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72956-09-3 molecular structure
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[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl][2-(2-methoxyphenoxy)ethyl]amine

ChemBase ID: 1007
Molecular Formular: C24H26N2O4
Molecular Mass: 406.47424
Monoisotopic Mass: 406.18925732
SMILES and InChIs

SMILES:
O(c1c2c3c([nH]c2ccc1)cccc3)CC(O)CNCCOc1c(OC)cccc1
Canonical SMILES:
COc1ccccc1OCCNCC(COc1cccc2c1c1ccccc1[nH]2)O
InChI:
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
InChIKey:
OGHNVEJMJSYVRP-UHFFFAOYSA-N

Cite this record

CBID:1007 http://www.chembase.cn/molecule-1007.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl][2-(2-methoxyphenoxy)ethyl]amine
IUPAC Traditional name
carvedilol
[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl][2-(2-methoxyphenoxy)ethyl]amine
Brand Name
Coreg
Coreg CR
Synonyms
Carvedilolum [Latin]
carvedilol
Carvedilol
Coreg
Dilatrend
1-(9H-Carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-2-propanol
BM-14190
Carvedilol
Artist
BM 14190
Cadilan
Carca
Cardivas
Carloc
Carvas
Carvediol
DQ 2466
Dimitone
Eucardic
Korvasan
Kredex
Querto
SKF 105517
Talliton
1-((9H-carbazol-4-yl)oxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)propan-2-ol
CAS Number
72956-09-3
MDL Number
MFCD00864692
PubChem SID
160964470
46505146
PubChem CID
2585

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 14.030432  H Acceptors
H Donor LogD (pH = 5.5) 0.48382187 
LogD (pH = 7.4) 2.069334  Log P 3.4248545 
Molar Refractivity 115.6377 cm3 Polarizability 47.905235 Å3
Polar Surface Area 75.74 Å2 Rotatable Bonds 10 
Lipinski's Rule of Five true 
Log P 3.05  LOG S -4.96 
Solubility (Water) 4.44e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO expand Show data source
DMSO: >20 mg/mL expand Show data source
Methanol expand Show data source
Practically insoluble (0.583 mg/L) expand Show data source
Apperance
White Solid expand Show data source
white to off-white solid expand Show data source
Melting Point
114-115°C expand Show data source
Hydrophobicity(logP)
3.8 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
UA8670000 expand Show data source
European Hazard Symbols
Nature polluting Nature polluting (N) expand Show data source
UN Number
3077 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
9 expand Show data source
Packing Group
3 expand Show data source
Risk Statements
51/53 expand Show data source
Safety Statements
61 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS09 expand Show data source
GHS Hazard statements
H411 expand Show data source
GHS Precautionary statements
P273 expand Show data source
Personal Protective Equipment
Eyeshields, Gloves expand Show data source
RID/ADR
UN 3077 9/PG 3 expand Show data source
Target
adrenergic receptor expand Show data source
Mechanism of Action
Beta-Adrenoceptor blocker expand Show data source
Calcium channel blocker expand Show data source
Purity
>98% expand Show data source
≥98% (HPLC) expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Vasodilator expand Show data source
Empirical Formula (Hill Notation)
C24H26N2O4 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB01136 external link
Item Information
Drug Groups approved; investigational
Description Carvedilol is a non-selective beta blocker indicated in the treatment of mild to moderate congestive heart failure (CHF). It blocks beta-1 and beta-2 adrenergic receptors as well as the alpha-1 adrenergic receptors.
Indication For the treatment of mild or moderate (NYHA class II or III) heart failure of ischemic or cardiomyopathic origin.
Pharmacology Carvedilol is a nonselective beta-adrenergic blocking agent with alpha1-blocking activity and is indicated for the treatment of hypertension and mild or moderate (NYHA class II or III) heart failure of ischemic or cardiomyopathic origin. Carvedilol is a racemic mixture in which nonselective b-adrenoreceptor blocking activity is present in the S(-) enantiomer and a-adrenergic blocking activity is present in both R(+) and S(-) enantiomers at equal potency. Carvedilol has no intrinsic sympathomimetic activity. The effect of carvedilol's b-adrenoreceptor blocking activity has been demonstrated in animal and human studies showing that carvedilol (1) reduces cardiac output in normal subjects; (2) reduces exercise-and/or isoproterenol-induced tachycardia and (3) reduces reflex orthostatic tachycardia.
Toxicity Not expected to be toxic following ingestion.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Carvedilol is metabolized primarily by aromatic ring oxidation and glucuronidation. The oxidative metabolites are further metabolized by conjugation via glucuronidation and sulfation. Demethylation and hydroxylation at the phenol ring produce three active metabolites with b-receptor blocking activity. The 4'-hydroxyphenyl metabolite is approximately 13 times more potent than carvedilol for b-blockade.
Absorption Carvedilol is rapidly and extensively absorbed following oral administration, with an absolute bioavailability of approximately 25% to 35% due to a significant degree of first-pass metabolism.
Half Life 7-10 hours
Protein Binding 98%
Elimination Carvedilol is extensively metabolized. Less than 2% of the dose was excreted unchanged in the urine.
Carvedilol is metabolized primarily by aromatic ring oxidation and glucuronidation. The oxidative metabolites are further metabolized by conjugation via glucuronidation and sulfation. The metabolites of carvedilol are excreted primarily via the bile into the feces.
Distribution * 115 L
Clearance * 500-700 mL/min
References
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]
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]
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]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1831 external link
Biological Activity:
Carvedilol is a non-selective beta blocker/alpha-1 blocker with an IC50 of 3.8 μM for inhibition of LDL oxidation. [1] Norepinephrine stimulates the nerves that control the muscles of the heart by binding to the β1- and β2-adrenergic receptors. Carvedilol blocks the binding to those receptors, which both slows the heart rhythm and reduces the force of the heart’s pumping. This lowers blood pressure and reduces heart failure. Norepinephrine also binds to the α1-adrenergic receptors on blood vessels, causing them to constrict and raise blood pressure. Carvedilol blocks this binding to the α1-adrenergic receptors too, which also lowers blood pressure. [2]
Sigma Aldrich - C3993 external link
Biochem/physiol Actions
Cavedilol is a non-selective β-adrenergic blocker with α1 blocking activity. Carvedilol is used specifically for the treatment of heart failure and high blood pressure. It has been shown to improve left ventricular ejection fraction and may reduce mortality.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C3993.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals - C184625 external link
Carvedilol is a nonselective β-adrenergic blocker with α1-blocking activity. Carvedilol is an antihypertensive used in the treatment of congestive heart failure.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
  • • 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
  • • 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
  • • http://en.wikipedia.org/wiki/Carvedilol
  • • Hirohashi, M., et al.: Arzneim.-Forsch., 40, 735 (1990)
  • • Packer, M., et al.: N. Engl. J. Med., 334, 1349 (1990)
  • • Ger. Pat., 1984, 2 815 926; CA, 92, 128716e, (synth)
  • • Ger. Pat., 1984, 3 319 027; CA, 102, 113292, (resoln)
  • • Cubeddu, L.X. et al., Clin. Pharmacol. Ther. (St. Louis), 1987, 41, 31, (pharmacol)
  • • Abshagen, U., J. Cardiovasc. Pharmacol., (Suppl. 11), 1987, 10, S23, (rev, pharmacol)
  • • Sponer, G. et al., J. Cardiovasc. Pharmacol., (Suppl. 11), 1987, 10, S49, (pharmacol)
  • • Reiff, K., J. Chromatogr., 1987, 413, 355, (hplc)
  • • Neugebauer, G. et al., Eur. J. Clin. Pharmacol., 1990, 38, S108, (pharmacol, isomers)
  • • Ruffolo, R.R. et al., Cardiovasc. Drug Rev., 1992, 10, 127, (rev)
  • • McTavish, D. et al., Drugs, 1993, 45, 232, (rev)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 632
  • • Beta-blockers in Clinical Practice, (Eds. Cruickshank, J.M. et al), 2nd edn., Churchill Livingstone, 1994, 1119, (book)
  • • Dunn, C.J., Drugs, 1997, 53, 161-185, (rev)
  • • Rabasseda, X. et al., Drugs of Today (Barcelona), 1998, 34, 905-926
  • • Wood, A.J.J. et al., N. Engl. J. Med., 1998, 339, 1759-1765, (rev)
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