139481-59-7 Usage
Description
Candesartan, also known as Atacand, is a benzimidazolecarboxylic acid derivative that functions as an angiotensin II receptor I (AT1) antagonist. It selectively inhibits angiotensin II-induced contractions and exhibits antihypertensive effects in animal models. Candesartan is clinically useful for treating hypertension and congestive heart failure, as well as ameliorating brain inflammation associated with Alzheimer's disease.
Uses
Used in Pharmaceutical Industry:
Candesartan is used as an antihypertensive agent for the treatment of hypertension. It acts as an angiotensin II type-1 receptor antagonist, inhibiting vasoconstriction and the production of aldosterone, leading to a decrease in water and sodium concentration in blood plasma.
Used in Cardiology:
Candesartan is used in the treatment of congestive heart failure. It prevents astrocyte and microglial activation and neuroinflammation, improving hippocampal neurogenesis and attenuating angiogenesis in hepatocellular carcinoma.
Used in Neurology:
Candesartan is used to ameliorate brain inflammation associated with Alzheimer's disease. It exhibits neuroprotective effects by inhibiting angiotensin II-induced contractions and reducing the maximal contractile response to angiostensin II.
Used in Oncology:
Candesartan has been shown to attenuate angiogenesis in hepatocellular carcinoma, potentially offering therapeutic benefits in cancer treatment.
Chemical Properties:
Candesartan is a crystalline solid with the CAS number 139481-59-7. It possesses an acidic tetrazole system, which likely plays a role in binding to the angiotensin II receptor, similar to the acidic groups of angiotensin II. The ester sidechain of candesartan facilitates hydrolysis, allowing for conversion to the free acid during absorption from the gastrointestinal tract.
Brand Name:
Atacand (AstraZeneca) is the brand name for candesartan, which is available in the pharmaceutical market for the treatment of hypertension and congestive heart failure.
References
1) 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
Check Digit Verification of cas no
The CAS Registry Mumber 139481-59-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,9,4,8 and 1 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 139481-59:
(8*1)+(7*3)+(6*9)+(5*4)+(4*8)+(3*1)+(2*5)+(1*9)=157
157 % 10 = 7
So 139481-59-7 is a valid CAS Registry Number.
InChI:InChI:1S/C24H20N6O3/c1-2-33-24-25-20-9-5-8-19(23(31)32)21(20)30(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-26-28-29-27-22/h3-13H,2,14H2,1H3,(H,31,32)(H,26,27,28,29)
139481-59-7Relevant articles and documents
Host-Guest Interactions between Candesartan and Its Prodrug Candesartan Cilexetil in Complex with 2-Hydroxypropyl-β-cyclodextrin: On the Biological Potency for Angiotensin II Antagonism
Ntountaniotis, Dimitrios,Andreadelis, Ioannis,Kellici, Tahsin F.,Karageorgos, Vlasios,Leonis, Georgios,Christodoulou, Eirini,Kiriakidi, Sofia,Becker-Baldus, Johanna,Stylos, Evgenios K.,Chatziathanasiadou, Maria V.,Chatzigiannis, Christos M.,Damalas, Dimitrios E.,Aksoydan, Busecan,Javornik, Uro?,Valsami, Georgia,Glaubitz, Clemens,Durdagi, Serdar,Thomaidis, Nikolaos S.,Kolocouris, Antonios,Plavec, Janez,Tzakos, Andreas G.,Liapakis, George,Mavromoustakos, Thomas
, p. 1255 - 1271 (2019/02/26)
Renin-angiotensin aldosterone system inhibitors are for a long time extensively used for the treatment of cardiovascular and renal diseases. AT1 receptor blockers (ARBs or sartans) act as antihypertensive drugs by blocking the octapeptide hormone Angiotensin II to stimulate AT1 receptors. The antihypertensive drug candesartan (CAN) is the active metabolite of candesartan cilexetil (Atacand, CC). Complexes of candesartan and candesartan cilexetil with 2-hydroxylpropyl-β-cyclodextrin (2-HP-β-CD) were characterized using high-resolution electrospray ionization mass spectrometry and solid state 13C cross-polarization/magic angle spinning nuclear magnetic resonance (CP/MAS NMR) spectroscopy. The 13C CP/MAS results showed broad peaks especially in the aromatic region, thus confirming the strong interactions between cyclodextrin and drugs. This experimental evidence was in accordance with molecular dynamics simulations and quantum mechanical calculations. The synthesized and characterized complexes were evaluated biologically in vitro. It was shown that as a result of CAN's complexation, CAN exerts higher antagonistic activity than CC. Therefore, a formulation of CC with 2-HP-β-CD is not indicated, while the formulation with CAN is promising and needs further investigation. This intriguing result is justified by the binding free energy calculations, which predicted efficient CC binding to 2-HP-β-CD, and thus, the molecule's availability for release and action on the target is diminished. In contrast, CAN binding was not favored, and this may allow easy release for the drug to exert its bioactivity.
METHOD FOR PREPARING TRITYL CANDESARTAN
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Paragraph 0035, (2018/06/15)
The present invention uses a candesartan cyclic compound as a starting material and performs thereon a three-step reaction of forming tetrazole, hydrolysis and adding a protecting group to directly obtain trityl candesartan without separating an intermediate product via crystallization. The operating process is simple and thus is more applicable to industrial production.
Preparation method of candesartan
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, (2017/09/02)
The invention relates to a preparation method of candesartan. The preparation method comprises the steps of carrying out N-alkylation reaction, deprotection reaction and ester hydrolysis reaction on raw materials including 2-ethoxybenzimidazole-7-carboxylate and a tetrazole compound, so as to obtain the candesartan. According to the preparation method, compounds with high toxicity and large environmental protection pressure such as sodium azide, tributyl tin chloride or tributyl tin azide are not used; and compared with processes in the prior art, the preparation method is simple and convenient in operation and is beneficial to industrial large-scale production.