(5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate

• ChemBase编号: 160
• 分子式: C29H30N6O6
• 平均质量: 558.5851
• 单一同位素质量: 558.22268271
• SMILES: OC(c1nc(n(c1C(=O)OCc1oc(=O)oc1C)Cc1ccc(cc1)c1c(cccc1)c1n[nH]nn1)CCC)(C)C
• Canonical SMILES: CCCc1nc(c(n1Cc1ccc(cc1)c1ccccc1c1n[nH]nn1)C(=O)OCc1oc(=O)oc1C)C(O)(C)C
• InChI: InChI=1S/C29H30N6O6/c1-5-8-23-30-25(29(3,4)38)24(27(36)39-16-22-17(2)40-28(37)41-22)35(23)15-18-11-13-19(14-12-18)20-9-6-7-10-21(20)26-31-33-34-32-26/h6-7,9-14,38H,5,8,15-16H2,1-4H3,(H,31,32,33,34)
• InChIKey: UQGKUQLKSCSZGY-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate; (5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate
• IUPAC传统名: benicar; (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)imidazole-4-carboxylate; (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)imidazole-4-carboxylate; olmesartan; @olmesartan; (5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate
• 商标名: Benicar; Olmetec; Votum; Benicar HCT
• 别名: 4-(1-Hydroxy-1-methylethyl)-2-propyl-1-[[2’-(1H-tetazol-5-yl)[1,1’-biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxylic Acid (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester; CS-866; (5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate; Olmesartan medoxomil; (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl] 4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate; Olmesartan medoximil; Olmesartan medoxomil; DE-092; Olmesartan; Benicar; Olmetec; Olmesartan

登记号

• CAS号: 144689-63-4; 144689-24-7
• MDL号: MFCD00944911
• PubChem SID: 160963623
• PubChem CID: 130881

理论计算性质

JChem

• Acid pKa: 7.399751
• 质子受体: 8
• 质子供体: 2
• LogD (pH = 5.5): 5.5291805
• LogD (pH = 7.4): 5.25633
• Log P: 5.5455294
• 摩尔折射率: 163.4584 cm^3
• 极化性: 58.660378 Å^3
• 极化表面积: 154.34 Å^2
• 可自由旋转的化学键: 11
• 里宾斯基五规则: false

ALOGPS 2.1

• Log P: 4.31
• LOG S: -4.86
• 溶解度: 7.75e-03 g/l

分子性质

理化性质

• 溶解度: DMSO; Ethanol; Methanol
• 外观: White Solid
• 熔点: 180-182°C (dec.)
• 疏水性(logP): 2.66; 5.9

安全信息

• 保存条件: -20°C; -20°C Freezer
• 保存注意事项: IRRITANT
• TSCA收录: false

药理学性质

• 作用靶点: Angiotensin receptor; RAAS
• 生物活性机理: Angiotensin II receptor antagonists; Block the binding of angiotension II to the AT1 receptors in vascular muscle; Prodrug-type angiotensin II receptor antagonist

产品相关信息

• 纯度: 95%; 95+%
• 成盐信息: Free Base
• 应用领域: Antihypertensive agent

详细说明

DrugBank - DB00275

• Drug Groups: approved; investigational
• Description: Olmesartan is an antihypertensive agent which belongs to the class of medicines called angiotensin II receptor antagonists. It acts rapidly to lower high blood pressure. It is marketed worldwide by Daiichi Sankyo, Ltd. and in the United States by Daiichi Sankyo, Inc. and Forest Laboratories.
• Indication: For the treatment of hypertension.
• Pharmacology: Olmesartan, a specific angiotensin II type 1 antagonist, is used alone or with other antihypertensive agents to treat hypertension. Unlike the angiotensin receptor antagonist losartan, olmesartan does not have an active metabolite or possess uricosuric effects. Blockade of the angiotensin II receptor inhibits the negative regulatory feedback of angiotensin II on renin secretion, but the resulting increased plasma renin activity and circulating angiotensin II levels do not overcome the effect of olmesartan on blood pressure.
• Toxicity: Symptoms of overdose include dehydration (dry mouth, excessive thirst, muscle pain or cramps, nausea and vomiting, weakness), dizziness, low blood pressure, and slow or irregular heartbeat.
• Affected Organisms: Humans and other mammals
• Biotransformation: Olmesartan is rapidly and completely bioactivated by ester hydrolysis to olmesartan during absorption from the gastrointestinal tract. There is virtually no further metabolism of olmesartan.
• Absorption: Bioavailability is about 26%. Food does not affect the bioavailability of olmesartan.
• Half Life: Approximately 13 hours
• Protein Binding: Highly bound to plasma proteins (99%) and does not penetrate red blood cells.
• Distribution: * 17 L
• Clearance: * Total plasma cl=1.3 L/h; * Renal cl=0.6 L/h
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1587

Research Area: Cardiovascular Disease
Biological Activity:
Olmesartan is an angiotensin II receptor antagonist with an IC50 of 7.7 nM. It is used to treat high blood pressure. Olmesartan works by blocking the binding of angiotensin II to the AT1 receptors in vascular muscle; it is therefore independent of angiotensin II synthesis pathways, unlike ACE inhibitors. By blocking binding rather than synthesis of angiotensin II, olmesartan inhibits the negative regulatory feedback on renin secretion. As a result of this blockage, olmesartan reduces vasoconstriction and the secretion of aldosterone. This lowers blood pressure by producing vasodilation, and decreasing peripheral resistance. [1]

Selleck Chemicals - S1604

Research Area: Cancer
Biological Activity:
Olmesartan medoxomil (Benicar) is a compound which is hydrolyzed to olmesartan that is a selective AT1 subtype angiotensin II receptor antagonist.Olmesartan medoxomil (Benicar) was converted to olmesartan  during absorption from the gastrointestinal tract. Olmesartan is indicated for the treatment of hypertension. It may be used alone or in combination with other antihypertensive agents. Olmesartan medoxomil (Benicar) exerts its pharmacological functions via blocking the binding of angiotensin II to the AT1 receptors in vascular muscle; it is therefore independent of angiotensin II synthesis pathways, unlike ACE inhibitors. By blocking the binding rather than the synthesis of angiotensin II, olmesartan prevents the negative regulatory feedback on renin secretion. As a result of this blockage, olmesartan attenuates vasoconstriction and the secretion of aldosterone. Olmesartan lowers blood pressure by producing vasodilation, and decreasing peripheral resistance.

Toronto Research Chemicals - O550000

An angiotensin II receptor antagonist. Used as an anti-hypertensive.

参考文献

• http://en.wikipedia.org/wiki/Olmesartan
• Yanagisawa, H., et al.: J. Med. Chem., 39, 323 (1996)
• Puchler, K., et al.: J. Hypertens., 15, 1809 (1996)
• Eur. Pat., 1992, Sankyo, 503 785; CA, 118, 22240k, (CS 866, RNH 6270, synth, pharmacol)
• Mizuno, M. et al., Eur. J. Pharmacol., 1995, 285, 181-188, (pharmacol, CS 866, RNH 6270)
• Yanagisawa, H. et al., J. Med. Chem., 1996, 39, 323-328, (synth, CS 866, RNH 6270, pmr, ir, pharmacol)