CLOPROSTENOL

Possibly Marketed Outside US

Details

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

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H](COC1=CC(Cl)=CC=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

Molecular Formula	C22H29ClO6
Molecular Weight	424.915
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26908917 | https://www.ncbi.nlm.nih.gov/pubmed/15971828

Cloprostenol is a synthetic prostaglandin analogue structurally related to Prostaglandin F2α (PGF2α), for use in cattle and horses. As a potent luteolytic agent it causes functional and morphological regression of the corpus luteum (luteolysis) in cattle and horses followed by return to oestrus and normal ovulation.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin F2-alpha receptor 12 Target ID: P43088 Gene ID: 5737.0 Gene Symbol: PTGFR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14729360 \| https://www.ncbi.nlm.nih.gov/pubmed/10915040	Agonist 2752		10.0 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Estrous cycles in cattle 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15971828	Preventing		Approved 8583	GONABREED Approved Use GONABREED, for estrous synchrony in lactating dairy cows and beef cows. GONABREED (Abbreviated New Animal Application 200-541) is a sterile injectable solution of gonadorelin acetate, and when used with cloprostenol sodium as part of a synchronization regimen, the drug can be used to synchronize estrous cycles to allow for fixed time artificial insemination in lactating dairy cows and beef cows. Launch Date 2013
Anoestrus due to persistent corpus luteum, suboestrus, luteal or follicular cysts in cattle 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28096623	Primary		Approved 8583	Cloprochem Approved Use Cattle: - Functional ovarian disorders such as anoestrus due to persistent corpus luteum, suboestrus, luteal or follicular cysts. - Synchronisation of oestrus. - Induction of parturition or abortion (associated increased incidence of retained foetal membranes, retentio secundinarum). Postpuerperium disorders of the uterus (e.g. pyometra, endometritis). Mares: - Induction of luteolysis following early foetal death and resorption - Termination of persistent dioestrus - Termination of pseudopregnancy - Treatment of lactation anoestrus - Induction of oestrus cycling in mares - Aid to stud management

PubMed

Title	Date	PubMed
Acquisition of luteolytic capacity involves differential regulation by prostaglandin F2alpha of genes involved in progesterone biosynthesis in the porcine corpus luteum.	2005-02	15713365
Vascular endothelial growth factor (VEGF) and fibroblast growth factor (FGF) expression during induced luteolysis in the bovine corpus luteum.	2004-04	14991729
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.	2002-04	11999132
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.	2000-01-17	10634944
Pharmacology of [3H]prostaglandin E1/[3H]prostaglandin E2 and [3H]prostaglandin F2alpha binding to EP3 and FP prostaglandin receptor binding sites in bovine corpus luteum: characterization and correlation with functional data.	1998-08	9694973

Patents

Sample Use Guides

In Vivo Use Guide

2 ml per single or repeated dose in cattle and horses

Route of Administration: Intramuscular

In Vitro Use Guide

In the cultured bovine luteal cells, [Ca2+]i increased after treatment with 1 ug/mL of Cloprostenol 15 s after treatment with 140% of the control.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:30:43 GMT 2025` Edited by `admin` on `Mon Mar 31 18:30:43 GMT 2025`
Record UNII	4208238832
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

(±)-CLOPROSTENOL

Preferred Name

English

CLOPROSTENOL

Official Name

English

RACEMIC CLOPROSTENOL

Common Name

English

cloprostenol [INN]

Common Name

English

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

Systematic Name

English

CLOPROSTENOL [MI]

Common Name

English

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

Common Name

English

CLOPROSTENOL, (±)-

Common Name

English

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

Systematic Name

English

5-HEPTENOIC ACID, 7-(2-(4-(3-CHLOROPHENOXY)-3-HYDROXY-1-BUTENYL)-3,5-DIHYDROXYCYCLOPENTYL)-, (1A(Z),2B(1E,3R*),3.ALPHA.,5.ALPHA.),- (±)-

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78568