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Olmesartan Medoxomil

CAS No.
144689-63-4
Chemical Name:
Olmesartan Medoxomil
Synonyms
Benicar;Oimesartan;OLMESARTAN MEDOXIMIL;OMST;CS-866;Olmetec;Olmesartan API;Olmesartan Medoxomi;OlmesartanC29H30N6O6;Olmesartan MedoxomiI
CBNumber:
CB8254825
Molecular Formula:
C29H30N6O6
Molecular Weight:
558.59
MDL Number:
MFCD00944911
MOL File:
144689-63-4.mol
Last updated:2024-05-06 14:49:57

Olmesartan Medoxomil Properties

Melting point 180°C
Boiling point 804.2±75.0 °C(Predicted)
Density 1.38±0.1 g/cm3(Predicted)
Flash point 180°C
storage temp. 2-8°C
solubility DMSO: soluble20mg/mL, clear
pka 4.15±0.10(Predicted)
form powder
color white to beige
Decomposition 180 ºC
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)
FDA UNII 6M97XTV3HD
ATC code C09CA08

Pharmacokinetic data

Protein binding 99.7%
Excreted unchanged in urine 35-50%
Volume of distribution 0.24(L/kg)
Biological half-life 10-15 / 36

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H302+H312+H332
Precautionary statements  P261-P264-P280-P301+P312-P302+P352+P312-P304+P340+P312
RTECS  NI4014200
HS Code  2934990002
NFPA 704
0
3 0

Olmesartan Medoxomil price More Price(49)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR1851 Olmesartan medoxomil Pharmaceutical Secondary Standard; Certified Reference Material 144689-63-4 200mg $257 2024-03-01 Buy
Sigma-Aldrich 1478367 Olmesartan medoxomil United States Pharmacopeia (USP) Reference Standard 144689-63-4 100mg $919 2024-03-01 Buy
TCI Chemical O0510 Olmesartan Medoxomil >98.0%(HPLC)(T) 144689-63-4 1g $103 2024-03-01 Buy
TCI Chemical O0510 Olmesartan Medoxomil >98.0%(HPLC)(T) 144689-63-4 5g $308 2024-03-01 Buy
Cayman Chemical 11614 Olmesartan Medoxomil ≥98% 144689-63-4 10mg $32 2024-03-01 Buy
Product number Packaging Price Buy
PHR1851 200mg $257 Buy
1478367 100mg $919 Buy
O0510 1g $103 Buy
O0510 5g $308 Buy
11614 10mg $32 Buy

Olmesartan Medoxomil Chemical Properties,Uses,Production

Description

Olmesartan medoxomil was launched in the US as benicar(R), 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 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.

Definition

ChEBI: Olmesartan medoxomil is a member of biphenyls.

brand name

Benicar

General Description

Olmesartan Medoxomil is a synthetic imidazole derivative prodrug with an antihypertensive property. Upon hydrolysis, olmesartan medoxomil is converted to olmesartan. Olmesartan selectively binds to the angiotensin type 1 (AT1) receptor of angiotensin II in vascular smooth muscle and adrenal gland, thereby competing angiotensin II binding to the receptor. This prevents angiotensin II-induced vasoconstriction and decreases aldosterone production, thereby preventing aldosterone-stimulated sodium retention and potassium excretion.

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

Olmesartan Medoxomil can be synthesized in 8 steps from diaminomaleonitrile by successive reactions with trialkylorthopropanoate to access 2-propyl-imidazole-45dicarbonitrile, conversion of the two nitrile functions to the corresponding ethyl esters, followed by methylmagnesium bromide addition to give the corresponding 4-(1-hydroxyalkyl)imidazole derivative.
synthesis of Olmesartan Medoxomil
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.

144690-92-6
144689-63-4
Synthesis of Olmesartan Medoxomil from Trityl olmesartan
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View Lastest Price from Olmesartan Medoxomil manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Olmesartan Medoxomil pictures 2024-06-07 Olmesartan Medoxomil
144689-63-4
US $0.00-0.00 / g 1g 99% 100kg Wuhan Cell Pharmaceutical Co., Ltd
Olmesartan Medoxomil pictures 2024-06-04 Olmesartan Medoxomil
144689-63-4
US $0.00 / Kg/Bag 2Kg/Bag 99% up, High Density 20 tons Sinoway Industrial co., ltd.
Olmesartan Medoxomil pictures 2024-05-06 Olmesartan Medoxomil
144689-63-4
US $0.00-0.00 / KG 1KG 99%, USP, EP 5,000KG Hangzhou Hyper Chemicals Limited

Olmesartan Medoxomil Spectrum

(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-((2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl] 4-yl)methyl)-4-( OlMesartan MedoxoMil SynoyM: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 OLMESARTAN MEDOXOMIL USP ORGANIC CHEMICA OMST 1H-Imidazole-5-carboxylic acid, 4-(1-hydroxy-1-methylethyl)-2-propyl-1-[[2'-(2H-tetrazol-5-yl)[1,1'-biphenyl]-4-yl]methyl]-, (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester Olmesartan medoxomil for system suitability Olmesartan MedoxomiI Olmesartan Medoxomi (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-((2'-(2H-tetrazol-5-yl)biphenyl-4-yl)methyl)-4-(2-hyd 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 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 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 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 Sanguisorba officinalis L. Olmesartan Medoxomil (100 mg) (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 OlMesartan MedoxoMil (Benicar) (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 Medoxomil USP/EP/BP olmesartan medoxomil olmetec 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 esterEuEEuE Olmesartan Medoxomil-USP 4-(1-Hydroxy-1-methylethyl)-2-propyl-1-[[2’-(2H-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 (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(2Htetrazol-5-yl)phenyl]phenyl]methyl]imidazole-4-carboxylate Good Quality Olmesartan Medoxomil CAS?144689-63-4?Omst for Anti-Hypertensive (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-((2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate Olmesartan Medoxomil (CS 866) 5-(2-hydroxypropan-2-yl)-2-propyl-3-[[4-[2-(2H-tetrazol-5-yl)phenyl]phenyl]methyl]-4-imidazolecarboxylic acid (5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester Olmesartan medoxomil CRS Olmesartan medoxomil for system suitability CRS Olmesartan Medoxomil RS olmesartan medoxomil olmetec 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 esterEuEE Olmesartan medoxomil (Y0001405) Olmesartan MedoxomilQ: What is Olmesartan Medoxomil Q: What is the CAS Number of Olmesartan Medoxomil Q: What is the storage condition of Olmesartan Medoxomil Olmesartan Medoxomil (1478367) Benicar Oimesartan OLMESARTAN MEDOXIMIL Benzenesulfonylchloride,8-(acetylamino)- Olmesartan Medoxomile OLMESARTAN MEDOXOMIL 13.33 % GRANULES OLEMISARTAN MEDAXMIL Olmesartan API Olmesartan Medoxomil (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 Olmesartan medoxomil API (5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 1-((2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-4-(2-hydroxypropan-2-yl)-2-propyl-1H-imidazole-5-carboxylate 144689-63-4 144689-63-5 C29H30N6O C29H30N6O6 Cardiovascular APIs OMNICEF API Inhibitor