ANA-12

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H21N3O3S
Molecular Weight	407.485
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O=C(NC1=C(C=CC=C1)C(=O)NC2CCCCNC2=O)C3=CC4=CC=CC=C4S3

InChI

InChIKey=TUSCYCAIGRVBMD-UHFFFAOYSA-N

InChI=1S/C22H21N3O3S/c26-20(25-17-10-5-6-12-23-21(17)27)15-8-2-3-9-16(15)24-22(28)19-13-14-7-1-4-11-18(14)29-19/h1-4,7-9,11,13,17H,5-6,10,12H2,(H,23,27)(H,24,28)(H,25,26)

HIDE SMILES / InChI

Molecular Formula	C22H21N3O3S
Molecular Weight	407.485
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21505263

ANA-12 is a low-molecular weight antagonist of tropomyosin-related kinase B (TrkB), which is the main receptor of neurotrophin brain-derived neurotrophic factor (BDNF). TrkB and BDNF are both the key mediators in the pathophysiology of several mood disorders, including anxiety and depression. ANA-12 showed direct and selective binding to TrkB and inhibited processes downstream of TrkB without altering TrkA and TrkC functions. It was shown, that mice administered ANA-12 demonstrated reduced anxiety- and depression-related behaviors on a variety of tests predictive of anxiolytic and antidepressant properties in humans.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Neurotrophic tyrosine kinase receptor 5 Target ID: CHEMBL3559684 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21505263	Antagonist 2778		12.0 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 267 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21505263	Primary		Preclinical	Unknown Approved Use Unknown
Depression 235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21505263	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
BDNF-TrkB signaling in the nucleus accumbens shell of mice has key role in methamphetamine withdrawal symptoms.	2015 Oct 27	26506052

Sample Use Guides

In Vivo Use Guide

F1 hybrids obtained by crossing C57BL/6 and 129SveV mice were used: a volume of 10 μl/g body weight was injected i.p. for saline and ANA-12 (0.5 mg/kg body weight) solutions.

Route of Administration: Intraperitoneal

In Vitro Use Guide

ANA-12 directly binds and selectively modulates TrkB. Bodipy–ANA-12 (100 μM) was incubated with increasing amounts of TrkBECD-Fc, IgG-Fc, BSA, or nothing. At concentrations up to 10–100 μM, ANA-12 completely abolished the effects of BDNF since no single neurite or branching could be observed even after 3 days of incubation. To assess the selectivity of the compound toward TrkB, there were used 2 other nnr5-PC12 cell lines expressing either TrkA or TrkC for which neurite outgrowth is dependent on NGF and NT-3, respectively. In these cell lines, ANA-12 had no effect on neurite outgrowth. Three days incubation with concentrations as high as 100 μM of ANA-12 did not affect NGF- and NT-3–dependent neurite length and branching, confirming its specificity to TrkB-related signaling.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:59:48 UTC 2023` Edited by `admin` on `Sat Dec 16 16:59:48 UTC 2023`
Record UNII	54S4JPT8JX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ANA-12

Common Name

English

BENZO(B)THIOPHENE-2-CARBOXAMIDE, N-(2-(((HEXAHYDRO-2-OXO-1H-AZEPIN-3-YL)AMINO)CARBONYL)PHENYL)-

Systematic Name

English

N-(2-(((HEXAHYDRO-2-OXO-1H-AZEPIN-3-YL)AMINO)CARBONYL)PHENYL)BENZO(B)THIOPHENE-2-CARBOXAMIDE

Systematic Name

English

Code System Code Type Description

FDA UNII

54S4JPT8JX