Structure via PubChem · Public domain (PubChem)
carbetocin
Sign in to saveAlso known as 1-butyric acid-2-(3-(p-methoxyphenyl)-L-alanine)oxytocin, deamino-2-O-methyltyrosine-1-carbaoxytocin, 1-butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocin, 1-Butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocin, Carbetocinum, 1-Butyric acid-2-(3-(P-methoxyphenyl)-L-alanine)oxytocin, Deamino-2-O-methyltyrosine-1-carbaoxytocin
Carbetocin, sold under the brand names Pabal among others, is a medication used to prevent excessive bleeding after childbirth, particularly following Cesarean section. It appears to work as well as oxytocin. Due to it being less economical than other options, use is not recommended by NHS Scotland. It is given by injection into a vein or muscle.
Chemical data
- Formula
- C45H69N11O12S
- Molecular weight
- 988.2 g/mol
- IUPAC name
- (2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-1-[(3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-[(2S)-butan-2-yl]-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl]pyrrolidine-2-carboxamide
- SMILES
- CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSCCCC(=O)N[C@H](C(=O)N1)CC2=CC=C(C=C2)OC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
- InChIKey
- NSTRIRCPWQHTIA-DTRKZRJBSA-N
- XLogP
- -1.1
- Polar surface area
- 388 Ų
- H-bond donors
- 10
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Protein
- Admin. routes
- parenteral
- Indications
- postpartum hemorrhage, Prader-Willi syndrome, Uterine Inertia, uterine fibroid
via ChEMBL · EBI
Research
430 papers- Intranasal Carbetocin Reduces Hyperphagia, Anxiousness, and Distress in Prader-Willi Syndrome: CARE-PWS Phase 3 Trial.The Journal of clinical endocrinology and metabolism · 2023
- Carbetocin: Worth the extra expense?Best practice & research. Clinical obstetrics & gynaecology · 2019
- Carbetocin for preventing postpartum haemorrhage.The Cochrane database of systematic reviews · 2012
- Carbetocin versus oxytocin in prevention of postpartum hemorrhage after cesarean delivery in high-risk women. A systematic review and meta-analysis.Archives of gynecology and obstetrics · 2025
- Effect of Carbetocin on Postpartum Hemorrhage after Vaginal Delivery: A Meta-Analysis.Computational and mathematical methods in medicine · 2022
via PubMed
Wikidata facts
- Mass
- 987.484788
- Has use
- medication
Show 5 more facts
- chemical formula
- C₄₅H₆₉N₁₁O₁₂S
- isomeric SMILES
- CC[C@H](C)[C@H]1C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@@H](CSCCCC(=O)N[C@H](C(=O)N1)CC2=CC=C(C=C2)OC)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
- canonical SMILES
- CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(CSCCCC(=O)NC(C(=O)N1)CC2=CC=C(C=C2)OC)C(=O)N3CCCC3C(=O)NC(CC(C)C)C(=O)NCC(=O)N)CC(=O)N)CCC(=O)N
- World Health Organisation international non-proprietary name
- carbetocin
- defined daily dose
- 0.1
Sources (2)
via Wikidata · CC0
~8 min read
Encyclopedic overview
11 sectionsContents
- Medical uses
- Comparison with other medication
- Adverse effects
- Interactions
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Society and culture
- Legal status
- Brand names
- References
Carbetocin, sold under the brand names Pabal among others, is a medication used to prevent excessive bleeding after childbirth, particularly following Cesarean section. It appears to work as well as oxytocin. Due to it being less economical than other options, use is not recommended by NHS Scotland. It is given by injection into a vein or muscle.
Side effects differ little from that of no treatment or placebo. Use is not recommended in people with epilepsy or eclampsia. Carbetocin is a manufactured long acting form of oxytocin. It works by activating the oxytocin receptor which causes the uterus to contract.
Excerpted from Wikipedia’s “carbetocin” article, available under the CC BY-SA 4.0 licence.