(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 ID: 160
• Molecular Formular: C29H30N6O6
• Molecular Mass: 558.5851
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: 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
• Brand Name: Benicar; Olmetec; Votum; Benicar HCT
• Synonyms: 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

Database IDs

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

CALCULATED PROPERTIES

JChem

• Acid pKa: 7.399751
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 5.5291805
• LogD (pH = 7.4): 5.25633
• Log P: 5.5455294
• Molar Refractivity: 163.4584 cm^3
• Polarizability: 58.660378 Å^3
• Polar Surface Area: 154.34 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 4.31
• LOG S: -4.86
• Solubility (Water): 7.75e-03 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: 180-182°C (dec.)
• Hydrophobicity(logP): 2.66; 5.9

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Target: Angiotensin receptor; RAAS
• Mechanism of Action: Angiotensin II receptor antagonists; Block the binding of angiotension II to the AT1 receptors in vascular muscle; Prodrug-type angiotensin II receptor antagonist

Product Information

• Purity: 95%; 95+%
• Salt Data: Free Base
• Application(s): Antihypertensive agent

DETAILS

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.

REFERENCES

• 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)