Candoxatrilat
Basic information
- CAS
123122-54-3- Standard SMILES
COCCOC[C@H](CC1(C(=O)NC2CCC(C(=O)O)CC2)CCCC1)C(=O)O- InChIKey
ACZWIDANLCXHBM-HRCADAONSA-N- Molecular formula
- C20H33NO7
- Average molar mass
- 399.5 g/mol
- Monoisotopic mass
- 399.22570239
Overview
Candoxatrilat is a dicarboxylic acid monoamide obtained by formal condensation between the amino group of cis-4-aminocyclohexanecarboxylic acid and the cyclopentanecarboxylic acid group of 1-[(2S)-2-carboxy-3-(2-methoxyethoxy)propyl]cyclopentanecarboxylic acid. A potent inhibitor of neutral endopeptidase (NEP, neprilysin, EC 3.4.24.11), it is used as its 2,3-dihydro-1H-inden-5-yl ester prodrug in the treatment of chronic heart failure. It has a role as an EC 3.4.24.* (metalloendopeptidase) inhibitor. It is a dicarboxylic acid and a dicarboxylic acid monoamide.
Names & identifiers
- Preferred name
- Candoxatrilat
- IUPAC
- 4-[[1-[(2S)-2-carboxy-3-(2-methoxyethoxy)propyl]cyclopentanecarbonyl]amino]cyclohexane-1-carboxylic acid
- English name
- Candoxatrilat
- Molecular formula
- C20H33NO7
- Molecular weight
- 399.481
Names & synonyms
candoxatrilat123122-54-3candoxatrilateCandoxatril diacidUK-739677WU8BZ90THUK-73,967CHEMBL4344924-[[1-[(2S)-2-carboxy-3-(2-methoxyethoxy)propyl]cyclopentanecarbonyl]amino]cyclohexane-1-carboxylic acidcis-4-[({1-[(2S)-2-carboxy-3-(2-methoxyethoxy)propyl]cyclopentyl}carbonyl)amino]cyclohexanecarboxylic acidUNII-7WU8BZ90THCandoxatrilat [USAN:INN:BAN]
Show more names
U 73967Candoxatrilat (UK 73967)4α-[[[1-[(S)-2-Carboxy-3-(2-methoxyethoxy)propyl]cyclopentyl]carbonyl]amino]cyclohexane-1α-carboxylic acid(1s,4s)-4-{1-[(2S)-2-carboxy-2-[(2-methoxyethoxy)methyl]ethyl]cyclopentaneamido}cyclohexane-1-carboxylic acidCyclohexanecarboxylic acid, 4-(((1-((2S)-2-carboxy-3-(2-methoxyethoxy)propyl)cyclopentyl)carbonyl)amino)-, cis-
(alphaS)-1-((cis-4-Carboxycyclohexyl)carbamoyl)-alpha-((2-methoxyethoxy)methyl)cyclopentanepropionic acid(alphaS)-1-[(cis-4-Carboxycyclohexyl)carbamoyl]-alpha-[(2-methoxyethoxy)methyl]cyclopentanepropionic acidU 73967; UK69578UK 73967UK 73,967CANDOXATRILAT [INN]Candoxatrilat (USAN/INN)CANDOXATRILAT [USAN]
Properties
Computed structural properties
- XLogP
- 1.3
- Topological polar surface area
- 122 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 11
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 537
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 108.5 · 108.5-109.1°
- alpha
- 1.4 ° · D +1.4° (c = 1 in methanol)
- Boiling point
- 642.1 · 642.1±55.0 °C(Predicted)
- Density
- 1.22 · 1.22±0.1 g/cm3(Predicted)
- pka
- 4.32 · 4.32±0.11(Predicted)
- FDA UNII
- 7 WU8BZ90TH · 7WU8BZ90TH
Chemistry & industry
Applications
UsesAntihypertensive.
Additional notes
DefinitionChEBI: Candoxatrilat is a dicarboxylic acid monoamide obtained by formal condensation between the amino group of cis-4-aminocyclohexanecarboxylic acid and the cyclopentanecarboxylic acid group of 1-[(2S)-2-carboxy-3-(2-methoxyethoxy)propyl]cyclopentanecarboxylic acid. A potent inhibitor of neutral endopeptidase (NEP, neprilysin, EC 3.4.24.11), it is used as its 2,3-dihydro-1H-inden-5-yl ester prodrug in the treatment of chronic heart failure. It has a role as an EC 3.4.24.* (metalloendopeptidase) inhibitor. It is a dicarboxylic acid and a dicarboxylic acid monoamide.
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