Candesartan

Candesartan Basic information
Product Name:Candesartan
Synonyms:1-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)Methyl)-2-ethoxy-1H-benzo[d]iMidazole-7-carboxylic acid;2-ethoxy-3-[[4-[2-(1h-tetrazol-5-yl)phenyl]phenyl]methyl]-3h-benzoimidazole-4-carboxylic acid;3-[[2'-(1H-Tetrazol-5-yl)biphenyl-4-yl]Methyl]-2-ethoxy-3H-benziMidazole-4- carboxylic Acid;Candesartan M1;2-ETHOXY1-2(1H-TETRAZOL-5YL)1,1-BIPHENYL)-4-YL)-4-YL)METHYL)1H-BENZIMIDAZOLE-7-CARBOXYLIC ACID;Candesartan Cilexetil EP IMpurity G;1-((2'-(1H-Tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylic;1H-Benzimidazole-7-carboxylic acid, 2-ethoxy-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-
CAS:139481-59-7
MF:C24H20N6O3
MW:440.45
EINECS:604-138-8
Product Categories:Isotope;Pharmaceutical raw material;Aromatics;Heterocycles;Bases & Related Reagents;Intermediates & Fine Chemicals;Nucleotides;Pharmaceuticals;Candesartan Cilexatil;Candesartan Cilexetil;API intermediates;Active Pharmaceutical Ingredients
Mol File:139481-59-7.mol
Candesartan Structure
Candesartan Chemical Properties
Melting point 183-185°C
Boiling point 754.8±70.0 °C(Predicted)
density 1.41±0.1 g/cm3(Predicted)
RTECS DD6671000
storage temp. Inert atmosphere,Store in freezer, under -20°C
solubility Soluble in DMSO (up to 40 mg/ml)
form solid
pka2.06±0.10(Predicted)
color White
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).
Stability:Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months.
CAS DataBase Reference139481-59-7(CAS DataBase Reference)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38
Safety Statements 26-36-60-36/37-9
HS Code 29419000
Hazardous Substances Data139481-59-7(Hazardous Substances Data)
Candesartan Usage And Synthesis
DescriptionCandesartan (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.
Chemical PropertiesCrystalline Solid
UsesCandesartan 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%.
Usesantihypertensive, angiotensin II inhibitor
UsesAn angiotensin II type-1 receptor antagonist. Used in treatment of congestive heart failure. Antihypertensive
DefinitionChEBI: A benzimidazolecarboxylic acid that is 1H-benzimidazole-7-carboxylic acid substituted by an ethoxy group at position 2 and a ({2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl}methyl) group at position 1. It is a angiotensin eceptor antagonist used for the treatment of hypertension.
Brand nameAtacand (AstraZeneca).
General DescriptionCandesartan, (+)-1-[[(cyclohexyloxy)carbonyl]-oxy]ethyl 2- ethoxy-1-[[2'-(1H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-benzimidazole-7-carboxylate(Atacand), like losartan, possesses the acidic tetrazole system,which most likely plays a role in binding to the angiotensin IIreceptor similarly to the acidic groups of angiotensin II. Also,the imidazole system has been replaced with a benzimidazolepossessing an ester at position. This ester must be hydrolyzedto the free acid. Fortunately, this conversion takesplace fairly easily because of the carbonate in the ester sidechain. This facilitates hydrolysis of the ester so much thatconversion to the free acid takes place during absorption fromthe gastrointestinal tract.
storageStore at RT
References1) Shibouta?et al.?(1993),?Pharmacological profile of a highly potent and long-acting angiotension II receptor antagonist, 2-ethoxy-1-[[2’-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimidazol-7-carboxylic acid (CV-11974), and its prodrug, (+/-)-1-(cyclohexyloxycarbonyloxy)-ethyl 2-ethoxy-1-[[2’-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1H-benzimidazole-7-carboxylate (TCV-116); J. Pharmacol. Exp. Therap.,?266?114 2) Bhat?et al. (2017),?Angiotensin receptor Blockade by Inhibiting Glial Activation Promotes Hippocampal Neurogenesis Via Activation of Wnt/B-Catenin signaling in hypertension; Mol. Neurobiol.,?55 5282 3) Fan?et al.?(2016),?Candesartan attenuates angiogenesis in hepatocellular carcinoma via downregulating AT1R/VEGF pathway; Biomed. Pharmacother.,?83?704 4) Torika?et al.?(2018),?Candesartan ameliorates brain inflammation associated with Alzheimer’s disease; CNS Neurosci. Ther.?24?231
Candesartan Preparation Products And Raw materials
Raw materialsThionyl chloride-->Potassium carbonate-->Trifluoroacetic acid-->tert-Butanol-->Sodium azide-->Benzyl bromide-->Mineral oil-->3-Nitrophthalic acid
TRITYL CANDESARTAN Methyl 1-[(2'-cyanobiphenyl-4-yl)methyl]-2-ethoxy-1H-benzimidazole-7-carboxylate Ethyl -2-ethoxy-1-[[(2-(1Htetrazol-5-yl)biphenyl-4-yl-) methyl] Ethyl-2-Ethoxy-1-[[(2'-Cyanobiphenyl-4-yl) Methyl] Benzimidazole]-7-Carboxylate Methyl CANDESARTAN CILEXETIL=ATACAND Ethyl-2-Ethoxy-1-[[(2'-(1h-Tetrazol-5-Yl)Biphenyl-4-Yl)Methyl]Benzimidazole]-7-Carboxylate CANDESARTAN CILEXETIL-D11 CANDESARTAN-D4 TRITYL CANDESARTAN CILETEXITIL,TRITYL CANDESARTAN CILEXETIL CANDERSARTAN CILEXETIL [3H(G)] Ethoxyquin Kresoxim-methyl PHENYL VALERATE Ethoxy Thiophanate-methyl METSULFURON METHYL CANDESARTAN-D5

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