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Cloxazolam

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Also known as: Cloxazolazepam, Sepazon, Olcadil, 24166-13-0, Enadel, Cloxazolamum

Molecular Formula

C₁₇H₁₄Cl₂N₂O₂

Molecular Weight

349.2 g/mol

InChI Key

ZIXNZOBDFKSQTC-UHFFFAOYSA-N

FDA UNII

GYL649Z0HY

Cloxazolam is a benzodiazepine with anxiolytic, sedative/hypnotic, muscle relaxant, and antiepileptic effects. It is marketed in the Argentina, Australia, Portugal, Belgium, Switzerland, Luxembourg, Germany, Taiwan and Japan -- mainly for anti-anxiety. The usual dose of cloxazolam in adults is 3-12mg/day for anti-anxiety. Although less commonly noted, it has also been reported as clinically effective in the treatment of depression, schizophrenia, and neurosis. As well, it has also been studied in Japan in doses of 15-30mg/day as an adjunct in the treatment of intractable epilepsy, for which it has demonstrated effectiveness.

1 2D Structure

Cloxazolam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

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

2.1.2 InChI

InChI=1S/C17H14Cl2N2O2/c18-11-5-6-15-13(9-11)17(12-3-1-2-4-14(12)19)21(7-8-23-17)10-16(22)20-15/h1-6,9H,7-8,10H2,(H,20,22)

2.1.3 InChI Key

ZIXNZOBDFKSQTC-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1COC2(N1CC(=O)NC3=C2C=C(C=C3)Cl)C4=CC=CC=C4Cl

2.2 Other Identifiers

2.2.1 UNII

GYL649Z0HY

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 10-chloro-11b-(2-chlorophenyl)-2,3,5,6,7,11b-hexahydrobenzo(6,7)-1,4-diazepino(5,4-b)oxazol-6-one

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

3. Cs 370

4. Former Cas Registry Number Of Cloxazolam

5. Mt 14-411

6. Olcadil

2.3.2 Depositor-Supplied Synonyms

1. Cloxazolazepam

2. Sepazon

3. Olcadil

4. 24166-13-0

5. Enadel

6. Cloxazolamum

7. Betavel

8. Lubalix

9. Tolestan

10. Cs 370

11. Mt 14-411

12. Gyl649z0hy

13. Chebi:31426

14. 10-chloro-11b-(2-chlorophenyl)-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6-one

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

16. 10-chloro-11b-(o-chlorophenyl)-2,3,7,11b-tetrahydro-oxazolo(3,2-d) (1,4)benzodiazepin-6(5h)-one

17. Cloxam

18. Cloxazolam [inn:jan]

19. Cloxazolamum [inn-latin]

20. Unii-gyl649z0hy

21. Brn 0569691

22. Sepazone

23. Dea No. 2753

24. 10-chloro-11b-(o-chlorophenyl)-2,3,7,11b-tetrahydro-oxazolo[3,2-d] [1,4]benzodiazepin-6(5h)-one

25. Sepazon (tn)

26. Cloxazolam [mi]

27. Cloxazolam [inn]

28. Cloxazolam [jan]

29. Dsstox_cid_2854

30. Cloxazolam (jp17/inn)

31. Cloxazolam [mart.]

32. Cloxazolam [who-dd]

33. Dsstox_rid_97543

34. Dsstox_gsid_22854

35. Us9271961, Cloxazolam

36. Schembl157225

37. Chembl2107254

38. Dtxsid0022854

39. Bdbm220121

40. Tox21_113693

41. Db01553

42. Ncgc00249917-01

43. 10-chloro-11b-(2-chlorophenyl)-2,3,7,11b-tetrahydro[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6(5h)-one

44. 10-chloro-2,3,5,6,7,11b-hexahydro-11b-(o-chlorophenyl)benzo(6,7)-1,4-diazepino-(5,4-b)-oxazol-6-one

45. Cas-24166-13-0

46. D01268

47. Q4385221

48. 10-chloro-11 B-(2-chlorophenyl)- 2,3,5,11b-tetrahydrooxazolo[3,2-d] [1,4]benzodiazepin-6(7h)-one

49. 10-chloro-11b-(2-chlorophenyl)-2,3, 5,11b-tetrahydrooxazolo[3,2-d] [1,4]benzodiazepin-6(7h)-one

50. 10-chloro-11b-(2-chlorophenyl)-2,3,5,11b-tetrahydrooxazolo[3,2-d] [1,4]benzodiazepin-6(7h)-one

51. 10-chloro-11b-(2-chlorophenyl)-2,3,5,11b-tetrahydrooxazolo[3,2-d][1,4]benzodiazepin-6(7h)-one

52. 10-chloro-11b-(2-chlorophenyl)-2,3,7,11b-tetrahydro[1,3]oxazolo[3,2-d][1,4]benzodiazepin-6(5h)-one #

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₇H₁₄Cl₂N₂O₂
Molecular Weight	349.2 g/mol
XLogP3	3.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	348.0432331 g/mol
Monoisotopic Mass	348.0432331 g/mol
Topological Polar Surface Area	41.6 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	478
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Used primarily as an anti-anxiety agent. Typically used short term, and may be given as a single dose of up to 100mcg/kg to reduce anxiety and tension experienced prior to surgery.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Studies have shown a superiority of 4mg/day of cloxazepam to 12mg/day of bromazepam in terms of anxiety, depressed mood, and sleep; an insignificant difference in terms of sedative effect; and less muscle relaxant effects. [3] Cloxazolam, administered as a single oral dose of 3mg, when compared to a single 5 mg dose of diazepam in one study, showed similar subjective measures; however, there cloxazolam caused more fatigue, and less mood improvement. Cloxazolam also induced a significant increase in heart rate in the control group of this study. [3]

5.2 ATC Code

N05BA22

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N05 - Psycholeptics

N05B - Anxiolytics

N05BA - Benzodiazepine derivatives

N05BA22 - Cloxazolam

5.3 Absorption, Distribution and Excretion

Route of Elimination

Renal elimination.

5.4 Metabolism/Metabolites

Cloxazolam is metabolised by the liver into the active metabolite chlordesmethyldiazepam (delorazepam). [5]

5.5 Biological Half-Life

65 hours

5.6 Mechanism of Action

Cloxazolam is a long acting benzodiazepine. It acts as a prodrug, with pharmacologically active metabolites, which bind to to the GABAa receptor, which other benzodiazepines bind to, to illicit a physiological response. [wiki]

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