Structure via PubChem · Public domain (PubChem)
carboprost
Sign in to saveCarboprost (INN, trade names for the tromethamine salts Hemabate, Tham) is a synthetic prostaglandin analogue of PGF2α (specifically, it is 15-methyl-PGF2α) with oxytocic properties.
Chemical data
- Formula
- C21H36O5
- Molecular weight
- 368.5 g/mol
- IUPAC name
- (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3S)-3-hydroxy-3-methyloct-1-enyl]cyclopentyl]hept-5-enoic acid
- 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
- InChIKey
- DLJKPYFALUEJCK-IIELGFQLSA-N
- XLogP
- 2.9
- Polar surface area
- 98 Ų
- H-bond donors
- 4
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 1979
- Admin. routes
- parenteral
via ChEMBL · EBI
Research
309 papers- Uterotonic Medications: Oxytocin, Methylergonovine, Carboprost, Misoprostol.Anesthesiology clinics · 2017
- Postpartum Haemorrhage and Carboprost for Its Prevention: A Narrative Review.Cureus · 2024
- Sufentanil for carboprost-induced adverse reactions during cesarean delivery under combined spinal-epidural anesthesia.Ginekologia polska · 2023
- Preventing postpartum hemorrhage with combined therapy rather than oxytocin alone.American journal of obstetrics & gynecology MFM · 2023
- Carboprost versus Oxytocin as the first-line treatment of primary postpartum haemorrhage (COPE): protocol for a phase IV, double-blind, double-dummy, randomised controlled trial and economic analysis.BMJ open · 2025
via PubMed
Wikidata facts
- Subclass of
- prostaglandins
- Mass
- 368.256
Show 5 more facts
- chemical formula
- C₂₁H₃₆O₅
- isomeric 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
- canonical SMILES
- CCCCCC(C)(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
- medical condition treated
- cystitis
- defined daily dose
- 2.5
via Wikidata · CC0
~2 min read
Encyclopedic overview
9 sectionsContents
- Indication
- Contraindication
- Precautions
- Adverse effects
- Storage and availability
- Synthesis
- References
- Further reading
- External links
Carboprost (INN, trade names for the tromethamine salts Hemabate, Tham) is a synthetic prostaglandin analogue of PGF2α (specifically, it is 15-methyl-PGF2α) with oxytocic properties.
Carboprost's main use is to reduce postpartum bleeding during the obstetrical emergency of postpartum hemorrhage.
Excerpted from Wikipedia’s “carboprost” article, available under the CC BY-SA 4.0 licence.