Cloprostenol sodium
[CAS# 55028-72-3]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: Cloprostenol sodium
• Synonyms: Sodium [1alpha(Z),2beta(1E,3R*),3alpha,5alpha]-(+/-)-7-[2-[4-(3-chlorophenoxy)-3-hydroxybut-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoate
• Molecular Formula: C₂₂H₂₈ClNaO₆
• Molecular Weight: 446.90
• CAS Registry Number: 55028-72-3
• EC Number: 259-439-3
• SMILES: C1[C@@H]([C@@H]([C@H]([C@@H]1O)/C=C/[C@H](COC2=CC(=CC=C2)Cl)O)C/C=CCCCC(=O)[O-])O.[Na+]

Properties

• Solubility: 20mM (water)
• Melting point: 68-70 °C

Safety Data

• Hazard Symbols: GHS08 Danger
• Risk Statements: H334-H360-H370-H372
• Safety Statements: P203-P233-P260-P264-P270-P271-P280-P284-P304+P340-P308+P316-P318-P319-P321-P342+P316-P403-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	1B	H360
Respiratory sensitization	Resp. Sens.	1	H334
Specific target organ toxicity - single exposure	STOT SE	1	H370
Specific target organ toxicity - repeated exposure	STOT RE	1	H372
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2	H319
Skin sensitization	Skin Sens.	1	H317

Discovery and Applications

Cloprostenol sodium is a synthetic prostaglandin F2α analogue that has gained significant importance in veterinary and human medicine due to its diverse pharmacological effects. The compound was first developed in the late 1970s, during a period of intensive research into prostaglandins and their analogues, aimed at exploring their therapeutic potential. Its discovery was driven by the need for effective treatments in reproductive medicine, particularly for conditions related to fertility and the estrous cycle in animals.

The chemical structure of cloprostenol sodium mimics that of natural prostaglandins, specifically targeting the prostaglandin F2α receptor. This mechanism allows cloprostenol to elicit various physiological responses, including smooth muscle contraction, which is particularly beneficial in the reproductive system. Its ability to induce luteolysis— the regression of the corpus luteum— has made it a critical tool in managing reproductive health.

In veterinary medicine, cloprostenol sodium is extensively used for synchronizing estrus in cattle, sheep, and swine. By inducing luteolysis, it effectively brings animals into heat, facilitating timed artificial insemination and improving overall reproductive efficiency. This application is particularly valuable in livestock production, where managing breeding cycles can enhance productivity and economic returns.

Additionally, cloprostenol is utilized in treating conditions such as pyometra, a serious uterine infection in dogs and cats. By promoting uterine contractions and expelling retained uterine contents, cloprostenol aids in the medical management of this potentially life-threatening condition. Furthermore, its applications extend to equine medicine, where it is employed to induce abortion or manage reproductive disorders.

In human medicine, cloprostenol sodium has also found applications, particularly in obstetrics and gynecology. It is used off-label for inducing labor by stimulating uterine contractions, thus facilitating childbirth. Its effects on smooth muscle contraction are harnessed in various medical settings, showcasing its versatility as a pharmacological agent.

The availability of cloprostenol sodium in both injectable and topical formulations allows for flexibility in administration, depending on the clinical situation and patient needs. The compound has been well-studied, with a favorable safety profile when used as directed, though it is essential to follow recommended dosages to avoid adverse effects, such as gastrointestinal disturbances.

Research into cloprostenol sodium continues to evolve, with ongoing studies aimed at optimizing its use in various species and exploring its potential in treating additional conditions. Its ability to mimic natural prostaglandins and modulate reproductive processes underscores its significance in both veterinary and human medicine. The discovery and application of cloprostenol sodium represent a crucial advancement in pharmacotherapy, particularly in reproductive health.

References

2024. Early induction of luteolysis in a timed AI protocol increases reproductive performance in beef cows. Domestic Animal Endocrinology, 87(1).
DOI: 10.1016/j.domaniend.2024.106853

2024. Cloprostenol effect with and without male stimulation on oestrus synchronization in Peru guinea pigs. Reproduction in Domestic Animals, 59(5).
DOI: 10.1111/rda.14574

2000. Use of cloprostenol as an abortifacient in the llama (Lama glama). Theriogenology, 54(4).
DOI: 10.1016/s0093-691x(00)00365-4