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Bromazepam
Also known as: Lexotanil, Compedium, Durazanil, Lectopam, Lexotan, Creosedin
Molecular Formula
C14H10BrN3O
Molecular Weight
316.15  g/mol
InChI Key
VMIYHDSEFNYJSL-UHFFFAOYSA-N
FDA UNII
X015L14V0O

One of the BENZODIAZEPINES that is used in the treatment of ANXIETY DISORDERS.
1 2D Structure

Bromazepam

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
7-bromo-5-pyridin-2-yl-1,3-dihydro-1,4-benzodiazepin-2-one
2.1.2 InChI
InChI=1S/C14H10BrN3O/c15-9-4-5-11-10(7-9)14(17-8-13(19)18-11)12-3-1-2-6-16-12/h1-7H,8H2,(H,18,19)
2.1.3 InChI Key
VMIYHDSEFNYJSL-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1C(=O)NC2=C(C=C(C=C2)Br)C(=N1)C3=CC=CC=N3
2.2 Other Identifiers
2.2.1 UNII
X015L14V0O
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Anxyrex

2. Apo Bromazepam

3. Apo-bromazepam

4. Beta, Bromazepam

5. Bromalich

6. Bromaz 1a Pharma

7. Bromazanil

8. Bromazep Von Ct

9. Bromazepam Al

10. Bromazepam Beta

11. Bromazepam Heumann

12. Bromazepam Neuraxpharm

13. Bromazepam Ratiopharm

14. Bromazepam-neuraxpharm

15. Bromazepam-ratiopharm

16. Durazanil

17. Gen Bromazepam

18. Gen-bromazepam

19. Lexatin

20. Lexomil

21. Lexotan

22. Lexotanil

23. Ro 5-3350

24. Ro 53350

25. Von Ct, Bromazep

2.3.2 Depositor-Supplied Synonyms

1. Lexotanil

2. Compedium

3. Durazanil

4. Lectopam

5. Lexotan

6. Creosedin

7. Lexaurin

8. Lexilium

9. Lekotam

10. Lexomil

11. 1812-30-2

12. Calmepam

13. Compendium

14. Normoc

15. La Xvii

16. Ro 5-3350

17. Bromazepamum [inn-latin]

18. Lexatin

19. 7-bromo-5-(2-pyridyl)-3h-1,4-benzodiazepin-2(1h)-one

20. 7-bromo-1,3-dihydro-5-(2-pyridyl)-2h-1,4-benzodiazepin-2-one

21. Bromazepam Civ

22. 2h-1,4-benzodiazepin-2-one, 7-bromo-1,3-dihydro-5-(2-pyridinyl)-

23. Nsc 140669

24. 7-bromo-5-pyridin-2-yl-1,3-dihydro-1,4-benzodiazepin-2-one

25. Ultramidol

26. 7-bromo-1,3-dihydro-5-(2-pyridyl)-2h-1,4-benzdiazepin-2-one

27. Nsc-140669

28. 1,3-dihydro-7-bromo-5-(2-pyridyl)-2h-1,4-benzodiazepin-2-one

29. 2h-1,4-benzodiazepin-2-one, 1,3-dihydro-7-bromo-5-(2-pyridyl)-

30. X015l14v0o

31. 2h-1,4-benzodiazepin-2-one, 7-bromo-1,3-dihydro-5-(2-pyridyl)-

32. 7-bromo-5-(2-pyridyl)-3h-1,4-benzodiaxepin-2(1h)-one

33. Bromazepamum

34. Bromazepamum [latin]

35. Ro-5-3350

36. Bromazepam [usan:inn:ban:jan]

37. Lectopam (tn)

38. Einecs 217-322-4

39. Ro 53350

40. Ro 4-9253

41. Brn 0618645

42. 7-bromo-5-[2-pyridyl]-3h-1,4-benzodiaxepin-2[1h]-one

43. Unii-x015l14v0o

44. Dea No. 2748

45. Bromazepam [mi]

46. Bromazepam [inn]

47. Bromazepam [jan]

48. Bromazepam [usan]

49. Bromazepam [mart.]

50. Bromazepam [who-dd]

51. Schembl43933

52. 5-26-05-00078 (beilstein Handbook Reference)

53. Mls003899212

54. Bromazepam, Analytical Standard

55. Chembl277062

56. Zinc1051

57. Bromazepam (jp17/usan/inn)

58. Bromazepam Civ [usp-rs]

59. Chebi:31302

60. Bromazepam [ep Monograph]

61. Dtxsid40171081

62. 7-bromo-1,4-benzodiazepin-2-one

63. Bromazepam 0.1 Mg/ml In Methanol

64. Bromazepam 1.0 Mg/ml In Methanol

65. Nsc140669

66. Db01558

67. Smr000058724

68. Wln: T67 Gmv Jn Ihj Ce K- Bt6nj

69. D01245

70. 2h-1, 7-bromo-1,3-dihydro-5-(2-pyridyl)-

71. 2h-1, 7-bromo-1,3-dihydro-5-(2-pyridinyl)-

72. 812b302

73. Bromazepam, Drug Standard, 1.0 Mg/ml In Methanol

74. Q422435

75. Bromazepam, European Pharmacopoeia (ep) Reference Standard

76. Bromazepam, United States Pharmacopeia (usp) Reference Standard

77. 7-bromo-5-(pyridin-2-yl)-1h-benzo[e][1,4]diazepin-2(3h)-one

78. 7-bromo-5-(pyridin-2-yl)-2,3-dihydro-1h-1,4-benzodiazepin-2-one

79. (e)-7-bromo-5-(pyridin-2-yl)-1h-benzo[e][1,4]diazepin-2(3h)-one

80. 7-bromo-5-(2-pyridinyl)-1,3-dihydro-2h-1,4-benzodiazepin-2-one #

81. Bromazepam Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 316.15 g/mol
Molecular Formula C14H10BrN3O
XLogP31.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass315.00072 g/mol
Monoisotopic Mass315.00072 g/mol
Topological Polar Surface Area54.4 Ų
Heavy Atom Count19
Formal Charge0
Complexity385
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Indication

For the short-term treatment of insomnia, short-term treatment of anxiety or panic attacks, if a benzodiazepine is required, and the alleviation of the symptoms of alcohol- and opiate-withdrawal.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Bromazepam is a lipophilic, long-acting benzodiazepine and with sedative, hypnotic, anxiolytic and skeletal muscle relaxant properties. It does not possess any antidepressant qualities. Bromazepam, like other benzodiazepines, presents a risk of abuse, misuse, and dependence. According to many psychiatric experts, Bromazepam has a greater abuse potential than other benzodiazepines because of fast resorption and rapid onset of action.


5.2 MeSH Pharmacological Classification

GABA Modulators

Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here. (See all compounds classified as GABA Modulators.)


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

N05BA08

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

N05BA08 - Bromazepam


5.4 Absorption, Distribution and Excretion

Absorption

Bioavailability is 84% following oral administration. The time to peak plasma level is 1 - 4 hours. Bromazepam is generally well absorbed after oral administration.


Route of Elimination

Urine (69%), as metabolites


Volume of Distribution

1.56 L/kg


Clearance

0.82 mL/min/kg.


5.5 Metabolism/Metabolites

Hepatically, via oxidative pathways (via an enzyme belonging to the Cytochrome P450 family of enzymes). One of the main metabolites is 3-hydroxybromazepam. It is pharmacologically active and the half life is similar to that of the parent compound.


Bromazepam has known human metabolites that include 3-Hydroxybromazepam.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.6 Biological Half-Life

10-20 hours


5.7 Mechanism of Action

Bromazepam binds to the GABA-A receptor producing a conformational change and potentiating its inhibitory effects. Other neurotransmitters are not influenced.


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