ETAZOLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H19N5O2
Molecular Weight	289.333
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)C1=CN=C2N(CC)N=CC2=C1NN=C(C)C

InChI

InChIKey=OPQRBXUBWHDHPQ-UHFFFAOYSA-N

InChI=1S/C14H19N5O2/c1-5-19-13-10(8-16-19)12(18-17-9(3)4)11(7-15-13)14(20)21-6-2/h7-8H,5-6H2,1-4H3,(H,15,18)

HIDE SMILES / InChI

Molecular Formula	C14H19N5O2
Molecular Weight	289.333
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18397369 | https://clinicaltrials.gov/ct2/show/NCT00880412 | https://www.ncbi.nlm.nih.gov/pubmed/29107895

Etazolate (EHT-0202) is a selective, positive GABAA receptor modulator has completed phase II clinical trials in patients with Alzheimer's disease. It is also a selective phosphodiesterase-4 inhibitor that is specific for cAMP. Etazolate showed anxiolytic and antidepressant activity and could be useful in managing post-traumatic stress disorder.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; anion channel 202 Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18397369	Positive Allosteric Modulator 179
Phosphodiesterase 4 52 Target ID: CHEMBL2093863 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23384434	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21222604	Primary		Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
activator 80 inhibitor 1587	inhibitor 1767	inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 60 CYP1A2 1524 CYP2C19 1478

Drug as perpetrator

Target	Modality	Activity
CYP19A1 60	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/899#sid=11113501	no
CYP2C19 1553	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/1851#sid=11111137	no
CYP2C9 1819	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/884#sid=11111137	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/891#sid=11113501	no
CYP3A4 1925	activator 214 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/885#sid=11111137	no
CYP1A2 1692	inhibitor 3277	yes [IC50 0.501 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://pubchem.ncbi.nlm.nih.gov/bioassay/884#sid=11111137	yes [IC50 12.5893 uM]

Sourcing

Vendor/Aggregator	ID	URL
Angene	AGN-PC-0WH4BE	http://www.angenechemical.com/productshow/AGN-PC-0WH4BE.html
ApexBio Technology	B6304	https://www.apexbt.com/catalogsearch/result/?q=B6304
BOC Sciences	35838-58-5	http://www.bocsci.com/description.asp?cas=35838-58-5
BOC Sciences	51022-77-6	http://www.bocsci.com/description.asp?cas=51022-77-6
MolPort	MolPort-003-666-862	https://www.molport.com/shop/molecule-link/MolPort-003-666-862
MuseChem	I010208	https://www.musechem.com/product/I010208.html
MuseChem	R020745	https://www.musechem.com/product/R020745.html
Oakwood	M01713	http://www.oakwoodchemical.com/ProductsList.aspx?txtSearch=M01713
Princeton BioMolecular Research	PBMR221698	http://www.princetonbio.com/order_online?common_id=PBMR221698
Tetrahedron	TS63362	http://www.thsci.com/search.do?q=TS63362
Tocris	438	https://www.tocris.com/search.php?Type=QuickSearch&Value=0438
Toronto Research Chemicals	E889250	https://www.trc-canada.com/product-detail/?CatNum=E889250
Toronto Research Chemicals	I821845	https://www.trc-canada.com/product-detail/?CatNum=I821845
eMolecules	299999093	https://orderbb.emolecules.com/search/#?query=299999093
eMolecules	537926	https://orderbb.emolecules.com/search/#?query=537926
eMolecules	739256	https://orderbb.emolecules.com/search/#?query=739256
mcule	MCULE-3211063713	https://mcule.com/MCULE-3211063713/

PubMed

Title	Date	PubMed
Interaction of allosteric ligands with GABAA receptors containing one, two, or three different subunits.	1996 Apr 22	8773466
Global expression profiling of theophylline response genes in macrophages: evidence of airway anti-inflammatory regulation.	2005 Aug 8	16083514
Etazolate, a neuroprotective drug linking GABA(A) receptor pharmacology to amyloid precursor protein processing.	2008 Jul	18397369
A cell protection screen reveals potent inhibitors of multiple stages of the hepatitis C virus life cycle.	2010 Feb 23	20142494
EHT0202 in Alzheimer's disease: a 3-month, randomized, placebo-controlled, double-blind study.	2011 Mar	21222604

Patents

Sample Use Guides

In Vivo Use Guide

2 capsules of study treatment (capsules of EHT0202 (ETAZOLATE) 40mg and or 80mg and/or placebo) are taken twice a day during breakfast and dinner over a 3-month treatment period.

Route of Administration: Oral

In Vitro Use Guide

Etazolate (20 nM-2 microM) dose-dependently protected rat cortical neurons against Abeta-induced toxicity. The neuroprotective effects of etazolate were fully blocked by GABA(A) receptor antagonists indicating that this neuroprotection was due to GABA(A) receptor signalling

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:53:25 UTC 2023` Edited by `admin` on `Sat Dec 16 17:53:25 UTC 2023`
Record UNII	I89Y79062L
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETAZOLATE

Official Name

English

etazolate [INN]

Common Name

English

1H-PYRAZOLO(3,4-B)PYRIDINE-5-CARBOXYLIC ACID, 1-ETHYL-4-((1-METHYLETHYLIDENE)HYDRAZINO)-, ETHYL ESTER

Common Name

English

ETHYL 1-ETHYL-4-(ISOPROPYLIDENEHYDRAZINO)-1H-PYRAZOLO(3,4-B)PYRIDINE-5-CARBOXYLATE

Systematic Name

English

EHT-0202

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C28197