ADINAZOLAM

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H18ClN5
Molecular Weight	351.833
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(C)CC1=NN=C2CN=C(C3=CC=CC=C3)C4=C(C=CC(Cl)=C4)N12

InChI

InChIKey=GJSLOMWRLALDCT-UHFFFAOYSA-N

InChI=1S/C19H18ClN5/c1-24(2)12-18-23-22-17-11-21-19(13-6-4-3-5-7-13)15-10-14(20)8-9-16(15)25(17)18/h3-10H,11-12H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C19H18ClN5
Molecular Weight	351.833
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/6320036 | https://www.ncbi.nlm.nih.gov/pubmed/3298327 | https://www.ncbi.nlm.nih.gov/pubmed/9600717 | https://www.ncbi.nlm.nih.gov/pubmed/27535017

Adinazolam, a benzodiazepine agonist, is an effective anxiolytic agent with antidepressant properties. It was shown, that adinazolam by itself had relatively weak benzodiazepine agonist activity, and much of the pharmacological activity belonged to its active metabolite N-desmethyladinazolam (NDMAD). Adinazolam has never been FDA approved, but it is sold as a research chemical.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
GABA-A receptor; benzodiazepine site 38 Target ID: CHEMBL2109243 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6148400	Agonist 2678

PubMed

Title	Date	PubMed
Pharmacological profile of the antidepressant adinazolam, a triazolobenzodiazepine.	1983 Nov	6320036
Determination of biological activity of adinazolam and its metabolites.	1984 Aug	6148400
Triazolobenzodiazepines antagonize the effects of anxiogenic drugs mediated at three different central nervous system sites.	1985 Oct 24	2867497
The effects of chronic antidepressant treatment in an animal model of anxiety.	1988	3137614
Inhibition of the binding and the behavioral effects of thyrotropin-releasing hormone (TRH) by the triazolobenzodiazepines.	1988 May	2845442
Double-blind comparison of alprazolam and adinazolam for panic and phobic disorders.	1989 Feb	2651489
The early acquisition of two-way (shuttle-box) avoidance as an anxiety-mediated behavior: psychopharmacological validation.	1991 Jan	1673080
Regulation of serotonin type 2 (5-HT2) and beta-adrenergic receptors in rat cerebral cortex following novel and classical antidepressant treatment.	1991 Nov	1664741
Platelet alpha-2 adrenoreceptor activity pre-treatment and post-treatment in major depressive disorder with melancholia.	1991 Oct	1666199
Ranitidine does not alter adinazolam pharmacokinetics or pharmacodynamics.	1992 Aug	1527233
Benzodiazepine suppression of corticotropin-releasing factor (CRF)-induced beta-endorphin release from rat neurointermediate pituitary.	1992 Sep-Oct	1480515
Downregulation of serotonin receptor subtypes by nortriptyline and adinazolam in major depressive disorder: neuroendocrine and platelet markers.	1993	8131152
Evidence that decreased function of lymphocyte beta adrenoreceptors reflects regulatory and adaptive processes in panic disorder with agoraphobia.	1993 Aug	8392297
Flumazenil prevents the anxiolytic effects of diazepam, alprazolam and adinazolam on the early acquisition of two-way active avoidance.	1993 Jul-Aug	8234145
Kinetic characterization and identification of the enzymes responsible for the hepatic biotransformation of adinazolam and N-desmethyladinazolam in man.	1998 Mar	9600717
The open field as a paradigm to measure the effects of drugs on anxiety-like behaviors: a review.	2003 Feb 28	12600700
Kinetics and dynamics of intravenous adinazolam, N-desmethyl adinazolam, and alprazolam in healthy volunteers.	2005 May	15831776
Evaluation of a basic physiologically based pharmacokinetic model for simulating the first-time-in-animal study.	2007 Jul	17481865
The effect of sympathetic antagonists on the antidepressant action of alprazolam.	2008 Jun 1	21499463
The enduring effects of an adolescent social stressor on synaptic density, part II: Poststress reversal of synaptic loss in the cortex by adinazolam and MK-801.	2008 Mar	18081181
Prediction of modified release pharmacokinetics and pharmacodynamics from in vitro, immediate release, and intravenous data.	2009 Jun	19430911
Recent trends in the impurity profile of pharmaceuticals.	2010 Jul	22247862

Patents

Sample Use Guides

In Vivo Use Guide

from 90 to 40 mg/day.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:45:49 GMT 2023` Edited by `admin` on `Sat Dec 16 17:45:49 GMT 2023`
Record UNII	KN08449444
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ADINAZOLAM

Official Name

English

ADINAZOLAM [MI]

Common Name

English

U-41,123

Code

English

Adinazolam [WHO-DD]

Common Name

English

4H-(1,2,4)TRIAZOLO(4,3-A)(1,4)BENZODIAZEPINE-1-METHANAMINE, 8-CHLORO-N-N-DIMETHYL-6-PHENYL-

Common Name

English

U-41123

Code

English

adinazolam [INN]

Common Name

English

8-Chloro-1-[(dimethylamino)methyl]-6-phenyl-4H-S-triazolo[4,3-a][1,4]benzodiazepine

Systematic Name

English

ADINAZOLAM [USAN]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QN05BA07