ISOPROPYL CLOPROSTENATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H35ClO6
Molecular Weight	466.995
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)OC(=O)CCC\C=C/C[C@H]1[C@@H](O)C[C@@H](O)[C@@H]1\C=C\[C@@H](O)COC2=CC=CC(Cl)=C2

InChI

InChIKey=OCNSAYQJDKJOLH-AHTXBMBWSA-N

InChI=1S/C25H35ClO6/c1-17(2)32-25(30)11-6-4-3-5-10-21-22(24(29)15-23(21)28)13-12-19(27)16-31-20-9-7-8-18(26)14-20/h3,5,7-9,12-14,17,19,21-24,27-29H,4,6,10-11,15-16H2,1-2H3/b5-3-,13-12+/t19-,21-,22-,23+,24-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28532844

D-cloprostenol, also called (+)-cloprostenol is a highly potent prostaglandin F2-alpha receptor agonist. (+)-Cloprostenol is a 15(R) enantiomer of cloprostenol responsible for the majority of its biological activity and is commonly used in bovine reproduction that increases myometral contractility.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin F2-alpha receptor 12 Target ID: P37289 Gene ID: 282020.0 Gene Symbol: PTGFR Target Organism: Bos taurus (Bovine) Sources: https://www.ncbi.nlm.nih.gov/pubmed/7707491	Agonist 2678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Effects of d-cloprostenol on different layers and regions of the bovine uterus during the follicular and luteal phases.	2017 Jul 1	28532844

Sample Use Guides

In Vivo Use Guide

dairy goats: Trial 1 comprised 54 goats allocated to receive two 37.5μg d-cloprostenol doses at intervals of seven (T7, n=19), 10 (T10, n=18), and 11.5 (T11.5, n=17) days. Trial 2 comprised 62 goats allocated to receive injections at T7 (n=30) and T11.5 (n=32). All females showed progesterone concentrations >1ng/mL before both d-cloprostenol injections. The largest follicle diameter present on ovaries was similar (P>0.05) among treatments at the first and second dose. The second largest follicle diameter was superior (P<0.05) to T7 than to T10 and T11.5 goats at first dose only.

Route of Administration: Other

In Vitro Use Guide

Prostaglandin F2 alpha receptors (PGF2 alpha Rs) were measured in bovine corpus luteum and myometrial cell membranes using a radiometric method. The inhibition of labelled PGF2 alpha binding exerted by d-cloprostenol, dl-cloprostenol, PGF2 alpha and PGE1 (10(-11) M to 10(-4) M) was evaluated in vitro. Results strongly suggest that cloprostenol binding to PGF2 alpha Rs is stereospecific. d-Cloprostenol and PGF2 alpha were equipotent, about 150 times more potent than dl-cloprostenol (P < 0.05) and approximately 280 times more potent than PGE1 (P < 0.05) in inhibiting [3H]PGF2 alpha binding to corpus luteum cell membranes.

Name

Type

Language

ISOPROPYL CLOPROSTENATE

Official Name

English

5-HEPTENOIC ACID, 7-(2-(4-(3-CHLOROPHENOXY)-3-HYDROXY-1-BUTENYL)-3,5-DIHYDROXYCYCLOPENTYL)-, 1-METHYLETHYL ESTER, (1R-(1.ALPHA.(Z),2.BETA.(1E,3R*),3.ALPHA.,5.ALPHA.))-

Common Name

English

ISOPROPYL CLOPROSTENOL

Brand Name

English

CLOPROSTENOL ISOPROPYL ESTER

Common Name

English

CPG-6112-95

Code

English

ISOPROPYL CLOPROSTENATE [INCI]

Common Name

English

CPG-611295

Common Name

English

5-HEPTENOIC ACID, 7-((1R,2R,3R,5S)-2-((1E,3R)-4-(3-CHLOROPHENOXY)-3-HYDROXY-1-BUTENYL)-3,5-DIHYDROXYCYCLOPENTYL)-, 1-METHYLETHYL ESTER, (5Z)-

Common Name

English

5-HEPTENOIC ACID, 7-((1R,2R,3R,5S)-2-((1E,3R)-4-(3-CHLOROPHENOXY)-3-HYDROXY-1-BUTEN-1-YL)-3,5-DIHYDROXYCYCLOPENTYL)-, 1-METHYLETHYL ESTER, (5Z)-

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID10935652