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Ketazolam

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FINISHED DOSAGE FORMULATIONS

14 FDF Dossiers, 10 Europe, 2 South Africa, 2 Listed Dossiers

14 FDF Dossiers
10 Europe
2 South Africa
2 Listed Dossiers

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Synopsis

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Chemistry

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Also known as: Unakalm, Ansieten, Loftran, Anxon, 27223-35-4, Anseren

Molecular Formula

C₂₀H₁₇ClN₂O₃

Molecular Weight

368.8 g/mol

InChI Key

PWAJCNITSBZRBL-UHFFFAOYSA-N

FDA UNII

424J5HGB8E

Ketazolam is a benzodiazepine derivative with anxiolytic, anticonvulsant, sedative and skeletal muscle relaxant activity. Ketazolam is not approved in Canada or America.

1 2D Structure

Ketazolam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

11-chloro-2,8-dimethyl-12b-phenyl-6H-[1,3]oxazino[3,2-d][1,4]benzodiazepine-4,7-dione

2.1.2 InChI

InChI=1S/C20H17ClN2O3/c1-13-10-18(24)23-12-19(25)22(2)17-9-8-15(21)11-16(17)20(23,26-13)14-6-4-3-5-7-14/h3-11H,12H2,1-2H3

2.1.3 InChI Key

PWAJCNITSBZRBL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC(=O)N2CC(=O)N(C3=C(C2(O1)C4=CC=CC=C4)C=C(C=C3)Cl)C

2.2 Other Identifiers

2.2.1 UNII

424J5HGB8E

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Marcen

2. Mi 49001

3. Sedotime

4. Solatran

5. U 28,774

6. Unakalm

2.3.2 Depositor-Supplied Synonyms

1. Unakalm

2. Ansieten

3. Loftran

4. Anxon

5. 27223-35-4

6. Anseren

7. U-28,774

8. (+)-ketazolam

9. (-)-ketazolam

10. Nsc 338158

11. U 28774

12. Ketazolam, (+)-

13. Ketazolam, (-)-

14. Nsc-338158

15. 424j5hgb8e

16. 92a214md7y

17. 9zbh5g9835

18. 11-chloro-2,8-dimethyl-12b-phenyl-6h-[1,3]oxazino[3,2-d][1,4]benzodiazepine-4,7-dione

19. U-28774

20. 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4h-(1,3)oxazino(3,2-d)(1,4)benzodiazepine-4,7(6h)-dione

21. 4h-(1,3)oxazino(3,2-d)(1,4)benzodiazepine-4,7(6h)-dione, 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-

22. 4h-(1,3)oxazino(3,2-d)(1,4)benzodiazepine-4,7(6h)-dione, 8,12b-dihydro-11-chloro-2,8-dimethyl-12b-phenyl-

23. 4h-[1,3]oxazino[3,2-d][1,4]benzodiazepine-4,7(6h)-dione, 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-

24. Ketazolamum

25. Ketazolamum [inn-latin]

26. 106938-99-2

27. 106939-00-8

28. 4h-(1,3)oxazino(3,2-d)(1,4)benzodiazepine-4,7(6h)-dione, 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-, (+)-

29. 4h-(1,3)oxazino(3,2-d)(1,4)benzodiazepine-4,7(6h)-dione, 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-, (-)-

30. Einecs 248-346-3

31. Sedotime

32. Ketazolam [usan:inn:ban]

33. Unii-92a214md7y

34. Ketazolam [inn]

35. Ketazolam [mi]

36. Ketazolam (usan/inn)

37. Ketazolam [usan]

38. Ketazolam [mart.]

39. Ketazolam [who-dd]

40. (+/-)-ketazolam

41. Unii-424j5hgb8e

42. 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4h-(1,3)-oxazino(3,2-d)(1,4)benzodiazepine-4,7(6h)dione

43. Schembl157329

44. Unii-9zbh5g9835

45. Chembl2104356

46. Dtxsid20865350

47. Chebi:135556

48. Hy-a0242

49. Nsc338158

50. Cs-6737

51. Db01587

52. 4h-(1,3)-oxazino(3,2-d)(1,4)benzodiazepine-4,7(6h)-dione, 11-chloro-8,12b-dihydro-2,8-dimethyl-

53. D04650

54. Q2397253

55. 4h-[1,2-d]-[1,4]benzodiazepine-4,7(6h)-dione, 11-chloro-8,12b-dihydro-2,8-dimethyl-

56. 11-chloro-2,8-dimethyl-12b-phenyl-8,12b-dihydro-4h-[1,3]oxazino[3,2-d][1,4]benzodiazepine-4,7(6h)-dione

57. 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4h-(1,3)-oxazino(3,2-d)-(1,4)benzodiazepine-4,7(6h)dione

58. 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4h-(1,3)-oxazino(3,2-d)[1,4]benzodiazepine-4,7(6h)-dione

59. 11-chloro-8,8-dimethyl-12b-phenyl-4h-[1,3]-oxazino[3,2-d]-[1,4]benzodiazepine-4,7(6h)dione

60. 14-chloro-4,10-dimethyl-2-phenyl-3-oxa-7,10-diazatricyclo[9.4.0.0^{2,7}]pentadeca-1(11),4,12,14-tetraene-6,9-dione

61. 4h-(1,3)-oxazino(3,2-d)-(1,4)benzodiazepine-4,7(6h)-dione, 11-chloro-8,12b-dihydro-2,8-dimethyl-

62. 4h-[1,2-d][1,4]benzodiazepine-4,7(6h)-dione, 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-

63. Ketazolam; 11-chloro-2,8-dimethyl-12b-phenyl-6h-[1,3]oxazino[3,2-d][1,4]benzodiazepine-4,7-quinone; 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4h-(1,3)-oxazino(3,2-d)(1,4)benzodiazepine-4,7(6h)dione; 11-chloro-8,12b-dihydro-2,8-dimethyl-12b-phenyl-4h

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₇ClN₂O₃
Molecular Weight	368.8 g/mol
XLogP3	3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	368.0927701 g/mol
Monoisotopic Mass	368.0927701 g/mol
Topological Polar Surface Area	49.8 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	631
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

Ketazolam could be used for the treatment of anxiety. In approved countries, it is indicated for the treatment of anxiety, tension, irritability and similar stress related symptoms.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Benzodiazepines enhance the effect of the neurotransmitter gamma-aminobutyric acid (GABA), which results in sedative, hypnotic, anxiolytic, anticonvulsant, muscle relaxant and amnesic action. Benzodiazepines bind nonspecifically to benzodiazepine receptors which mediate sleep, affects muscle relaxation, anticonvulsant activity, motor coordination, and memory. As benzodiazepine receptors are thought to be coupled to gamma-aminobutyric acid-A (GABA_A) receptors, this enhances the effects of GABA by increasing GABA affinity for the GABA receptor. Binding of GABA to the site opens the chloride channel, resulting in a hyperpolarized cell membrane that prevents further excitation of the cell.

5.2 MeSH Pharmacological Classification

Anti-Anxiety Agents

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)

5.3 ATC Code

N - Nervous system

N05 - Psycholeptics

N05B - Anxiolytics

N05BA - Benzodiazepine derivatives

N05BA10 - Ketazolam

5.4 Absorption, Distribution and Excretion

Route of Elimination

Diazepam and its metabolites are excreted mainly in the urine, predominantly as their glucuronide conjugates.

5.5 Metabolism/Metabolites

Ketazolam is metabolized to diazepam, followed by demoxepam, and finally desmethyldiazepam.

5.6 Biological Half-Life

26-200 hours

5.7 Mechanism of Action

Benzodiazepines share a similar chemical structure and their effects in humans are mainly produced by the allosteric modification of a specific kind of neurotransmitter receptor, the GABAA receptor, which increases the conductance of this inhibitory channel; this results in the various therapeutic effects as well as adverse effects of benzodiazepines. Binding of benzodiazepines to this receptor complex promotes binding of GABA, which in turn increases the conduction of chloride ions across the neuronal cell membrane. This increased conductance raises the membrane potential of the neuron resulting in inhibition of neuronal firing. In addition, different GABAA receptor subtypes have varying distributions within different regions of the brain and therefore control distinct neuronal circuits. Hence, activation of different GABAA receptor subtypes by benzodiazepines may result in distinct pharmacological actions.

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