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Carvedilol

July 24, 2017
Common Name

Carvedilol Description

Carvedilol is only found in individuals that have used or taken this drug. It is a non-selective beta blocker indicated in the treatment of mild to moderate congestive heart failure (CHF).Carvedilol is a racemic mixture in which nonselective beta-adrenoreceptor blocking activity is present in the S(-) enantiomer and alpha-adrenergic blocking activity is present in both R(+) and S(-) enantiomers at equal potency. Carvedilols beta-adrenergic receptor blocking ability decreases the heart rate, myocardial contractility, and myocardial oxygen demand. Carvedilol also decreases systemic vascliar resistance via its alpha adrenergic receptor blocking properties. Carvedilol and its metabolite BM-910228 (a less potent beta blocker, but more potent antioxidant) have been shown to restore the inotropic responsiveness to Ca2+ in OH– free radical-treated myocardium. Carvedilol and its metabolites also prevent OH– radical-induced decrease in sarcoplasmic reticlium Ca2+-ATPase activity. Therefore, carvedilol and its metabolites may be beneficial in chronic heart failure by preventing free radical damage. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+-)-1-(Carbazol-4-yloxy)-3-((2-(O-methoxyphenoxy)ethyl)amino)-2-propanolChEBI CarvedilolumChEBI SKF 105517ChEBI CoregMeSH DilatrendMeSH KredexMeSH Carvedilol, (R)-isomerMeSH Carvedilol, 14C-labeledMeSH CoropresMeSH EucardicMeSH Carvedilol hydrochlorideMeSH Carvedilol, (+-)-isomerMeSH QuertoMeSH Carvedilol, (S)-isomerMeSH

Chemical Formlia

C24H26N2O4 Average Molecliar Weight

406.4742 Monoisotopic Molecliar Weight

406.18925733 IUPAC Name

1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol Traditional Name

1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol CAS Registry Number

72956-09-3 SMILES

COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2

InChI Identifier

InChI=1S/C24H26N2O4/c1-28-21-10-4-5-11-22(21)29-14-13-25-15-17(27)16-30-23-12-6-9-20-24(23)18-7-2-3-8-19(18)26-20/h2-12,17,25-27H,13-16H2,1H3

InChI Key

OGHNVEJMJSYVRP-UHFFFAOYSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as carbazoles. These are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. Kingdom

Organic compounds Super Class

Organoheterocyclic compounds Class

Indoles and derivatives Sub Class

Carbazoles Direct Parent

Carbazoles Alternative Parents

  • Indoles
  • Phenoxy compounds
  • Methoxybenzenes
  • Anisoles
  • Alkyl aryl ethers
  • Pyrroles
  • Heteroaromatic compounds
  • Secondary alcohols
  • 1,2-aminoalcohols
  • Dialkylamines
  • Azacyclic compounds
  • Organopnictogen compounds
  • Hydrocarbon derivatives

    • Substituents

  • Carbazole
  • Indole
  • Phenoxy compound
  • Anisole
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Secondary amine
  • Azacycle
  • Secondary aliphatic amine
  • Ether
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Alcohol
  • Aromatic heteropolycyclic compound

    • Molecliar Framework

    Aromatic heteropolycyclic compounds External Descriptors

  • secondary alcohol (CHEBI:3441 )
  • secondary amino compound (CHEBI:3441 )
  • carbazoles (CHEBI:3441 )

    • Ontology Status

    Expected but not Quantified Origin

  • Drug

    • Biofunction

  • Adrenergic Agents
  • Adrenergic alpha-Antagonists
  • Adrenergic beta-Antagonists
  • Antihypertensive Agents
  • Vasodilator Agents

    • Application

  • Pharmaceutical

    • Cellliar locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point114 – 115 °CNot Available Boiling PointNot AvailableNot Available Water Solubility4.44e-03 g/LNot Available LogP3.8Not Available

    Predicted Properties

    Property Value Source Water Solubility0.0044 mg/mLALOGPS logP3.05ALOGPS logP3.42ChemAxon logS-5ALOGPS pKa (Strongest Acidic)14.03ChemAxon pKa (Strongest Basic)8.74ChemAxon Physiological Charge1ChemAxon Hydrogen Acceptor Count5ChemAxon Hydrogen Donor Count3ChemAxon Polar Surface Area75.74 Å2ChemAxon Rotatable Bond Count10ChemAxon Refractivity115.64 m3·mol-1ChemAxon Polarizability45.03 Å3ChemAxon Number of Rings4ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0a4i-1662900000-f901a62f255da92e9a09View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – , positivesplash10-0a4i-0220900000-5821022307fc5077033bView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, PositiveNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, NegativeNot Available Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, NegativeNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Extracellliar
  • Membrane

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Carvedilol PathwaySMP00367Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01136

  • 21059682

    • details UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01136

  • 21059682

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    DB01136 DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    Not Available KNApSAcK ID

    Not Available Chemspider ID

    2487 KEGG Compound ID

    C06875 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Carvedilol NuGOwiki Link

    HMDB15267 Metagene Link

    HMDB15267 METLIN ID

    Not Available PubChem Compound

    2585 PDB ID

    Not Available ChEBI ID

    3441

    Product: TMB

    References Synthesis Reference Not Available Material Safety Data Sheet (MSDS) Not Available General References
    1. Vanderhoff BT, Ruppel HM, Amsterdam PB: Carvedilol: the new role of beta blockers in congestive heart failure. Am Fam Physician. 1998 Nov 1;58(7):1627-34, 1641-2. [PubMed:9824960 ]
    2. Packer M, Coats AJ, Fowler MB, Katus HA, Krum H, Mohacsi P, Rouleau JL, Tendera M, Castaigne A, Roecker EB, Schultz MK, DeMets DL: Effect of carvedilol on survival in severe chronic heart failure. N Engl J Med. 2001 May 31;344(22):1651-8. [PubMed:11386263 ]
    3. Packer M, Fowler MB, Roecker EB, Coats AJ, Katus HA, Krum H, Mohacsi P, Rouleau JL, Tendera M, Staiger C, Holcslaw TL, Amann-Zalan I, DeMets DL: Effect of carvedilol on the morbidity of patients with severe chronic heart failure: results of the carvedilol prospective randomized cumulative survival (COPERNICUS) study. Circulation. 2002 Oct 22;106(17):2194-9. [PubMed:12390947 ]

    PMID: 10640519

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