TRACAZOLATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H24N4O2
Molecular Weight	304.3874
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCNC1=C(C(=O)OCC)C(C)=NC2=C1C=NN2CC

InChI

InChIKey=PCTRYMLLRKWXGF-UHFFFAOYSA-N

InChI=1S/C16H24N4O2/c1-5-8-9-17-14-12-10-18-20(6-2)15(12)19-11(4)13(14)16(21)22-7-3/h10H,5-9H2,1-4H3,(H,17,19)

HIDE SMILES / InChI

Molecular Formula	C16H24N4O2
Molecular Weight	304.3874
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/11901225 | https://www.ncbi.nlm.nih.gov/pubmed/6121710 | https://www.ncbi.nlm.nih.gov/pubmed/6121711 | https://www.ncbi.nlm.nih.gov/pubmed/2866547

Tracazolate (ICI 136,753), a pyrazolopyridine, is a non-benzodiazepine with anxiolytic-like activity in animal models. It is known to interact with gamma-aminobutyric acid (GABA)(A) receptors, adenosine receptors, and phosphodiesterases. Its intrinsic efficacy, potentiation, or inhibition is determined by the nature of the third subunit (gamma1-3, delta, or epsilon) within the GABA(A) receptor complex.

CNS Activity

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/11901225\|https://www.ncbi.nlm.nih.gov/pubmed/6121711\|https://www.ncbi.nlm.nih.gov/pubmed/6121710	Modulator 828

PubMed

Title	Date	PubMed
Tracazolate reveals a novel type of allosteric interaction with recombinant gamma-aminobutyric acid(A) receptors.	2002 Apr	11901225
Role of the alpha subunit in the modulation of GABA(A) receptors by anabolic androgenic steroids.	2005 Sep	15993433
alpha1beta2delta, a silent GABAA receptor: recruitment by tracazolate and neurosteroids.	2008 Mar	18204487
Dihydropyrimidinone positive modulation of delta-subunit-containing gamma-aminobutyric acid type A receptors, including an epilepsy-linked mutant variant.	2010 Jun 15	20450160
Kinetic and structural determinants for GABA-A receptor potentiation by neuroactive steroids.	2010 Mar	20808543
Limiting activity at beta1-subunit-containing GABAA receptor subtypes reduces ataxia.	2010 Mar	19940102

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:15:54 GMT 2023` Edited by `admin` on `Sat Dec 16 05:15:54 GMT 2023`
Record UNII	NH0HPL3U1T
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TRACAZOLATE

Official Name

English

ETHYL 4-(BUTYLAMINO)-1-ETHYL-6-METHYL-1H-PYRAZOL(3,4-B)PYRIDINE-5-CARBOXYLATE

Common Name

English

ICI-136,753

Common Name

English

ICI 136,753

Code

English

1H-PYRAZOLO(3,4-B)PYRIDINE-5-CARBOXYLIC ACID, 4-(BUTYLAMINO)-1-ETHYL-6-METHYL-, ETHYL ESTER

Common Name

English

TRACAZOLATE [USAN]

Common Name

English

ICI-136753

Code

English

tracazolate [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C28197