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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:16:38 UTC
HMDB IDHMDB0015267
Secondary Accession Numbers
  • HMDB15267
Metabolite Identification
Common NameCarvedilol
DescriptionCarvedilol 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. Carvedilol's beta-adrenergic receptor blocking ability decreases the heart rate, myocardial contractility, and myocardial oxygen demand. Carvedilol also decreases systemic vascular 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 reticulum Ca2+-ATPase activity. Therefore, carvedilol and its metabolites may be beneficial in chronic heart failure by preventing free radical damage.
Structure
Thumb
Synonyms
ValueSource
(+-)-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 FormulaC24H26N2O4
Average Molecular Weight406.4742
Monoisotopic Molecular Weight406.18925733
IUPAC Name1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol
Traditional Name1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol
CAS Registry Number72956-09-3
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 KeyOGHNVEJMJSYVRP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassCarbazoles
Direct ParentCarbazoles
Alternative Parents
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
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point114 - 115 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0044 g/LNot Available
LogP3.8Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0044 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity115.64 m³·mol⁻¹ChemAxon
Polarizability45.03 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-2930000000-265c376e802c07cf1f2dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-001i-5911100000-80d7548a1e9097537fe6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-1662900000-f901a62f255da92e9a09View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-0220900000-5821022307fc5077033bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0641900000-b122718c07e709b6e644View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-2970100000-e3a225c7d81ac86276beView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pvi-5900000000-8e6d7ab1b80d6492009dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a59-0920700000-a59fa070af5b3d3fc223View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0900000000-3815ea3eac5b157a1da0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-001i-1900000000-1853ce1e2c70f7955fbeView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01136 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01136 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01136
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2487
KEGG Compound IDC06875
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCarvedilol
METLIN IDNot Available
PubChem Compound2585
PDB IDNot Available
ChEBI ID3441
References
Synthesis ReferenceNot 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 ]