Fenprostalene |
![]() Last updated: 16/09/2025 |
![]() |
(Not known by any other names) |
|
![]() |
|
A synthetic analogue of prostaglandin F2alpha with veterinary applications | |
---|---|---|
|
Used as an abortifacient and for estrus synchronization | |
|
Cattle; Pigs; Dogs |
Approval status |
|
Not approved | |
---|---|---|
|
Not approved |
Chemical structure |
|
Fenprostalene exhibits complex stereoisomerism due to its multiple chiral centres and conjugated double bonds. It exists as a mixture of stereoisomers, including both enantiomers and diastereomers, which differ in their spatial arrangement and influence biological activity. The molecule also shows geometric (E/Z) isomerism around its double bonds, further contributing to its structural diversity. | |
---|---|---|
|
C₂₃H₃₀O₆ | |
|
COC(=O)CCC=C=CC[C@@H]1[C@H](O)C[C@H](O)[C@H]1\C=C\[C@H](O)COC1=CC=CC=C1 | |
|
COC(=O)CCC=C=CC[C@@H]1[C@@H](C[C@@H]([C@H]1/C=C/[C@@H](COC2=CC=CC=C2)O)O)O | |
|
BYNHBQROLKAEDQ-CNDPCGPLSA-N | |
|
InChI=1S/C23H30O6/c1-28-23(27)12-8-3-2-7-11-19-20(22(26)15-21(19)25)14-13-17(24)16-29-18-9-5-4-6-10-18/h3-7,9-10,13-14,17,19-22,24-26H,8,11-12,15-16H2,1H3/b14-13+/t2?,17-,19-,20-,21+,22-/m0/s1 | |
|
Yes |
General status |
|
- | |
---|---|---|
|
Phenol ether | |
|
- | |
|
- | |
|
Synthetic | |
|
- | |
|
[Prostaglandin F2-alpha receptor, Agonist] | |
|
69381-94-8 | |
|
273-982-3 | |
|
- | |
|
- | |
|
72734332 | |
|
Prostaglandins | |
|
QG02AD92 | |
|
No | |
|
- | |
|
402.49 | |
|
- | |
|
methyl 7-[(1S,2S,3S,5R)-3,5-dihydroxy-2-[(3S)-3-hydroxy-4-phenoxybut-1-en-1-yl]cyclopentyl]hepta-4,5-dienoate | |
|
- | |
|
- | |
|
- | |
|
- | |
|
- |
Commercial |
|
|
|||
---|---|---|---|---|
|
Current | |||
|
Mid 1970s, first synthesised; 1990s, clinical livestock trials; Late 1990s, first approvals USA | |||
|
- | |||
|
- | |||
|
- | |||
|
The production of fenprostalene involves a multi-step synthetic process designed to construct its complex prostaglandin-like structure with precise stereochemistry. It typically begins with a bicyclic ketone precursor, which undergoes stereoselective oxidation using Baeyer–Villiger monooxygenase to introduce key oxygen functionalities. This is followed by diastereoselective ketone reduction using ketoreductase enzymes to establish the correct configuration at multiple chiral centres. Subsequent steps include regioselective p-phenylbenzoylation of a secondary alcohol and strategic formation of the conjugated dienoate side chain. The synthesis culminates with final esterification to yield fenprostalene with the desired pharmacological profile. | |||
|
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. |
|
![]() |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
- | |||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
Release into the environment may occur via the excreta of treated animals |
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 |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | |||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
- | |||||||||||
|
- | - | - | ||||||||
- | |||||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - |
Aquatic ecotoxicology |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - |
|
- | - | - | |||
|
- | - | - |
|
![]() |
General |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | |||||||||
|
- | ||||||||||
|
The majority of the administered dose (approx. 60–85%) is excreted via urine within 72 hours. With the reminder of the dose is eliminated through faeces. | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
- |
Health issues |
|
|
||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
No information available |
Handling issues |
|
|
|||
---|---|---|---|---|
|
No information available | |||
|
- | |||
|
- | |||
|
- | |||
|
- | |||
|
- |
|
![]() |
|
|
||
---|---|---|---|
|
fenprostalene | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- |
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 |