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Adinazolam

Adinazolam structure

CAS No:
37115-32-5
Formula:
C19H18ClN5
Chemical Name:
Adinazolam
Synonyms:
4H-[1,2,4]Triazolo[4,3-a][1,4]benzodiazepine-1-methanamine,8-chloro-N,N-dimethyl-6-phenyl-;8-Chloro-N,N-dimethyl-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepine-1-methanamine;Adinazolam;U 41123;1-(8-Chloro-6-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-1-yl)-N,N-dimethylmethanamine;53416-44-7
Categories:
Pharmaceutical Intermediates > Bulk Drug Intermediates

Description

Solid

Adinazolam is a triazolo[4,3-a][1,4]benzodiazepine having a dimethylaminomethyl group at the 1-position, a phenyl group at the 6-position and a chloro substituent at the 8-position. It has a role as a sedative, an anxiolytic drug, an anticonvulsant and an antidepressant.|Adinazolam (Deracyn®) is a benzodiazepine derivative with anxiolytic, anticonvulsant, sedative, and antidepressant properties. Adinazolam was first developed to enhance the antidepressant effects of [alprazolam]. It has never been approved by the FDA for clinical use.

Adinazolam Basic Attributes

Molecular Weight：

351.83

Exact Mass：

351.83

UNII：

KN08449444

DSSTox ID：

DTXSID40190611

ATC Code：

N - Nervous system

Characteristics

PSA：

46.3 Å²

XLogP3：

4.4

Density：

1.31±0.1 g/cm3

Melting Point：

171-172.5 °C

Boiling Point：

527.0±60.0 °C(Predicted)

Water Solubility：

6.72e-02 g/L

PKA：

pKa 6.2 (D2O/DClor D2O/NaOD ) (Uncertain);5.8±0.1(D2O/DClor D2O/NaOD ) (Uncertain)

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

3249

Toxicity

Toxicity Summary：

Signs of overdose may include muscle weakness, ataxia, dysarthria and particularly in children paradoxical excitement. In more severe cases diminished reflexes, confusion, and coma may ensue.

Drug Information

Drug Indication：

For the treatment of anxiety and status epilepticus.

Pharmacology：

Adinazolam is a benzodiazepine derivative used to treat anxiety, status epilepticus, and for sedation induction and anterograde amnesia. Adinazolam binds with high affinity to the GABA benzodiazepine receptor complex. Considerable evidence suggest that the central pharmacologic/therapeutic actions of alprazolam are mediated via interaction with this receptor complex.

MeSH：

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)

Metabolism/Metabolites：

The drug primarily undergoes hepatic metabolism to form the main metabolite N-desmethyladinazolam, alpha-hydroxyalprazolam, and estazolam.|Adinazolam has known human metabolites that include N-demethyladinazolam.

Biological Half-Life：

Less than 3 hours.

Mechanism of Action：

Adinazolam binds to peripheral-type benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways.

MeSH Entry Terms：

adinazolam

Adinazolam Use and Manufacturing

Antidepressant; sedative-hypnotic.

Computed Properties

Molecular Weight:351.8
XLogP3:1.6
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:3
Exact Mass:351.1250733
Monoisotopic Mass:351.1250733
Topological Polar Surface Area:46.3
Heavy Atom Count:25
Complexity:490
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes