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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 of ISOPROPYL CLOPROSTENATE

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

Molecular Formula C25H35ClO6
Molecular Weight 466.995
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 2
Optical Activity UNSPECIFIED

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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P37289
Gene ID: 282020.0
Gene Symbol: PTGFR
Target Organism: Bos taurus (Bovine)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Effects of d-cloprostenol dose and corpus luteum age on ovulation, luteal function, and morphology in nonlactating dairy cows with early corpora lutea.
2012 Aug

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 20:10:50 GMT 2023
Edited
by admin
on Sat Dec 16 20:10:50 GMT 2023
Record UNII
765298537G
Record Status Validated (UNII)
Record Version
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Name Type Language
ISOPROPYL CLOPROSTENATE
INCI  
INCI  
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
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
PRIMARY
SMS_ID
300000034591
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
PRIMARY
PUBCHEM
59938277
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
PRIMARY
CAS
157283-66-4
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
PRIMARY
FDA UNII
765298537G
Created by admin on Sat Dec 16 20:10:50 GMT 2023 , Edited by admin on Sat Dec 16 20:10:50 GMT 2023
PRIMARY
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