DrugBank: Carbetocin (DB01282)

targets (1)

Identification

Name

Carbetocin

Accession Number

DB01282

Type

small molecule

Groups

approved

Description

Carbetocin is a drug used to control postpartum hemorrhage, bleeding after giving birth. It is an analogue of oxytocin, and its action is similar to that of oxytocin — it causes contraction of the uterus.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Carbetocino [inn-spanish]
Carbetocinum [inn-latin]

Synonyms

Carbetocino [inn-spanish]
Carbetocinum [inn-latin]

Salts

Not Available

Brand names

Not Available

Brand mixtures

Not Available

Categories

Anti-tocolytic Agents
Labor Induction Agents

CAS number

37025-55-1

Weight

Average: 988.161
Monoisotopic: 987.484787417

Chemical Formula

C₄₅H₆₉N₁₁O₁₂S

InChI Key

InChIKey=NSTRIRCPWQHTIA-DTRKZRJBSA-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

Plain Text

IUPAC Name

(2S)-2-{[(2S)-1-{[(3R,6S,9S,12S,15S)-12-[(2S)-butan-2-yl]-9-(2-carbamoylethyl)-6-(carbamoylmethyl)-15-[(4-methoxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentaazacycloicosan-3-yl]carbonyl}pyrrolidin-2-yl]formamido}-N-(carbamoylmethyl)-4-methylpentanamide

SMILES

[H][C@]1(NC(=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)N1CCC[C@H]1C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)[C@@H](C)CC

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

Used to control postpartum hemorrhage and bleeding after giving birth.

Pharmacodynamics

Carbetocin is a drug used to control postpartum hemorrhage, bleeding after giving birth. It is sold under the trade name Duratocin. It is an analogue of oxytocin, and its action is similar to that of oxytocin; it causes contraction of the uterus.

Mechanism of action

Carbetocin binds to oxytocin receptors present on the smooth musculature of the uterus, resulting in rhythmic contractions of the uterus, increased frequency of existing contractions, and increased uterine tone. The oxytocin receptor content of the uterus is very low in the non-pregnant state, and increases during pregnancy, reaching a peak at the time of delivery.

Absorption

Bioavailability is 80% following intramuscular injection.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

40 minutes

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Liquid	Intravenous

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Property	Value	Source
logP	-2	PhysProp

Predicted Properties

Property	Value	Source
water solubility	2.65e-02 g/l	ALOGPS
logP	0.14	ALOGPS
logP	-3.6	ChemAxon Molconvert
logS	-4.6	ALOGPS
pKa	11.83	ChemAxon Molconvert
hydrogen acceptor count	12	ChemAxon Molconvert
hydrogen donor count	10	ChemAxon Molconvert
polar surface area	362.51	ChemAxon Molconvert
rotatable bond count	18	ChemAxon Molconvert
refractivity	250.18	ChemAxon Molconvert
polarizability	101	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D07229
ChEBI	59204
ChEMBL	59204
Therapeutic Targets Database	DAP000269
PharmGKB	PA10038
Drug Product Database	2231593
Wikipedia	http://en.wikipedia.org/wiki/Carbetocin

ATC Codes

H01BB03

AHFS Codes

76:00.00

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug

Interaction

Dinoprostone

Dinoprostone may enhance the therapeutic effect of carbetocin. Avoid concomitant use of carbetocin with dinoprostone. The oxytocic activity of carbetocin (oxytocin analogue) may be augmented by agents used to promote cervical ripening (eg, dinoprostone, misoprostol). Dinoprostone (vaginal insert) prescribing information recommends waiting at least 30 minute following its removal before initiating treatment with oxytocic agents. A similar approach might be anticipated with misoprostol use.

Misoprostol

Misoprostol may enhance the therapeutic effect of Carbetocin. Avoid the concomitant use of carbetocin and misoprostol. The oxytocic activity of carbetocin (oxytocin analogue) may be augmented by agents used to promote cervical ripening (eg, dinoprostone, misoprostol). Dinoprostone (vaginal insert) prescribing information recommends waiting at least 30 minute following its removal before initiating treatment with oxytocic agents. A similar approach might be anticipated with misoprostol use.

Food Interactions

Not Available

Targets
1. Oxytocin receptor Pharmacological action: yes Actions: agonist Receptor for oxytocin. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol- calcium second messenger system Organism class: human UniProt ID: P30559 Gene: OXTR Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Engstrom T, Barth T, Melin P, Vilhardt H: Oxytocin receptor binding and uterotonic activity of carbetocin and its metabolites following enzymatic degradation. Eur J Pharmacol. 1998 Aug 21;355(2-3):203-10. Pubmed Gimpl G, Postina R, Fahrenholz F, Reinheimer T: Binding domains of the oxytocin receptor for the selective oxytocin receptor antagonist barusiban in comparison to the agonists oxytocin and carbetocin. Eur J Pharmacol. 2005 Mar 7;510(1-2):9-16. Pubmed Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Targets

1. Oxytocin receptor

Pharmacological action: yes
Actions: agonist

Receptor for oxytocin. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol- calcium second messenger system

Organism class: human
UniProt ID: P30559 Link_out

Gene: OXTR Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Engstrom T, Barth T, Melin P, Vilhardt H: Oxytocin receptor binding and uterotonic activity of carbetocin and its metabolites following enzymatic degradation. Eur J Pharmacol. 1998 Aug 21;355(2-3):203-10. Pubmed
Gimpl G, Postina R, Fahrenholz F, Reinheimer T: Binding domains of the oxytocin receptor for the selective oxytocin receptor antagonist barusiban in comparison to the agonists oxytocin and carbetocin. Eur J Pharmacol. 2005 Mar 7;510(1-2):9-16. Pubmed
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Comments

Drug created on May 17, 2007 10:46 / Updated on April 19, 2012 13:17