(+)-Cloprostenol sodium
[CAS# 62561-03-9]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: (+)-Cloprostenol sodium
• Synonyms: (5Z)-7-[(1R,2R,3R,5S)-2-[(1E,3R)-4-(3-Chlorophenoxy)-3-hydroxy-1-buten-1-yl]-3,5-dihydroxycyclopentyl]-5-heptenoic acid sodium salt
• Molecular Formula: C₂₂H₂₈ClNaO₆
• Molecular Weight: 446.90
• CAS Registry Number: 62561-03-9
• EC Number: 682-027-3
• 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)

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
Acute toxicity	Acute Tox.	4	H302

Discovery and Applications

(+)-Cloprostenol sodium is a synthetic prostaglandin analog that is primarily used in veterinary medicine for its ability to induce estrus and facilitate parturition in livestock. This compound belongs to the class of prostaglandin F2α analogs, which are important in various reproductive processes. The development of cloprostenol can be traced back to the need for effective reproductive management strategies in the agricultural sector.

The discovery of cloprostenol sodium emerged from research aimed at understanding and manipulating reproductive hormones in animals. Prostaglandins play a crucial role in the regulation of reproductive functions, including the initiation of labor, regulation of the estrous cycle, and luteolysis. The synthetic analogs were designed to mimic the actions of natural prostaglandins while offering enhanced stability and potency. (+)-Cloprostenol sodium was first synthesized in the 1970s, and subsequent studies demonstrated its efficacy in various animal species.

In practical applications, cloprostenol sodium is commonly administered to cattle and swine to synchronize estrus and optimize breeding schedules. This is particularly valuable in large-scale agricultural operations, where managing the timing of breeding can significantly impact productivity and economic outcomes. The compound is administered via injection, and its effects can lead to the contraction of the uterine muscles, facilitating the expulsion of the corpus luteum and thus allowing the animal to return to estrus.

Beyond its role in reproductive management, cloprostenol sodium has also found applications in the treatment of certain medical conditions in animals. For instance, it is used to manage conditions related to the uterus, such as pyometra, a serious infection that can occur in female dogs and cats. By promoting uterine contractions, cloprostenol sodium helps in expelling retained products and addressing complications associated with this condition.

Research continues to explore the broader implications of cloprostenol sodium and its analogs in both veterinary and human medicine. Studies are underway to assess their potential uses in reproductive health and to evaluate their safety and efficacy in various populations. The compound has also been the subject of interest in studies investigating its mechanisms of action and potential interactions with other hormones and treatments.

Overall, (+)-cloprostenol sodium represents a significant advancement in reproductive management in veterinary medicine. Its discovery has contributed to the optimization of breeding practices in livestock, enhancing productivity and welfare in animal husbandry.

References

2000. The induction of parturition in the bitch using sodium cloprostenol. Theriogenology, 54(2).
DOI: 10.1016/s0093-691x(00)00362-9

2005. Responsiveness to Progestagen‐eCG‐Cloprostenol Treatment in Goat Food Restricted for Long Period and Refed. Reproduction in Domestic Animals, 40(2).
DOI: 10.1111/j.1439-0531.2004.00561.x

2024. Effect of the Application of PGF2α Associated With Ovulation Induction in a Fixed‐Time Superovulation Programme for Precocious Nellore Heifers. Reproduction in Domestic Animals, 59(10).
DOI: 10.1111/rda.14734