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Avagacestat

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
Avagacestat
DrugBank Accession Number
DB11893
Background

Avagacestat has been investigated for the basic science and treatment of Alzheimer Disease.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 520.88
Monoisotopic: 520.0595166
Chemical Formula
C20H17ClF4N4O4S
Synonyms
  • Avagacestat
External IDs
  • BMS 708163
  • BMS-708163
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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
AGamma-secretase subunit APH-1A
modulator
Humans
AGamma-secretase subunit PEN-2
modulator
Humans
APresenilin-1
modulator
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 phenyloxadiazoles. These are polycyclic aromatic compounds containing a benzene ring linked to a 1,2,4-oxadiazole ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Oxadiazoles
Direct Parent
Phenyloxadiazoles
Alternative Parents
Alpha amino acids and derivatives / Benzenesulfonamides / Benzenesulfonyl compounds / Fluorobenzenes / Chlorobenzenes / Organosulfonamides / Aryl chlorides / Aryl fluorides / Fatty amides / Aminosulfonyl compounds
show 11 more
Substituents
Alkyl fluoride / Alkyl halide / Alpha-amino acid or derivatives / Aminosulfonyl compound / Aromatic heteromonocyclic compound / Aryl chloride / Aryl fluoride / Aryl halide / Azacycle / Benzenesulfonamide
show 29 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
TQ44WWY45Q
CAS number
1146699-66-2
InChI Key
XEAOPVUAMONVLA-QGZVFWFLSA-N
InChI
InChI=1S/C20H17ClF4N4O4S/c21-14-3-5-15(6-4-14)34(31,32)29(17(18(26)30)7-8-20(23,24)25)10-13-2-1-12(9-16(13)22)19-27-11-33-28-19/h1-6,9,11,17H,7-8,10H2,(H2,26,30)/t17-/m1/s1
IUPAC Name
(2R)-5,5,5-trifluoro-2-(N-{[2-fluoro-4-(1,2,4-oxadiazol-3-yl)phenyl]methyl}4-chlorobenzenesulfonamido)pentanamide
SMILES
NC(=O)[C@@H](CCC(F)(F)F)N(CC1=CC=C(C=C1F)C1=NOC=N1)S(=O)(=O)C1=CC=C(Cl)C=C1

References

General References
Not Available
PubChem Compound
46883536
PubChem Substance
347828228
ChemSpider
24670668
ChEMBL
CHEMBL1090771
ZINC
ZINC000043202993
PDBe Ligand
EN9
PDB Entries
6lqg

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns
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2CompletedTreatmentAlzheimer's Disease (AD)1somestatusstop reasonjust information to hide
2TerminatedTreatmentAlzheimer's Disease (AD)1somestatusstop reasonjust information to hide
1CompletedNot AvailableAlzheimer's Disease (AD)4somestatusstop reasonjust information to hide
1CompletedNot AvailableAlzheimer's Disease (AD) / Healthy Volunteers (HV)1somestatusstop reasonjust information to hide
1CompletedBasic ScienceAlzheimer's Disease (AD)4somestatusstop 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 Solubility0.0269 mg/mLALOGPS
logP3.17ALOGPS
logP3.96Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)14.02Chemaxon
pKa (Strongest Basic)-2.4Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area119.39 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity125.98 m3·mol-1Chemaxon
Polarizability44.96 Å3Chemaxon
Number of Rings3Chemaxon
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/MSsplash10-00di-0001090000-c3c385887bd7390fab88
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0400390000-1403983036668c976cdf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00b9-0002970000-8a8b6e32ea353fe65c96
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-8602960000-c6a401c2fede41ef0aa4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0902720000-64203a6b8fe361793fb7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9100100000-dcb0dee79aad134c8bb5
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-207.2965
predicted
DeepCCS 1.0 (2019)
[M+H]+209.69206
predicted
DeepCCS 1.0 (2019)
[M+Na]+215.6046
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Gamma-secretase subunit APH-1A
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Modulator
General Function
Non-catalytic subunit of the gamma-secretase complex, an endoprotease complex that catalyzes the intramembrane cleavage of integral membrane proteins such as Notch receptors and APP (amyloid-beta precursor protein) (PubMed:12297508, PubMed:12522139, PubMed:12679784, PubMed:12763021, PubMed:25043039, PubMed:26280335, PubMed:30598546, PubMed:30630874). Required for normal gamma-secretase assembly (PubMed:12471034, PubMed:12522139, PubMed:12763021, PubMed:19369254). The gamma-secretase complex plays a role in Notch and Wnt signaling cascades and regulation of downstream processes via its role in processing key regulatory proteins, and by regulating cytosolic CTNNB1 levels (Probable)
Specific Function
Endopeptidase activator activity
Gene Name
APH1A
Uniprot ID
Q96BI3
Uniprot Name
Gamma-secretase subunit APH-1A
Molecular Weight
28995.7 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. Gamma-secretase subunit PEN-2
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Modulator
General Function
Essential subunit of the gamma-secretase complex, an endoprotease complex that catalyzes the intramembrane cleavage of integral membrane proteins such as Notch receptors and APP (amyloid-beta precursor protein) (PubMed:12522139, PubMed:12679784, PubMed:12740439, PubMed:12763021, PubMed:24941111, PubMed:30598546, PubMed:30630874). The gamma-secretase complex plays a role in Notch and Wnt signaling cascades and regulation of downstream processes via its role in processing key regulatory proteins, and by regulating cytosolic CTNNB1 levels (Probable). PSENEN modulates both endoproteolysis of presenilin and gamma-secretase activity (PubMed:12522139, PubMed:12679784, PubMed:12740439, PubMed:12763021, PubMed:24941111)
Specific Function
Endopeptidase activator activity
Gene Name
PSENEN
Uniprot ID
Q9NZ42
Uniprot Name
Gamma-secretase subunit PEN-2
Molecular Weight
12029.01 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]
Details3. Presenilin-1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Modulator
General Function
Catalytic subunit of the gamma-secretase complex, an endoprotease complex that catalyzes the intramembrane cleavage of integral membrane proteins such as Notch receptors and APP (amyloid-beta precursor protein) (PubMed:10206644, PubMed:10545183, PubMed:10593990, PubMed:10811883, PubMed:10899933, PubMed:12679784, PubMed:12740439, PubMed:15274632, PubMed:20460383, PubMed:25043039, PubMed:26280335, PubMed:28269784, PubMed:30598546, PubMed:30630874). Requires the presence of the other members of the gamma-secretase complex for protease activity (PubMed:15274632, PubMed:25043039, PubMed:26280335, PubMed:30598546, PubMed:30630874). Plays a role in Notch and Wnt signaling cascades and regulation of downstream processes via its role in processing key regulatory proteins, and by regulating cytosolic CTNNB1 levels (PubMed:10593990, PubMed:10811883, PubMed:10899933, PubMed:9738936). Stimulates cell-cell adhesion via its interaction with CDH1; this stabilizes the complexes between CDH1 (E-cadherin) and its interaction partners CTNNB1 (beta-catenin), CTNND1 and JUP (gamma-catenin) (PubMed:11953314). Under conditions of apoptosis or calcium influx, cleaves CDH1 (PubMed:11953314). This promotes the disassembly of the complexes between CDH1 and CTNND1, JUP and CTNNB1, increases the pool of cytoplasmic CTNNB1, and thereby negatively regulates Wnt signaling (PubMed:11953314, PubMed:9738936). Required for normal embryonic brain and skeleton development, and for normal angiogenesis (By similarity). Mediates the proteolytic cleavage of EphB2/CTF1 into EphB2/CTF2 (PubMed:17428795, PubMed:28269784). The holoprotein functions as a calcium-leak channel that allows the passive movement of calcium from endoplasmic reticulum to cytosol and is therefore involved in calcium homeostasis (PubMed:16959576, PubMed:25394380). Involved in the regulation of neurite outgrowth (PubMed:15004326, PubMed:20460383). Is a regulator of presynaptic facilitation, spike transmission and synaptic vesicles replenishment in a process that depends on gamma-secretase activity. It acts through the control of SYT7 presynaptic expression (By similarity)
Specific Function
Aspartic endopeptidase activity, intramembrane cleaving
Gene Name
PSEN1
Uniprot ID
P49768
Uniprot Name
Presenilin-1
Molecular Weight
52667.34 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 20:58 / Updated at August 27, 2024 19:15