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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:55 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
Data?1582753277
Synonyms
ValueSource
(+-)-1-(Carbazol-4-yloxy)-3-((2-(O-methoxyphenoxy)ethyl)amino)-2-propanolChEBI
CarvedilolumChEBI
SKF 105517ChEBI
ArtistKegg
CoregKegg
DilatrendHMDB
KredexHMDB
Carvedilol, (R)-isomerHMDB
Carvedilol, 14C-labeledHMDB
CoropresHMDB
EucardicHMDB
Carvedilol hydrochlorideHMDB
Carvedilol, (+-)-isomerHMDB
QuertoHMDB
Carvedilol, (S)-isomerHMDB
Carvedilol, (-)HMDB
Carvedilol, 14C labeledHMDB
Carvedilol, (-)-isomerHMDB
14C-Labeled carvedilolHMDB
Carvedilol, (+)HMDB
Carvedilol, (+)-isomerHMDB
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
Description Belongs to the class of organic compounds known as carbazoles. Carbazoles 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
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point114 - 115 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.0044 g/LNot Available
LogP3.8Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM190.030932474
[M+H]+Not Available189.08http://allccs.zhulab.cn/database/detail?ID=AllCCS00001030
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+194.28331661259
DarkChem[M-H]-193.80731661259
DeepCCS[M+H]+185.36530932474
DeepCCS[M-H]-183.00730932474
DeepCCS[M-2H]-217.33430932474
DeepCCS[M+Na]+193.39530932474
AllCCS[M+H]+201.532859911
AllCCS[M+H-H2O]+198.932859911
AllCCS[M+NH4]+203.932859911
AllCCS[M+Na]+204.632859911
AllCCS[M-H]-199.332859911
AllCCS[M+Na-2H]-199.332859911
AllCCS[M+HCOO]-199.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CarvedilolCOC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N24685.1Standard polar33892256
CarvedilolCOC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N23553.6Standard non polar33892256
CarvedilolCOC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N23815.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Carvedilol,1TMS,isomer #1COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C3724.9Semi standard non polar33892256
Carvedilol,1TMS,isomer #2COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)[Si](C)(C)C3763.0Semi standard non polar33892256
Carvedilol,1TMS,isomer #3COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C3749.0Semi standard non polar33892256
Carvedilol,2TMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C)[Si](C)(C)C3781.2Semi standard non polar33892256
Carvedilol,2TMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C)[Si](C)(C)C3546.1Standard non polar33892256
Carvedilol,2TMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C)[Si](C)(C)C4541.5Standard polar33892256
Carvedilol,2TMS,isomer #2COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C3669.4Semi standard non polar33892256
Carvedilol,2TMS,isomer #2COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C3397.3Standard non polar33892256
Carvedilol,2TMS,isomer #2COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C4300.7Standard polar33892256
Carvedilol,2TMS,isomer #3COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)[Si](C)(C)C3715.0Semi standard non polar33892256
Carvedilol,2TMS,isomer #3COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)[Si](C)(C)C3472.2Standard non polar33892256
Carvedilol,2TMS,isomer #3COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)[Si](C)(C)C4495.5Standard polar33892256
Carvedilol,3TMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C3742.9Semi standard non polar33892256
Carvedilol,3TMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C3443.8Standard non polar33892256
Carvedilol,3TMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C)O[Si](C)(C)C)[Si](C)(C)C4170.4Standard polar33892256
Carvedilol,1TBDMS,isomer #1COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C(C)(C)C3937.6Semi standard non polar33892256
Carvedilol,1TBDMS,isomer #2COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)[Si](C)(C)C(C)(C)C4015.0Semi standard non polar33892256
Carvedilol,1TBDMS,isomer #3COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C3888.2Semi standard non polar33892256
Carvedilol,2TBDMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4219.5Semi standard non polar33892256
Carvedilol,2TBDMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3904.1Standard non polar33892256
Carvedilol,2TBDMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1[NH]2)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4569.6Standard polar33892256
Carvedilol,2TBDMS,isomer #2COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4001.0Semi standard non polar33892256
Carvedilol,2TBDMS,isomer #2COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3776.6Standard non polar33892256
Carvedilol,2TBDMS,isomer #2COC1=CC=CC=C1OCCNCC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C4339.3Standard polar33892256
Carvedilol,2TBDMS,isomer #3COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4086.7Semi standard non polar33892256
Carvedilol,2TBDMS,isomer #3COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3808.7Standard non polar33892256
Carvedilol,2TBDMS,isomer #3COC1=CC=CC=C1OCCN(CC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4501.1Standard polar33892256
Carvedilol,3TBDMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4280.5Semi standard non polar33892256
Carvedilol,3TBDMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C3952.6Standard non polar33892256
Carvedilol,3TBDMS,isomer #1COC1=CC=CC=C1OCCN(CC(COC1=CC=CC2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C4245.4Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Carvedilol GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-2930000000-265c376e802c07cf1f2d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carvedilol GC-MS (1 TMS) - 70eV, Positivesplash10-001i-5911100000-80d7548a1e9097537fe62017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Carvedilol GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Carvedilol , positive-QTOFsplash10-0a4i-1662900000-f901a62f255da92e9a092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carvedilol , positive-QTOFsplash10-0a4i-0220900000-5821022307fc5077033b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carvedilol 35V, Negative-QTOFsplash10-0a59-0700900000-db48a63e0af377a4fd9a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Carvedilol 35V, Positive-QTOFsplash10-05gi-0590400000-262b3137ced7d5771dd12021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 10V, Positive-QTOFsplash10-0a4i-0641900000-b122718c07e709b6e6442016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 20V, Positive-QTOFsplash10-001i-2970100000-e3a225c7d81ac86276be2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 40V, Positive-QTOFsplash10-0pvi-5900000000-8e6d7ab1b80d6492009d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 10V, Negative-QTOFsplash10-0a59-0920700000-a59fa070af5b3d3fc2232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 20V, Negative-QTOFsplash10-001i-0900000000-3815ea3eac5b157a1da02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 40V, Negative-QTOFsplash10-001i-1900000000-1853ce1e2c70f7955fbe2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 10V, Positive-QTOFsplash10-0a59-0371900000-e534eced6a6fe12ecec42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 20V, Positive-QTOFsplash10-0kcr-0981300000-ba8dc2f3b7ba5097647c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 40V, Positive-QTOFsplash10-0udi-2910000000-f102425e265c4b7f88452021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 10V, Negative-QTOFsplash10-0a4i-0400900000-d652673d45eb1d8b982c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 20V, Negative-QTOFsplash10-053r-2941300000-60c60407d2e97777ae0b2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Carvedilol 40V, Negative-QTOFsplash10-001i-0900000000-dcfc85c30b0adee491ca2021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01136 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]