Carbetocin
(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
Molecular Identity
Carbetocin
(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
PubChem CID: 16681432
Carbetocin is oxytocin in which the hydrogen on the phenolic hydroxy group is substituted by methyl, the amino group on the cysteine residue is substituted by hydrogen, and the sulfur of the cysteine residue is replaced by a methylene group. A synthetic carba-analogue of oxytocin, it is used to control bleeding after giving birth. Like oxytocin, it causes contraction of the uterus. It has a role as an oxytocic.
2D Structure
Properties
C45H69N11O12S
Molecular Formula
988.20
Molecular Weight
g/mol
987.4848
Exact Mass
Da
-1.1
XLogP
Drug-like (Lipinski: < 5)
388
TPSA
May have limited oral absorption
10
H-Bond Donors
13
H-Bond Acceptors
1850
Complexity
SMILES
Canonical SMILES
SMILES: Synonyms(20)
Carbetocin37025-55-1PabalCarbetocinoCarbetocinumDuratocincarbetocineCarbetocinadeamino-2-O-methyltyrosine-1-carbaoxytocinLV-101CHEBI:59204DTXSID9089752788TWF8015Y1-butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocin1-Butyric acid-2-(3-(p-methoxyphenyl)-L-alanine)oxytocin
Data from PubChem (NCBI)
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Drug Network
Trials and conditions connected to Carbetocin
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