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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H69N11O12S
Molecular Weight 988.161
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CARBETOCIN

SMILES

CCC(C)[C@@H]1NC(=O)[C@H](CC2=CC=C(OC)C=C2)NC(=O)CCCSC[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(N)=O)NC1=O)C(=O)N3CCC[C@H]3C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O

InChI

InChIKey=NSTRIRCPWQHTIA-DTRKZRJBSA-N
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

HIDE SMILES / InChI

Molecular Formula C45H69N11O12S
Molecular Weight 988.161
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Carbetocin is a synthetic analogue of human peptide hormone, oxytocin. Like oxytocin, it stimulate oxytocin receptors and is used to facilitate childbirth. The drug is being marketed in Europe under the name Pabal for the prevention of uterine atony following delivery of the infant by Caesarean section. If untreated by carbetocin, uterine atony may lead to postpartum haemorrhage.

CNS Activity

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
48.8 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
PABAL

PubMed

Sample Use Guides

In Vivo Use Guide
100 ug of carbetocin must be administered slowly, over 1 minute only after delivery of the infant by Caesarean section.
Route of Administration: Intravenous
In Vitro Use Guide
Myometrial strips from women undergoing elective cesarean deliveries were bathed in physiological salt solution or oxytocin (10(-5) M) for 2 hours and then subjected to a dose-response testing with increasing concentrations of carbetocin in a pattern of 1 log molar increase every 10 min from 10 (-10) to 10 (-5) M.
Substance Class Chemical
Record UNII
88TWF8015Y
Record Status Validated (UNII)
Record Version