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.
In the Vinony graph
Within Vinony's link graph, carboprost is referenced by 239 other articles, and connects out to postpartum hemorrhage, methylergonovine and prostaglandin F2α.
It is catalogued under topics including Chemical articles with multiple CAS registry numbers, Chemicals using indexlabels and Drugboxes which contain changes to verified fields.
Its subject is documented across 7 Wikipedia language editions.
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.