| Identification | More | [Name]
CS-866 | [CAS]
144689-63-4 | [Synonyms]
OLMESARTAN
4-(1-hydroxy-1-methylethyl)-2-propyl-1-((2'-(1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl-1H-Imidazole-5-carboxylic acid, (5-methyl-2-oxo-1,3-dioxol-4-yl) methyl ester
Benicar
OlmesartanC29H30N6O6
CS-866, 4-(1-Hydroxy-1-methylethyl)-2-propyl-1-[[2(1H-tetazol-5-yl)[1,1biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxylic Acid (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl Ester
Oimesartan
4-(1-Hydroxy-1-methylethyl)-2-propyl-1-[[2'-(1H-tetazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-carboxylicacid(5-Methyl-2-oxo-1,3-dioxol-4-yl)methylester
CS-866
Olmesartan medoxomil
Olmetec
OLMESARTAN MEDOXIMIL
5-(1-HYDROXY-1-METHYLETHYL)-2-PROPYL-3-[2''-(1H-TETRAZOL-5-YL)-BIPHENYL-4-YLMETHYL]-3H-IMIDAZOLE-4-CARBOXYLIC ACID 5-METHYL-2-OXO-[1,3]DIOXOL-4-YLMETHYL ESTER
5-(1-Hydroxy-1-methylethyl)-2-propyl-3-[2'-(1H-tet | [EINECS(EC#)]
604-433-1 | [Molecular Formula]
C24H26N6O3 | [MDL Number]
MFCD00914967 | [Molecular Weight]
446.5 | [MOL File]
144689-63-4.mol |
| Chemical Properties | Back Directory | [Appearance]
White to off-white crystalline powder | [Melting point ]
180°C | [Boiling point ]
804.2±75.0 °C(Predicted) | [density ]
1.38±0.1 g/cm3(Predicted) | [Fp ]
180°C | [storage temp. ]
2-8°C | [solubility ]
DMSO: soluble20mg/mL, clear | [form ]
powder | [pka]
4.15±0.10(Predicted) | [color ]
white to beige | [Decomposition ]
180 ºC | [Usage]
An angiotensin II receptor antagonist. Used as an anti-hypertensive | [InChIKey]
UQGKUQLKSCSZGY-UHFFFAOYSA-N | [SMILES]
C1(CCC)N(CC2=CC=C(C3=CC=CC=C3C3=NNN=N3)C=C2)C(C(OCC2=C(C)OC(=O)O2)=O)=C(C(O)(C)C)N=1 | [CAS DataBase Reference]
144689-63-4(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Olmesartan medoxomil(144689-63-4) was launched in the US as benicar@, an orally administered treatment for hypertension. Olmesartan, is a new selective and competitive nonpeptide angiotensin II type 1 receptor antagonist and potently inhibits the Ang.ll-induced pressor responses. The drug competitively inhibited binding of [125I1]-All to AT1 receptors in bovine adrenal cortical membranes, but had no effect on binding to AT2 receptors in bovine cerebellar membranes. In comparative clinical studies in patients with essential hypertension, olmesartan reduced sitting cuff diastolic blood pressure significantly more than losartan, valdesartan and ibesartan, while reductions in systolic blood pressure were similar for all treatments. Olmesartan medoxomil was also shown to reduce blood pressure significantly more effectively than losartan and the ACE inhibitor captopril and as effectively as the pbloker atenolol.
| [Chemical Properties]
White to off-white crystalline powder | [Originator]
Sanky (Japan) | [Uses]
Olmesartan medoxomil(144689-63-4) is an angiotensin II receptor antagonist used to treat high blood pressure. Olmesartan works by blocking the binding of angiotensin II to the AT1 receptors in vascular muscle. By blocking the binding rather than the synthesis of angiotensin II, olmesartan inhibits the negative regulatory feedback on renin secretion.
Olmesartan medoxomil is a pro-drug that is de-esterified to the active metabolite, olmesartan. Olmesartan has a dual method of elimination, with about 60% eliminated by the liver and the remainder by the kidney. In situations of impaired renal or hepatic function, the alternative excretion pathway can compensate for the compromised one. Olmesartan is not metabolized by the cytochrome P450 enzyme system and therefore has a low potential for metabolic drug interactions, a feature that may be of importance when treating patients on multiple drug regimens, such as the elderly. Olmesartan is well tolerated and has an excellent safety profile that is comparable to that of placebo. In addition, olmesartan provides 24-h blood pressure control with a once-daily dosing. In head-to-head studies, olmesartan delivered superior blood pressure reduction when compared with other angiotensin-II receptor antagonists at their recommended doses.
| [Uses]
An angiotensin II receptor antagonist. Used as an anti-hypertensive | [Definition]
ChEBI: Olmesartan medoxomil is a member of biphenyls. | [Brand name]
Benicar | [General Description]
Pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to the preparation of in-house working standards | [Biochem/physiol Actions]
Olmesartan medoxomil is a selective Angiotensin II Type I receptor blocker and antihypertensive drug. Olmesartan medoxomil is converted enzymatically to the active form olmesartan. | [Clinical Use]
Angiotensin-II receptor antagonist:
Hypertension | [Side effects]
Dizziness or lightheadedness may occur as your body adjusts to the medication. If any of these effects persist or worsen, tell your doctor or pharmacist promptly. To reduce the risk of dizziness and lightheadedness, get up slowly when rising from a sitting or lying position. | [Synthesis]
The imidazole ring of olmesartan (18)
was constructed with diaminomaleonitrile 155 and
trimethylorthobutyrate (156) in CH3CN then xylene to give
157 in 96% yield. Acid hydrolysis of 157 in 6N HCl
gave the dicarboxylic acid intermediate. After esterification
of the diacid in ethanol in the presence of HCl, diester 158
was treated with MeMgCl to give 4-(1-hydroxyalkyl)
imidazole 159 in 95% yield. Alkylation of 159 with
biphenyl bromide 160 in the presence of potassium tbutoxide
afforded 161 in 80% yield. Ester 161 was then
hydrolyzed to free carboxylic acid 162 under basic conditions, and 162 was treated with chloride 163 in the
presence of K2CO3 to give ester 164 in 88% yield from 161.Lastly, the trityl group was removed with 25% aqueous
acetic acid to give olmesartan (18) in 81% yield.
| [Drug interactions]
Potentially hazardous interactions with other drugs
Anaesthetics: enhanced hypotensive effect.
Analgesics: antagonism of hypotensive effect and
increased risk of renal impairment with NSAIDs;
hyperkalaemia with ketorolac and other NSAIDs.
Antihypertensives: increased risk of hyperkalaemia
hypotension and renal impairment with ACE-Is and
aliskiren.
Ciclosporin: increased risk of hyperkalaemia and
nephrotoxicity.
Diuretics: enhanced hypotensive effect;
hyperkalaemia with potassium-sparing diuretics.
ESAs: increased risk of hyperkalaemia; antagonism
of hypotensive effect.
Lithium: reduced excretion (possibility of enhanced
lithium toxicity).
Potassium salts: increased risk of hyperkalaemia.
Tacrolimus: increased risk of hyperkalaemia and
nephrotoxicity. | [Metabolism]
Olmesartan medoxomil is an ester prodrug that is
hydrolysed during absorption from the gastrointestinal
tract to the active form olmesartan.
It is excreted in the urine and the bile as olmesartan;
about 35-50% of the absorbed dose is excreted in the
urine and the remainder in the bile. |
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