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Identification
NameCarbetocin
Accession NumberDB01282
TypeSmall Molecule
GroupsApproved
DescriptionCarbetocin 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
Thumb
Synonyms
1-Butanoic acid-2-(O-methyl-L-tyrosine)-1-carbaoxytocin
1-Butyric acid-2-(3-(P-methoxyphenyl)-L-alanine)oxytocin
Carbetocino
Carbetocinum
Deamino-2-O-methyltyrosine-1-carbaoxytocin
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Duratocin Injectionliquid100 mcgintravenousFerring Inc1999-08-01Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII88TWF8015Y
CAS number37025-55-1
WeightAverage: 988.161
Monoisotopic: 987.484787417
Chemical FormulaC45H69N11O12S
InChI KeyInChIKey=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)[[email protected]](CC2=CC=C(OC)C=C2)NC(=O)CCCSC[[email protected]](NC(=O)[[email protected]](CC(N)=O)NC(=O)[[email protected]](CCC(N)=O)NC1=O)C(=O)N1CCC[[email protected]]1C(=O)N[C@@H](CC(C)C)C(=O)NCC(N)=O)[C@@H](C)CC
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Cyclic alpha peptide
  • N-acyl-alpha amino acid or derivatives
  • Macrolactam
  • Alpha-amino acid amide
  • N-substituted-alpha-amino acid
  • Methoxybenzene
  • Pyrrolidine-2-carboxamide
  • Pyrrolidine carboxylic acid or derivatives
  • Phenol ether
  • N-acylpyrrolidine
  • Anisole
  • Alkyl aryl ether
  • Fatty acyl
  • Benzenoid
  • N-acyl-amine
  • Fatty amide
  • Monocyclic benzene moiety
  • Tertiary carboxylic acid amide
  • Pyrrolidine
  • Cyclic alcohol
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Primary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Dialkylthioether
  • Thioether
  • Ether
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed to control postpartum hemorrhage and bleeding after giving birth.
PharmacodynamicsCarbetocin 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 actionCarbetocin 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.
Related Articles
AbsorptionBioavailability is 80% following intramuscular injection.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life40 minutes
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Liquidintravenous100 mcg
PricesNot Available
PatentsNot Available
Properties
StateSolid
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 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesH01BB03
AHFS Codes
  • 76:00.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
Carboprost TromethamineThe risk or severity of adverse effects can be increased when Carboprost Tromethamine is combined with Carbetocin.
DinoprostoneThe risk or severity of adverse effects can be increased when Dinoprostone is combined with Carbetocin.
MisoprostolThe risk or severity of adverse effects can be increased when Misoprostol is combined with Carbetocin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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
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. [PubMed:9760035 ]
  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. [PubMed:15740719 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Comments
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Drug created on May 17, 2007 10:46 / Updated on August 17, 2016 12:23