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Cas Database

72956-09-3

72956-09-3

Identification

  • Product Name:Carvedilol

  • CAS Number: 72956-09-3

  • EINECS:1308068-626-2

  • Molecular Weight:496.517

  • Molecular Formula: C24H26N2O4

  • HS Code:2933995300

  • Mol File:72956-09-3.mol

Synonyms:2-Propanol, 1-(9H-carbazol-4-yloxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)-, (+-)-;Carvedilolum [Latin];Carvedilol [USAN:BAN:INN:JAN];Coreg (TN);Carvedilol (JAN/USAN);2-Propanol,1-(9H-carbazol-4-yloxy)-3-[[2- (2-methoxyphenoxy)ethyl]amino]-;SKF 105517;(+-)-1-(Carbazol-4-yloxy)-3-((2-(o-methoxyphenoxy)ethyl)amino)-2-propanol;DQ 2466;1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethylamino]propan-2-ol;

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Safety information and MSDS view more

  • Pictogram(s):HarmfulXn, DangerousN

  • Hazard Codes:N,Xn

  • Signal Word:No signal word.

  • Hazard Statement:H411 Toxic to aquatic life with long lasting effects

  • First-aid measures: General adviceConsult a physician. Show this safety data sheet to the doctor in attendance.If inhaled If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician. In case of skin contact Wash off with soap and plenty of water. Consult a physician. In case of eye contact Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician. If swallowed Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.

  • Fire-fighting measures: Suitable extinguishing media Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide. Wear self-contained breathing apparatus for firefighting if necessary.

  • Accidental release measures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. For personal protection see section 8. Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Pick up and arrange disposal. Sweep up and shovel. Keep in suitable, closed containers for disposal.

  • Handling and storage: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Avoid exposure - obtain special instructions before use.Provide appropriate exhaust ventilation at places where dust is formed. For precautions see section 2.2. Store in cool place. Keep container tightly closed in a dry and well-ventilated place.

  • Exposure controls/personal protection:Occupational Exposure limit valuesBiological limit values Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday. Eye/face protection Safety glasses with side-shields conforming to EN166. Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU). Skin protection Wear impervious clothing. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace. Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique(without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands. The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and the standard EN 374 derived from it. Respiratory protection Wear dust mask when handling large quantities. Thermal hazards

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  • Manufacture/Brand:Usbiological
  • Product Description:Carvedilol
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  • Product Description:Carvedilol
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  • Product Description:Carvedilol ≥99%(HPLC)
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  • Product Description:Carvedilol European Pharmacopoeia (EP) Reference Standard
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  • Product Description:Carvedilol ≥98% (HPLC), solid
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  • Product Description:Carvedilol United States Pharmacopeia (USP) Reference Standard
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Relevant articles and documentsAll total 45 Articles be found

In-situ and one-step preparation of protein film in capillary column for open tubular capillary electrochromatography enantioseparation

Li, Ling,Xue, Xuqi,Zhang, Huige,Lv, Wenjuan,Qi, Shengda,Du, Hongying,Manyande, Anne,Chen, Hongli

supporting information, p. 2139 - 2142 (2021/04/07)

In this work, the phase-transitioned BSA (PTB) film using the mild and fast fabrication process adhered to the capillary inner wall uniformly, and the fabricated PTB film-coated capillary column was applied to realize open tubular capillary electrochromatography (OT-CEC) enantioseparation. The enantioseparation ability of PTB film-coated capillary was evaluated with eight pairs of chiral analytes including drugs and neurotransmitters, all achieving good resolution and symmetrical peak shape. For three consecutive runs, the relative standard deviations (RSD) of migration time for intra-day, inter-day, and column-to-column repeatability were in the range of 0.3%–3.5%, 0.2%–4.9% and 2.1%–7.7%, respectively. Moreover, the PTB film-coated capillary column ran continuously over 300 times with high separation efficiency. Therefore, the coating method based on BSA self-assembly supramolecular film can be extended to the preparation of other proteinaceous capillary columns.

Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC

Shuang, Yazhou,Liao, Yuqin,Wang, Hui,Wang, Yuanxing,Li, Laisheng

, p. 168 - 184 (2019/11/25)

A triazole-bridged bis(β-cyclodextrin) was synthesized via a high-yield Click Chemistry reaction between 6-azido-β-cyclodextrin and 6-propynylamino-β-cyclodextrin, and then it was bonded onto ordered silica gel SBA-15 to obtain a novel triazole-bridged bis (β-cyclodextrin)–bonded chiral stationary phase (TBCDP). The structures of the bridged cyclodextrin and TBCDP were characterized by the infrared spectroscopy, mass spectrometry, elemental analysis, and thermogravimetric analysis. The chiral performance of TBCDP was evaluated by using chiral pesticides and drugs as probes including triazoles, flavanones, dansyl amino acids and β-blockers. Some effects of the composition in mobile phase and pH value on the enantioseparations were investigated in different modes. The nine triazoles, eight flavanones, and eight dansyl amino acids were successfully resolved on TBCDP under the reversed phase with the resolutions of hexaconazole, 2′-hydroxyflavanone, and dansyl-DL-tyrosine, which were 2.49, 5.40, and 3.25 within 30 minutes, respectively. The ten β-blockers were also separated under the polar organic mode with the resolution of arotinolol reached 1.71. Some related separation mechanisms were discussed preliminary. Compared with the native cyclodextrin stationary phase (CDSP), TBCDP has higher enantioselectivity to separate more analytes, which benefited from the synergistic inclusion ability of the two adjacent cavities and bridging linker of TBCDP, thereby enabling it a promising prospect in chiral drugs and food analysis.

Drug repurposing and rediscovery: Design, synthesis and preliminary biological evaluation of 1-arylamino-3-aryloxypropan-2-ols as anti-melanoma agents

Chang, Qi,Long, Jing,Hu, Liqing,Chen, Zhuo,Li, Qianbin,Hu, Gaoyun

, (2020/04/09)

Malignant melanoma (MM) presents as the highest morbidity and mortality type in skin cancer. Herein, inspired by the previously reported anti-melanoma effect of propranolol, a widely applied β adrenergic receptor antagonist as cardiovascular drug, we set out to exploit its potential as anti-melanoma therapy based on the drug repurposing strategy. Structural optimization of propranolol yielded 5m, which exhibits dramatically improved potency on human melanoma cell growth (1.98–3.70 μM), compared to propranolol (59.5–75.8 μM). Further investigation demonstrated that 5m could inhibit colony formation of melanoma cell line (completely abolished at 2 μM for 5m, partially inhibited at 50 μM for propranolol), induce cell apoptosis and cell cycle arrest in the G2/M phase (both observed at 1 μM). Preliminary mechanism study indicated that 5m could disrupt the cellular microtubule network, which suggested tubulin as a potential target. Docking study provided a structural insight into the interaction between 5m and tubulin. In summary, our study presents a drug repurposing case that redirects a cardiovascular agent to an anti-melanoma agent.

Hybridization of β-Adrenergic Agonists and Antagonists Confers G Protein Bias

Stanek, Markus,Picard, Louis-Philippe,Schmidt, Maximilian F.,Kaindl, Jonas M.,Hübner, Harald,Bouvier, Michel,Weikert, Dorothée,Gmeiner, Peter

, p. 5111 - 5131 (2019/05/28)

Starting from the β-adrenoceptor agonist isoprenaline and beta-blocker carvedilol, we designed and synthesized three different chemotypes of agonist/antagonist hybrids. Investigations of ligand-mediated receptor activation using bioluminescence resonance energy transfer biosensors revealed a predominant effect of the aromatic head group on the intrinsic activity of our ligands, as ligands with a carvedilol head group were devoid of agonistic activity. Ligands composed of a catechol head group and an antagonist-like oxypropylene spacer possess significant intrinsic activity for the activation of Gαs, while they only show weak or even no β-arrestin-2 recruitment at both β1- and β2-AR. Molecular dynamics simulations suggest that the difference in G protein efficacy and β-arrestin recruitment of the hybrid (S)-22, the full agonist epinephrine, and the β2-selective, G protein-biased partial agonist salmeterol depends on specific hydrogen bonding between Ser5.46 and Asn6.55, and the aromatic head group of the ligands.

Discovery of novel small molecule TLR4 inhibitors as potent anti-inflammatory agents

Xu, Yao,Chen, Shujun,Cao, Ying,Zhou, Pingzheng,Chen, Zhipeng,Cheng, Kui

, p. 253 - 266 (2018/05/29)

Toll-like receptor 4 (TLR4) initiates innate immune response to release inflammatory cytokines and has been pathologically linked to variety of inflammatory diseases. Recently, we found that Carvedilol, as the classic anti-heart failure and anti-inflammatory clinic drug, could inhibit the TLR4 signaling in the TLR4 overexpressed cells. Herein, we have designed and synthesized a small library of novel Carvedilol derivatives and investigated their potential inhibitory activity. The results indicate that the most potent compound 8a (SMU-XY3) could effectively inhibited TLR4 protein and the LPS triggered alkaline phosphatase signaling in HEK-Blue hTLR4 cells. It down regulated the nitric oxide (NO) in both RAW264.7 cells and BV-2 microglial cells, in addition to blocking the TNF-α signaling in ex-vivo human peripheral blood mononuclear cells (PBMC). More interestingly, 8a shows higher affinity to hyperpolarization-activated cyclic nucleotide-gated 4 (HCN4) over HCN2, which probably indicates the new application of TLR4 inhibitor 8a in heart failure, coronary heart disease, and other inflammatory diseases.

Process route upstream and downstream products

Process route

4-(2,3-epoxypropoxy)carbazole
51997-51-4,95093-96-2

4-(2,3-epoxypropoxy)carbazole

carvedilol
72956-09-3

carvedilol

Conditions
Conditions Yield
2-[(2-methoxy)phenoxy]ethylamine hydrochloride; With potassium carbonate; In isopropyl alcohol; at 35 ℃; for 0.25h;
4-(2,3-epoxypropoxy)carbazole; In isopropyl alcohol; at 83 ℃; for 5h;
45%
Multi-step reaction with 3 steps
1: potassium carbonate / N,N-dimethyl-formamide / 4 h / 140 °C
2: methylamine / water / 2 h / 80 °C
3: potassium carbonate / toluene / 80 - 85 °C
With potassium carbonate; methylamine; In water; N,N-dimethyl-formamide; toluene;
Multi-step reaction with 4 steps
1: hydrogenchloride / water; methanol / 0 - 30 °C
2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 90 - 95 °C
3: methylamine / water / 2 h / 80 °C
4: dipotassium hydrogenphosphate; N-benzyl-N,N,N-triethylammonium chloride / toluene / 5 h / Reflux
With hydrogenchloride; dipotassium hydrogenphosphate; N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate; methylamine; In methanol; water; N,N-dimethyl-formamide; toluene;
Multi-step reaction with 3 steps
1: 4-methoxypyridine N-oxide; sodium sulfate / dichloromethane / 60 h / 20 °C
2: potassium carbonate / toluene / 60 h / Reflux
3: tetrabutyl ammonium fluoride / tetrahydrofuran / 17 h / 30 - 40 °C
With 4-methoxypyridine N-oxide; tetrabutyl ammonium fluoride; potassium carbonate; sodium sulfate; In tetrahydrofuran; dichloromethane; toluene;
Multi-step reaction with 2 steps
1: water; hydrogen bromide / isopropyl alcohol / 25 - 60 °C
2: triethylamine / isopropyl alcohol / 60 °C
With water; hydrogen bromide; triethylamine; In isopropyl alcohol;
(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol salicylate
787598-91-8

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

C<sub>39</sub>H<sub>39</sub>N<sub>3</sub>O<sub>6</sub>
918903-20-5

C39H39N3O6

carvedilol
72956-09-3

carvedilol

Conditions
Conditions Yield
With sodium hydroxide; In water; isopropyl alcohol; at 50 - 70 ℃; for 0.75h;
91.21%
(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol salicylate; With triethylamine; In ethyl acetate; at 10 - 35 ℃; for 1h;
With sodium chloride; In water; ethyl acetate; for 0.5h;
(+/-) 1-(9H-carbazol-4-yloxy)-3-[2-(2-methoxyphenoxy)ethyl]amino-2-propanol oxalate
72956-09-3

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

carvedilol
72956-09-3

carvedilol

Conditions
Conditions Yield
With ammonia; In dichloromethane; water; at 20 ℃; for 1h; pH=9.0 - 9.3;
63.2%
2-(2-methoxy-phenoxy)-ethylamine
1836-62-0

2-(2-methoxy-phenoxy)-ethylamine

4-(2,3-epoxypropoxy)carbazole
51997-51-4,95093-96-2

4-(2,3-epoxypropoxy)carbazole

carvedilol
72956-09-3

carvedilol

Conditions
Conditions Yield
In isopropyl alcohol; for 5h; Inert atmosphere; Reflux;
81%
With N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; at 80 - 85 ℃;
36.26%
With sulfuric acid; potassium carbonate; In isopropyl alcohol; at 80 ℃; for 6h;
In ethyl acetate; at 78 ℃; for 6h; Product distribution / selectivity;
With sodium carbonate; In water; ethyl acetate;
With sodium carbonate; In water; ethyl acetate;
In dimethyl sulfoxide; at 68 - 72 ℃; for 18 - 20h; Product distribution / selectivity;
In ethyl acetate; for 24h; Reflux;
lithium bromide; In 1,2-dimethoxyethane; at 50 ℃; for 24h;
In 1,2-dimethoxyethane; ethyl acetate;
In isopropyl alcohol; for 2h; Reflux;
With lithium bromide;
In ethanol; for 24h; Reflux;
176 mg
In ethyl acetate; for 24h; Reflux;
2-(2-methoxy-phenoxy)-ethylamine
1836-62-0

2-(2-methoxy-phenoxy)-ethylamine

4-(2,3-epoxypropoxy)carbazole
51997-51-4,95093-96-2

4-(2,3-epoxypropoxy)carbazole

C<sub>39</sub>H<sub>39</sub>N<sub>3</sub>O<sub>6</sub>
918903-20-5

C39H39N3O6

carvedilol
72956-09-3

carvedilol

Conditions
Conditions Yield
In dimethyl sulfoxide; at 68 - 72 ℃; for 18 - 20h;
58%
2-[(2-methoxy)phenoxy]ethylamine hydrochloride
64464-07-9

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

4-(2,3-epoxypropoxy)carbazole
51997-51-4,95093-96-2

4-(2,3-epoxypropoxy)carbazole

carvedilol
72956-09-3

carvedilol

Conditions
Conditions Yield
2-[(2-methoxy)phenoxy]ethylamine hydrochloride; With sodium hydroxide; In water; at 20 ℃; pH=9 - 9.5;
4-(2,3-epoxypropoxy)carbazole; In water; at 80 - 85 ℃; for 0.75 - 1h; Product distribution / selectivity;
45.99%
2-[(2-methoxy)phenoxy]ethylamine hydrochloride; With sodium hydroxide; In water; isopropyl alcohol; at 20 ℃; pH=9 - 9.5;
4-(2,3-epoxypropoxy)carbazole; In water; isopropyl alcohol; for 4 - 5h; Product distribution / selectivity; Heating / reflux;
43.05%
With potassium carbonate; In i-Amyl alcohol; at 80 - 85 ℃; for 7h;
41%
With calcium carbonate; In isopropyl alcohol; at 80 ℃; for 4h;
(+/-)-1-(9H-carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)-ethyl]-amino]-2-propanol tolsylate
1016214-10-0

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

carvedilol
72956-09-3

carvedilol

Conditions
Conditions Yield
With sodium carbonate; In water; ethyl acetate; Product distribution / selectivity;
88%
With sodium carbonate; In water; ethyl acetate;
80%
With sodium hydroxide; water; In isopropyl alcohol; Product distribution / selectivity;
1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol
143412-40-2,143412-41-3,72955-96-5

1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol

2-(2-methoxyphenoxy)ethyl4-methylbenzenesulfonate

2-(2-methoxyphenoxy)ethyl4-methylbenzenesulfonate

carvedilol
72956-09-3

carvedilol

Conditions
Conditions Yield
With dipotassium hydrogenphosphate; N-benzyl-N,N,N-triethylammonium chloride; In toluene; for 5h; Reflux;
1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol
143412-40-2,143412-41-3,72955-96-5

1-amino-3-(9H-carbazol-4-yloxy)-propan-2-ol

1-(2-chloroethoxy)-2-methoxybenzene
53815-60-4

1-(2-chloroethoxy)-2-methoxybenzene

carvedilol
72956-09-3

carvedilol

Conditions
Conditions Yield
With potassium carbonate; In toluene; at 80 - 85 ℃;
83%
4-[2-(tert-butyldiphenylsilyloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propyloxy]carbazole

4-[2-(tert-butyldiphenylsilyloxy)-3-(2-(2-methoxyphenoxy)ethylamino)propyloxy]carbazole

carvedilol
72956-09-3

carvedilol

Conditions
Conditions Yield
With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 30 - 40 ℃; for 17h;
67%

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