Carbetocin

Title: Carbetocin
CAS Registry Number: 37025-55-1
CAS Name: 1-Butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocin
Additional Names: 1-butyric acid-2-[3-(p-methoxyphenyl)-L-alanine]oxytocin; deamino-2-O-methyltyrosine-1-carbaoxytocin; 1-thia-4,7,10,13,16-pentaazacycloeicosane cyclic peptide deriv; 1-desamino-1-monocarba-[2-tyr(OMe)]-OT; (2-O-methyltyrosine)deamino-1-carbaoxytocin; d(COMOT)
Trademarks: Decomoton (Aesculaap); Depotocin (Spofa)
Molecular Formula: C45H69N11O12S
Molecular Weight: 988.16
Percent Composition: C 54.70%, H 7.04%, N 15.59%, O 19.43%, S 3.24%
Literature References: Synthetic carba-analog of oxytocin, q.v. Prepn: I. Fric et al., Collect. Czech. Chem. Commun. 39, 1290 (1974); J. H. Cort et al., DE 2732175 (1976 to Czech. Akad. Ved.). Chromatographic properties: M. Lebl, Collect. Czech. Chem. Commun. 45, 2927 (1980). Uterotonic and galactogogic activity: T. Barth et al., ibid. 3045; T. Barth et al., ibid. 46, 2441 (1981). Pharmacokinetics in lactating sows: N. Cort et al., Am. J. Vet. Res. 42, 1804 (1981). Use in regulation of bovine labor: Z. Veznik et al., ibid. 40, 425 (1979). Effect on milk let-down in sows: N. Cort et al., ibid. 43, 1283 (1982).
Properties: Solid from methanol with ether [a]D -69.0° (c = 0.25 in 1M acetic acid).
Optical Rotation: [a]D -69.0° (c = 0.25 in 1M acetic acid)
Therap-Cat-Vet: Oxytocic, stimulates milk let-down.
Carbic Anhydride Carbimazole Carbinoxamine Carbiphene Carbitol?

Carbetocin
Carbetocin.svg
Systematic (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
Clinical data
Trade names Duratocin, Pabal, Lonactene
AHFS/Drugs.com Micromedex Detailed Consumer Information
Legal status POM (UK) Not available (U.S.)
Routes Intravenous, intramuscular
Pharmacokinetic data
Bioavailability 80% (IM)
Half-life 40 minutes
Identifiers
CAS number 37025-55-1 YesY
ATC code H01BB03
PubChem CID 71715
DrugBank DB01282
ChemSpider 64765 YesY
UNII 88TWF8015Y YesY
KEGG D07229 N
Chemical data
Formula C45H69N11O12S 
Mol. mass 988.162 g/mol
 N (what is this?)  (verify)

Carbetocin (trade names Duratocin, Pabal, Lonactene) is an obstetric drug used to control postpartum hemorrhage and bleeding after giving birth, particularly following Cesarean section.[1] It is an eight amino long oxytocin analogue (oxytocin is a nonapeptide) and its action is similar to that of oxytocin.[2][3] Carbetocin primarily agonizes peripherally expressed oxytocin receptors. Carbetocin is manufactured by Ferring Pharmaceuticals and is available in Canada and the United Kingdom, but not in the United States.