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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
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 Weight 363.2 g/mol
Molecular Formula C18H16Cl2N2O2
XLogP33.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass362.0588831 g/mol
Monoisotopic Mass362.0588831 g/mol
Topological Polar Surface Area41.6 Ų
Heavy Atom Count24
Formal Charge0
Complexity505
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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 Tmax 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.


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18-Oct-2021
20-Sep-2024
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