Carvedilol

Base Information

• Chemical Name: Carvedilol
• CAS No.: 72956-09-3
• Deprecated CAS: 107741-96-8
• Molecular Formula: C24H26N2O4
• Molecular Weight: 496.517
• Hs Code.: 2933995300
• European Community (EC) Number: 615-871-8,658-032-1
• NSC Number: 758694
• UNII: 0K47UL67F2
• DSSTox Substance ID: DTXSID8022747
• Nikkaji Number: J33.955E
• Wikipedia: Carvedilol
• Wikidata: Q412534
• NCI Thesaurus Code: C28906
• RXCUI: 20352
• Pharos Ligand ID: BM9MKM694U27
• Metabolomics Workbench ID: 43359
• ChEMBL ID: CHEMBL723
• Mol file: 72956-09-3.mol

Synonyms:14C-labeled Carvedilol;BM 14190;BM-14190;BM14190;carvedilol;carvedilol hydrochloride;Carvedilol, (+);Carvedilol, (+)-isomer;carvedilol, (+-)-isomer;Carvedilol, (-);Carvedilol, (-)-isomer;carvedilol, (R)-isomer;carvedilol, (S)-isomer;Carvedilol, 14C labeled;carvedilol, 14C-labeled;Coreg;Coropres;Dilatrend;Eucardic;Kredex;Querto

Chemical Property of Carvedilol

Chemical Property:

• Appearance/Colour: colourless crystalline powder
• Vapor Pressure: 1.14E-32mmHg at 25°C
• Melting Point: 113-117 °C
• Boiling Point: 655.2 °C at 760 mmHg
• PKA: 13.90±0.20(Predicted)
• Flash Point: 350.1 °C
• PSA: 75.74000
• Density: 1.25 g/cm³
• LogP: 4.12890
• Storage Temp.: Store at +4°C
• Solubility.: DMSO: >20mg/mL
• Water Solubility.: 449.2ug/L(22.5 oC)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 406.18925731
• Heavy Atom Count: 30
• Complexity: 508

Purity/Quality:

99% min ^*data from raw suppliers

Carvedilol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, N
• Hazard Codes: N,Xn
• Statements: 51/53-36/37/38-20/21/22
• Safety Statements: 61-36-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Beta-Adrenergic Receptor Antagonists
• Canonical SMILES: COC1=CC=CC=C1OCCNCC(COC2=CC=CC3=C2C4=CC=CC=C4N3)O
• Recent ClinicalTrials: A Prospective Study of Breast Cancer Patients With Abnormal Strain Imaging
• Recent EU Clinical Trials: Danish trial of beta blocker treatment after myocardial infarction without reduced ejection fraction (DANBLOCK)
• Recent NIPH Clinical Trials: Effect of postoperative landiolol for atrial fibrillation
• 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. 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 .
• Uses: A nonselective -adrenergic blocker with a1-blocking activity. An antihypertensive used in the treatment of congestive heart failure. antibacterial Carvedilol is a nonselective β-adrenergic blocker with α1-blocking activity. Carvedilol is an antihypertensive used in the treatment of congestive heart failure. veterinary use For the treatment of mild or moderate (NYHA class II or III) heart failure of ischemic or cardiomyopathic origin. An α1- and β-adrenergic receptor antagonist.
• Therapeutic Function: Beta-adrenergic blocker
• 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.
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Analgesics: NSAIDs antagonise hypotensive effect. Anti-arrhythmics: increased risk of myocardial depression and bradycardia; increased risk of bradycardia, myocardial depression and AV block with amiodarone; increased risk of myocardial depression and bradycardia with flecainide. Antibacterials: concentration reduced by rifampicin. Antidepressants: enhanced hypotensive effect with MAOIs. Antihypertensives; enhanced hypotensive effect; increased risk of withdrawal hypertension with clonidine; increased risk of first dose hypotensive effect with post-synaptic alpha-blockers such as prazosin. Antimalarials: increased risk of bradycardia with mefloquine. Antipsychotics enhanced hypotensive effect with phenothiazines. Calcium-channel blockers: increased risk of bradycardia and AV block with diltiazem; hypotension and heart failure possible with nifedipine and nisoldipine; asystole, severe hypotension and heart failure with verapamil. Ciclosporin: increased trough concentration, reduce dose by 20% in affected patients. Cytotoxics: possible increased risk of bradycardia with crizotinib. Diuretics: enhanced hypotensive effect. Fingolimod: possibly increased risk of bradycardia. Moxisylyte: possible severe postural hypotension. Sympathomimetics: severe hypertension with adrenaline and noradrenaline and possibly with dobutamine.

Technology Process of Carvedilol

There total 57 articles about Carvedilol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.21%

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol salicylate (787598-91-8) → C39H39N3O6 (918903-20-5) + carvedilol (72956-09-3)

Guidance literature:

With sodium hydroxide; In water; isopropyl alcohol; at 50 - 70 ℃; for 0.75h;

Reference yield: 88.0%

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol tolsylate (1016214-10-0) → carvedilol (72956-09-3)

Guidance literature:

With sodium carbonate; In water; ethyl acetate; Product distribution / selectivity;

Reference yield: 83.0%

1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol (143412-40-2,143412-41-3,72955-96-5) + 1-(2-chloroethoxy)-2-methoxybenzene (53815-60-4) → carvedilol (72956-09-3)

Guidance literature:

With potassium carbonate; In toluene; at 80 - 85 ℃;

upstream raw materials:

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol salicylate

2-[(2-methoxy)phenoxy]ethylamine hydrochloride

4-(2,3-epoxypropoxy)carbazole

2-(2-methoxy-phenoxy)-ethylamine

Downstream raw materials:

(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol tolsylate

1-(9H-carbazol-4-yloxy)-3-{[2-(2-methoxyphenoxy)ethyl]methylamino}-2-propanol

5-(((9H-carbazol-4-yl)oxy)methyl)-3-(2-(2-methoxyphenoxy)ethyl)oxazolidin-2-one

(+)-Carvedilol

Refernces

• 1、 Chang, Qi,Long, Jing,Hu, Liqing,Chen, Zhuo,Li, Qianbin,Hu, Gaoyun. "Drug repurposing and rediscovery: Design, synthesis and preliminary biological evaluation of 1-arylamino-3-aryloxypropan-2-ols as anti-melanoma agents". . . Retrieved 2020/04/09.
• 2、 Stanek, Markus,Picard, Louis-Philippe,Schmidt, Maximilian F.,Kaindl, Jonas M.,Hübner, Harald,Bouvier, Michel,Weikert, Dorothée,Gmeiner, Peter. "Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias". . p. 5111 - 5131. Retrieved 2019/05/28.