Carvedilol

Identification

Summary

Carvedilol is a non selective beta-adrenergic antagonist used to treat mild to severe chronic heart failure, hypertension, and left ventricular dysfunction following myocardial infarction in clinically stable patients.

Brand Names

Coreg

Generic Name

Carvedilol

DrugBank Accession Number

DB01136

Background

Carvedilol is a racemic mixture where the S(-) enantiomer is both a beta and alpha-1 adrenoceptor blocker, and the R(+) enantiomer is an alpha-1 adrenoceptor blocker.^5,6 It is currently used to treat heart failure, left ventricular dysfunction, and hypertension.^5,6 The dual action of carvedilol is advantageous in combination therapies as moderate doses of 2 drugs have a decreased incidence of adverse effects compared to high dose monotherapy in the treatment of moderate hypertension.⁴

Carvedilol was granted FDA approval on 14 September 1995.⁵

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 406.4742
Monoisotopic: 406.18925733
Chemical Formula: C₂₄H₂₆N₂O₄

Synonyms

(+-)-1-(Carbazol-4-yloxy)-3-((2-(o-methoxyphenoxy)ethyl)amino)-2-propanol
Carvedilol
Carvédilol
Carvedilolum

External IDs

SKF 105517

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Pharmacology

Indication

Carvedilol is indicated to treat mild to severe heart failure, left ventricular dysfunction after myocardial infarction with ventricular ejection fraction ≤40%, or hypertension.^5,6

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Associated Conditions

Indication Type	Indication	Approval Level
Management of	Atrial fibrillation	••• •••••
Management of	Chronic stable angina pectoris	••• •••••
Management of	Hypertension	••••••••••••
Management of	Lvef ≤40% left ventricular dysfunction	••••••••••••
Management of	Mild heart failure	••••••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Carvedilol reduces tachycardia through beta adrenergic antagonism and lowers blood pressure through alpha-1 adrenergic antagonism.^5,6 It has a long duration of action as it is generally taken once daily and has a broad therapeutic index as patients generally take 10-80mg daily.^5,6 Patients taking carvedilol should not abruptly stop taking this medication as this may exacerbate coronary artery disease.^5,6

Mechanism of action

Carvedilol inhibits exercise induce tachycardia through its inhibition of beta adrenoceptors.⁴ Carvedilol's action on alpha-1 adrenergic receptors relaxes smooth muscle in vasculature, leading to reduced peripheral vascular resistance and an overall reduction in blood pressure.^1,4 At higher doses, calcium channel blocking and antioxidant activity can also be seen.¹ The antioxidant activity of carvedilol prevents oxidation of low density lipoprotein and its uptake into coronary circulation.¹

Target	Actions	Organism
ABeta-1 adrenergic receptor	antagonist	Humans
AAlpha-1A adrenergic receptor	antagonist potentiator	Humans
AAlpha-1 adrenergic receptors	inhibitor	Humans
UNADH dehydrogenase [ubiquinone] 1 subunit C2	inhibitor	Humans
UBeta-2 adrenergic receptor	antagonist	Humans
UVascular endothelial growth factor A	other	Humans
UNatriuretic peptides B	other	Humans
UGap junction alpha-1 protein	other	Humans
UPotassium voltage-gated channel subfamily H member 2	inhibitor	Humans
UVascular cell adhesion protein 1	inhibitor	Humans
UAlpha-1D adrenergic receptor	antagonist	Humans
UAlpha-1B adrenergic receptor	antagonist	Humans
UAlpha-2C adrenergic receptor	antagonist	Humans
UAlpha-2B adrenergic receptor	antagonist	Humans
UAlpha-2A adrenergic receptor	antagonist	Humans
UE-selectin	inhibitor	Humans
UHypoxia-inducible factor 1-alpha	modulator	Humans
UInward rectifier potassium channel 4	inhibitor	Humans
UInward rectifier potassium channel 2	inhibitor	Humans

Absorption

Carvedilol has a bioavailability of 25-35%.^4,5,6 Carvedilol has a T_max of 1 to 2 hours.⁴ Taking carvedilol with a meal increases T_max without increasing AUC.⁴ Carvedilol doses of 50mg lead to a C_max of 122-262µg/L and an AUC of 717-1600µg/L*h.⁴ Carvedilol doses of 25mg lead to a C_max of 24-151µg/L and an AUC of 272-947µg/L*h.⁴ Carvedilol doses of 12.5mg lead to a C_max of 58-69µg/L and an AUC of 208-225µg/L*h.⁴

Volume of distribution

Carvedilol has a volume of distribution of 1.5-2L/kg⁴ or 115L.⁶

Protein binding

Carvedilol is 98% protein bound in plasma.^5,6 95% of carvedilol is bound to serum albumin.⁴

Metabolism

Carvedilol can be hydroxlated at the 1 position by CYP2D6, CYP1A2, or CYP1A1 to form 1-hydroxypheylcarvedilol; at the 4 position by CYP2D6, CYP2E1, CYP2C9, or CYP3A4 to form 4'-hydroxyphenylcarvedilol; at the 5 position by CYP2D6, CYP2C9, or CYP3A4 to form 5'-hydroxyphenylcarvedilol; and at the 8 position by CYP1A2, CYP3A4, and CYP1A1 to form 8-hydroxycarbazolylcarvedilol.² Carvedilol can also be demethylated by CYP2C9, CYP2D6, CYP1A2, or CYP2E1 to form O-desmethylcarvedilol.² Carvedilol and its metabolites may undergo further sulfate conjugation or glucuronidation before elimination.² Carvedilol can be O-glucuronidated by UGT1A1, UGT2B4, and UGT2B7 to form carvedilol glucuronide.³

Hover over products below to view reaction partners

Carvedilol

Route of elimination

16% of carvedilol is excreted in the urine with <2% excreted as unmetabolized drug.⁴ Carvedilol is primarily excreted in the bile and feces.^5,6

Half-life

The half life of carvedilol is between 7-10 hours, though significantly shorter half lives have also been reported.^4,5,6

Clearance

The plasma clearance of carvedilol has been reported as 0.52L/kg⁴ or 500-700mL/min.^5,6

Adverse Effects

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Toxicity

Patients experiencing an overdose may present with hypotension, bradycardia, cardiac insufficiency, cardiogenic shock, and cardiac arrest.^5,6 Patients should remain in a supine position and may be given atropine for bradycardia and glucagon followed by sympathomimetics to support cardiovascular function.^5,6

Pathways

Pathway	Category
Carvedilol Action Pathway	Drug action

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Interacting Gene/Enzyme	Allele name	Genotype(s)	Defining Change(s)	Type(s)	Description	Details
Beta-1 adrenergic receptor	---	(C;C) / (C;G) / (A;A)	C Allele, homozygous	Effect Directly Studied	Patients with this genotype in ADRB1 have an increased likelihood of responding to carvedilol for the treatment of increased blood pressure.	Details
Cytochrome P450 2D6	CYP2D6*3	Not Available	C allele	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*4	Not Available	C allele	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*5	Not Available	Whole-gene deletion	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*6	Not Available	1707delT	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*7	Not Available	2935A>C	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*8	Not Available	1758G>T	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*11	Not Available	883G>C	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*12	Not Available	124G>A	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*13	Not Available	CYP2D7/2D6 hybrid gene structure	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*14A	Not Available	1758G>A	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*15	Not Available	137insT, 137_138insT	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*19	Not Available	2539_2542delAACT	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*20	Not Available	1973_1974insG	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*21	Not Available	2573insC	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*31	Not Available	-1770G>A / -1584C>G … show all	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*36	Not Available	100C>T / -1426C>T … show all	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*38	Not Available	2587_2590delGACT	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*40	Not Available	1863_1864ins(TTT CGC CCC)2	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*42	Not Available	3259_3260insGT	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*44	Not Available	2950G>C	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*47	Not Available	100C>T / -1426C>T … show all	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*51	Not Available	-1584C>G / -1235A>G … show all	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*56	Not Available	3201C>T	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*57	Not Available	100C>T / 310G>T … show all	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*62	Not Available	4044C>T	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*68A	Not Available	-1426C>T / -1235A>G … show all	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*68B	Not Available	Similar but not identical switch region compared to CYP2D668A. Found in tandem arrangement with CYP2D64.	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*69	Not Available	2988G>A / -1426C>T … show all	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*92	Not Available	1995delC	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*100	Not Available	-1426C>T / -1235A>G … show all	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details
Cytochrome P450 2D6	CYP2D6*101	Not Available	-1426C>T / -1235A>G … show all	Effect Inferred	Poor drug metabolizer, increased dizziness.	Details

Interactions

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This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abaloparatide	The risk or severity of adverse effects can be increased when Carvedilol is combined with Abaloparatide.
Abametapir	The serum concentration of Carvedilol can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Carvedilol can be increased when combined with Abatacept.
Abemaciclib	The serum concentration of Abemaciclib can be increased when it is combined with Carvedilol.
Abiraterone	The serum concentration of Carvedilol can be increased when it is combined with Abiraterone.

Food Interactions

Take with food. Food slows the absorption and reduces the incidence of adverse effects.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Carvedilol phosphate	EQT531S367	610309-89-2	LHNYXTULDSJZRB-UHFFFAOYSA-N

Product Images

International/Other Brands

COREGCR

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Carvedilol	Tablet	25 mg	Oral	Sanis Health Inc	2011-06-10	Not applicable
Carvedilol	Tablet	12.5 mg	Oral	Pro Doc Limitee	2009-06-12	Not applicable
Carvedilol	Tablet	25 mg	Oral	Sivem Pharmaceuticals Ulc	2004-04-06	Not applicable
Carvedilol	Tablet	3.125 mg	Oral	Sanis Health Inc	2011-06-10	Not applicable
Carvedilol	Tablet	3.125 mg	Oral	Sivem Pharmaceuticals Ulc	2004-04-06	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Apo-carvedilol	Tablet	25 mg	Oral	Apotex Corporation	2003-08-06	Not applicable
Apo-carvedilol	Tablet	3.125 mg	Oral	Apotex Corporation	2003-08-06	Not applicable
Apo-carvedilol	Tablet	12.5 mg	Oral	Apotex Corporation	2003-08-06	Not applicable
Apo-carvedilol	Tablet	6.25 mg	Oral	Apotex Corporation	2003-08-06	Not applicable
Auro-carvedilol	Tablet	12.5 mg	Oral	Auro Pharma Inc	2014-02-06	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Co-Dilatrend 25 mg/12,5 mg - Filmtabletten	Carvedilol (25 mg) + Hydrochlorothiazide (12.5 mg)	Tablet, film coated	Oral	Cheplapharm Arzneimittel Gmb H	1998-06-18	Not applicable

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Hypertenevide-12.5	Carvedilol (12.5 mg/1) + Arginine (60 mg/1)	Kit	Oral	Physician Therapeutics Llc	2011-07-07	Not applicable

Chemical Identifiers

UNII: 0K47UL67F2
CAS number: 72956-09-3
InChI Key: OGHNVEJMJSYVRP-UHFFFAOYSA-N
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
IUPAC Name: 1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol
SMILES: COC1=CC=CC=C1OCCNCC(O)COC1=CC=CC2=C1C1=CC=CC=C1N2

References

Synthesis Reference

Ilan Kor, "Crystalline solids of carvedilol and processes for their preparation." U.S. Patent US20030166702, issued September 04, 2003.

US20030166702

General References

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. [Article]
Oldham HG, Clarke SE: In vitro identification of the human cytochrome P450 enzymes involved in the metabolism of R(+)- and S(-)-carvedilol. Drug Metab Dispos. 1997 Aug;25(8):970-7. [Article]
Takekuma Y, Yagisawa K, Sugawara M: Mutual inhibition between carvedilol enantiomers during racemate glucuronidation mediated by human liver and intestinal microsomes. Biol Pharm Bull. 2012;35(2):151-63. doi: 10.1248/bpb.35.151. [Article]
Morgan T: Clinical pharmacokinetics and pharmacodynamics of carvedilol. Clin Pharmacokinet. 1994 May;26(5):335-46. doi: 10.2165/00003088-199426050-00002. [Article]
FDA Approved Drug Products: Carvedilol Oral Tablets [Link]
FDA Approved Drug Products: Carvedilol Oral Extended Release Capsules [Link]

External Links

Human Metabolome Database: HMDB0015267
KEGG Drug: D00255
KEGG Compound: C06875
PubChem Compound: 2585
PubChem Substance: 46505146
ChemSpider: 2487
BindingDB: 25759
RxNav: 20352
ChEBI: 3441
ChEMBL: CHEMBL723
Therapeutic Targets Database: DAP000135
PharmGKB: PA448817
Guide to Pharmacology: GtP Drug Page
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Carvedilol

FDA label

Download (1.25 MB)

MSDS

Download (32.9 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Basic Science	Acute Coronary Syndrome (ACS)	1
4	Completed	Basic Science	Dilated Cardiomyopathies, Idiopathic	1
4	Completed	Diagnostic	Cardiomyopathy / Heart Failure	1
4	Completed	Diagnostic	Diabetes	1
4	Completed	Other	Cardiac Failure / Cardiovascular Disease (CVD) / Heart Failure / Heart Failure With Preserved Ejection Fraction (HFpEF) / Heart Failure, Diastolic	2

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Actavis Group
Advantage Dose LLC
Amerisource Health Services Corp.
Apotex Inc.
A-S Medication Solutions LLC
Atlantic Biologicals Corporation
Aurobindo Pharma Ltd.
Bryant Ranch Prepack
Cadila Healthcare Ltd.
Caraco Pharmaceutical Labs
Cardinal Health
Caremark LLC
Dept Health Central Pharmacy
DHHS Program Support Center Supply Service Center
Dispensing Solutions
Diversified Healthcare Services Inc.
Doctor Reddys Laboratories Ltd.
GlaxoSmithKline Inc.
Glenmark Generics Ltd.
Hikma Pharmaceuticals
Kaiser Foundation Hospital
Lupin Pharmaceuticals Inc.
Major Pharmaceuticals
Mckesson Corp.
Murfreesboro Pharmaceutical Nursing Supply
Mylan
Ohm Laboratories Inc.
Patheon Inc.
PD-Rx Pharmaceuticals Inc.
Physicians Total Care Inc.
Prepak Systems Inc.
Ranbaxy Laboratories
Rebel Distributors Corp.
Remedy Repack
Resource Optimization and Innovation LLC
Sandoz
Shasun Chemicals & Drugs Ltd.
Solco Healthcare US LLC
Southwood Pharmaceuticals
Taro Pharmaceuticals USA
Teva Pharmaceutical Industries Ltd.
UDL Laboratories
Vangard Labs Inc.
West-Ward Pharmaceuticals
Zydus Pharmaceuticals

Dosage Forms

Form	Route	Strength
Tablet	Oral
Tablet	Oral	25.000 mg
Tablet	Oral	1250000 mg
Tablet	Oral	2500000 mg
Tablet, film coated	Oral
Tablet, film coated	Oral	12.5 MG
Tablet, film coated	Oral	25 MG
Tablet, film coated	Oral	6.25 MG
Tablet	Oral	12.5 mg/1
Tablet	Oral	25 mg/1
Tablet	Oral	25.0 mg
Tablet	Oral	3.125 mg/1
Tablet	Oral	6.25 mg/1
Tablet, coated	Oral	12.5 mg/1
Tablet, coated	Oral	25 mg/1
Tablet, coated	Oral	3.125 mg/1
Tablet, coated	Oral	6.25 mg/1
Tablet, film coated	Oral	12.5 mg/1
Tablet, film coated	Oral	12.5 mg/301
Tablet, film coated	Oral	25 mg/1
Tablet, film coated	Oral	3.125 mg/1
Tablet, film coated	Oral	6.25 mg/1
Tablet	Oral
Tablet, film coated	Oral
Tablet, coated	Oral	12.5 mg
Tablet, coated	Oral	2500000 mg
Tablet, coated	Oral	6.25 mg
Tablet, film coated	Oral	3.125 MG
Tablet	Oral	3125 MG
Tablet, film coated	Oral	3125 MG
Tablet	Oral	25 MG
Capsule, extended release	Oral	10 mg/1
Capsule, extended release	Oral	20 mg/1
Capsule, extended release	Oral	40 mg/1
Capsule, extended release	Oral	80 mg/1
Tablet	Oral	6.250 mg
Tablet	Oral	50 mg
Tablet	Oral	625000 mg
Kit	Oral
Tablet	Oral	3.125 mg
Tablet, coated	Oral	25 mg
Tablet, film coated	Oral	12.500 mg
Tablet, film coated	Oral	25.000 mg
Tablet, film coated	Oral	6.250 mg
Tablet	Oral	12.5 mg
Tablet	Oral	6.25 mg

Prices

Unit description	Cost	Unit
Coreg CR 10 mg 24 Hour Capsule	4.77USD	capsule
Coreg CR 20 mg 24 Hour Capsule	4.77USD	capsule
Coreg CR 40 mg 24 Hour Capsule	4.77USD	capsule
Coreg CR 80 mg 24 Hour Capsule	4.77USD	capsule
Coreg cr 10 mg capsule	4.59USD	capsule
Coreg cr 20 mg capsule	4.59USD	capsule
Coreg cr 40 mg capsule	4.59USD	capsule
Coreg cr 80 mg capsule	4.59USD	capsule
Coreg 12.5 mg tablet	2.54USD	tablet
Coreg 25 mg tablet	2.54USD	tablet
Coreg 3.125 mg tablet	2.54USD	tablet
Coreg 6.25 mg tablet	2.54USD	tablet
Carvedilol 12.5 mg tablet	2.18USD	tablet
Carvedilol 25 mg tablet	2.18USD	tablet
Carvedilol 3.125 mg tablet	2.18USD	tablet
Carvedilol 6.25 mg tablet	2.18USD	tablet
Apo-Carvedilol 12.5 mg Tablet	0.84USD	tablet
Apo-Carvedilol 25 mg Tablet	0.84USD	tablet
Apo-Carvedilol 3.125 mg Tablet	0.84USD	tablet
Apo-Carvedilol 6.25 mg Tablet	0.84USD	tablet
Phl-Carvedilol 12.5 mg Tablet	0.79USD	tablet
Phl-Carvedilol 3.125 mg Tablet	0.79USD	tablet
Phl-Carvedilol 6.25 mg Tablet	0.79USD	tablet
Pms-Carvedilol 12.5 mg Tablet	0.79USD	tablet
Pms-Carvedilol 25 mg Tablet	0.79USD	tablet
Pms-Carvedilol 3.125 mg Tablet	0.79USD	tablet
Pms-Carvedilol 6.25 mg Tablet	0.79USD	tablet
Ran-Carvedilol 12.5 mg Tablet	0.79USD	tablet
Ran-Carvedilol 25 mg Tablet	0.79USD	tablet
Ran-Carvedilol 3.125 mg Tablet	0.79USD	tablet
Ran-Carvedilol 6.25 mg Tablet	0.79USD	tablet
Ratio-Carvedilol 12.5 mg Tablet	0.79USD	tablet
Ratio-Carvedilol 25 mg Tablet	0.79USD	tablet
Ratio-Carvedilol 3.125 mg Tablet	0.79USD	tablet
Ratio-Carvedilol 6.25 mg Tablet	0.79USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US7268156	Yes	2007-09-11	2023-12-27
US8101209	Yes	2012-01-24	2026-03-11
US6022562	Yes	2000-02-08	2016-04-17
USRE40000	Yes	2008-01-08	2015-12-07

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	114.5 °C	http://www.chemspider.com/Chemical-Structure.2487.html
water solubility	88mg/mL	http://www.chemspider.com/Chemical-Structure.2487.html
logP	3.8	https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6361727/

Predicted Properties

Property	Value	Source
Water Solubility	0.00444 mg/mL	ALOGPS
logP	3.05	ALOGPS
logP	3.42	Chemaxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.03	Chemaxon
pKa (Strongest Basic)	8.74	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	75.74 Å²	Chemaxon
Rotatable Bond Count	10	Chemaxon
Refractivity	115.64 m³·mol^-1	Chemaxon
Polarizability	45.03 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.9706
Blood Brain Barrier	-	0.6814
Caco-2 permeable	-	0.6308
P-glycoprotein substrate	Substrate	0.8552
P-glycoprotein inhibitor I	Non-inhibitor	0.8729
P-glycoprotein inhibitor II	Non-inhibitor	0.6521
Renal organic cation transporter	Non-inhibitor	0.5405
CYP450 2C9 substrate	Non-substrate	0.7517
CYP450 2D6 substrate	Substrate	0.8918
CYP450 3A4 substrate	Substrate	0.5408
CYP450 1A2 substrate	Inhibitor	0.524
CYP450 2C9 inhibitor	Non-inhibitor	0.8496
CYP450 2D6 inhibitor	Non-inhibitor	0.7274
CYP450 2C19 inhibitor	Non-inhibitor	0.5676
CYP450 3A4 inhibitor	Non-inhibitor	0.6352
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.6048
Ames test	Non AMES toxic	0.8261
Carcinogenicity	Non-carcinogens	0.9692
Biodegradation	Not ready biodegradable	0.963
Rat acute toxicity	2.4566 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.5725
hERG inhibition (predictor II)	Inhibitor	0.8889

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-001j-2930000000-265c376e802c07cf1f2d
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a4i-1662900000-f901a62f255da92e9a09
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a4i-0220900000-5821022307fc5077033b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0540-0191400000-6ca107cb7cfb8a8df480
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-1920100000-260ea815e32284b67e6e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0uyi-0692100000-94603f19885f76f25d91
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-0910000000-fdc780b7f84ab5fc815b
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0c0r-3921000000-87acb72afee99d28a2e1
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-001i-0900000000-6537a5cf26732e4e5abf
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[M-H]-	198.3687664	predicted	DarkChem Lite v0.1.0
[M-H]-	183.00732	predicted	DeepCCS 1.0 (2019)
[M+H]+	198.7501664	predicted	DarkChem Lite v0.1.0
[M+H]+	185.36533	predicted	DeepCCS 1.0 (2019)
[M+Na]+	198.3830664	predicted	DarkChem Lite v0.1.0
[M+Na]+	193.39514	predicted	DeepCCS 1.0 (2019)

Targets

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Property	Measurement	pH	Temperature (°C)	References
Kd (nM)	1.76	7.4	37	A15307
Ki (nM)	1.7	N/A	N/A	A15544

Details1. Beta-1 adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist

General Function: Receptor signaling protein activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Gene Name: ADRB1
Uniprot ID: P08588
Uniprot Name: Beta-1 adrenergic receptor
Molecular Weight: 51322.1 Da

References

Nichols AJ, Gellai M, Ruffolo RR Jr: Studies on the mechanism of arterial vasodilation produced by the novel antihypertensive agent, carvedilol. Fundam Clin Pharmacol. 1991;5(1):25-38. [Article]
Nichols AJ, Sulpizio AC, Ashton DJ, Hieble JP, Ruffolo RR Jr: In vitro pharmacologic profile of the novel beta-adrenoceptor antagonist and vasodilator, carvedilol. Pharmacology. 1989;39(5):327-36. [Article]
Nichols AJ, Sulpizio AC, Ashton DJ, Hieble JP, Ruffolo RR Jr: The interaction of the enantiomers of carvedilol with alpha 1- and beta 1-adrenoceptors. Chirality. 1989;1(4):265-70. [Article]
de Mey C, Breithaupt K, Schloos J, Neugebauer G, Palm D, Belz GG: Dose-effect and pharmacokinetic-pharmacodynamic relationships of the beta 1-adrenergic receptor blocking properties of various doses of carvedilol in healthy humans. Clin Pharmacol Ther. 1994 Mar;55(3):329-37. [Article]

Details2. Alpha-1A adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist
Potentiator
Curator comments: This drug is a non-selective alpha antagonist.

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name: ADRA1A
Uniprot ID: P35348
Uniprot Name: Alpha-1A adrenergic receptor
Molecular Weight: 51486.005 Da

References

O'Connell TD, Jensen BC, Baker AJ, Simpson PC: Cardiac alpha1-adrenergic receptors: novel aspects of expression, signaling mechanisms, physiologic function, and clinical importance. Pharmacol Rev. 2013 Dec 24;66(1):308-33. doi: 10.1124/pr.112.007203. Print 2014. [Article]
Jensen BC, Swigart PM, De Marco T, Hoopes C, Simpson PC: {alpha}1-Adrenergic receptor subtypes in nonfailing and failing human myocardium. Circ Heart Fail. 2009 Nov;2(6):654-63. doi: 10.1161/CIRCHEARTFAILURE.108.846212. Epub 2009 Aug 6. [Article]

Details3. Alpha-1 adrenergic receptors (Protein Group)

Kind: Protein group
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...

Components:

Name	UniProt ID
Alpha-1A adrenergic receptor	P35348
Alpha-1B adrenergic receptor	P35368
Alpha-1D adrenergic receptor	P25100

References

O'Connell TD, Jensen BC, Baker AJ, Simpson PC: Cardiac alpha1-adrenergic receptors: novel aspects of expression, signaling mechanisms, physiologic function, and clinical importance. Pharmacol Rev. 2013 Dec 24;66(1):308-33. doi: 10.1124/pr.112.007203. Print 2014. [Article]

Details4. NADH dehydrogenase [ubiquinone] 1 subunit C2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Nadh dehydrogenase (ubiquinone) activity
Specific Function: Accessory subunit of the mitochondrial membrane respiratory chain NADH dehydrogenase (Complex I), that is believed not to be involved in catalysis. Complex I functions in the transfer of electrons ...
Gene Name: NDUFC2
Uniprot ID: O95298
Uniprot Name: NADH dehydrogenase [ubiquinone] 1 subunit C2
Molecular Weight: 14187.33 Da

References

Oliveira PJ, Santos DJ, Moreno AJ: Carvedilol inhibits the exogenous NADH dehydrogenase in rat heart mitochondria. Arch Biochem Biophys. 2000 Feb 15;374(2):279-85. [Article]

Details5. Beta-2 adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Protein homodimerization activity
Specific Function: Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately ...
Gene Name: ADRB2
Uniprot ID: P07550
Uniprot Name: Beta-2 adrenergic receptor
Molecular Weight: 46458.32 Da

References

Irodova NL, Krasnikova TL, Masenko VP, Kochetov AG, Chazova IE: [Carvedilol in treating primary pulmonary hypertension patients: effect on severity of cardiac failure, degree of pulmonary hypertension, concentration of catecholamines in blood plasma and dependence of cyclic AMP synthesis in lymphocytes on beta-adrenergic receptors]. Ter Arkh. 2002;74(8):30-4. [Article]
Maebara C, Ohtani H, Sugahara H, Mine K, Kubo C, Sawada Y: Nightmares and panic disorder associated with carvedilol overdose. Ann Pharmacother. 2002 Nov;36(11):1736-40. [Article]
Okajima K, Harada N, Uchiba M, Isobe H: Activation of capsaicin-sensitive sensory neurons by carvedilol, a nonselective beta-blocker, in spontaneous hypertensive rats. J Pharmacol Exp Ther. 2004 May;309(2):684-91. Epub 2004 Feb 5. [Article]
Nichols AJ, Gellai M, Ruffolo RR Jr: Studies on the mechanism of arterial vasodilation produced by the novel antihypertensive agent, carvedilol. Fundam Clin Pharmacol. 1991;5(1):25-38. [Article]

Details6. Vascular endothelial growth factor A

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Other

General Function: Vascular endothelial growth factor receptor binding
Specific Function: Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of...
Gene Name: VEGFA
Uniprot ID: P15692
Uniprot Name: Vascular endothelial growth factor A
Molecular Weight: 27042.205 Da

References

de Boer RA, Siebelink HJ, Tio RA, Boomsma F, van Veldhuisen DJ: Carvedilol increases plasma vascular endothelial growth factor (VEGF) in patients with chronic heart failure. Eur J Heart Fail. 2001 Jun;3(3):331-3. [Article]
Saijonmaa O, Nyman T, Fyhrquist F: Carvedilol inhibits basal and stimulated ACE production in human endothelial cells. J Cardiovasc Pharmacol. 2004 May;43(5):616-21. [Article]
Shyu KG, Lu MJ, Chang H, Sun HY, Wang BW, Kuan P: Carvedilol modulates the expression of hypoxia-inducible factor-1alpha and vascular endothelial growth factor in a rat model of volume-overload heart failure. J Card Fail. 2005 Mar;11(2):152-9. [Article]
Shyu KG, Liou JY, Wang BW, Fang WJ, Chang H: Carvedilol prevents cardiac hypertrophy and overexpression of hypoxia-inducible factor-1alpha and vascular endothelial growth factor in pressure-overloaded rat heart. J Biomed Sci. 2005;12(2):409-20. [Article]

Details7. Natriuretic peptides B

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Other

General Function: Receptor binding
Specific Function: Cardiac hormone which may function as a paracrine antifibrotic factor in the heart. Also plays a key role in cardiovascular homeostasis through natriuresis, diuresis, vasorelaxation, and inhibition...
Gene Name: NPPB
Uniprot ID: P16860
Uniprot Name: Natriuretic peptides B
Molecular Weight: 14725.825 Da

References

Ohta Y, Watanabe K, Nakazawa M, Yamamoto T, Ma M, Fuse K, Ito M, Hirono S, Tanabe T, Hanawa H, Kato K, Kodama M, Aizawa Y: Carvedilol enhances atrial and brain natriuretic peptide mRNA expression and release in rat heart. J Cardiovasc Pharmacol. 2000;36 Suppl 2:S19-23. [Article]
Richards AM, Doughty R, Nicholls MG, MacMahon S, Sharpe N, Murphy J, Espiner EA, Frampton C, Yandle TG: Plasma N-terminal pro-brain natriuretic peptide and adrenomedullin: prognostic utility and prediction of benefit from carvedilol in chronic ischemic left ventricular dysfunction. Australia-New Zealand Heart Failure Group. J Am Coll Cardiol. 2001 Jun 1;37(7):1781-7. [Article]
Konishi H, Nishio S, Tsutamoto T, Minouchi T, Yamaji A: Serum carvedilol concentration and its relation to change in plasma brain natriuretic peptide level in the treatment of heart failure: a preliminary study. Int J Clin Pharmacol Ther. 2003 Dec;41(12):578-86. [Article]
Takeda Y, Fukutomi T, Suzuki S, Yamamoto K, Ogata M, Kondo H, Sugiura M, Shigeyama J, Itoh M: Effects of carvedilol on plasma B-type natriuretic peptide concentration and symptoms in patients with heart failure and preserved ejection fraction. Am J Cardiol. 2004 Aug 15;94(4):448-53. [Article]
Frantz RP, Olson LJ, Grill D, Moualla SK, Nelson SM, Nobrega TP, Hanna RD, Backes RJ, Mookadam F, Heublein D, Bailey KR, Burnett JC: Carvedilol therapy is associated with a sustained decline in brain natriuretic peptide levels in patients with congestive heart failure. Am Heart J. 2005 Mar;149(3):541-7. [Article]

Details8. Gap junction alpha-1 protein

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Other

General Function: Signal transducer activity
Specific Function: Gap junction protein that acts as a regulator of bladder capacity. A gap junction consists of a cluster of closely packed pairs of transmembrane channels, the connexons, through which materials of ...
Gene Name: GJA1
Uniprot ID: P17302
Uniprot Name: Gap junction alpha-1 protein
Molecular Weight: 43008.005 Da

References

Yeh HI, Lee PY, Su CH, Tian TY, Ko YS, Tsai CH: Reduced expression of endothelial connexins 43 and 37 in hypertensive rats is rectified after 7-day carvedilol treatment. Am J Hypertens. 2006 Feb;19(2):129-35. [Article]
Fan SY, Ke YN, Zeng YJ, Wang Y, Cheng WL, Yang JR: [Effects and the mechanism of carvedilol on gap junctional intercellular communication in rat myocardium]. Zhonghua Xin Xue Guan Bing Za Zhi. 2005 Dec;33(12):1141-5. [Article]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	10471	N/A	N/A	A18337
IC 50 (nM)	350	N/A	N/A	A18340
IC 50 (nM)	10471.29	N/A	N/A	A27428 / A27431
IC 50 (nM)	12589.25	N/A	N/A	A27558

Details9. Potassium voltage-gated channel subfamily H member 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
Specific Function: Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
Gene Name: KCNH2
Uniprot ID: Q12809
Uniprot Name: Potassium voltage-gated channel subfamily H member 2
Molecular Weight: 126653.52 Da

References

Karle CA, Kreye VA, Thomas D, Rockl K, Kathofer S, Zhang W, Kiehn J: Antiarrhythmic drug carvedilol inhibits HERG potassium channels. Cardiovasc Res. 2001 Feb 1;49(2):361-70. [Article]
Kawakami K, Nagatomo T, Abe H, Kikuchi K, Takemasa H, Anson BD, Delisle BP, January CT, Nakashima Y: Comparison of HERG channel blocking effects of various beta-blockers-- implication for clinical strategy. Br J Pharmacol. 2006 Mar;147(6):642-52. [Article]

Details10. Vascular cell adhesion protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Primary amine oxidase activity
Specific Function: Important in cell-cell recognition. Appears to function in leukocyte-endothelial cell adhesion. Interacts with integrin alpha-4/beta-1 (ITGA4/ITGB1) on leukocytes, and mediates both adhesion and si...
Gene Name: VCAM1
Uniprot ID: P19320
Uniprot Name: Vascular cell adhesion protein 1
Molecular Weight: 81275.43 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Chen JW, Lin FY, Chen YH, Wu TC, Chen YL, Lin SJ: Carvedilol inhibits tumor necrosis factor-alpha-induced endothelial transcription factor activation, adhesion molecule expression, and adhesiveness to human mononuclear cells. Arterioscler Thromb Vasc Biol. 2004 Nov;24(11):2075-81. Epub 2004 Sep 16. [Article]

Details11. Alpha-1D adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Alpha1-adrenergic receptor activity
Specific Function: This alpha-adrenergic receptor mediates its effect through the influx of extracellular calcium.
Gene Name: ADRA1D
Uniprot ID: P25100
Uniprot Name: Alpha-1D adrenergic receptor
Molecular Weight: 60462.205 Da

References

Koshimizu TA, Tsujimoto G, Hirasawa A, Kitagawa Y, Tanoue A: Carvedilol selectively inhibits oscillatory intracellular calcium changes evoked by human alpha1D- and alpha1B-adrenergic receptors. Cardiovasc Res. 2004 Sep 1;63(4):662-72. [Article]
Van Tassell BW, Rondina MT, Huggins F, Gilbert EM, Munger MA: Carvedilol increases blood pressure response to phenylephrine infusion in heart failure subjects with systolic dysfunction: evidence of improved vascular alpha1-adrenoreceptor signal transduction. Am Heart J. 2008 Aug;156(2):315-21. doi: 10.1016/j.ahj.2008.04.004. Epub 2008 Jun 20. [Article]

Details12. Alpha-1B adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Protein heterodimerization activity
Specific Function: This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name: ADRA1B
Uniprot ID: P35368
Uniprot Name: Alpha-1B adrenergic receptor
Molecular Weight: 56835.375 Da

References

Koshimizu TA, Tsujimoto G, Hirasawa A, Kitagawa Y, Tanoue A: Carvedilol selectively inhibits oscillatory intracellular calcium changes evoked by human alpha1D- and alpha1B-adrenergic receptors. Cardiovasc Res. 2004 Sep 1;63(4):662-72. [Article]

Details13. Alpha-2C adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Protein homodimerization activity
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins.
Gene Name: ADRA2C
Uniprot ID: P18825
Uniprot Name: Alpha-2C adrenergic receptor
Molecular Weight: 49521.585 Da

References

Koshimizu TA, Tsujimoto G, Hirasawa A, Kitagawa Y, Tanoue A: Carvedilol selectively inhibits oscillatory intracellular calcium changes evoked by human alpha1D- and alpha1B-adrenergic receptors. Cardiovasc Res. 2004 Sep 1;63(4):662-72. [Article]

Details14. Alpha-2B adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Epinephrine binding
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is clonidine...
Gene Name: ADRA2B
Uniprot ID: P18089
Uniprot Name: Alpha-2B adrenergic receptor
Molecular Weight: 49565.8 Da

References

Koshimizu TA, Tsujimoto G, Hirasawa A, Kitagawa Y, Tanoue A: Carvedilol selectively inhibits oscillatory intracellular calcium changes evoked by human alpha1D- and alpha1B-adrenergic receptors. Cardiovasc Res. 2004 Sep 1;63(4):662-72. [Article]

Details15. Alpha-2A adrenergic receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Antagonist

General Function: Thioesterase binding
Specific Function: Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name: ADRA2A
Uniprot ID: P08913
Uniprot Name: Alpha-2A adrenergic receptor
Molecular Weight: 48956.275 Da

References

Koshimizu TA, Tsujimoto G, Hirasawa A, Kitagawa Y, Tanoue A: Carvedilol selectively inhibits oscillatory intracellular calcium changes evoked by human alpha1D- and alpha1B-adrenergic receptors. Cardiovasc Res. 2004 Sep 1;63(4):662-72. [Article]

Details16. E-selectin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Transmembrane signaling receptor activity
Specific Function: Cell-surface glycoprotein having a role in immunoadhesion. Mediates in the adhesion of blood neutrophils in cytokine-activated endothelium through interaction with PSGL1/SELPLG. May have a role in ...
Gene Name: SELE
Uniprot ID: P16581
Uniprot Name: E-selectin
Molecular Weight: 66654.575 Da

References

Chen JW, Lin FY, Chen YH, Wu TC, Chen YL, Lin SJ: Carvedilol inhibits tumor necrosis factor-alpha-induced endothelial transcription factor activation, adhesion molecule expression, and adhesiveness to human mononuclear cells. Arterioscler Thromb Vasc Biol. 2004 Nov;24(11):2075-81. Epub 2004 Sep 16. [Article]

Details17. Hypoxia-inducible factor 1-alpha

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Modulator

General Function: Ubiquitin protein ligase binding
Specific Function: Functions as a master transcriptional regulator of the adaptive response to hypoxia. Under hypoxic conditions, activates the transcription of over 40 genes, including erythropoietin, glucose transp...
Gene Name: HIF1A
Uniprot ID: Q16665
Uniprot Name: Hypoxia-inducible factor 1-alpha
Molecular Weight: 92669.595 Da

References

Shyu KG, Lu MJ, Chang H, Sun HY, Wang BW, Kuan P: Carvedilol modulates the expression of hypoxia-inducible factor-1alpha and vascular endothelial growth factor in a rat model of volume-overload heart failure. J Card Fail. 2005 Mar;11(2):152-9. [Article]

Details18. Inward rectifier potassium channel 4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Pdz domain binding
Specific Function: Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentratio...
Gene Name: KCNJ4
Uniprot ID: P48050
Uniprot Name: Inward rectifier potassium channel 4
Molecular Weight: 49499.61 Da

References

Ferrer T, Ponce-Balbuena D, Lopez-Izquierdo A, Arechiga-Figueroa IA, de Boer TP, van der Heyden MA, Sanchez-Chapula JA: Carvedilol inhibits Kir2.3 channels by interference with PIP(2)-channel interaction. Eur J Pharmacol. 2011 Oct 1;668(1-2):72-7. doi: 10.1016/j.ejphar.2011.05.067. Epub 2011 Jun 6. [Article]

Details19. Inward rectifier potassium channel 2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Probably participates in establishing action potential waveform and excitability of neuronal and muscle tissues. Inward rectifier potassium channels are characterized by a greater tendency to allow potassium to flow into the cell rather than out of it. Their voltage dependence is regulated by the concentration of extracellular potassium; as external potassium is raised, the voltage range of the channel opening shifts to more positive voltages. The inward rectification is mainly due to the blockage of outward current by internal magnesium. Can be blocked by extracellular barium or cesium.
Specific Function: Identical protein binding
Gene Name: KCNJ2
Uniprot ID: P63252
Uniprot Name: Inward rectifier potassium channel 2
Molecular Weight: 48287.82 Da

References

Ferrer T, Ponce-Balbuena D, Lopez-Izquierdo A, Arechiga-Figueroa IA, de Boer TP, van der Heyden MA, Sanchez-Chapula JA: Carvedilol inhibits Kir2.3 channels by interference with PIP(2)-channel interaction. Eur J Pharmacol. 2011 Oct 1;668(1-2):72-7. doi: 10.1016/j.ejphar.2011.05.067. Epub 2011 Jun 6. [Article]

Enzymes

Details1. Cytochrome P450 1A2

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A2
Uniprot ID: P05177
Uniprot Name: Cytochrome P450 1A2
Molecular Weight: 58293.76 Da

References

Oldham HG, Clarke SE: In vitro identification of the human cytochrome P450 enzymes involved in the metabolism of R(+)- and S(-)-carvedilol. Drug Metab Dispos. 1997 Aug;25(8):970-7. [Article]
Parker BM, Rogers SL, Lymperopoulos A: Clinical pharmacogenomics of carvedilol: the stereo-selective metabolism angle. Pharmacogenomics. 2018 Sep 1;19(14):1089-1093. doi: 10.2217/pgs-2018-0115. Epub 2018 Aug 8. [Article]
Abrudan MB, Popa DS, Muntean DM, Gheldiu AM, Vlase L: Pharmacokinetic interactions study between carvedilol and some antidepressants in rat liver microsomes - a comparative study. Med Pharm Rep. 2019 Apr;92(2):158-164. doi: 10.15386/mpr-1225. Epub 2019 Apr 25. [Article]
FDA label, Carvedilol [File]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Wang Z, Wang L, Xu RA, Zhan YY, Huang CK, Dai DP, Cai JP, Hu GX: Role of cytochrome P450 2D6 genetic polymorphism in carvedilol hydroxylation in vitro. Drug Des Devel Ther. 2016 Jun 8;10:1909-16. doi: 10.2147/DDDT.S106175. eCollection 2016. [Article]
Oldham HG, Clarke SE: In vitro identification of the human cytochrome P450 enzymes involved in the metabolism of R(+)- and S(-)-carvedilol. Drug Metab Dispos. 1997 Aug;25(8):970-7. [Article]
Carvedilol Therapy and CYP2D6 Genotype [Link]

Details3. Cytochrome P450 1A1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Vitamin d 24-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP1A1
Uniprot ID: P04798
Uniprot Name: Cytochrome P450 1A1
Molecular Weight: 58164.815 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]

Details4. Cytochrome P450 2E1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name: CYP2E1
Uniprot ID: P05181
Uniprot Name: Cytochrome P450 2E1
Molecular Weight: 56848.42 Da

References

Oldham HG, Clarke SE: In vitro identification of the human cytochrome P450 enzymes involved in the metabolism of R(+)- and S(-)-carvedilol. Drug Metab Dispos. 1997 Aug;25(8):970-7. [Article]
Carvedilol Therapy and CYP2D6 Genotype [Link]

Details5. UDP-glucuronosyltransferase 1-1

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Steroid binding
Specific Function: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
Gene Name: UGT1A1
Uniprot ID: P22309
Uniprot Name: UDP-glucuronosyltransferase 1-1
Molecular Weight: 59590.91 Da

References

Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [Article]

Details6. UDP-glucuronosyltransferase 2B4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Glucuronosyltransferase activity
Specific Function: UDPGTs are of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isozyme is active on polyhydroxylated estrogens (such as...
Gene Name: UGT2B4
Uniprot ID: P06133
Uniprot Name: UDP-glucuronosyltransferase 2B4
Molecular Weight: 60512.035 Da

References

Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [Article]

Details7. UDP-glucuronosyltransferase 2B7

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Glucuronosyltransferase activity
Specific Function: UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
Gene Name: UGT2B7
Uniprot ID: P16662
Uniprot Name: UDP-glucuronosyltransferase 2B7
Molecular Weight: 60694.12 Da

References

Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [Article]

Details8. Cytochrome P450 2C9

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name: CYP2C9
Uniprot ID: P11712
Uniprot Name: Cytochrome P450 2C9
Molecular Weight: 55627.365 Da

References

Pan PP, Weng QH, Zhou CJ, Wei YL, Wang L, Dai DP, Cai JP, Hu GX: The role of CYP2C9 genetic polymorphism in carvedilol O-desmethylation in vitro. Eur J Drug Metab Pharmacokinet. 2016 Feb;41(1):79-86. doi: 10.1007/s13318-014-0245-2. Epub 2014 Dec 5. [Article]
Laura Dean, MD (2012). Medical Genetics Summaries : Carvedilol Therapy and CYP2D6 Genotype. National Center for Biotechnology Information (US).
Carvedilol Therapy and CYP2D6 Genotype [Link]
Carvedilol FDA [File]

Details9. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
Flockhart Table of Drug Interactions [Link]
Carvedilol Therapy and CYP2D6 Genotype [Link]

Details10. Xanthine dehydrogenase/oxidase

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Xanthine oxidase activity
Specific Function: Key enzyme in purine degradation. Catalyzes the oxidation of hypoxanthine to xanthine. Catalyzes the oxidation of xanthine to uric acid. Contributes to the generation of reactive oxygen species. Ha...
Gene Name: XDH
Uniprot ID: P47989
Uniprot Name: Xanthine dehydrogenase/oxidase
Molecular Weight: 146422.99 Da

References

Yue TL, McKenna PJ, Gu JL, Cheng HY, Ruffolo RE Jr, Feuerstein GZ: Carvedilol, a new vasodilating beta adrenoceptor blocker antihypertensive drug, protects endothelial cells from damage initiated by xanthine-xanthine oxidase and neutrophils. Cardiovasc Res. 1994 Mar;28(3):400-6. [Article]

Carriers

Details1. Serum albumin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Binder

General Function: Toxic substance binding
Specific Function: Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name: ALB
Uniprot ID: P02768
Uniprot Name: Serum albumin
Molecular Weight: 69365.94 Da

References

FDA Approved Drug Products: Carvedilol Oral Tablets [Link]
FDA Approved Drug Products: Carvedilol Oral Extended Release Capsules [Link]

Transporters

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	4600	N/A	N/A	A15813
IC 50 (nM)	6600	N/A	N/A	A15813
IC 50 (nM)	6000	N/A	N/A	A15813

Details1. P-glycoprotein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Inhibitor

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [Article]
Takara K, Kakumoto M, Tanigawara Y, Funakoshi J, Sakaeda T, Okumura K: Interaction of digoxin with antihypertensive drugs via MDR1. Life Sci. 2002 Feb 15;70(13):1491-500. [Article]
Jonsson O, Behnam-Motlagh P, Persson M, Henriksson R, Grankvist K: Increase in doxorubicin cytotoxicity by carvedilol inhibition of P-glycoprotein activity. Biochem Pharmacol. 1999 Dec 1;58(11):1801-6. [Article]
Neuhoff S, Langguth P, Dressler C, Andersson TB, Regardh CG, Spahn-Langguth H: Affinities at the verapamil binding site of MDR1-encoded P-glycoprotein: drugs and analogs, stereoisomers and metabolites. Int J Clin Pharmacol Ther. 2000 Apr;38(4):168-79. [Article]
Hokama N, Hobara N, Sakai M, Kameya H, Ohshiro S, Sakanashi M: Influence of nicardipine and nifedipine on plasma carvedilol disposition after oral administration in rats. J Pharm Pharmacol. 2002 Jun;54(6):821-5. [Article]
Kakumoto M, Sakaeda T, Takara K, Nakamura T, Kita T, Yagami T, Kobayashi H, Okamura N, Okumura K: Effects of carvedilol on MDR1-mediated multidrug resistance: comparison with verapamil. Cancer Sci. 2003 Jan;94(1):81-6. [Article]
Brodde OE, Kroemer HK: Drug-drug interactions of beta-adrenoceptor blockers. Arzneimittelforschung. 2003;53(12):814-22. [Article]
FDA Drug Development and Drug Interactions: Table of Substrates, Inhibitors and Inducers [Link]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55

Carvedilol

Identification

Structure for Carvedilol (DB01136)

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Properties

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Enzymes

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Carriers

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