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
Structure for Carbetocin (DB01282)
- 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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- Contraindications & Blackbox Warnings
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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.
Target Actions Organism AOxytocin receptor agonistHumans - 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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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbaloparatide The risk or severity of adverse effects can be increased when Carbetocin is combined with Abaloparatide. Acebutolol The risk or severity of adverse effects can be increased when Acebutolol is combined with Carbetocin. Aldesleukin The risk or severity of adverse effects can be increased when Aldesleukin is combined with Carbetocin. Aliskiren The risk or severity of adverse effects can be increased when Carbetocin is combined with Aliskiren. Ambrisentan Carbetocin may increase the hypotensive activities of Ambrisentan. Amifostine The risk or severity of adverse effects can be increased when Amifostine is combined with Carbetocin. Amiloride The risk or severity of adverse effects can be increased when Amiloride is combined with Carbetocin. Amiodarone The risk or severity of adverse effects can be increased when Amiodarone is combined with Carbetocin. Amlodipine The risk or severity of adverse effects can be increased when Amlodipine is combined with Carbetocin. Amobarbital Amobarbital may increase the hypotensive activities of Carbetocin. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Carbetocin Injection Solution 100 mcg / mL Intravenous Juno Pharmaceuticals Corp. 2020-01-21 Not applicable Canada 
Duratocin Solution 100 mcg / mL Intravenous Ferring Pharmaceuticals 1999-08-01 2021-05-18 Canada Duratocin Solution 100 mcg / mL Intramuscular; Intravenous Ferring Pharmaceuticals 2020-08-05 Not applicable Canada
Categories
- ATC Codes
- H01BB03 — Carbetocin
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Delayed-Action Preparations
- Drug Delivery Systems
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hypotensive Agents
- Oxytocin and Analogues
- Peptide Hormones
- Peptides
- Pharmaceutical Preparations
- Pituitary and Hypothalamic Hormones and Analogues
- Pituitary Hormones
- Pituitary Hormones, Posterior
- Posterior Pituitary Lobe Hormones
- Reproductive Control Agents
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Uterotonic agents
- 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
- External Links
- 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
Phase Status Purpose Conditions Count 4 Completed Not Available Postpartum Haemorrhage (PPH) 1 4 Completed Diagnostic Arrhythmia 1 4 Completed Prevention Abdominal Myomectomy 1 4 Completed Prevention Blood Loss During Surgery / Intrapartum Hemorrhage 1 4 Completed Prevention Bloodloss / Postpartum Haemorrhage (PPH) 1 4 Completed Prevention Complications; Cesarean Section / Hemodynamics Instability 1 4 Completed Prevention Postpartum Haemorrhage (PPH) 4 4 Completed Prevention Pregnancy, Complications 1 4 Completed Prevention Primary Postpartum Haemorrhage 1 4 Completed Prevention Uterus Myoma 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Parenteral Solution Intramuscular; Intravenous 100 cg Injection, solution Solution Intramuscular; Intravenous 100 mcg / mL Solution Intravenous 100 mcg / mL Injection Intravenous 100 mcg/ml Injection, solution 100 mcg/mL Injection, solution Intravenous 100 mcg/ml Solution Intramuscular; Intravenous 100 mcg Solution Intravenous 100.00 mcg Solution Intravenous 100.000 mcg Injection, solution Intramuscular; Intravenous 100 mcg/1ml Solution Parenteral 100.000 mcg Injection Intravenous 0.1 mg/ml Injection, solution Intravenous Solution Intravenous 100.000 µg Solution Parenteral 100 mcg Solution 100 mcg/1ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP -2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0265 mg/mL ALOGPS logP 0.14 ALOGPS logP -3.6 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 11.42 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 10 Chemaxon Polar Surface Area 362.51 Å2 Chemaxon Rotatable Bond Count 18 Chemaxon Refractivity 250.18 m3·mol-1 Chemaxon Polarizability 101.2 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9806 Blood Brain Barrier - 0.9678 Caco-2 permeable - 0.774 P-glycoprotein substrate Substrate 0.8748 P-glycoprotein inhibitor I Inhibitor 0.5541 P-glycoprotein inhibitor II Non-inhibitor 0.8748 Renal organic cation transporter Non-inhibitor 0.8938 CYP450 2C9 substrate Non-substrate 0.8785 CYP450 2D6 substrate Non-substrate 0.7363 CYP450 3A4 substrate Substrate 0.6535 CYP450 1A2 substrate Non-inhibitor 0.8997 CYP450 2C9 inhibitor Non-inhibitor 0.7966 CYP450 2D6 inhibitor Non-inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.7442 CYP450 3A4 inhibitor Non-inhibitor 0.8166 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9196 Ames test Non AMES toxic 0.8318 Carcinogenicity Non-carcinogens 0.8517 Biodegradation Not ready biodegradable 0.9703 Rat acute toxicity 3.2094 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9403 hERG inhibition (predictor II) Inhibitor 0.6577
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
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
- 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]
- 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]
- 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 December 03, 2023 06:20