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 ;
	(what is this?) (verify)

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.

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