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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
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
48.8 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
PABAL

Approved Use

PABAL is indicated for the prevention of uterine atony following delivery of the infant by Caesarean section under epidural or spinal anaesthesia.
PubMed

PubMed

TitleDatePubMed
Ascending dose tolerance study of intramuscular carbetocin administered after normal vaginal birth.
1998 Apr
Patents

Sample Use Guides

100 ug of carbetocin must be administered slowly, over 1 minute only after delivery of the infant by Caesarean section.
Route of Administration: Intravenous
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
Created
by admin
on Fri Dec 15 15:49:26 UTC 2023
Edited
by admin
on Fri Dec 15 15:49:26 UTC 2023
Record UNII
88TWF8015Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CARBETOCIN
INN   MART.   MI   WHO-DD  
USAN   INN  
Official Name English
1-BUTYRIC ACID-2-(3-(P-METHOXYPHENYL)-L-ALANINE)OXYTOCIN
Common Name English
CARBETOCIN [MI]
Common Name English
O-METHYL-N-(4-SULFANYLBUTANOYL)-L-TYROSYL-L-ISOLEUCYL-L-GLUTAMINYL-L-ASPARAGINYL-L-CYSTEINYL-L-PROLYL-L-LEUCYL-GLYCINAMIDE CYCLIC (1->5)-THIOETHER
Systematic Name English
PABAL
Brand Name English
DURATOCIN
Brand Name English
Carbetocin [WHO-DD]
Common Name English
CARBETOCIN [USAN]
Common Name English
FE-992097
Code English
CARBETOCIN [MART.]
Common Name English
carbetocin [INN]
Common Name English
LV-101
Code English
GLYCINAMIDE, N-(4-MERCAPTO-1-OXOBUTYL)-O-METHYL-L-TYROSYL-L-ISOLEUCYL-L-GLUTAMINYL-L-ASPARAGINYL-L-CYSTEINYL-L-PROLYL-L-LEUCYL-, CYCLIC (1->5)-THIOETHER
Systematic Name English
Classification Tree Code System Code
WHO-VATC QH01BB03
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
EU-Orphan Drug EU/3/12/975
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
FDA ORPHAN DRUG 423014
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
WHO-ATC H01BB03
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
NCI_THESAURUS C548
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
Code System Code Type Description
CHEBI
59204
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
ECHA (EC/EINECS)
253-312-6
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
WIKIPEDIA
Carbetocin
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
DRUG CENTRAL
495
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
EVMPD
SUB06125MIG
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
INN
5014
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
FDA UNII
88TWF8015Y
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
NCI_THESAURUS
C96858
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
SMS_ID
100000081320
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
MESH
C020731
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
ChEMBL
CHEMBL3301668
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
EPA CompTox
DTXSID90897527
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
USAN
HI-212
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
CAS
37025-55-1
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
DRUG BANK
DB01282
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
PUBCHEM
16681432
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY
MERCK INDEX
m3066
Created by admin on Fri Dec 15 15:49:26 UTC 2023 , Edited by admin on Fri Dec 15 15:49:26 UTC 2023
PRIMARY Merck Index
Related Record Type Details
TARGET -> AGONIST
Related Record Type Details
ACTIVE MOIETY