Carboprost Tromethamine

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Cat Number

API58551692

CAS Number

58551-69-2

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Product Detail Description Scientific Support Customer Q&A

CAS Number

58551-69-2

EINECS

638-806-5

Storage

Store at 2-8°C

Synonyms

Hemabate; carboprost trometamol; U-32921E; U4526F86FJ; PROSTIN/15M; Carboprost tromethamine salt; DTXSID601015618

Molecular Formula

C25H47NO8

Molecular Weight

489.6

Smiles

CCCCC[C@@](C)(/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\\CCCC(=O)O)O)O)O.C(C(CO)(CO)N)O

Appearance

White to off-white crystalline powder

Melting Point

95-105°C

Boiling Point

536.6°C at 760 mmHg

Relative Density

1.153

General Description

Carboprost tromethamine is a synthetic analogue of prostaglandin F2α (PGF2α), with a 15-methyl group substitution that protects the molecule from rapid enzymatic degradation by 15-hydroxyprostaglandin dehydrogenase, prolonging its half-life. The tromethamine salt provides water solubility. Carboprost is a white to off-white crystalline powder with a molecular weight of 475.6 Da (as the tromethamine salt).

Mechanism of Action

Carboprost acts as a potent agonist at the FP prostaglandin receptor, stimulating uterine smooth muscle contraction through increased intracellular calcium and phospholipase C activation. This causes powerful myometrial contractions, increasing uterine tone and reducing bleeding. The drug also has vasoconstrictive effects on uterine vessels and may induce gastrointestinal motility and bronchoconstriction at higher doses.

Application

Carboprost is indicated for the treatment of postpartum hemorrhage (PPH) due to uterine atony that is unresponsive to conventional management, such as oxytocin, ergonovine, or manual massage. It is also used for the induction of second-trimester abortion. The drug is administered intramuscularly and is effective in reducing blood loss and the need for surgical intervention.

In 90 women undergoing laparoscopic myomectomy, carboprost tromethamine (250 µg IM) plus oxytocin infusion significantly reduced operative time (24.3 vs 30.4 min), blood loss (51.1 vs 108.4 mL), and postoperative hemoglobin drop (6.9 vs 14.1 g/L) compared to carboprost alone or vasopressin. Uterine contraction pain was more common with carboprost, but other side effects were similar. Carboprost plus oxytocin is effective for reducing blood loss during myomectomy.

Fig. 1 Time of bowel deflation and postoperative hospital stay in the different groups. Each bar represents the mean ± standard deviation. (Zhang R, et al., 2015)

References

Zhang R, et al. Assessment of carboprost tromethamine for reducing hemorrhage in laparoscopic intramural myomectomy. Exp Ther Med. 2015;10(3):1171-1174.

Does Carboprost Tromethamine require refrigerated storage as a prostaglandin analog?

Yes, it must be stored at 2-8°C. At room temperature, thermal degradation via dehydration and oxidation of the cyclopentane ring occurs.

Is Carboprost Tromethamine sensitive to light and oxygen during handling?

Yes, it is photosensitive and prone to oxidation. Store in light-resistant containers under inert gas (nitrogen) to prevent degradation.

What is the stability of Carboprost Tromethamine after dilution for intramuscular use?

Diluted solutions are stable for up to 24 hours under refrigeration when protected from light.

How is the impurity carboprost 15-keto (an oxidative degradation product) monitored?

This degradation product is specifically quantified using a stability-indicating HPLC method, ensuring it remains within ICH limits.