Description In vitro In vivo
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ANA12

Description In vitro In vivo
Product Name
ANA12
CAS No.
219766-25-3
Chemical Name
ANA12
Synonyms
ANA12;CS-1732;ANA 12;ANA12;ANA12 USP/EP/BP;N-(2-((2-oxoazepan-3-yl)carbamoyl)phenyl)benzo[b]thiophene-2-carboxamide;N-{2-[(2-OXO-3-AZEPANYL)CARBAMOYL]PHENYL}-1-BENZOTHIOPHENE-2-CARB OXAMIDE;N-[2-[[(Hexahydro-2-oxo-1H-azepin-3-yl)amino]carbonyl]phenyl]-benzo[b]thiophene-2-carboxamide;Benzo[b]thiophene-2-carboxamide, N-[2-[[(hexahydro-2-oxo-1H-azepin-3-yl)amino]carbonyl]phenyl]-
CBNumber
CB62730549
Molecular Formula
C22H21N3O3S
Formula Weight
407.49
MOL File
219766-25-3.mol
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ANA12 Property

Boiling point:
639.2±55.0 °C(Predicted)
Density 
1.36±0.1 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: ≥5mg/mL at 60°C
form 
powder
pka
12.09±0.70(Predicted)
color 
white to beige
Stability:
Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 2 months.
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Safety

Hazard Codes 
Xn
Risk Statements 
22
WGK Germany 
3
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0209
Product name
ANA-12
Purity
≥98% (HPLC)
Packaging
5mg
Price
$144
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0209
Product name
ANA-12
Purity
≥98% (HPLC)
Packaging
25mg
Price
$598
Updated
2024/03/01
Sigma-Aldrich
Product number
5.06304
Product name
TrkB Antagonist, ANA-12 - CAS 219766-25-3 - Calbiochem
Packaging
25MG
Price
$282
Updated
2022/05/15
Cayman Chemical
Product number
14309
Product name
ANA 12
Purity
≥98%
Packaging
1mg
Price
$33
Updated
2024/03/01
Cayman Chemical
Product number
14309
Product name
ANA 12
Purity
≥98%
Packaging
5mg
Price
$106
Updated
2024/03/01
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ANA12 Chemical Properties,Usage,Production

Description

ANA-12 is a selective TrkB antagonist with Kd of 10 nM and 12 μM for the high and low affinity sites, respectively.

In vitro

ANA-12 binds directly and selectively to TrkB and inhibits processes downstream of TrkB without altering TrkA and TrkC functions. In nnr5 PC12-TrkB cells, ANA-12 prevents brain-derived neurotrophic factor (BDNF)-induced neurite outgrowth at concentrations as low as 10 nM. In DRG neurons, ANA-12 eliminates the effect of BDNF on increasing inward current.

In vivo

In adult C57BL6/129SveV F1s mice, ANA-12 (0.5 mg/kg, i.p.) decreases TrKB activity in the brain and reduces the anxiety- and depression-related behaviors without affecting the neuron survival. In male C57BL/6 mice, ANA-12 (0.5 mg/kg, i.p.) shows antidepressant-like effects on lipopolysaccharide-induced depression-like behavior. In male Sprague-Dawley rats, ANA-12 (3 μg/dose) blocks the effect of medial nucleus tractus solitarius (mNTS) BDNF on reducing food intake. In male wild-type mice, ANA-12 reverses ethanol intake and induces D3 receptor downregulation, but is ineffective in D3R-/- mice. In male CocSired rats, ANA-12 (0.5 mg/kg, i.p.) reverses the diminished self-administration of cocaine.

Description

ANA-12 (219755-25-3) is a TrkB receptor antagonist. Binds to two distinct receptor sites preventing activation by BDNF non-competitively, IC50?= 45.6 nM and 41.1 μM for the high and low affinity sites respectively. Systemic administration to adult mice decreased TrkB activity in the brain without affecting neuronal survival or altering TrkA and TrkC functions. ANA-12 displays antidepressant and anxiolytic properties in mouse models after systemic administration.1?Shows antidepressant effects on LPS-induced depression-like behavior in mice.2?ANA-12 has been used to elucidate the role of BDNF in improvement of cognitive decline during calorie restriction3?and in the discovery of new neurotrophic agents4.

Uses

ANA-12 was used to inhibit TrkB in primary mouse cortical neurons and primary rat hippocampal cultures.

Definition

ChEBI: ANA-12 is a secondary carboxamide that is anthranilic acid in which the carboxy group has undergone condensation with the primary amino group of alpha-amino-epsilon-caprolactam, while the aryl-amino group has undergone condensation with the carboxy group of 1-benzothiophene-2-carboxylic acid. It is a selective, non-competitive antagonist of tropomyosin receptor kinase B (TrkB, also known as tyrosine receptor kinase B). It has a role as a tropomyosin-related kinase B receptor antagonist, an antidepressant and an anxiolytic drug. It is a secondary carboxamide, a member of caprolactams and a member of 1-benzothiophenes. It is functionally related to a 2-aminohexano-6-lactam and an anthranilic acid.

Biochem/physiol Actions

The neurotrophin brain-derived neurotrophic factor (BDNF) and its receptor tropomyosin-related kinase B (TrkB) have emerged as key mediators in the pathophysiology of several mood disorders, including anxiety and depression. ANA-12 is a TrkB ligand that prevents activation of the receptor by BDNF with a high potency. It binds selectively to TrkB and inhibits processes downstream of TrkB without altering TrkA and TrkC functions. In adult mice model ANA-12 decreases TrkB activity in the brain without affecting neuronal survival. Mice dosed with ANA-12 show reduced anxiety- and depression related behaviors on a variety of tests predictive of anxiolytic and antidepressant properties in humans. ANA-12 may be a valuable tool for studying BDNF/TrkB signaling and may constitute a lead compound for developing the next generation of therapeutic agents for the treatment of mood disorders. There is also N-T19, which is less potent.

storage

Store at +4°C

References

1) Cazorla?et al. (2011),?Identification of a low-molecular weight TrkB antagonist with anxiolytic and antidepressant activity in mice; J. Clin. Invest.,?121?1846 2) Zhang?et al. (2014),?Antidepressant effects of TRKB ligands on depression-like behavior and dendritic changes in mice after inflammation; J. Neuropsychopharmacol.,?18?pyu077 3) Kishi?et al. (2015),?Calorie restriction improves cognitive decline via up-regulation of brain-derived neurotrophic factor: tropomyosin-related kinase B in hippocampus of obesity-induced hypertensive rats; Int. Heart J.,?56?110 4) Chakravarty?et al.?(2015) A?novel natural product inspired scaffold with robust neurotrophic, neurogenic and neuroprotective action; Sci. Rep.,?5?14134

ANA12 Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from ANA12 manufacturers

Career Henan Chemical Co
Product
ANA12 219766-25-3
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
20kg
Release date
2019-12-23

219766-25-3, ANA12Related Search:


  • ANA12
  • N-(2-((2-oxoazepan-3-yl)carbamoyl)phenyl)benzo[b]thiophene-2-carboxamide
  • N-[2-[[(Hexahydro-2-oxo-1H-azepin-3-yl)amino]carbonyl]phenyl]-benzo[b]thiophene-2-carboxamide
  • ANA 12;ANA12
  • CS-1732
  • N-{2-[(2-OXO-3-AZEPANYL)CARBAMOYL]PHENYL}-1-BENZOTHIOPHENE-2-CARB OXAMIDE
  • Benzo[b]thiophene-2-carboxamide, N-[2-[[(hexahydro-2-oxo-1H-azepin-3-yl)amino]carbonyl]phenyl]-
  • ANA12 USP/EP/BP
  • 219766-25-3
  • Inhibitors
  • API