31868-18-5

Basic information

• Product Name: mexazolam
• Synonyms: mexazolam;CS 386;Melex;Oxazolo[3,2-d][1,4]benzodiazepin-6(5H)-one, 10-chloro-11b-(2-chlorophenyl)-2,3,7,11b-tetrahydro-3-methyl- (9CI);10-Chloro-11b-(2-chlorophenyl)-2,3,7,11b-tetrahydro-3-methyloxazolo[3,2-d][1,4]benzodiazepin-6(5H)-one;10-Chloro-11b-(o-chlorophenyl)-2,3,7,11b-tetrahydro-3-methyloxazolo[3,2-d][1,4]benzodiazepin-6(5H)-one;10-Chloro-2,3,7,11b-tetrahydro-3-methyl-11b-(o-chlorophenyl)oxazolo[3,2-d][1,4]benzodiazepin-6(5H)-one;10-chloro-11b-(2-chlorophenyl)-3-methyl-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-one
• CAS NO: 31868-18-5
• Molecular Formula: C₁₈H₁₆Cl₂N₂O₂
• Molecular Weight: 363.26
• Mol File: 31868-18-5.mol
• Article Data: 3

Chemical Properties

• Melting Point: 172-175°
• Boiling Point: 522.2 °C at 760 mmHg
• Flash Point: 269.6 °C
• Appearance: /
• Density: 1.3817 (rough estimate)
• Vapor Pressure: 5.29E-11mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• PKA: 6.69(at 25℃)
• CAS DataBase Reference: mexazolam(CAS DataBase Reference)
• NIST Chemistry Reference: mexazolam(31868-18-5)
• EPA Substance Registry System: mexazolam(31868-18-5)

Safety Data

• Hazardous Substances Data: 31868-18-5(Hazardous Substances Data)

Usage

Description

Mexazolam, also known by the brand name MELEX, is a benzodiazepine anxiolytic closely related to flutazolam. It is a pharmaceutical compound that has been investigated for its therapeutic value in treating anxiety and other related conditions. Mexazolam is known to be metabolized via the CYP3A4 pathway, which plays a crucial role in its effectiveness and potential interactions with other medications.

Uses

Used in Pharmaceutical Industry:
Mexazolam is used as an anxiolytic (anti-anxiety agent) for the treatment of various anxiety-related conditions. It is particularly effective against psychosomatic essential hypertension, peptic ulcer, irritable colon, and autonomic dystonia. Its anxiolytic properties make it a valuable compound in the management of stress and anxiety, contributing to the overall well-being of patients.
Used in Medical Treatment:
In the medical field, mexazolam is utilized for its calming and sedative effects. It can be prescribed to patients suffering from severe anxiety, panic attacks, or other conditions that require short-term relief from heightened stress levels. Its effectiveness in treating these conditions makes it a valuable tool for healthcare professionals in managing patient care.
Used in Research and Development:
Mexazolam is also used in research and development for the study of benzodiazepine compounds and their effects on the central nervous system. Understanding the mechanisms of action and potential applications of mexazolam can lead to the development of new therapeutic strategies and medications for anxiety and related disorders.

Originator

Sankyo (Japan)

InChI:InChI=1/C18H16Cl2N2O2/c1-11-10-24-18(13-4-2-3-5-15(13)20)14-8-12(19)6-7-16(14)21-17(23)9-22(11)18/h2-8,11H,9-10H2,1H3,(H,21,23)

Synthetic route

2-Amino-1-propanol (6168-72-5) + 2-(2-bromo-acetylamino)-5,2'-dichloro-benzophenone (5504-92-7) → mexazolam (31868-18-5)

Conditions	Yield
(i) CH2Cl2, (ii) AcOH, EtOH; Multistep reaction;

7-Chloro-5-(2-chloro-phenyl)-4-(2-hydroxy-1-methyl-ethyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-4-ium → mexazolam (31868-18-5)

Conditions	Yield
With borate buffer (pH=8-10.5) In ethanol; water Equilibrium constant; Mechanism; variation of pH and buffers.;
In ethanol; water at 25℃; Rate constant;

mexazolam (31868-18-5) + methyl iodide (74-88-4) → 10-chloro-11b-(2-chloro-phenyl)-3,7-dimethyl-2,3,7,11b-hexahydro-benzo[f]oxazolo[3,2-e][1,4]diazepin-6-one (32711-03-8)

Conditions	Yield
(i) NaOMe, MeOH, (ii) /BRN= 969135/, DMF; Multistep reaction;

mexazolam (31868-18-5) → 7-Chloro-5-(2-chloro-phenyl)-4-(2-hydroxy-1-methyl-ethyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-4-ium

Conditions	Yield
With hydrogenchloride In ethanol; water Equilibrium constant; Mechanism; variation of pH and buffers.;
In ethanol; water at 25℃; Rate constant;

Upstream product

• 6168-72-5 2-Amino-1-propanol 
• 5504-92-7 2-(2-bromo-acetylamino)-5,2'-dichloro-benzophenone 

Relevant articles and documents

Kinetics and mechanism of the acid-base equilibrium of mexazolam and comparison with those of other commercial benzodiazepinooxazole drugs

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Anxiolytic sedatives. 1. Synthesis and pharmacology of benzo[6,7]-1,4-diazepino[5,4-b]oxazole derivatives and analogs.

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