,6AS)-4-((1E,3S)-3-CYCLOHEXYL-3-HYDROXY-1-PROPENYL)HEXAHYDRO-5-HYDROXY-2H-CYCLOPENTA(B)FURAN-2-YLIDENE)METHYL)-, MONOSODIUM SALT

Systematic Name

English

RHEOCYCLAN

Brand Name

English

TAPROSTENE SODIUM SALT [MI]

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID9049033