Candoxatril

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

What is the Candoxatril?

The molecule Candoxatril presents a molecular formula of C29H41NO7 and its IUPAC name is 4-[[1-[(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-(2-methoxyethoxymethyl)-3-oxopropyl]cyclopentanecarbonyl]amino]cyclohexane-1-carboxylic acid.

Candoxatril (trade name Invoril) is an ACE inhibitor developed by Boehringer Ingelheim. It was approved in Germany in 1996, but is not available in the United States..

Candoxatril is the first member of a new class of ACE inhibitors, the oxadiazoles. It differs from other ACE inhibitors in that it has a much longer half-life in the body and is not metabolized by the liver..

Candoxatril has been shown to be more effective than other ACE inhibitors in reducing blood pressure and is also more effective in reducing left ventricular mass in patients with hypertension..

In a large clinical trial, candoxatril was shown to be as effective as captopril in reducing blood pressure, but with a lower incidence of side effects such as dry cough and angioedema..

Candoxatril is well tolerated, with a low incidence of side effects. The most common side effects are headache, dizziness, and fatigue..

Candoxatril is a safe and effective ACE inhibitor that is more effective than other ACE inhibitors in reducing blood pressure and left ventricular mass. It is well tolerated, with a low incidence of side effects..

3D structure

Cartesian coordinates

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

2D drawing

 

Candoxatril ZTWZVMIYIIVABD-RZMWZJFBSA-N chemical compound 2D structure molecule svg
Candoxatril

 

Molecule descriptors

 
IUPAC name4-[[1-[(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-(2-methoxyethoxymethyl)-3-oxopropyl]cyclopentanecarbonyl]amino]cyclohexane-1-carboxylic acid
InChI codeInChI=1S/C29H41NO7/c1-35-15-16-36-19-23(27(33)37-25-12-9-20-5-4-6-22(20)17-25)18-29(13-2-3-14-29)28(34)30-24-10-7-21(8-11-24)26(31)32/h9,12,17,21,23-24H,2-8,10-11,13-16,18-19H2,1H3,(H,30,34)(H,31,32)/t21?,23-,24?/m0/s1
InChI KeyZTWZVMIYIIVABD-RZMWZJFBSA-N
SMILESCOCCOC[C@H](CC1(C(=O)NC2CCC(C(=O)O)CC2)CCCC1)C(=O)Oc1ccc2c(c1)CCC2

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.

  • (.ALPHA.S)-1-((CIS-4-CARBOXYCYCLOHEXYL)CARBAMOYL)-.ALPHA.-((2-METHOXYETHOXY)METHYL)CYCLOPENTANEPROPIONIC ACID, .ALPHA.-5-INDANYL ESTER
  • (S)-cis-4-{1 -[2-(5-Indanyloxycarbonyl)-3-(2-methoxyethoxy)-propyl]-1-cyclopentanecarboxamido}-1-cyclohexanecarboxylic acid
  • (S)-cis-4-{1 -[2-(5-Indanyloxycarbonyl)-3-(2-methoxyethoxy)propyl]-1-cyclopentanecarboxamido}-1-cyclohexanecarboxylic acid
  • (alphaS)-1-((cis-4-Carboxycyclohexyl)carbamoyl)-alpha-((2-methoxyethoxy)methyl)cyclopentanepropionic acid, alpha-5-indanyl ester
  • 123122-55-4
  • 4-({1-[(S)-2-(Indan-5-yloxycarbonyl)-3-(2-methoxy-ethoxy)-propyl]-cyclopentanecarbonyl}-amino)-cyclohexanecarboxylic acid
  • 4-[[1-[(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-(2-methoxyethoxymethyl)-3-oxopropyl]cyclopentanecarbonyl]amino]cyclohexane-1-carboxylic acid
  • ACP75508EE
  • BCP28764
  • CIS-4-(1-(2-(5-INDANYLOXYCARBONYL)-3-(2-METHOXYETHOXY)PROPYL)-1-CYCLOPENTANECARBOXAMIDO)-1-CYCLOHEXANECARBOXYLIC ACID L-
  • CS-0016160
  • Candoxatril
  • Candoxatril (JAN/USAN/INN)
  • Cyclohexanecarboxylic acid, 4-(((1-(3-((2,3-dihydro-1H-inden-5-yl)oxy)-2-((2-methoxyethoxy)methyl)-3-oxopropyl)cyclopentyl)carbonyl)amino)-, (4(S)-cis)-
  • Cyclohexanecarboxylic acid, 4-[[[1-[(2S)-3-[(2,3-dihydro-1H-inden-5-yl)oxy]-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentyl]carbonyl]amino]-, cis-
  • D01070
  • DB00616
  • DSSTox_CID_27286
  • DSSTox_GSID_47286
  • DSSTox_RID_82240
  • GTPL6492
  • HY-19649
  • NCGC00248052-01
  • NCGC00254350-01
  • Q5032033
  • UK 79300 pound>> UK-79300 pound>> UK79300
  • UK-79,300
  • UK-79300
  • [4(S)-cis]-4-[[[1-[3-[(2,3-dihydro-1H-indeb5-yl)oxy]-2-[(2-methoxyethoxy)methyl]-3-oxopropyl]cyclopentyl]carbonyl]amino]cyclohexanecarboxylic acid
  • cis-4-{[(1-{(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-[(2-methoxyethoxy)methyl]-3-oxopropyl}cyclopentyl)carbonyl]amino}cyclohexanecarboxylic acid

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3774999
  • ZINC100036919
  • ZINC253733842
  • CAS-123122-55-4
  • UNII-ACP75508EE
  • DTXSID6047286
  • CHEMBL35084
  • CHEBI:3353
  • Tox21_300450
  • SCHEMBL121666
  • SCHEMBL1649937

Physico-Chemical properties

IUPAC name4-[[1-[(2S)-3-(2,3-dihydro-1H-inden-5-yloxy)-2-(2-methoxyethoxymethyl)-3-oxopropyl]cyclopentanecarbonyl]amino]cyclohexane-1-carboxylic acid
Molecular formulaC29H41NO7
Molecular weight515.638
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity139.55
LogP4.5
Topological polar surface area111.2

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.