Azilsartan

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Azilsartan are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Azilsartan?

The molecule Azilsartan presents a molecular formula of C25H20N4O5 and its IUPAC name is 2-ethoxy-3-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid.

Azilsartan (INN; trade name Edarbi) is an angiotensin II receptor antagonist (AT1 subtype) used in the management of hypertension. It was developed by Takeda..

Azilsartan is the first in a new class of antihypertensive agents, the azilsartan potassium class, that selectively blocks the binding of angiotensin II to the AT1 receptor. This results in vasodilation and lowering of blood pressure..

Azilsartan has greater affinity for the AT1 receptor than other available ARBs. It has about 33% greater binding affinity than candesartan and about double the binding affinity of valsartan, irbesartan, and losartan..

Azilsartan has about the same potency as candesartan. The half-life of azilsartan is about 12 hours, which is similar to other ARBs..

Azilsartan is well tolerated. The most common adverse effect is dizziness (1.4%)..

Azilsartan exists as tablets of 20, 40, and 80 mg in several countries..

3D structure

Cartesian coordinates

Geometry of Azilsartan in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Azilsartan KGSXMPPBFPAXLY-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Azilsartan

 

Molecule descriptors

 
IUPAC name2-ethoxy-3-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid
InChI codeInChI=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)
InChI KeyKGSXMPPBFPAXLY-UHFFFAOYSA-N
SMILESCCOc1nc2cccc(C(=O)O)c2n1Cc1ccc(-c2ccccc2-c2nc(=O)o[nH]2)cc1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 1-[[2'-(2,5-Dihydro-5-oxo-1,2,4-oxadiazol-3-yl) [1,1'-biphenyl]-4-yl]methyl]-2-ethoxy-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-1H-benzimidazole-7-carboxylic Acid
  • 1346599-45-8
  • 147403-03-0
  • 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-
  • 2-ETHOXY-1-((2'-(5-OXO-2,5-DIHYDRO-1,2,4-OXADIAZOL-3-YL)BIPHENYL-4-YL)METHYL)-1H-BENZIMIDAZOLE-7-CARBOXYLIC ACID
  • 2-Ethoxy-1-((2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-biphenyl-4-yl)methyl)-1H-benzimidazole-7-carboxylic acid
  • 2-Ethoxy-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)- 1H-benzimidazole-7-carboxylic acid
  • 2-Ethoxy-1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid
  • 2-Ethoxy-1-[[2'-(2,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl4-yl]methyl]benzimidazole-7-carboxylic acid
  • 2-Ethoxy-1-[[2'-(4,5-dihydro-5-oxo-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic Acid
  • 2-Ethoxy-3-[2''-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid
  • 2-Ethoxy-3-[2'-(5-oxo-2,5-dihydro-[1,2,4]oxadiazol-3-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid
  • 2-Ethoxy-3-[2'-(5-oxo-4,5-dihydro-[1,2,4]oxadiazol-3-yl)-biphenyl-4-ylmethyl]-3H-benzoimidazole-4-carboxylic acid
  • 2-ethoxy-1-((2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl)methyl)-1H-benzo[d]imidazole-7-carboxylic acid
  • 2-ethoxy-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylic acid
  • 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid
  • 2-ethoxy-3-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid
  • 403A030
  • AB01566867_01
  • AC-25912
  • AM84439
  • AMY4360
  • Azilsartan
  • Azilsartan (JAN/USAN/INN)
  • Azilsartan (TAK-536)
  • Azilsartan free acid
  • Azilsartan- Bio-X
  • BA164233
  • BCP03826
  • BCP0726000135
  • BCP9000002
  • BDBM50055441
  • CCG-269296
  • CS-1396
  • CX1016
  • D08864
  • DB-063707
  • F9NUX55P23
  • FT-0662457
  • FT-0662458
  • GTPL6901
  • HMS3651J16
  • HMS3747I09
  • HSDB 8208
  • HY-14914
  • KS-5381
  • L001451
  • MFCD20278186
  • NCGC00386206-03
  • NCGC00386206-04
  • Q27074832
  • SB20804
  • SW219493-1
  • TAK 536
  • TAK-536
  • TAK536
  • WDC59945
  • s3046

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC598390
  • UNII-F9NUX55P23
  • AKOS007930882
  • AKOS024458220
  • DTXSID70163712
  • CHEMBL57242
  • CHEBI:68850
  • SCHEMBL167538

Physico-Chemical properties

IUPAC name2-ethoxy-3-[[4-[2-(5-oxo-4H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylic acid
Molecular formulaC25H20N4O5
Molecular weight456.45
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity125.29
LogP4.2
Topological polar surface area123.2

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.