Carboprost
[CAS# 35700-23-3]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Prostaglandins
• Name: Carboprost
• Synonyms: 15-Methyl prostaglandin F2alpha; (Z)-7-[(3R,5S)-3,5-Dihydroxy-2-[(E,3S)-3-hydroxy-3-methyl-oct-1-enyl]cyclopentyl]hept-5-enoic acid
• Molecular Formula: C₂₁H₃₆O₅
• Molecular Weight: 368.51
• CAS Registry Number: 35700-23-3
• SMILES: CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=CCCCC(=O)O)O)O)O

Properties

• Solubility: 2 mg/mL (water)

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P280-P301+P312-P302+P352-P305+P351+P338

Discovery and Applications

Carboprost, also known as carboprost tromethamine, is a synthetic analogue of prostaglandin F2α, which is primarily used in obstetrics and gynecology for its potent uterotonic properties. It was first synthesized in the late 1970s by researchers aiming to develop more effective medications for inducing labor and managing postpartum hemorrhage. The need for improved agents stemmed from the limitations of natural prostaglandins, which are often unstable and have a short half-life in the human body.

The discovery of carboprost was part of a broader effort to explore the therapeutic potential of prostaglandin analogues. Researchers found that by modifying the natural structure of prostaglandin F2α, they could enhance its pharmacokinetic profile, making it more effective for clinical use. Carboprost exhibits a longer duration of action compared to its natural counterpart, allowing for more predictable and controllable effects in medical settings.

One of the primary applications of carboprost is in obstetrics, where it is utilized to induce labor in women who require medical intervention to initiate childbirth. The drug stimulates uterine contractions, facilitating the labor process and helping to ensure a safe delivery. Additionally, carboprost is employed to treat postpartum hemorrhage, a potentially life-threatening condition characterized by excessive bleeding following childbirth. By promoting uterine contractions, carboprost effectively helps to reduce blood loss and stabilize the mother’s condition.

Beyond its obstetric applications, carboprost has also been investigated for its potential use in medical abortions. The drug’s ability to induce contractions and expel uterine contents makes it a valuable option for terminating pregnancies in certain clinical scenarios. Its efficacy and safety profile have contributed to its acceptance in reproductive health practices.

Research continues into the broader implications of carboprost and its analogues in various therapeutic areas. The compound’s influence on smooth muscle contraction and its role in inflammatory responses have led scientists to explore its potential applications in treating conditions such as asthma and pulmonary hypertension. Ongoing studies aim to elucidate these effects further and potentially expand the therapeutic use of carboprost beyond obstetrics.

In conclusion, carboprost represents a significant advancement in the field of reproductive medicine, providing effective options for inducing labor and managing postpartum hemorrhage. Its development exemplifies the potential of synthetic analogues of natural compounds to enhance clinical outcomes in specific medical contexts.

References

1979. Luteolysis and termination of early pregnancy in the rhesus monkey with prostalene, a synthetic prostaglandin analog. Prostaglandins and Medicine.
DOI: 10.1016/0161-4630(79)90036-3

2021. Prostaglandins for Postpartum Hemorrhage: Pharmacology, Application, and Current Opinion. Pharmacology.
DOI: 10.1159/000516631

2023. Structures of human prostaglandin F2α receptor reveal the mechanism of ligand and G protein selectivity. Nature Communications.
DOI: 10.1038/s41467-023-43922-8