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Carvedilol

CAS：72956-09-3
MW:406.48
MF：C24H26N2O4

Carvedilol is a vasodilating beta-blocker useful in the treatment of hypertension andangina pectoris. In addition to lowering blood pressure, carvedilol decreases totalvascular resistance without the reflex tachycardia usually occurring with vasodilators.It is reported to be well tolerated with renal sparing effects. View more+

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Names and ldentifier
Properties
Use and Manufacturing
Safety and Handling
Msds
Other Information
Computational chemical data
Related Questions
Realated Product Infomation

1. Names and Identifiers

1.1 Name: Carvedilol

1.2 Synonyms: (±)-1-(9H-Carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-2-propanol; 1-(9h-carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-2-propano; 1-(9H-carbazol-4-yloxy)-3-[(2-{[2-(methyloxy)phenyl]oxy}ethyl)amino]propan-2-ol; 1-(9H-CARBAZOL-4-YLOXY)-3-[[2-(2-METHOXYPHENOXY)ETHYL]AMINO]-2-PROPANOL; 1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxy-phenoxy)-ethylamino]-propan-2-ol; 1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-ol; 1-(9H-carbazol-4-yloxy)-3-{[2-(2-méthoxyphénoxy)éthyl]amino}propan-2-ol; 1-(9H-Carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}-2-propanol; 1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]amino}propan-2-ol; 1-(9H-carbazol-4-yloxy)-3-{2-(2-methoxyphenoxy)ethylamino}propan-2-ol; 1-[carbazolyl-(4)-oxy]-3-[(2-methoxyphenoxyethyl)amino]-propanol-(2); 2-Propanol, 1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-; 2-propanol, 1-(9H-carbazol-4-yloxy)-3-2-(2-methoxyphenoxy)ethylamino-; BM-14190; Carvedilolum; Carvedilolum [Latin]; COREG; Coropress; DILATREND; DIMITONE; DQ-2466; Eucardic; Kredex; MFCD00864692; Querto;

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1.3 CAS No.: 72956-09-3

1.4 CID: 2585

1.5 EINECS: 615-871-8

1.6 Molecular Formula: C24H26N2O4

1.7 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

1.8 InChkey: OGHNVEJMJSYVRP-UHFFFAOYSA-N

1.9 Canonical Smiles: COC1=CC=CC=C1OCCNCC(COC2=CC=CC3=C2C4=CC=CC=C4N3)O

1.10 Isomers Smiles: COC1=CC=CC=C1OCCNCC(COC2=CC=CC3=C2C4=CC=CC=C4N3)O

2. Properties

2.1 Solubility: DMSO: >20mg/mL

2.2 Appearance: colourless crystalline powder

2.3 Chemical Properties: Colourless Crystalline Solid

2.4 Color/Form: Powder

2.5 pKa: 13.90±0.20(Predicted)

2.6 Water Solubility: Insoluble

2.7 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A member of the class of carbazoles that is an adrenergic antagonist with non-selective beta- and alpha-1 receptor blocking properties which helps in the management of congestive heart failure.

3.2 Description: Carvedilol(BM14190) is a non-selective beta blocker/alpha-1 blocker with an IC50 of 3.8 μM for inhibition of LDL oxidation.IC50 Value: 3.8 μM ( inhibition of LDL oxidation)Target: beta Adrenergic ReceptorCarvedilol is a nonselective-blocking agent and is used in the treatment of hypertension and angina pectoris. As a third-generation β-adrenergic blocker (β-blocker), Carvedilol is able to reverse cardiac structural remodeling. Recentresults demonstrated that the effect caused by Carvedil

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3.3 Usage: A nonselective -adrenergic blocker with a1-blocking activity. An antihypertensive used in the treatment of congestive heart failure.

4. Safety and Handling

4.1 Safety: Hazard Codes of Carvedilol (CAS NO.72956-09-3):?N,Xn
Risk Statements: 51/53-36/37/38-20/21/22
R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment.?
R36/37/38: Irritating to eyes, respiratory system and skin.?
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 61-36-26
S61: Avoid release to the environment. Refer to special instructions / safety data sheets.?
S36: Wear suitable protective clothing.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 3077 9/PG 3
RTECS: UA8670000

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4.2 Specification: ?Carvedilol ,?its cas register number is 72956-09-3. It also can be called?(+-)-1-(Carbazol-4-yloxy)-3-((2-(o-
methoxyphenoxy)ethyl)amino)-2-propanol ; (+-)-1-Carbazol-4-yloxy)-3-((2-(o-methoxyphenoxy)ethyl)amino)-2-propanol ;
?2-Propanol, 1-(9H-carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-, (+-)- ; BM 14190 ; Carvedilolum ; Coreg ;
?DQ 2466 ; HSDB 7044 ; SKF 105517 ; UNII-0K47UL67F2?.?Carvedilol (CAS NO.72956-09-3) is a?colourless crystalline solid.?Side effects of carvedilol were observed to include nightmares,sleep disturbances and anxiety and panic attacks. This is based on a single case report of a patient already diagnosed with anxiety disorder and using the drug improperly before bedtime at elevated doses.

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4.3 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
dog	LD50	oral	> 1gm/kg (1000mg/kg)	GASTROINTESTINAL: NAUSEA OR VOMITING	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 1181, 1989.
mouse	LD50	intraperitoneal	364mg/kg (364mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA	New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
mouse	LD50	intravenous	27mg/kg (27mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LIVER: OTHER CHANGES	New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
mouse	LDLo	oral	8gm/kg (8000mg/kg)	SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 1181, 1989.
rat	LD50	intraperitoneal	769mg/kg (769mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LUNGS, THORAX, OR RESPIRATION: ACUTE PULMONARY EDEMA	New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
rat	LD50	intravenous	25mg/kg (25mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) LIVER: OTHER CHANGES	New Cardiovascular Drugs. Vol. 5, Pg. 135, 1987.
rat	LDLo	oral	8gm/kg (8000mg/kg)	GASTROINTESTINAL: ULCERATION OR BLEEDING FROM STOMACH BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE	Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 20, Pg. 1181, 1989.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	No signal word.
Hazard statement(s)	H411 Toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P273 Avoid release to the environment.
Response	P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. Synthesis Route

72956-09-3Total: 25 Synthesis Route

90-05-1 331 Suppliers

72956-09-3 362 Suppliers

1836-62-0 166 Suppliers

72956-09-3 362 Suppliers

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7. Precursor and Product

precursor:

52602-39-8

90-05-1

1836-62-0

51997-51-4

374779-43-8

72956-09-3

72955-94-3

180987-80-8

53815-60-4

143412-40-2

product:

72956-09-3

95093-99-5

72956-44-6

95094-00-1

8. Computed Properties

Molecular Weight：406.48g/mol
Molecular Formula：C₂₄H₂₆N₂O₄
Compound Is Canonicalized：True
XLogP3-AA：406.18925731
Monoisotopic Mass：406.18925731
Complexity：508
Rotatable Bond Count：10
Hydrogen Bond Donor Count：3
Hydrogen Bond Acceptor Count：5
Topological Polar Surface Area：75.7
Heavy Atom Count：：30
Defined Atom Stereocenter Count：0
Undefined Atom Stereocenter Count：1
Defined Bond Stereocenter Count：0
Undefined Bond Stereocenter Count：0
Isotope Atom Count：0
Covalently-Bonded Unit Count：1
CACTVS Substructure Key Fingerprint：AAADceB7OAAAAAAAAAAAAAAAAAAAAWAAAAAwYMAAAAAAAFgB/AAAHgAQCAAADBzhngYyxvLJlgCgAyRiRACCiCAhIiAImaA+7JgPNuLEsZuHOCrm0Bnb6Aew0OMOgAAAAgAKQAAAAAAEABSAAAAAAAAAAA==

9.Other Information

Merck: 14,1873

Description: Carvedilol is a vasodilating beta-blocker useful in the treatment of hypertension and angina pectoris. In addition to lowering blood pressure, carvedilol decreases total vascular resistance without the reflex tachycardia usually occurring with vasodilators. It is reported to be well tolerated with renal sparing effects.

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Description: Carvedilol (Item No. 26286) is an analytical reference standard categorized as a β-adrenergic receptor antagonist and vasodilator. Formulations containing carvedilol have been used to enhance physical performance in athletes. This product is intended for use in analytical forensic applications. This product is also available as a general research tool (Item No. 15418).

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Chemical Properties: Colourless Crystalline Solid

Originator: Boehringer Mannheim (Germany)

Uses: A nonselective -adrenergic blocker with a1-blocking activity. An antihypertensive used in the treatment of congestive heart failure.

Uses: antibacterial

Uses: Carvedilol is a nonselective β-adrenergic blocker with α1-blocking activity. Carvedilol is an antihypertensive used in the treatment of congestive heart failure.

Uses: veterinary use

Uses: For the treatment of mild or moderate (NYHA class II or III) heart failure of ischemic or cardiomyopathic origin.

Uses: An α1- and β-adrenergic receptor antagonist.

Definition: ChEBI: A member of the class of carbazoles that is an adrenergic antagonist with non-selective beta- and alpha-1 receptor blocking properties which helps in the management of congestive heart failure.

Manufacturing Process: 1-(9H-Carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-2-propanol may be synthesized by the method of preparation of S-(-)-(1-carbazol-4- yloxy)-3-[2-(2-methoxyphenoxy)]ethylaminopropan-2-ol (Patent US 4,697,022 and 4,824,963).
27.5 g 4-hydroxycarbazole are dissolved in a mixture of 150 ml 1 N aqueous sodium hydroxide solution and 70 ml dimethylsulfoxide. To this is added at ambient temperature 13.9 g epichlorohydrin, followed by stirring for 18 hours at ambient temperature. 280 ml water are then added thereto, followed by stirring for 15 min and filtering off with suction. The filter residue is washed with 0.1 N aqueous sodium hydroxide solution and water and subsequently dissolved in methylene chloride. The methylene chloride solution is dried over anhydrous sodium sulfate, treated with active charcoal and floridin and evaporated. 4-(2,3-Epoxypropoxy)-carbazole is purified by recrystallising twice from ethyl acetate. From the mother liquors there are isolated a further 4- (2,3-epoxypropoxy)-carbazole.
10 g 4-(2,3-epoxypropoxy)-carbazole are, together with 13.97 g o-methoxyphenoxyethylamine, heated under reflux in 70 ml isopropanol for 2 hours. The solvent is evaporated off and the residue is stirred for 2 hours with a mixture of 115 ml toluene, 35 ml cyclohexane and 40 ml ethyl acetate. After filtering off with suction, the (1-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)]-ethylaminopropan-2-ol is recrystallised from 150 ml ethyl acetate.

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Brand name: Coreg (GlaxoSmithKline);Dilatrend.

Therapeutic Function: Beta-adrenergic blocker

General Description: Carvedilol (Coreg) is a β-blocker that hasa unique pharmacological profile. Like labetalol, it is aβ-blocker that possesses α1-blocking activity. Only the(S) enantiomer possesses the β-blocking activity, althoughboth enantiomers are blockers of the α1-receptor. Overall,its β-blocking activity is 10- to 100-fold of its α-blocking activity.

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Biological Activity: Potent β -adrenoceptor and α 1 -adrenoceptor antagonist (K i values are 0.81, 0.96 and 2.2 nM for β 1 -, β 2 - and α 1 -adrenoceptors respectively) that displays antihypertensive and peripheral vasodilatory activity. Blocks cardiac inward-rectifier K + (K IR ) channels, voltage-dependent Ca 2+ channels and exhibits antioxidant properties at higher concentrations.

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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.

Clinical Use: Carvedilol is also unique in that it possesses antioxidantactivity and an antiproliferative effect on vascular smoothmuscle cells. It thus has a neuroprotective effect and the abilityto provide major cardiovascular organ protection. It isused in treating hypertension and congestive heart failure.

Veterinary Drugs and Treatments: Carvedilol may be useful as adjunctive therapy in the treatment of heart failure (dilated cardiomyopathy) in dogs. There is a fair amount of controversy at present among veterinary cardiologists as to whether this drug will find a therapeutic niche.

10. Toltal 319 Suppliers View more

Baoji Guokang Healthchem co.,ltd

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Amitychem Corporation

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Wuhan Circle Star Chem-medical Technology Co.,Ltd

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Fuao Chemical Technology Co., Ltd.

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Chinese manufacturer supply Carvedilol CAS 72956-09-3 with favorable price

Wuhan Fortuna Chemical Co., Ltd.

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11. Related Questions

: Is the Position of β-Blockers in Heart Failure Management Unshakable?It is well known that β-blockers are the cornerstone of standard treatment for heart failure. They not only improve symptoms and quality of life, but also reduce the risk of death, hospitalization, a..; Does Carvedilol have dosage requirements for treating heart failure?Carvedilol is a commonly used medication for treating primary hypertension and heart failure. It is a white tablet that can be taken directly with warm water. Carvedilol is a long-term medication, and..; Is Carvedilol associated with severe adverse reactions?When choosing a medication, it is important to consider not only its therapeutic effects but also its safety. Even if a medication has good treatment outcomes, it is not recommended to blindly use it ..; Is β-Blocker the Best Treatment for Heart Failure?Heart failure is the only cardiovascular disease with a continuously increasing incidence rate, associated with significant mortality and causing a considerable economic burden. Traditionally, β-bloc..

12. Realated Product Infomation