Mexazolam

Synopsis, Chemistry

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Also known as: Melex, 31868-18-5, Cs-386, Chebi:31842, S5969b6237, 10-chloro-11b-(2-chlorophenyl)-2,3,7,11b-tetrahydro-3-methyloxazolo(3,2-d)(1,4)benzodiazepin-6(5h)-one

Molecular Formula

C₁₈H₁₆Cl₂N₂O₂

Molecular Weight

363.2 g/mol

InChI Key

ANUCDXCTICZJRH-UHFFFAOYSA-N

FDA UNII

S5969B6237

Mexazolam (CS-386) is a benzodiazepine indicated for the treatment of anxiety with or without psychoneurotic conditions. Mexazolam's structure is similar to that of other benzodiazepines such as [oxazolam] and [cloxazolam]. The use of benzodiazepines in the treatment of anxiety is generally a second line measure.

1 2D Structure

Mexazolam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

10-chloro-11b-(2-chlorophenyl)-3-methyl-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-one

2.1.2 InChI

InChI=1S/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)

2.1.3 InChI Key

ANUCDXCTICZJRH-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1COC2(N1CC(=O)NC3=C2C=C(C=C3)Cl)C4=CC=CC=C4Cl

2.2 Other Identifiers

2.2.1 UNII

S5969B6237

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 10-chloro-2,3,7,11b-tetrahydro-3-methyl-11b-(2-chlorophenyl)oxazolo(3,2-d)(1,4)benzodiazepin-6(5h)-one

2. Cs 386

3. Cs-386

2.3.2 Depositor-Supplied Synonyms

1. Melex

2. 31868-18-5

3. Cs-386

4. Chebi:31842

5. S5969b6237

6. 10-chloro-11b-(2-chlorophenyl)-2,3,7,11b-tetrahydro-3-methyloxazolo(3,2-d)(1,4)benzodiazepin-6(5h)-one

7. 10-chloro-11b-(o-chlorophenyl)-2,3,7,11b-tetrahydro-3-methyloxazolo(3,2-d)(1,4)benzodiazepin-6(5h)-one

8. Mexazolamum

9. Mexazolam [inn:jan]

10. Mexazolamum [inn-latin]

11. Cs 386

12. 10-chloro-11b-(2-chlorophenyl)-3-methyl-2,3,7,11b-tetrahydrobenzo[f]oxazolo[3,2-d][1,4]diazepin-6(5h)-one

13. Brn 1091849

14. Sedoxil

15. Unii-s5969b6237

16. Melex (tn)

17. Mexazolam (jan/inn)

18. Mexazolam [inn]

19. Mexazolam [jan]

20. Mexazolam [mi]

21. Mexazolam [mart.]

22. Mexazolam [who-dd]

23. Dsstox_cid_31504

24. Dsstox_rid_97389

25. Dsstox_gsid_57715

26. 10-chloro-11b-(2-chlorophenyl)-3-methyl-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-one

27. Schembl218453

28. Chembl1743261

29. Dtxsid9057715

30. Tox21_113740

31. Db15489

32. Ncgc00253606-01

33. Oxazolo(3,2-d)(1,4)benzodiazepin-6(5h)-one, 10-chloro-11b-(2-chlorophenyl)-2,3,7,11b-tetrahydro-3-methyl-

34. Cas-31868-18-5

35. D01316

36. Q6148446

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₆Cl₂N₂O₂
Molecular Weight	363.2 g/mol
XLogP3	3.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	362.0588831 g/mol
Monoisotopic Mass	362.0588831 g/mol
Topological Polar Surface Area	41.6 Å²
Heavy Atom Count	24
Formal Charge	0
Complexity	505
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Mexazolam is indicated for the treatment of anxiety with or without psychoneurotic conditions.

5 Pharmacology and Biochemistry

5.1 ATC Code

N - Nervous system

N05 - Psycholeptics

N05B - Anxiolytics

N05BA - Benzodiazepine derivatives

N05BA25 - Mexazolam

5.2 Absorption, Distribution and Excretion

Absorption

The active metabolite chloronordiazepam has a T_max of 1-2h.

Route of Elimination

Mexazolam is mainly eliminated in the bile and feces, with <10% eliminated as metabolites in the urine. >50% of a dose of mexazolam is eliminated as the metabolite chloroxazepam.

5.3 Metabolism/Metabolites

Mexazolam is rapidly metabolized to the active metabolites chloronordiazepam and chloroxazepam.

5.4 Biological Half-Life

Mexazolam follows a 2 compartment model with a first half life of 1.4h and a second half life of 76h.

5.5 Mechanism of Action

Mexazolam is a benzodiazepine that binds to benzodiazepine-type receptors, inhibiting gamma-aminobutyric acid.