NAV

Varespladib methyl

Identification

Generic Name
Varespladib methyl
DrugBank Accession Number
DB05737
Background

Varespladib methyl has been investigated for the treatment of Acute Coronary Syndrome. Studies showed that Varespladib methyl treatment resulted in significant positive changes on lipoproteins and inflammation.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 394.427
Monoisotopic: 394.152871816
Chemical Formula
C22H22N2O5
Synonyms
  • Varespladib methyl
  • Varespladib methyl ester
External IDs
  • A-002
  • LY-333013
  • LY333013
  • S-3013
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Pharmacology

Indication

Investigated for use/treatment in atherosclerosis and coronary artery disease.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

A–002 is an orally administered‚ potent inhibitor of secretory phospholipase spla2(spla2)‚ including groups IIA‚ V‚ and X. Atherosclerosis is a disease of the arteries that results from inflammation and the build-up of plaque under the lining of the blood vessel. This build-up can cause vascular swelling and eventual rupture. spla2 levels have been shown to be elevated in patients with both stable and unstable coronary artery disease. Higher levels of the enzyme have been shown to predict an increased risk for future cardiovascular events such as heart attacks and stroke.

TargetActionsOrganism
UPhospholipase A2, membrane associatedNot AvailableHumans
UGroup 10 secretory phospholipase A2Not AvailableHumans
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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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

Products

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International/Other Brands
Varespladib

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenoxyacetic acid derivatives. These are compounds containing an anisole where the methane group is linked to an acetic acid or a derivative.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenoxyacetic acid derivatives
Direct Parent
Phenoxyacetic acid derivatives
Alternative Parents
N-alkylindoles / Indoles / Phenol ethers / Aryl ketones / Alkyl aryl ethers / Substituted pyrroles / Vinylogous amides / Methyl esters / Heteroaromatic compounds / Primary carboxylic acid amides
show 5 more
Substituents
Alkyl aryl ether / Aromatic heteropolycyclic compound / Aryl ketone / Azacycle / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Carboxylic acid ester / Ether / Heteroaromatic compound
show 19 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
0NB98NBX3D
CAS number
172733-08-3
InChI Key
VJYDOJXJUCJUHL-UHFFFAOYSA-N
InChI
InChI=1S/C22H22N2O5/c1-3-15-20(21(26)22(23)27)19-16(24(15)12-14-8-5-4-6-9-14)10-7-11-17(19)29-13-18(25)28-2/h4-11H,3,12-13H2,1-2H3,(H2,23,27)
IUPAC Name
methyl 2-{[1-benzyl-3-(carbamoylcarbonyl)-2-ethyl-1H-indol-4-yl]oxy}acetate
SMILES
CCC1=C(C(=O)C(N)=O)C2=C(OCC(=O)OC)C=CC=C2N1CC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
9886917
PubChem Substance
347827740
ChemSpider
8062590
ChEMBL
CHEMBL2105659
ZINC
ZINC000001550156
Wikipedia
Varespladib_methyl

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3TerminatedTreatmentAcute Coronary Syndrome (ACS)1
2CompletedPreventionCoronary Artery Disease (CAD)3
2CompletedTreatmentAcute Coronary Syndrome (ACS)1
2CompletedTreatmentEnvenomation, Snake / Envenoming / Envenoming, Snake / Snake Bite1
2RecruitingTreatmentEnvenoming, Snake / Snake Bite1

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 Solubility0.00343 mg/mLALOGPS
logP3.34ALOGPS
logP2.92Chemaxon
logS-5.1ALOGPS
pKa (Strongest Acidic)13.81Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area100.62 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity107.66 m3·mol-1Chemaxon
Polarizability41.16 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
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/MSsplash10-0ab9-0009000000-b888ea2a35cd45722691
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00or-0097000000-5874401b5e2315b473cd
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004l-3019000000-205416385926fd98c4ca
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014l-2059000000-32c13993148c09a6a849
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-6091000000-7751cb93ecafee4e1417
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004l-0090000000-a4853f45c747eea42d50
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-188.05835
predicted
DeepCCS 1.0 (2019)
[M+H]+190.41634
predicted
DeepCCS 1.0 (2019)
[M+Na]+197.08113
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Phospholipase A2, membrane associated
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phospholipid binding
Specific Function
Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-ph...
Gene Name
PLA2G2A
Uniprot ID
P14555
Uniprot Name
Phospholipase A2, membrane associated
Molecular Weight
16082.525 Da
Details2. Group 10 secretory phospholipase A2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Phospholipase activity
Specific Function
PA2 catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides. Has a powerful potency for releasing arachidonic acid from cell membrane phospholipids. Prefers phosph...
Gene Name
PLA2G10
Uniprot ID
O15496
Uniprot Name
Group 10 secretory phospholipase A2
Molecular Weight
18153.04 Da

Drug created at November 18, 2007 18:27 / Updated at February 21, 2021 18:51