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=CC=CC=C1C(=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 2 Target ID: CHEMBL3559684 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21505263	Antagonist 2849		12.0 µM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anxiety 275 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21505263	Primary		Preclinical	Unknown Approved Use Unknown
Depression 240 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.	2015-10-27	26506052
Physical exercise and environment exploration affect synaptogenesis in adult-generated neurons in the rat dentate gyrus: possible role of BDNF.	2013-10-09	23973748
Identification of a low-molecular weight TrkB antagonist with anxiolytic and antidepressant activity in mice.	2011-05	21505263

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 `Wed Apr 02 08:41:05 GMT 2025` Edited by `admin` on `Wed Apr 02 08:41:05 GMT 2025`
Record UNII	54S4JPT8JX
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Preferred Name

English

ANA-12

Common 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