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Delorazepam

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Synopsis

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Chemistry

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Also known as: 2894-67-9, Chlordemethyldiazepam, B1, benzodiazepine, Delorazepam [inn], Cl-dmdz, Clordesmetildiazepam

Molecular Formula

C₁₅H₁₀Cl₂N₂O

Molecular Weight

305.2 g/mol

InChI Key

CHIFCDOIPRCHCF-UHFFFAOYSA-N

FDA UNII

O91W32476G

delorazepam is a natural product found in Solanum tuberosum, Triticum aestivum, and Artemisia dracunculus with data available.

1 2D Structure

Delorazepam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-chloro-5-(2-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one

2.1.2 InChI

InChI=1S/C15H10Cl2N2O/c16-9-5-6-13-11(7-9)15(18-8-14(20)19-13)10-3-1-2-4-12(10)17/h1-7H,8H2,(H,19,20)

2.1.3 InChI Key

CHIFCDOIPRCHCF-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1C(=O)NC2=C(C=C(C=C2)Cl)C(=N1)C3=CC=CC=C3Cl

2.2 Other Identifiers

2.2.1 UNII

O91W32476G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2'-chloronordiazepam

2. 7-chloro-5-(2-chlorophenyl) 1,3-dihydro-2h-1,4-benzodiazepin-2-one

3. Chlordemethyldiazepam

4. Chlordesmethyldiazepam

5. Chlorodesmethyldiazepam

2.3.2 Depositor-Supplied Synonyms

1. 2894-67-9

2. Chlordemethyldiazepam

3. B1, Benzodiazepine

4. Delorazepam [inn]

5. Cl-dmdz

6. Clordesmetildiazepam

7. En [anticonvulsant]

8. Dadumir

9. Ro 5-3027

10. 2h-1,4-benzodiazepin-2-one, 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-

11. 7-chloro-5-(2-chloro-phenyl)-1,3-dihydro-2h-1,4-benzodiazepin-2-one

12. Nsc 169895

13. Rv-12165

14. 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-1,4-benzodiazepin-2-one

15. Nsc-169895

16. Chembl268254

17. 1,3-dihydro-7-chloro-5-(o-chlorophenyl)-2h-1,4-benzodiazepin-2-one

18. 2h-1,4-benzodiazepin-2-one, 7-chloro-5-(o-chlorophenyl)-1,3-dihydro-

19. 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-2h-1,4-benzodiazepin-2-one

20. 7-chloro-5-(o-chlorophenyl)-1,3-dihydro-2h-1,4-benzodiazepin-2-one

21. Delorazepam (inn)

22. O91w32476g

23. 2h-1,4-benzodiazepin-2-one, 1,3-dihydro-7-chloro-5-(2-chlorophenyl)-

24. 2-chloronordiazepam

25. 2'-chloronordiazepam

26. Delorazepamum

27. Delorazepamum [inn-latin]

28. Clordesmetildiazepam [spanish]

29. Einecs 220-771-9

30. Brn 0754062

31. Dea No. 2754

32. Unii-o91w32476g

33. Dadumir (tn)

34. Cambridge Id 6782587

35. Delorazepam [mart.]

36. Oprea1_689003

37. Delorazepam [who-dd]

38. 5-24-04-00331 (beilstein Handbook Reference)

39. Schembl157332

40. O-chlorodesmethyldiazepam

41. Delorazepam--dea Schedule Iv Item

42. Dtxsid70183137

43. Chebi:135295

44. Delorazepam 0.1 Mg/ml In Methanol

45. Zinc1255325

46. Bdbm50026858

47. Nsc169895

48. Stk072416

49. Stl149558

50. Akos002312613

51. Akos005749640

52. Db01511

53. Wln: T67 Gmv Jn Ihj Cg Kr Bg

54. Ac-15739

55. Db-008912

56. D07784

57. Ab00119043-01

58. 894d679

59. Sr-01000243030

60. 2h-1, 1,3-dihydro-7-chloro-5-(2-chlorophenyl)-

61. 2h-1, 7-chloro-5-(2-chlorophenyl)-1,3-dihydro-

62. 2h-1, 7-chloro-5-(o-chlorophenyl)-1,3-dihydro-

63. Q3705147

64. Sr-01000243030-1

65. W-107017

66. 7-chloro-5-(2-chlorophenyl)-3h-1,4-benzodiazepin-2-ol

67. 7-chloro-5-(2-chlorophenyl)-1h-benzo[e][1,4]diazepin-2(3h)-one

68. (e)-7-chloro-5-(2-chlorophenyl)-1h-benzo[e][1,4]diazepin-2(3h)-one

69. 1,3-dihydro-7-chloro-5-(2-chlorophenyl)-2h-1,4-benzodiazepin-2-one

70. 7-chloro-5-(2'-chlorophenyl)-1,3-dihydro-2h-1,4-benzodiazepin-2-one

71. 7-chloro-5-(2-chloro-phenyl)-1,3-dihydro-benzo[e][1,4]diazepin-2-one

72. Delorazepam Solution, 100 Mug/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₀Cl₂N₂O
Molecular Weight	305.2 g/mol
XLogP3	3.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	304.0170183 g/mol
Monoisotopic Mass	304.0170183 g/mol
Topological Polar Surface Area	41.5 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	413
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Mainly used as an anti-anxiety agent. Studies have found delorazepam to be more effective in the first 4 weeks of use than antidepressants; however, after 4 weeks, antidepressants showed superior anti-anxiety effects. Anti-anxiety effects also appear to be weaker in elderly patients. Effectiveness has also been observed in the treatment of alcohol withdrawal. Delorazapam was reported to be a manageable drug in that it did not exhibit severe side effects and did not require further therapies to control symptoms of withdrawal.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

5.2 Absorption, Distribution and Excretion

Absorption

77-87% oral bioavailability, with a relatively slow absorption rate. Reaches peak plasma levels within 1-2 hours of administration. Food may slow absorption, however other pharmacokinetic variables remain unchanged. After multiple doses delorazepam accumulates, although accumulation is slower in younger patients.

Route of Elimination

Renally eliminated.

Volume of Distribution

140 L/kg apparent volume of distribution in 11 patients with normal renal function; 47 L/kg in 11 patients with renal failure and on regular hemodialysis. In another study, apparent volume of distribution was 65 L/kg in 8 patients with liver disease and 118.4 L/kg in 12 healthy controls.

Clearance

Still detectable 72 hours after dosing in healthy patients. Patients with liver disease experienced a reduction in clearance from 0.13 to 0.25 ng/mLh.

5.3 Metabolism/Metabolites

Delorazepam is metabolized at a relatively slow pace by the liver. The major metabolite (15-34% of the parent drug) is lorazepam. Older patients metabolize delorazepam slower than younger patients.

5.4 Biological Half-Life

Very long elimination half life of 80-115 hours, varying with age. Elimination is slower as age increases. [1] Liver disease also impacts elimination half life, with impairment resulting in half lives up to 395 hours.

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