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| Trade names | Hemabate |
| AHFS/Drugs.com | Micromedex Detailed Consumer Information |
| MedlinePlus | a600042 |
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| Routes of administration | Intramuscular |
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| Chemical and physical data | |
| Formula | C21H36O5 |
| Molar mass | 368.514 g·mol−1 |
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Carboprost (INN, trade names for thetromethamine saltsHemabate,Tham) is a syntheticprostaglandin analogue ofPGF2α (specifically, it is 15-methyl-PGF2α) withoxytocic properties.
Carboprost's main use is to reducepostpartum bleeding during the obstetrical emergency ofpostpartum hemorrhage.
Carboprost is used in postpartum hemorrhage caused by uterine atony not controlled by other methods. One study has shown that carboprost tromethamine is more effective than oxytocin in preventing postpartum hemorrhage in high-risk patients undergoing cesarean delivery.[2]
Carboprost was the first drug widely used formedication abortions. It is still sometimes used for second trimester abortions, but has generally been supplanted by themifepristone/misoprostol combination.[3][4][5][6][7][8]
Carboprost is contraindicated in severe cardiovascular, renal, and hepatic disease. It is also contraindicated in acute pelvic inflammatory disease. Hypersensitivity to carboprost or any of its components is also a contraindication.[3]
Carboprost is supplied with its salt derivative tromethamine in 1-milliliter ampules containing a 250 mcg/mL solution of the active drug. The drug must be kept refrigerated at 2–8 °C (36–46 °F).[3]
A significant deactivating metabolic transformation of natural prostaglandins is enzymatic oxidation of the C-15 hydroxyl to the corresponding ketone. This is prevented, with retention of activity, by methylation to give the C-15 tertiary carbinol series.
This molecular feature is readily introduced at the stage of the Corey lactone (1) by reaction with methylGrignard reagent ortrimethylaluminium. The resulting mixture of tertiary carbinols (2) is transformed to oxytocic carboprost (3) by standard transformations, including separation of diastereomers, so that the final product is the C-15 analogue. This diastereomer is reputably freeer of prostaglandin side effects than the C-15 (S) isomer.
