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C3993

Sigma-Aldrich

Carvedilol

≥98% (HPLC), solid

Synonym(s):

1-(9H-Carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-2-propanol, BM-14190

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About This Item

Empirical Formula (Hill Notation):
C24H26N2O4
CAS Number:
72956-09-3
Molecular Weight:
406.47
MDL number:
MFCD00864692
UNSPSC Code:
12352200
PubChem Substance ID:
329775050
NACRES:
NA.77

assay

≥98% (HPLC)

form

solid

color

white to off-white

solubility

DMSO: >20 mg/mL

originator

GlaxoSmithKline

SMILES string

OC(COC1=CC=CC2=C1C3=C(C=CC=C3)N2)CNCCOC4=CC=CC=C4OC

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

Gene Information

human ... ADRA1A(148) , ADRA1B(147) , ADRA1D(146) , ADRB1(153) , ADRB2(154) , ADRB3(155)

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Application

Carvedilol has been used:
  • as a β blocker to determine its effect on hypoxia inducible factor (HIF)-mediated erythropoiesis under hypoxia in vivo
  • as a βAR antagonist for inhibition of bARs
  • as a β-blocker to examine airway mechanics in fungus-challenged mice

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.

Features and Benefits

This compound is featured on the β-Adrenoceptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by GlaxoSmithKline. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

pictograms

Health hazardEnvironment
GHS08,GHS09

signalword

Warning

hcodes

H373,H411

Hazard Classifications

Aquatic Chronic 2 - STOT RE 2

target_organs

Liver,spleen,Uterus (including cervix),Adrenal gland

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Hypoxia sensing through beta-adrenergic receptors
Cheong HI, et al.
JCI insight, 1(21) (2016)
Long-acting beta agonists enhance allergic airway disease
Knight JM, et al.
Testing, 10(11), e0142212-e0142212 (2015)
V J Thanawala et al.
British journal of pharmacology, 172(20), 4833-4846 (2015-07-28)
Our previous studies have shown the β2 -adrenoceptor and its endogenous ligand, adrenaline, are required for development of the asthma phenotype in murine asthma models. Chronic administration of some, but not other, β-blockers attenuated the asthma phenotype and led us
Visualizing dynamics of cell signaling in vivo with a phase separation-based kinase reporter
Zhang Q, et al.
Molecular Cell, 69(2), 334-346 (2018)
Samantha L Payne et al.
EBioMedicine, 75, 103767-103767 (2021-12-22)
There is a critical need to better understand the mechanisms that drive local cell invasion and metastasis to develop new therapeutics targeting metastatic disease. Bioelectricity is an important mediator of cellular processes and changes in the resting membrane potential (RMP)
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