ChemicalBook > CAS DataBase List > Olmesartan Medoxomil

Olmesartan Medoxomil

Product Name
Olmesartan Medoxomil
CAS No.
144689-63-4
Chemical Name
Olmesartan Medoxomil
Synonyms
Benicar;Oimesartan;OLMESARTAN MEDOXIMIL;OMST;CS-866;Olmetec;Olmesartan API;Omesartan ester;Olmesartan Medoxomi;Olmesartn Medoxomil
CBNumber
CB8254825
Molecular Formula
C29H30N6O6
Formula Weight
558.59
MOL File
144689-63-4.mol
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Olmesartan Medoxomil Property

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
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
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)
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Safety

RTECS 
NI4014200
HS Code 
2934990002
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR1851
Product name
Olmesartan medoxomil
Purity
Pharmaceutical Secondary Standard; Certified Reference Material
Packaging
200mg
Price
$257
Updated
2024/03/01
Sigma-Aldrich
Product number
1478367
Product name
Olmesartan medoxomil
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
100mg
Price
$919
Updated
2024/03/01
TCI Chemical
Product number
O0510
Product name
Olmesartan Medoxomil
Purity
>98.0%(HPLC)(T)
Packaging
1g
Price
$103
Updated
2024/03/01
TCI Chemical
Product number
O0510
Product name
Olmesartan Medoxomil
Purity
>98.0%(HPLC)(T)
Packaging
5g
Price
$308
Updated
2024/03/01
Cayman Chemical
Product number
11614
Product name
Olmesartan Medoxomil
Purity
≥98%
Packaging
10mg
Price
$32
Updated
2024/03/01
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Olmesartan Medoxomil Chemical Properties,Usage,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.

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.

Olmesartan Medoxomil Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Olmesartan Medoxomil manufacturers

Sinoway Industrial co., ltd.
Product
Olmesartan Medoxomil 144689-63-4
Price
US $0.00/Kg/Bag
Min. Order
2Kg/Bag
Purity
99% up, High Density
Supply Ability
20 tons
Release date
2023-11-14
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Olmesartan Medoxomil 144689-63-4
Price
US $0.00/KG
Min. Order
1KG
Purity
99.0%,USP/EP
Supply Ability
500KG/month
Release date
2021-07-03
HEBEI SHENGSUAN CHEMICAL INDUSTRY CO.,LTD
Product
Olmesartan Medoxomil 144689-63-4
Price
US $980.00-750.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
5000
Release date
2024-08-15

144689-63-4, Olmesartan MedoxomilRelated Search:

Olmesartan Olmesartan OlMesartan Lactone IMpurity 1-(4-(2-hydroxypropan-2-yl)-2-propyl-1-((2'-(1-trityl-1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-1H-imidazol-5-yl)ethanone Losartan potassium Irbesartan Olmesartan Rebeprazole sodium Valganciclovir hydrochloride 4-(1-Methoxy-1-methylethyl)-2-propyl-1H-Imidazole-5-carboxylic acid ethyl ester Anastrozole Tasosartan EPROSARTAN 4,5-Bismethylene-1,3-dioxolan-2-one Dehydro Olmesartan OlMesartan MedoxoMil Ethyl Methyl Analog Diethyl 2-propylImidazoledicarbonate OlMesartan MedoxoMil Butyl IMpurity

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