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Avoralstat

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

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Data Packages
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Identification

Generic Name
Avoralstat
DrugBank Accession Number
DB12120
Background

Avoralstat has been used in trials studying the prevention of HAE and Hereditary Angioedema.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 513.554
Monoisotopic: 513.201218989
Chemical Formula
C28H27N5O5
Synonyms
  • 3-(2-((4-Carbamimidoylphenyl)carbamoyl)-4-ethenyl-5-methoxyphenyl)-6-((cyclopropylmethyl)carbamoyl)pyridine-2-carboxylic acid
  • 3-[2-(4-carbamimidoyl-phenylcarbamoyl)-5-methoxy-4-vinyl-phenyl]-6-(cyclopropylmethyl-carbamoyl)-pyridine-2-carboxylic acid
  • 3-[2-[(4-carbamimidoylphenyl)carbamoyl]-4-ethenyl-5-methoxyphenyl]-6-(cyclopropylmethylcarbamoyl)pyridine-2-carboxylic acid
  • Avoralstat
  • BCX-4161
  • BCX4161
External IDs
  • BCX-4161
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AKallikrein-2
inhibitor
Humans
AKininogen-1
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 benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Benzanilides
Alternative Parents
Phenylpyridines / Benzamides / Pyridinecarboxylic acids / 2-heteroaryl carboxamides / Anisoles / Styrenes / Benzoyl derivatives / Methoxybenzenes / Phenoxy compounds / Alkyl aryl ethers
show 8 more
Substituents
2-heteroaryl carboxamide / 3-phenylpyridine / Alkyl aryl ether / Amidine / Anisole / Aromatic heteromonocyclic compound / Azacycle / Benzamide / Benzanilide / Benzoic acid or derivatives
show 23 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
UX17773O15
CAS number
918407-35-9
InChI Key
TUWMKPVJGGWGNL-UHFFFAOYSA-N
InChI
InChI=1S/C28H27N5O5/c1-3-16-12-21(26(34)32-18-8-6-17(7-9-18)25(29)30)20(13-23(16)38-2)19-10-11-22(33-24(19)28(36)37)27(35)31-14-15-4-5-15/h3,6-13,15H,1,4-5,14H2,2H3,(H3,29,30)(H,31,35)(H,32,34)(H,36,37)
IUPAC Name
3-{2-[(4-carbamimidoylphenyl)carbamoyl]-4-ethenyl-5-methoxyphenyl}-6-[(cyclopropylmethyl)carbamoyl]pyridine-2-carboxylic acid
SMILES
COC1=CC(=C(C=C1C=C)C(=O)NC1=CC=C(C=C1)C(N)=N)C1=CC=C(N=C1C(O)=O)C(=O)NCC1CC1

References

General References
Not Available
PubChem Compound
86566678
PubChem Substance
347828419
ChemSpider
34994574
ChEMBL
CHEMBL4297502
PDBe Ligand
DJY
PDB Entries
6bfp

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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3TerminatedPreventionHereditary Angioedema (HAE)1somestatusstop reasonjust information to hide
2CompletedPreventionHereditary Angioedema (HAE)1somestatusstop reasonjust information to hide
2, 3CompletedPreventionHereditary Angioedema (HAE)1somestatusstop reasonjust information to hide
1CompletedTreatmentHereditary Angioedema (HAE)2somestatusstop reasonjust information to hide

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00687 mg/mLALOGPS
logP2.58ALOGPS
logP1.63Chemaxon
logS-4.9ALOGPS
pKa (Strongest Acidic)0.55Chemaxon
pKa (Strongest Basic)11.49Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area167.49 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity154.82 m3·mol-1Chemaxon
Polarizability54.86 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
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/MSsplash10-01ox-1000940000-78c8580f8c3a2e49db45
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03yl-2204950000-b0eb4743cd159eb1e61d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0295-1001920000-24b838bdc1f1f0ba4835
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00r6-7009710000-96cea52f497a99782617
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-08or-5009410000-5bafcfd97ba5b44fc490
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9115720000-fa4b30270f2ea9c351b6
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-215.8549
predicted
DeepCCS 1.0 (2019)
[M+H]+218.25044
predicted
DeepCCS 1.0 (2019)
[M+Na]+224.16298
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Kallikrein-2
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Glandular kallikreins cleave Met-Lys and Arg-Ser bonds in kininogen to release Lys-bradykinin
Specific Function
serine-type endopeptidase activity
Gene Name
KLK2
Uniprot ID
P20151
Uniprot Name
Kallikrein-2
Molecular Weight
28670.77 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Details2. Kininogen-1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Kininogens are inhibitors of thiol proteases. HMW-kininogen plays an important role in blood coagulation by helping to position optimally prekallikrein and factor XI next to factor XII; HMW-kininogen inhibits the thrombin- and plasmin-induced aggregation of thrombocytes. LMW-kininogen inhibits the aggregation of thrombocytes. LMW-kininogen is in contrast to HMW-kininogen not involved in blood clotting
Specific Function
cysteine-type endopeptidase inhibitor activity
Gene Name
KNG1
Uniprot ID
P01042
Uniprot Name
Kininogen-1
Molecular Weight
71956.965 Da
References
  1. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]

Drug created at October 20, 2016 21:23 / Updated at October 03, 2024 04:25