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Azilsartan medoxomil

Azilsartan medoxomil structure

CAS No:
863031-21-4
Formula:
C30H24N4O8
Chemical Name:
Azilsartan medoxomil
Synonyms:
1H-Benzimidazole-7-carboxylic acid,1-[[2′-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)[1,1′-biphenyl]-4-yl]methyl]-2-ethoxy-,(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl ester;Azilsartan medoxomil;TAK 491;(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-1-[[2′-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]-1H-benzimidazole-7-carboxylate;Edarbi;(5-Methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate;Ipreziv
Categories:
Biochemical Engineering > Inhibitors

Description

Azilsartan medoxomil(TAK 491) is an orally administered angiotensin II receptor type 1 antagonist with IC50 of 0.62 nM, which used in the treatment of adults with essential hypertension. IC50 Value: 0.62 nM [2]Target: AT1 receptorin vitro: In aortic endothelial cells, azilsartan inhibited cell proliferation at concentrations as low as 1 μmol/l, whereas valsartan showed little or no antiproliferative effects at concentrations below 10 μmol/l. Antiproliferative effects of azilsartan were a

Azilsartan medoxomil is a carboxylic ester obtained by formal condensation of the carboxy group of azilsartan with the hydroxy group of 4-(hydroxymethyl)-5-methyl-1,3-dioxol-2-one. A prodrug for azilsartan, it is used for treatment of hypertension. It has a role as a prodrug, an angiotensin receptor antagonist and an antihypertensive agent. It is a member of benzimidazoles, a dioxolane, a cyclic carbonate ester, a 1,2,4-oxadiazole, an aromatic ether and a carboxylic ester. It derives from an azilsartan. It is a conjugate acid of an azilsartan medoxomil(1-).|Azilsartan medoxomil is an angiotensin II receptor antagonist indicated for the treatment of mild to moderate essential hypertension. Azilsartan medoxomil is a prodrug of Azilsartan marketed as "Edarbi" by Takeda. Azilsartan medoxomil has so far been shown to be superior to olmesartan and valsartan in lowering blood pressure.|Azilsartan Medoxomil is a medoxomil prodrug of azilsartan, an angiotensin II receptor antagonist with antihypertensive activity. Upon hydrolysis, azilsartan selectively and competitively binds to the AT1 subtype angiotensin II receptor and blocks the binding of angiotensin II to the receptor, thus promoting vasodilatation and counteracting the effects of aldosterone. Converted from angiotensin I by angiotensin-converting enzyme (ACE), angiotensin II stimulates the adrenal cortex to synthesize and secrete aldosterone, decreasing sodium excretion and increasing potassium excretion, and acts as a vasoconstrictor in vascular smooth muscle.

Azilsartan medoxomil Basic Attributes

Molecular Weight：

568.53356

Exact Mass：

568.53

EC Number：

1308068-626-2

UNII：

LL0G25K7I2

DSSTox ID：

DTXSID10235482

NCI Thesaurus Code：

C75110

ATC Code：

C09CA09|C - Cardiovascular system

Characteristics

PSA：

140

XLogP3：

4.9

Density：

1.5±0.1 g/cm3

Melting Point：

212-214

Boiling Point：

748.0±70.0°C at 760 mmHg

Flash Point：

406.2±35.7 °C

Refractive Index：

1.680

Water Solubility：

Practically insoluble in water

PKA：

6.1None

Dissociation Constants：

6.1

Toxicity

Toxicity Summary：

Hypotension and diarrhea are most common.

Protein Binding：

Azilsartan medoxomil is 99% plasma protein bound.

Drug Information

Drug Indication：

Treatment of hypertension (alone or as an adjunct).|FDA Label|Edarbi is indicated for the treatment of essential hypertension in adults.|Ipreziv is indicated for the treatment of essential hypertension in adults.|Treatment of hypertension

Pharmacology：

Azilsartan medoxomil decreases the pressor effect of angiotensin II. In response, angiotensin I, angiotensin II, and renin are increased while aldosterone is decreased.

MeSH：

Agents that antagonize ANGIOTENSIN II TYPE 1 RECEPTOR. Included are ANGIOTENSIN II analogs such as SARALASIN and biphenylimidazoles such as LOSARTAN. Some are used as ANTIHYPERTENSIVE AGENTS. (See all compounds classified as Angiotensin II Type 1 Receptor Blockers.)

Absorption：

Azilsartan medoxomil is hydrolyzed to the active metabolite azilsartan in the GI tract. The presence of food does not affect oral absorption of azilsartan medoxomil, and the bioavailability is 60% for azilsartan. Maximum plasma concentrations are reached in 1.5 to 3 hours.|Renal clearance is 2.3 L/minute.|Azilsartan medoxomil has a Vd of 16L.|Fecal elimination accounts for 55%, urine excretion 42%, and unchanged drug 15%.

Metabolism/Metabolites：

Azilsartan is metabolized by CYP2C9. CYP2C9 carries out decarboxylation of azilsartan to M-I, and O-dealkylation of azilsartan to M-II. Both M-I and M-II have no pharmacologic activity.

Biological Half-Life：

The half-life is 11 hours, and it takes about 5 days to reach steady state concentrations.

Mechanism of Action：

Azilsartan medoxomil blocks the angiotensin II type 1 receptor preventing angiotensin II from binding and causing vasoconstriction. Azilsartan's ability to remain tightly bound to AT1 receptors for very long periods after drug washout is among its most unusual features.

MeSH Entry Terms：

azilsartan medoxomil

Azilsartan medoxomil Use and Manufacturing

Use Classification：

Human drugs -> Edarbi -> EMA Drug Category|Agents acting on the renin-angiotensin system -> Human pharmacotherapeutic group|Human drugs -> Ipreziv -> EMA Drug Category|Human Drugs -> EU pediatric investigation plans|Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:568.5
XLogP3:4.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:10
Exact Mass:568.15941374
Monoisotopic Mass:568.15941374
Topological Polar Surface Area:140
Heavy Atom Count:42
Complexity:1100
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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CAS No.: 863031-21-4

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CAS No.: 863031-21-4

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