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Azilsartan Medoxomil

HCID 135409642
새 노트새 반응견적 요청하기인쇄 미리보기
기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
863031-21-4
표준 SMILES
CCOc1nc2cccc(C(=O)OCc3oc(=O)oc3C)c2n1Cc1ccc(-c2ccccc2-c2noc(=O)[nH]2)cc1
InChIKey
QJFSABGVXDWMIW-UHFFFAOYSA-N
분자식
C30H24N4O8
평균 분자량
568.5 g/mol
단동위원소 질량
568.15941373

개요

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 an antihypertensive agent, a prodrug and an angiotensin receptor antagonist. It is a member of benzimidazoles, a carboxylic ester, an aromatic ether, a dioxolane, a 1,2,4-oxadiazole and a cyclic carbonate ester. It is functionally related to an azilsartan. It is a conjugate acid of an azilsartan medoxomil(1-).

이름 및 식별자

우선 이름
Azilsartan Medoxomil
IUPAC
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate
영어명
Azilsartan Medoxomil
분자식
C30H24N4O8
분자량
568.53

이름 및 동의어

AZILSARTAN MEDOXOMIL863031-21-4TAK 491TAK-491azilsartan medoxomiloIprezivAR-14LL0G25K7I2azilsartanum medoxomilumTAK491CHEBI:68845DTXSID10235482
이름 더 보기
Azilsartan MedoxiMilCS-306Azizartan esterAzilsaran medoxomilAzilsartan MedoxoMil(TAK 491)Azilsartan Kamedoxomil Form IAzilsartan Medoxomil USP/EP/BPAzilsartan Acid Medoxomil Ester
(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(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}-1-benzimidazole-7-carboxylate1H-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 ester1H-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(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)-1-benzimidazole-7-carboxylate(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-carboxylateRefChem:916599DTXCID10157973

물성

구조 계산 물성

XLogP
4.9
극성 표면적
140 Ų
수소 결합 공여자 수
1
수소 결합 수용자 수
10
회전 가능 결합 수
10
무거운 원자 수
42
형식 전하
0
복잡도
1,100

실험 및 물리화학적 성질

Drugs · 2건

Pharmaceuticals -> Listed in ZINC15

Pharmaceuticals -> Used in Switzerland

Solubility<1 mg/mL
Human Drugs · 2건

FDA approved drugs -> Active ingredient

EMA approved medicines: Human medicine

물리화학적 성질

녹는점
160 · 160-161oC
밀도
1.45 · 1.45
저장 조건
Refrigerator
용해도
DMSO (약간 용해됨), 메탄올(약간 용해됨,가열, 초음파 처리)
산도 계수 (pKa)
6.99 · 6.99±0.20(Predicted)
물리적 상태
고체
색상
흰색~밝은 베이지
InChIKey
QJFSABGVXDWMIW-UHFFFAOYSA-N
SMILES
C1(OCC)N(CC2=CC=C(C3=CC=CC=C3C3=NC(=O)ON3)C=C2)C2=C(C(OCC3=C(C)OC(=O)O3)=O)C=CC=C2N=1

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

안전 데이터

신호 어
Warning
유해·위험 문구
암호 유해·위험 문구 위험 등급 범주 신호 어 그림 문자 P- 코드 H302

화학 및 산업

약리 정보

ATC Code · 2건

C - Cardiovascular system

QC - Cardiovascular system

Protein BindingAzilsartan is >99% bound to human plasma proteins, mainly serum albumin. Protein binding is constant at azilsartan plasma concentrations well above the range achieved with recommended doses.
Pharmacodynamics · 1건

Pharmacodynamic effects of azilsartan medoxomil are mediated by its active metabolite, azilsartan. Azilsartan inhibits the pressor effects of an angiotensin II infusion in a dose-related manner. At a single 32 mg dose, azilsartan inhibited the maximal pressor effect by approximately 90% at peak plasma concentrations and by 60% at 24 hours after administration. In healthy subjects receiving single and repeated doses of azilsartan medoxomil, plasma angiotensin I and II concentrations and plasma renin activity increased, while plasma aldosterone concentrations decreased. Like other ARBs, azilsartan causes dose-dependent decrease in peripheral resistance and decreases smooth muscle vascular tone. As azilsartan blocks the angiotensin II receptor, the negative regulatory feedback of angiotensin II on renin secretion is inhibited; however, the resulting increased plasma renin activity and angiotensin II circulating levels do not overcome the blood pressure-lowering effect of azilsartan. Blood pressure-lowering effects of antihypertensive agents can be reduced in patients of African descent. However, there are no recommended dosage adjustment of azilsartan on the basis of a patient’s sex, race, or degree of renal or hepatic impairment. Azilsartan medoxomil has negligible effects on serum potassium or sodium levels. Azilsartan does not affect the biosynthesis of angiotensin II nor bradykinin levels. It also does not bind to any ion channels that are involved in cardiovascular regulation.

Mechanism of Action · 1건

The renin-angiotensin-aldosterone system regulates blood pressure. Angiotensin II is a peptide hormone that is a principal pressor agent in the renin-angiotensin-aldosterone system. It is a potent, direct vasoconstrictor that binds to the angiotensin II type 1 receptor (AT1 receptor) to stimulate the synthesis and release of aldosterone and promote cardiac stimulation. Angiotensin II promotes renal tubular reabsorption of sodium, resulting in water retention. It also inhibits further secretion of renin. AT1 receptors are highly expressed in vascular smooth muscle and the adrenal gland. Azilsartan medoxomil is a prodrug that is hydrolyzed to its active metabolite, azilsartan, in the gastrointestinal tract following oral administration. Azilsartan selectively binds to AT1 receptors as an antagonist, blocking vasoconstrictor and aldosterone-secreting effects of angiotensin II. Azilsartan has more than a 10,000-fold greater affinity for the AT1 receptor than for the AT2 receptor, which is predominantly involved in cardiovascular homeostasis. Azilsartan appears to dissociate from AT1 receptors much more slowly than other ARBs, which explains its longer duration of action when compared to other ARBs.

공급사

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공개 문의

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관련 반응

4건
반응 기록 만들기
HRID 254442 반응식
HRID 254442생성물로uspto-grants-2011_01
HRID 825651 반응식
HRID 825651생성물로Test data from https://doi.org/10.1039/C8SC04228D
HRID 1372373 반응식
HRID 1372373생성물로uspto-grants-2007_01
HRID 2101481 반응식
HRID 2101481생성물로uspto-grants-2009_08

화합물 노트

불러오는 중…

이 페이지에서기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트

데이터베이스 식별자

CAS
863031-21-4
PubChem CID
135409642
DTXSID
DTXSID10235482
ChEMBL
CHEMBL2028661
ChEBI
CHEBI:68845
UNII
LL0G25K7I2
Nikkaji
J2.748.955I
Biological Half-LifeThe elimination half-life of azilsartan is approximately 11 hours.
Metabolism/Metabolites · 1건

After azilsartan medoxomil is hydrolyzed into its active metabolite, azilsartan is metabolized to two primary metabolites, which are pharmacologically inactive. The major metabolite in plasma is metabolite M-II, which is formed via O-dealkylation mediated by CYP2C9. The minor metabolite is metabolite M-I, which is formed via decarboxylation mediated by CYP2C8 and CYP2B6. MII has approximately 50% systemic exposure of azilsartan, and MI has less than 1% systemic exposure of azilsartan.

FDA Pharmacological Classification · 2건

AZILSARTAN MEDOXOMIL

Angiotensin 2 Receptor Blocker [EPC]; Decreased Blood Pressure [PE]; Angiotensin 2 Type 1 Receptor Antagonists [MoA]

MeSH Pharmacological ClassificationAgents 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.
Absorption, Distribution and Excretion · 4건

During absorption, azilsartan medoxomil is hydrolyzed to azilsartan. The parent drug is not detectable in plasma after oral administration. The absolute bioavailability of azilsartan is estimated to be 60%. Tmax ranges from 1.5 to three hours. Steady-state levels of azilsartan are achieved within five days, and no accumulation in plasma occurs with repeated once-daily dosing.

Following oral administration of 14C-labeled azilsartan medoxomil, approximately 55% of radioactivity was recovered in feces and approximately 42% in urine. Of the recovered dose in urine, about 15% was excreted as azilsartan.

The volume of distribution of azilsartan is approximately 16 L. In rats, a minimal amount of radiolabelled drug crossed the blood-brain barrier. Azilsartan crossed the placental barrier in pregnant rats and was distributed to the fetus.

Renal clearance of azilsartan is approximately 2.3 mL/min.

응용 분야 · 1건

개요Azilsartan medoxomil (Edarbi), an angiotensin II receptor antagonist, was approved by the U.S. FDA in February 2011 for the treatment of hypertension in adults. The discovery of azilsartan was the result of a medicinal chemistry effort to identify an ARB with a different carboxylic acid isostere than the ones found in the marketed ARBs. Several of the marketed ARBs use a tetrazole group as a carboxylic acid isostere. The medicinal chemistry approach that led to azilsartan involved the replacement of this commonly used tetrazole with a 5-oxo-1,2,4-oxadiazole group. Azilsartan can be synthesized by Suzuki coupling of p-tolyl boronic acid to 2-bromobenzonitrile, followed by bromination of the methyl group. The bromide is displaced to introduce a protected 2-ethoxy-1H-benzo[d] imidazole-7-carboxylate. The cyano group is converted to a hydroxylamidine, followed by reaction with an alkyl-chloroformate and intramolecular cyclization to form the 5-oxo-1,2,4-oxadiazole ring. The acid is then deprotected and converted to a prodrug. The parent, azilsartan has been extensively characterized in vitro and compared with other marketed AT1 antagonists olmesartan, valsartan, telmisartan, irbesartan, and candesartan. Azilsartan was found to be a potent (IC50=2.6 nM), selective, inverse agonist of the AT1 receptor. From washout experiments, azilsartan was found have slow dissociation from the receptor and thus is characterized as an insurmountable antagonist.

추가 설명

정의ChEBI: 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.