Cloprostenol |
![]() Last updated: 16/09/2025 |
![]() |
(Not known by any other names) |
|
![]() |
|
Cloprostenol is an analogue of prostaglandin F2α (PGF2α) and used for its potemnt luteolytic properties | |
---|---|---|
|
Used to terminate pregnancy, induce parturition, and control the breeding pattern of a herd/flock or individual animals for effective stud management. | |
|
Cattle; Pigs; Sheep; Horses |
Approval status |
|
Approved - usually supplied as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
---|---|---|
|
Approved |
Chemical structure |
|
Cloprostenol exhibits double bond isomerism, specifically geometric (cis-trans or E/Z) isomerism, due to the presence of multiple carbon–carbon double bonds in its unsaturated side chains. These double bonds can adopt either cis (Z) or trans (E) configurations, which significantly affect the molecule’s three-dimensional shape and biological activity. For example, isomers such as cis-delta4, trans-delta5, and cis-delta13 analogues have been synthesised and studied, with the cis-delta4 isomer showing comparable luteolytic potency to cloprostenol, while others are markedly less active. Cloprostenol is typically marketed as a racemic mixture. | |
---|---|---|
|
C₂₂H₂₉ClO₆ | |
|
C1C(C(C(C1O)C=CC(COC2=CC(=CC=C2)Cl)O)CC=CCCCC(=O)O)O | |
|
C1[C@@H]([C@@H]([C@H]([C@@H]1O)/C=C/[C@H](COC2=CC(=CC=C2)Cl)O)C/C=C\CCCC(=O)O)O | |
|
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 | |
|
Yes |
General status |
|
Fertility drug, Medicinal drug | |
---|---|---|
|
Prostaglandin | |
|
~98% | |
|
- | |
|
Synthetic | |
|
Induces in a sharp fall in progesterone levels | |
|
[Prostaglandin F2-alpha receptor, Agonist] | |
|
54276-21-0 | |
|
40665-92-7 | |
|
255-028-8 | |
|
- | |
|
- | |
|
5311053 | |
|
Genito urinary system & sex hormones: Prostaglandins | |
|
QG02AD90 | |
|
No | |
|
Allowed substance (Table 1: Bovine, Porcine, Caprine, Equidae) | |
|
424.9 | |
|
- | |
|
(Z)-7-[(1R,2R,3R,5S)-2-[(E,3R)-4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid | |
|
- | |
|
- | |
|
- | |
|
- | |
|
White amorphous, hygroscopic powder | |
|
Commercial |
|
|
|||
---|---|---|---|---|
|
Current | |||
|
1970s, first synthesised; 1980s, initial vet use; 2008, approvals UK | |||
|
|
|||
|
|
|||
|
Usually supplied as solution for injection | |||
|
Cloprostenol is produced through a complex chemical synthesis that builds on the structural framework of prostaglandin F2alpha, its natural analogue. The process typically follows a modified Corey synthesis route, which involves constructing the cyclopentane ring and attaching the appropriate unsaturated side chains with precise stereochemistry. Key steps include alkylation of cyclopentadiene, oxidation, and stereoselective functional group additions to ensure the correct configuration at multiple chiral centres. One of the challenges in production is controlling double bond isomerism, as the molecule contains several conjugated double bonds that can easily isomerise under reaction conditions. The final compound is often converted to its sodium salt form for improved stability and solubility. | |||
|
Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
|
![]() |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
10 | E3 E = Manufacturers safety data sheets 3 = Unverified data of known source |
Moderate | ||||||||
|
50000 | Q3 Q = Miscellaneous data from online sources Ethanol3 = Unverified data of known source |
- | ||||||||
60000 | Q3 Q = Miscellaneous data from online sources DMSO3 = Unverified data of known source |
- | |||||||||
130000 | Q3 Q = Miscellaneous data from online sources Dimethylformamide3 = Unverified data of known source |
- | |||||||||
|
69 | E3 E = Manufacturers safety data sheets 3 = Unverified data of known source |
- | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
- | |||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
Max: 220nm, 275nm, 282nm | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
- | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- |
Degradation |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | ||||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
|
- |
Soil adsorption and mobility |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | ||||||||||
|
- | ||||||||||
|
- |
Fate indices |
|
|
|
|
||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||||||||||||||||||||
|
|
- | - | - | |||||||||||||||||||||||||
|
- | - |
Known metabolites |
None
|
![]() |
Terrestrial ecotoxicology |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
25 | E3 E = Manufacturers safety data sheets Rat3 = Unverified data of known source |
High | ||||||||
|
|
- | - | - | |||||||
|
- | - | |||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
- | |||||||||||
|
- | - | - | ||||||||
- | |||||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - |
Aquatic ecotoxicology |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - |
|
- | - | - | |||
|
- | - | - |
|
![]() |
General |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
High (class III) | - | - | ||||||||
|
25 | E3 E = Manufacturers safety data sheets Rat3 = Unverified data of known source |
High | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | |||||||||
|
May be absorbed through the skin | ||||||||||
|
Eliminated in approximately equal amounts via the kidney and in bile. Excretion in urine is partly as unchanged parent and partly as metabolites. | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
- |
Health issues |
|
|
||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
Possible sensitiser May cause vomiting and nausea |
Handling issues |
|
|
|||
---|---|---|---|---|
|
No information available | |||
|
- | |||
|
Not listed (Not listed) | |||
|
- | |||
|
- | |||
|
- |
|
![]() |
|
|
||
---|---|---|---|
|
cloprostenol | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- |
Record last updated: | 16/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |