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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 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
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

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

CNS Non-penetrant
1014
Curator's Comment: Cloprostenol doesn`t cross the blood-brain barrier in pigs

Originator

Cooper, M.J.|Walpole, A.I.
2
Sources: Practical Applications of Prostaglandins and their Synthesis Inhibitors, edited by S.M.M. Karim, 1979
Curator's Comment: 1975

Approval Year

1982
100
Targets

Targets

Primary TargetPharmacologyConditionPotency
Prostaglandin F2-alpha receptor
12
Target ID: P43088
Gene ID: 5737.0
Gene Symbol: PTGFR
Target Organism: Homo sapiens (Human)
Agonist
2678
 10.0 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Approved
8429
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

1.36918086E12
Primary
Approved
8429
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

PubMed

TitleDatePubMed
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 Aug
The utilization of recombinant prostanoid receptors to determine the affinities and selectivities of prostaglandins and related analogs.
2000 Jan 17
Cloned human EP1 prostanoid receptor pharmacology characterized using radioligand binding techniques.
2002 Apr
Vascular endothelial growth factor (VEGF) and fibroblast growth factor (FGF) expression during induced luteolysis in the bovine corpus luteum.
2004 Apr
Acquisition of luteolytic capacity involves differential regulation by prostaglandin F2alpha of genes involved in progesterone biosynthesis in the porcine corpus luteum.
2005 Feb
Patents

Patents

20040171155
2

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 Fri Dec 15 16:32:08 UTC 2023
Edited
by admin
on Fri Dec 15 16:32:08 UTC 2023
Record UNII
4208238832
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOPROSTENOL
INN   MI  
INN  
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
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
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
WHO-VATC QG02AD90
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
Code System Code Type Description
FDA UNII
4208238832
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
CAS
40665-92-7
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
MESH
D003008
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
ChEMBL
CHEMBL2220404
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
MERCK INDEX
m3658
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY Merck Index
SMS_ID
100000084020
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
RXCUI
2606
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID7048372
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
ECHA (EC/EINECS)
255-028-8
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
INN
3793
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
DAILYMED
4208238832
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
PUBCHEM
5311053
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
EVMPD
SUB06745MIG
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
NCI_THESAURUS
C79571
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
DRUG BANK
DB11507
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
WIKIPEDIA
Cloprostenol
Created by admin on Fri Dec 15 16:32:08 UTC 2023 , Edited by admin on Fri Dec 15 16:32:08 UTC 2023
PRIMARY
Related Record Type Details
PROSTAGLANDIN F2-ALPHA RECEPTOR
TARGET -> AGONIST
BINDING
Ki
PROSTAGLANDIN E2 RECEPTOR EP3 SUBTYPE
TARGET -> AGONIST
BINDING
Ki
Structure of CLOPROSTENOL, (+)-
ENANTIOMER -> RACEMATE
Structure of CLOPROSTENOL SODIUM
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of CLOPROSTENOL
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