Carbetocin

Carbetocin
Clinical data
Trade names	Duratocin, Pabal, Lonactene, others
Other names	(2-O-Methyltyrosine)deamino-1-carbaoxytocin; Deamino-2-O-methyltyrosine-1-carbaoxytocin; 1-Butanoic acid-2-(O-methy-L-tyrosine)-1-carbaoxytocin; 1-butyric acid-2-[3-(4-methoxyphenyl)-L-alanine]oxytocin
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of; administration	Intravenous, intramuscular
ATC code	H01BB03 (WHO) ;
Legal status
Legal status	UK: POM (Prescription only);
Pharmacokinetic data
Bioavailability	80% (IM)
Elimination half-life	85–100 minutes
Identifiers
	IUPAC name (2S)-1-[(3S,6S,9S,12S,15S)-12-[(2S)-butan-2-yl]-; 9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-; [(4-hydroxyphenyl)methyl]-16-methyl-5,8,11,14,17-; pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-; 3-carbonyl]-N-[(1S)-1-(carbamoylmethylcarbamoyl)-; 3-methyl-butyl]pyrrolidine-2-carboxamide;
CAS Number	37025-55-1 ;
PubChem CID	16681432;
DrugBank	DB01282 ;
ChemSpider	16736854 ;
UNII	88TWF8015Y;
KEGG	D07229 ;
CompTox Dashboard (EPA)	DTXSID90897527 ;
ECHA InfoCard	100.048.450
Chemical and physical data
Formula	C45H69N11O12S
Molar mass	988.17 g·mol−1
3D model (JSmol)	Interactive image;
	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)Cc2ccc(cc2)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;
	InChI InChI=1S/C45H69N11O12S/c1-6-25(4)38-44(66)51-28(15-16-34(46)57)40(62)52-31(21-35(47)58)41(63)54-32(23-69-18-8-10-37(60)50-30(42(64)55-38)20-26-11-13-27(68-5)14-12-26)45(67)56-17-7-9-33(56)43(65)53-29(19-24(2)3)39(61)49-22-36(48)59/h11-14,24-25,28-33,38H,6-10,15-23H2,1-5H3,(H2,46,57)(H2,47,58)(H2,48,59)(H,49,61)(H,50,60)(H,51,66)(H,52,62)(H,53,65)(H,54,63)(H,55,64)/t25-,28-,29-,30-,31-,32-,33-,38-/m0/s1 ; Key:NSTRIRCPWQHTIA-DTRKZRJBSA-N ;
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Carbetocin, sold under the brand names Pabal among others, is a medication used to prevent excessive bleeding after childbirth, particularly following Cesarean section.^[2] It appears to work as well as oxytocin.^[3] Due to it being less economical than other options, use is not recommended by NHS Scotland.^[2] It is given by injection into a vein or muscle.^[3]

Side effects differ little from that of no treatment or placebo.^[3] Use is not recommended in people with epilepsy or eclampsia.^[2] Carbetocin is a manufactured long acting form of oxytocin.^[3] It works by activating the oxytocin receptor which causes the uterus to contract.^[4]^[3]

Carbetocin was first described in 1974.^[5] It was approved for medical use in Canada and the United Kingdom in 1997.^[3] It is on the World Health Organization's List of Essential Medicines.^[6] It is not available in the United States or Japan.^[7]^[3]

^ MacDonald K, Feifel D (2015). "Helping Oxytocin Deliver: Considerations in the Development of Oxytocin-Based Therapeutics for Brain Disorders". In Shalev I, Ebstein RP (eds.). Social Hormones and Human Behavior: What Do We Know and Where Do We Go from Here. Frontiers Media SA. pp. 51–. ISBN 978-2-88919-407-0.
^ ^a ^b ^c British National Formulary: BNF 76 (76th ed.). Pharmaceutical Press. 2018. p. 804. ISBN 978-0-85711-338-2.
^ ^a ^b ^c ^d ^e ^f ^g "Proposal for Inclusion of Carbetocin in the Who List of Essential Medicines" (PDF). WHO. Retrieved 25 October 2019.
^ Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 65–. ISBN 978-94-011-4439-1.
^ Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 214–. ISBN 978-1-4757-2085-3.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ "Carbetocin Drug Information, Professional". Drugs.com. Archived from the original on 28 November 2020. Retrieved 12 November 2019.

[ShalevEbstein2015-1] MacDonald K, Feifel D (2015). "Helping Oxytocin Deliver: Considerations in the Development of Oxytocin-Based Therapeutics for Brain Disorders". In Shalev I, Ebstein RP (eds.). Social Hormones and Human Behavior: What Do We Know and Where Do We Go from Here. Frontiers Media SA. pp. 51–. ISBN 978-2-88919-407-0.

[BNF76-2] British National Formulary: BNF 76 (76th ed.). Pharmaceutical Press. 2018. p. 804. ISBN 978-0-85711-338-2.

[WHO_2019-3] ^ ^a ^b ^c ^d ^e ^f ^g "Proposal for Inclusion of Carbetocin in the Who List of Essential Medicines" (PDF). WHO. Retrieved 25 October 2019.

[Morton2012-4] Morton IK, Hall JM (2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 65–. ISBN 978-94-011-4439-1.

[Elks2014-5] Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 214–. ISBN 978-1-4757-2085-3.

[WHO21st-6] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[MMX2019-7] "Carbetocin Drug Information, Professional". Drugs.com. Archived from the original on 28 November 2020. Retrieved 12 November 2019.

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