NAV

Candoxatrilat

Identification

Generic Name
Candoxatrilat
DrugBank Accession Number
DB11623
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 399.484
Monoisotopic: 399.225702407
Chemical Formula
C20H33NO7
Synonyms
  • Candoxatrilat
  • Candoxatrilate
External IDs
  • UK-73,967
  • UK-73967

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ANeprilysin
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Dicarboxylic acids and derivatives
Direct Parent
Dicarboxylic acids and derivatives
Alternative Parents
Fatty amides / Secondary carboxylic acid amides / Dialkyl ethers / Carboxylic acids / Organopnictogen compounds / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic homomonocyclic compound / Carbonyl group / Carboxamide group / Carboxylic acid / Dialkyl ether / Dicarboxylic acid or derivatives / Ether / Fatty acyl / Fatty amide / Hydrocarbon derivative
Molecular Framework
Aliphatic homomonocyclic compounds
External Descriptors
dicarboxylic acid monoamide, dicarboxylic acid (CHEBI:3354)
Affected organisms
Not Available

Chemical Identifiers

UNII
7WU8BZ90TH
CAS number
123122-54-3
InChI Key
ACZWIDANLCXHBM-HRCADAONSA-N
InChI
InChI=1S/C20H33NO7/c1-27-10-11-28-13-15(18(24)25)12-20(8-2-3-9-20)19(26)21-16-6-4-14(5-7-16)17(22)23/h14-16H,2-13H2,1H3,(H,21,26)(H,22,23)(H,24,25)/t14-,15-,16+/m0/s1
IUPAC Name
(1s,4s)-4-{1-[(2S)-2-carboxy-2-[(2-methoxyethoxy)methyl]ethyl]cyclopentaneamido}cyclohexane-1-carboxylic acid
SMILES
COCCOC[C@H](CC1(CCCC1)C(=O)N[C@H]1CC[C@H](CC1)C(O)=O)C(O)=O

References

General References
Not Available
KEGG Drug
D03349
KEGG Compound
C11721
PubChem Compound
443380
PubChem Substance
347828015
ChemSpider
16736848
BindingDB
50281657
ChEBI
3354
ChEMBL
CHEMBL434492
Wikipedia
Candoxatril

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.766 mg/mLALOGPS
logP1.47ALOGPS
logP1.87Chemaxon
logS-2.7ALOGPS
pKa (Strongest Acidic)4.08Chemaxon
pKa (Strongest Basic)0.48Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area122.16 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity100.73 m3·mol-1Chemaxon
Polarizability42.2 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Neprilysin
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Thermolysin-like specificity, but is almost confined on acting on polypeptides of up to 30 amino acids (PubMed:15283675, PubMed:8168535). Biologically important in the destruction of opioid peptide...
Gene Name
MME
Uniprot ID
P08473
Uniprot Name
Neprilysin
Molecular Weight
85513.225 Da
References
  1. Alabaster CT, Machin I, Samuels GM, Sutton MR: The effects of UK-79,300, an orally-absorbed atriopeptidase inhibitor, in a conscious dog model of cardiac insufficiency. Br J Pharmacol. 1989 Dec;98 Suppl:823P. [Article]
  2. Sansoe G, Aragno M, Mastrocola R, Restivo F, Mengozzi G, Smedile A, Rosina F, Danni O, Parola M, Rizzetto M: Neutral endopeptidase (EC 3.4.24.11) in cirrhotic liver: a new target to treat portal hypertension? J Hepatol. 2005 Nov;43(5):791-8. Epub 2005 Jun 20. [Article]

Drug created at October 14, 2016 17:02 / Updated at February 21, 2021 18:53