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Details

Stereochemistry ACHIRAL
Molecular Formula C25H20N4O5
Molecular Weight 456.4501
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AZILSARTAN

SMILES

CCOC1=NC2=C(N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NOC(=O)N5)C(=CC=C2)C(O)=O

InChI

InChIKey=KGSXMPPBFPAXLY-UHFFFAOYSA-N
InChI=1S/C25H20N4O5/c1-2-33-24-26-20-9-5-8-19(23(30)31)21(20)29(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-27-25(32)34-28-22/h3-13H,2,14H2,1H3,(H,30,31)(H,27,28,32)

HIDE SMILES / InChI

Molecular Formula C25H20N4O5
Molecular Weight 456.4501
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Azilsartan medoxomil (trade name Edarb) is an angiotensin II receptor blocker (ARB) that lowers blood pressure by blocking the action of angiotensin II, a vasopressor hormone. It is indicated for the treatment of hypertension to lower blood pressure which reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. Azilsartan medoxomil may be used either alone or in combination with other antihypertensive agents such as chlorthalidone (CLD). As an ARB, azilsartan medoxomil selectively inhibits angiotensin II from binding to the angiotensin II type-1 receptor (AT1). This receptor inhibition provides the antihypertensive activity of azilsartan medoxomil because it blocks the pressor effects of angiotensin II. Azilsartan medoxomil is a prodrug of azilsartan. It is hydrolyzed to the active moiety, azilsartan, in the gastrointestinal (GI) tract during the absorption phase. Azilsartan medoxomil, in combination with the thiazide-like diuretic chlorthalidone, was more effective in lowering systolic BP than azilsartan plus HCTZ.

CNS Activity

Approval Year

TargetsConditions

Conditions

PubMed

PubMed

TitleDatePubMed
TAK-536, a new AT1 receptor blocker, improves glucose intolerance and adipocyte differentiation.
2007 May
Azilsartan Medoxomil (Edarbi): The Eighth Angiotensin II Receptor Blocker.
2011 Oct
Differential pharmacology and benefit/risk of azilsartan compared to other sartans.
2012
A systematic comparison of the properties of clinically used angiotensin II type 1 receptor antagonists.
2013 Apr
Azilsartan, aliskiren, and combination antihypertensives utilizing renin-angiotensin-aldosterone system antagonists.
2014 Sep-Oct
Patents

Sample Use Guides

In Vivo Use Guide
For 4 weeks during the run-in period, one tablet of TAK-536CCB (as TAK-536/ amlodipine, 20 mg/5 mg, respectively) will be orally administered once daily, before or after breakfast. For 48 weeks during 52 weeks of the treatment period, one tablet of TAK-536TCH (as TAK-536/ amlodipine/amlodipine, 20 mg/5 mg/12.5 mg, respectively) will be orally administered once daily, before or after breakfast. For the remaining 4 weeks of the treatment period, one tablet each of TAK-536CCB and HCTZ 12.5 mg will be orally administered once daily, before or after breakfast.
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Oct 21 21:26:16 UTC 2019
Edited
by admin
on Mon Oct 21 21:26:16 UTC 2019
Record UNII
F9NUX55P23
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZILSARTAN
INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
AZILSARTAN [MART.]
Common Name English
TAK-536
Code English
AZILSARTAN [MI]
Common Name English
AZILSARTAN [INN]
Common Name English
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-
Common Name English
AZILSARTAN [WHO-DD]
Common Name English
AZILSARTAN [JAN]
Common Name English
2-ETHOXY-1-((2'-(5-OXO-2,5-DIHYDRO-1,2,4-OXADIAZOL-3-YL)BIPHENYL-4-YL)METHYL)-1H-BENZIMIDAZOLE-7-CARBOXYLIC ACID
Systematic Name English
AZILSARTAN [VANDF]
Common Name English
AZILSARTAN [USAN]
Common Name English
Classification Tree Code System Code
NDF-RT N0000175561
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
NCI_THESAURUS C66930
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
LIVERTOX 82
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL57242
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
MERCK INDEX
M2173
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY Merck Index
INN
8724
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
NDF-RT
N0000178477
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY Decreased Blood Pressure [PE]
CAS
147403-03-0
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
EVMPD
SUB31561
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
EPA CompTox
147403-03-0
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
MESH
C521273
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
RXCUI
1091643
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY RxNorm
DRUG BANK
DB08822
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
NDF-RT
N0000180999
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY Angiotensin 2 Type 1 Receptor Antagonists [MoA]
NCI_THESAURUS
C75107
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
PUBCHEM
9825285
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
HSDB
147403-03-0
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
WIKIPEDIA
AZILSARTAN
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
LactMed
147403-03-0
Created by admin on Mon Oct 21 21:26:16 UTC 2019 , Edited by admin on Mon Oct 21 21:26:16 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
METABOLIC ENZYME -> SUBSTRATE
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
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IMPURITY -> PARENT
Probable human carcinogen.
IMPURITY -> PARENT
Priority toxic pollutant.
IMPURITY GENOTOXIC->PARENT
NDMA is an organic chemical that is in a family of potent carcinogens.
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Tmax PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC