Candesartan

Base Information

• Chemical Name: Candesartan
• CAS No.: 139481-59-7
• Molecular Formula: C24H20N6O3
• Molecular Weight: 440.461
• Hs Code.: 29419000
• European Community (EC) Number: 604-138-8
• NSC Number: 759858
• UNII: S8Q36MD2XX
• DSSTox Substance ID: DTXSID0022725
• Nikkaji Number: J540.291C
• Wikipedia: Candesartan
• Wikidata: Q415970
• NCI Thesaurus Code: C65284
• RXCUI: 214354
• Pharos Ligand ID: RWMN5HNLCSWF
• Metabolomics Workbench ID: 43087
• ChEMBL ID: CHEMBL1016
• Mol file: 139481-59-7.mol

Synonyms:2-ethoxy-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-benzimidazole-7-carboxylic acid;2-ethoxy-7-carboxy-1-(2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methylbenzimidazole;candesartan;CV 11974;CV-11974;CV11974

Chemical Property of Candesartan

Chemical Property:

• Appearance/Colour: crystalline solid
• Vapor Pressure: 4.39E-24mmHg at 25°C
• Melting Point: 183-185 °C
• Refractive Index: 1.746
• Boiling Point: 754.8 °C at 760 mmHg
• PKA: 2.06±0.10(Predicted)
• Flash Point: 410.3 °C
• PSA: 118.81000
• Density: 1.41 g/cm³
• LogP: 4.02860
• Storage Temp.: -20°C Freezer
• Solubility.: Soluble in DMSO (up to 40 mg/ml)
• Water Solubility.: Soluble in ethyl acetate, methanol, water (<1 mg/ml at 25°C), DMSO (88 mg/ml at 25°C), and ethanol (1 mg/ml at 25°C).
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 7
• Exact Mass: 440.15968852
• Heavy Atom Count: 33
• Complexity: 660

Purity/Quality:

99%+ ^*data from raw suppliers

Candesartan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36-60-36/37-9

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Angiotensin II Receptor Antagonists
• Canonical SMILES: CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NNN=N5)C(=O)O
• Recent ClinicalTrials: Candesartan for Migraine Prevention:
• Recent EU Clinical Trials: EARLY treatment with Candesartan vs Placebo in asymptomatic GENEtic carriers of Dilated Cardiomyopathy (EARLY-GENE trial)
• Recent NIPH Clinical Trials: J-TASTE trial
• Description: Candesartan (CAS 139481-59-7) is an angiotensin II receptor I (AT1) antagonist, IC50s=1.12 and 2.86 nM for bovine adrenal cortex and rabbit aorta respectively.1?Selectively inhibits angiotensin II-induced contraction of rabbit aortic strips with no effect on contraction induced by other agents such as norepinephrine, KCl, serotonin, PGF2αor endothelin. Prevents astrocyte and microglial activation and neuroinflammation and improves hippocampal neurogenesis.2?Attenuates angiogenesis in hepatocellular carcinoma.3?Clinically useful antihypertensive agent. Ameliorates brain inflammation associated with Alzheimer’s disease.4?Active?in vivo?and orally active.
• Uses: An angiotensin II type-1 receptor antagonist. Used in treatment of congestive heart failure. Antihypertensive antihypertensive, angiotensin II inhibitor Candesartan is a selective AT1 (angiotensin II receptor 1) antagonist. Antagonism of angiotensin receptors inhibits vasoconstriction and the production of aldosterone, leading to a decrease in water and sodium concentration in blood plasma. Exhibits antihypertensive effects in animal models. Used in treatment of congestive heart failure, as antihypertensive. Candesartan does not affect cell viability or proliferation but increases the expression of VEGF and interleukin-8 in the cultured medium of KU-19-19 cells. Candesartan (0.1 nM) could reduce the maximal contractile response to angiostensin II by approximately 50%.

Technology Process of Candesartan

There total 27 articles about Candesartan 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: 85.0%

ethyl 2-ethoxy-1-{[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl]-1,1'-biphenyl-4-yl}methyl]-benzimidazole-7-carboxylate (856414-35-2) → candesartan (139481-59-7)

Guidance literature:

With lithium hydroxide; In ethanol; at 80 ℃; for 3h;

Reference yield: 80.0%

ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylate (139481-58-6) → candesartan (139481-59-7)

Guidance literature:

ethyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]-methyl]benzimidazole-7-carboxylate; With sodium hydroxide; ethanol; water; for 24h; Heating / reflux;

With hydrogenchloride; In ethanol; water; pH=4 - 4.5;

Reference yield: 78.01%

candesartan cilexetil → methanol-methyl carbonate + candesartan (139481-59-7) + cyclohexanol (108-93-0)

Guidance literature:

With sodium hydroxide; In methanol; dichloromethane; at 30 ℃; for 8h;

DOI:10.1021/acs.molpharmaceut.8b01212

upstream raw materials:

methyl 2-ethoxy-1-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylate

methyl 2-carboxy-3-nitrobenzoate

acid chloride of 1-methylhydrogen-3-nitrophthalate

3-nitrophthalic acid

Downstream raw materials:

2-Ethoxy-1-[[2'-(N-triphenylmethyltetrazol-5-yl)-biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid

cilexetil trityl candesartan

1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carbaldehyde O-methyl oxime

1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carbaldehyde oxime

Refernces

• 1、 -. "Method for treating azide ions, non-genotoxic impurity Sartan raw material medicine and immediate thereof". Paragraph 0105; 0106. . Retrieved 2019/05/28.
• 2、 -. "A trityl protecting group by removing method of preparing losartan medicine". Paragraph 0032-0039; 0047-0051. . Retrieved 2018/07/30.