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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H29ClO6
Molecular Weight 424.915
Optical Activity ( + )
Defined Stereocenters 5 / 5
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of CLOPROSTENOL, (+)-

SMILES

O[C@@H](COC1=CC=CC(Cl)=C1)\C=C\[C@H]2[C@H](O)C[C@H](O)[C@@H]2C\C=C/CCCC(O)=O

InChI

InChIKey=VJGGHXVGBSZVMZ-QIZQQNKQSA-N
InChI=1S/C22H29ClO6/c23-15-6-5-7-17(12-15)29-14-16(24)10-11-19-18(20(25)13-21(19)26)8-3-1-2-4-9-22(27)28/h1,3,5-7,10-12,16,18-21,24-26H,2,4,8-9,13-14H2,(H,27,28)/b3-1-,11-10+/t16-,18-,19-,20+,21-/m1/s1

HIDE SMILES / InChI
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
Effects of d-cloprostenol on different layers and regions of the bovine uterus during the follicular and luteal phases.
2017 Jul 1
Reproductive parameters of dairy goats after receiving two doses of d-cloprostenol at different intervals.
2017 Jun

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.
Name Type Language
CLOPROSTENOL, (+)-
Common Name English
(+)-CLOPROSTENOL
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)-, (5Z)-
Systematic Name English
D-CLOPROSTENOL
Common Name English
DALMAZIN
Brand Name English
R-CLOPROSTENOL
Common Name English
DALMAPROST D
Brand Name English
5-HEPTENOIC ACID, 7-((1R,2R,3R,5S)-2-((1E,3R)-4-(3-CHLOROPHENOXY)-3-HYDROXY-1-BUTENYL)-3,5-DIHYDROXYCYCLOPENTYL)-, (5Z)-
Systematic Name English
16-(M-CHLOROPHENOXY)-17,18,19,20-TETRANORPROSTAGLANDIN F2.ALPHA.
Common Name English
Code System Code Type Description
SMS_ID
300000031271
Created by admin on Fri Dec 15 16:12:18 GMT 2023 , Edited by admin on Fri Dec 15 16:12:18 GMT 2023
PRIMARY
CAS
54276-21-0
Created by admin on Fri Dec 15 16:12:18 GMT 2023 , Edited by admin on Fri Dec 15 16:12:18 GMT 2023
PRIMARY
PUBCHEM
5311053
Created by admin on Fri Dec 15 16:12:18 GMT 2023 , Edited by admin on Fri Dec 15 16:12:18 GMT 2023
PRIMARY
FDA UNII
52EJR3Y9IN
Created by admin on Fri Dec 15 16:12:18 GMT 2023 , Edited by admin on Fri Dec 15 16:12:18 GMT 2023
PRIMARY