Carbetocin

Identification

Summary

Carbetocin is an oxytocin agent used to control postpartum hemorrhage and bleeding after giving birth.

Brand Names
Duratocin
Generic Name
Carbetocin
DrugBank Accession Number
DB01282
Background

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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 988.161
Monoisotopic: 987.484787417
Chemical Formula
C45H69N11O12S
Synonyms
  • 1-butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocin
  • 1-butyric acid-2-(3-(p-methoxyphenyl)-L-alanine)oxytocin
  • Carbetocin
  • Carbetocina
  • Carbetocino
  • Carbetocinum
  • deamino-2-O-methyltyrosine-1-carbaoxytocin
External IDs
  • LV-101

Pharmacology

Indication

Used to control postpartum hemorrhage and bleeding after giving birth.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Prophylaxis ofPostpartum hemorrhage••••••••••••
Prophylaxis ofUterine atony••••••••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AOxytocin receptor
agonist
Humans
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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Carbetocin is combined with Abaloparatide.
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Carbetocin.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Carbetocin.
AliskirenThe risk or severity of adverse effects can be increased when Carbetocin is combined with Aliskiren.
AmbrisentanCarbetocin may increase the hypotensive activities of Ambrisentan.
Food Interactions
No interactions found.

Products

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Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Carbetocin InjectionSolution100 mcg / mLIntravenousJuno Pharmaceuticals Corp.2020-01-21Not applicableCanada flag
DuratocinSolution100 mcg / mLIntravenousFerring Pharmaceuticals1999-08-012021-05-18Canada flag
DuratocinSolution100 mcg / mLIntramuscular; IntravenousFerring Pharmaceuticals2020-08-05Not applicableCanada flag

Categories

ATC Codes
H01BB03 — Carbetocin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Cyclic peptides / Leucine and derivatives / Proline and derivatives / Macrolactams / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Pyrrolidinecarboxamides / Anisoles / Phenoxy compounds / N-acylpyrrolidines
show 14 more
Substituents
Alkyl aryl ether / Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-oligopeptide / Anisole / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group
show 32 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
heterodetic cyclic peptide (CHEBI:59204)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
88TWF8015Y
CAS number
37025-55-1
InChI Key
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
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-pentaazacycloicosane-3-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

References

General References
Not Available
Human Metabolome Database
HMDB0015402
KEGG Drug
D07229
PubChem Compound
16681432
PubChem Substance
46509009
ChemSpider
16736854
BindingDB
50044677
ChEBI
59204
ChEMBL
CHEMBL3301668
ZINC
ZINC000150338703
Therapeutic Targets Database
DAP000269
PharmGKB
PA164743086
Wikipedia
Carbetocin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedNot AvailablePostpartum Haemorrhage (PPH)1
4CompletedDiagnosticArrhythmia1
4CompletedPreventionAbdominal Myomectomy1
4CompletedPreventionBlood Loss During Surgery / Intrapartum Hemorrhage1
4CompletedPreventionBloodloss / Postpartum Haemorrhage (PPH)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionParenteral
SolutionIntramuscular; Intravenous100 cg
Injection, solution
SolutionIntramuscular; Intravenous100 mcg / mL
SolutionIntravenous100 mcg / mL
InjectionIntravenous100 mcg/ml
Injection, solution100 mcg/mL
Injection, solutionIntravenous100 mcg/ml
SolutionIntramuscular; Intravenous100 mcg
SolutionIntravenous100.00 mcg
SolutionIntravenous100.000 mcg
Injection, solutionIntramuscular; Intravenous100 mcg/1ml
SolutionParenteral100.000 mcg
InjectionIntravenous0.1 mg/ml
Injection, solutionIntravenous
SolutionIntravenous100.000 µg
SolutionParenteral100 mcg
Solution100 mcg/1ml
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP-2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0265 mg/mLALOGPS
logP0.14ALOGPS
logP-3.6Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)11.42Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count10Chemaxon
Polar Surface Area362.51 Å2Chemaxon
Rotatable Bond Count18Chemaxon
Refractivity250.18 m3·mol-1Chemaxon
Polarizability101.2 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9806
Blood Brain Barrier-0.9678
Caco-2 permeable-0.774
P-glycoprotein substrateSubstrate0.8748
P-glycoprotein inhibitor IInhibitor0.5541
P-glycoprotein inhibitor IINon-inhibitor0.8748
Renal organic cation transporterNon-inhibitor0.8938
CYP450 2C9 substrateNon-substrate0.8785
CYP450 2D6 substrateNon-substrate0.7363
CYP450 3A4 substrateSubstrate0.6535
CYP450 1A2 substrateNon-inhibitor0.8997
CYP450 2C9 inhibitorNon-inhibitor0.7966
CYP450 2D6 inhibitorNon-inhibitor0.8931
CYP450 2C19 inhibitorNon-inhibitor0.7442
CYP450 3A4 inhibitorNon-inhibitor0.8166
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9196
Ames testNon AMES toxic0.8318
CarcinogenicityNon-carcinogens0.8517
BiodegradationNot ready biodegradable0.9703
Rat acute toxicity3.2094 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9403
hERG inhibition (predictor II)Inhibitor0.6577
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0000000019-faf8db32c23b578e18fd
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-029e-4010000039-1a2f733f51dced806199
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ei-2642000289-e3275757cc645a21194a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0200000194-a722d8b013365c876787
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0100-9620024533-912a3113d12bb1237983
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dl-3332023294-1ba4ff83ad9d2ceeb61d
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-305.5086005
predicted
DarkChem Lite v0.1.0
[M-H]-299.3112
predicted
DeepCCS 1.0 (2019)
[M+H]+307.3883005
predicted
DarkChem Lite v0.1.0
[M+H]+300.9644
predicted
DeepCCS 1.0 (2019)
[M+Na]+307.6758005
predicted
DarkChem Lite v0.1.0
[M+Na]+307.12122
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Vasopressin receptor activity
Specific Function
Receptor for oxytocin. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system.
Gene Name
OXTR
Uniprot ID
P30559
Uniprot Name
Oxytocin receptor
Molecular Weight
42770.99 Da
References
  1. 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. [Article]
  2. 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. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created at May 17, 2007 16:46 / Updated at March 18, 2024 16:48