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Chemistry

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Also known as: Benzalin, 146-22-5, Neozepam, Imeson, Mogadon, Remnos

Molecular Formula

C₁₅H₁₁N₃O₃

Molecular Weight

281.27 g/mol

InChI Key

KJONHKAYOJNZEC-UHFFFAOYSA-N

FDA UNII

9CLV70W7HS

A benzodiazepine derivative used as an anticonvulsant and hypnotic.

1 2D Structure

Nitrazepam

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

7-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one

2.1.2 InChI

InChI=1S/C15H11N3O3/c19-14-9-16-15(10-4-2-1-3-5-10)12-8-11(18(20)21)6-7-13(12)17-14/h1-8H,9H2,(H,17,19)

2.1.3 InChI Key

KJONHKAYOJNZEC-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1C(=O)NC2=C(C=C(C=C2)[N+](=O)[O-])C(=N1)C3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

9CLV70W7HS

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Alodorm

2. Dormalon

3. Dormo-puren

4. Eatan

5. Imadorm

6. Imeson

7. Mogadon

8. Nitrazadon

9. Nitrazep

10. Nitrazepam Al

11. Nitrazepam Neuraxpharm

12. Nitrazepam-neuraxpharm

13. Nitrodiazepam

14. Novanox

15. Radedorm

16. Remnos

17. Rhoxal Nitrazepam

18. Rhoxal-nitrazepam

19. Serenade

20. Somnite

2.3.2 Depositor-Supplied Synonyms

1. Benzalin

2. 146-22-5

3. Neozepam

4. Imeson

5. Mogadon

6. Remnos

7. Neuchlonic

8. Apodorm

9. Calsmin

10. Eunoctin

11. Imesont

12. Nitrados

13. Radedorm

14. Sonebon

15. Trazenin

16. Hipnax

17. Hipsal

18. Nelmat

19. Surem

20. Epibenzalin

21. Epinelbon

22. Nitrenpax

23. Somitran

24. Sonnolin

25. Unisomnia

26. Cerson

27. Dumolid

28. Nelbon

29. Paxisyn

30. Pelson

31. Relact

32. N-desmethylnimetazepam

33. Persopit

34. Gerson

35. Ibrovek

36. Eatan

37. Dormin-5

38. Nitrazepamum

39. 1,3-dihydro-7-nitro-5-phenyl-2h-1,4-benzodiazepin-2-one

40. Ro 4-5360

41. Mogadone

42. Magadon

43. Megadon

44. Mogadan

45. Ro 5-3059

46. Nitrazepamum [inn-latin]

47. 7-nitro-5-phenyl-2,3-dihydro-1h-1,4-benzodiazepin-2-one

48. La 1

49. Nsc-58775

50. 7-nitro-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one

51. 7-nitro-1,3-dihydro-5-phenyl-2h-1,4-benzodiazepin-2-one

52. 2h-1,4-benzodiazepin-2-one, 1,3-dihydro-7-nitro-5-phenyl-

53. S 2000

54. 7-nitro-5-phenyl-1,3-dihydro-2h-1,4-benzodiazepin-2-one

55. 2,3-dihydro-7-nitro-5-phenyl-1h-1,4-benzodiazepin-2-on

56. Dormo-puren

57. N05cd02

58. Mitidin

59. 9clv70w7hs

60. Chembl13209

61. Eatan N

62. Chebi:7581

63. Somnite

64. Nsc58775

65. Ro-45360

66. Ro-53059

67. Ncgc00159358-02

68. 2,3-dihydro-7-nitro-5-phenyl-1h-1,4-benzodiazepin-2-one

69. Calsamin

70. Eunoktin

71. Ipersed

72. Nitravet

73. Nitrempax

74. Noctesed

75. Pacisyn

76. Somnased

77. Somnibel

78. Ro-4-5360

79. Ro-5-3059

80. Dsstox_cid_3372

81. La 1 (van)

82. Dormicum (anticonvulsant)

83. Dsstox_rid_77000

84. Dsstox_gsid_23372

85. 7-nitro-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one

86. Nitrazepam [usan:inn:ban:jan]

87. Nitrazepam (tn)

88. Benzalin (tn)

89. Cas-146-22-5

90. Smr000058302

91. Ccris 1931

92. Einecs 205-665-2

93. Nsc 58775

94. Unii-9clv70w7hs

95. Brn 0757185

96. Dea No. 2834

97. Isopropylacetate/nitrazepam

98. Ro 53-60

99. Nitrazepam [mi]

100. Nitrazepam [inn]

101. Nitrazepam [jan]

102. Nitrazepam [usan]

103. Chemdiv1_022312

104. Nitrazepam [mart.]

105. Nitrazepam [who-dd]

106. Nitrazepam [who-ip]

107. Oprea1_476234

108. Schembl35202

109. 5-24-04-00344 (beilstein Handbook Reference)

110. Mls001304053

111. Mls001424061

112. Dtxsid5023372

113. Nitrazepam (jp17/usan/inn)

114. Hms650g04

115. Kjonhkayojnzec-uhfffaoysa-

116. Nitrazepam [ep Monograph]

117. 1, 3-dihydro-7-nitro-5-phenyl-2h-1,4-benzodiazepin-2-one

118. Hms2051f19

119. Hms2272g03

120. Hms3393f19

121. 7-nitro-1,4-benzodiazepin-2-one

122. Nitrazepam Methanol Solution

123. Nitrazepamum [who-ip Latin]

124. Zinc4311748

125. Tox21_111601

126. Bdbm50020856

127. Pdsp1_000120

128. Pdsp2_000120

129. Stk806322

130. Akos002254707

131. Nitrazepam 0.1 Mg/ml In Acetonitrile

132. Nitrazepam 1.0 Mg/ml In Acetonitrile

133. Tox21_111601_1

134. Wln: T67 Gmv Jn Ihj Cnw Kr

135. Ab02342

136. Ac-4537

137. Ccg-100977

138. Db01595

139. Nc00227

140. Ncgc00159358-03

141. 2h-1, 1,3-dihydro-7-nitro-5-phenyl-

142. 7-nitro-5-phenyl-2,4-benzodiazepin-2-one

143. Db-042832

144. C07487

145. D00531

146. 146n225

147. A808471

148. Q410078

149. 7-nitro-5-phenyl-1h-benzo[e][1,4]diazepin-2(3h)-one

150. Nitrazepam, British Pharmacopoeia (bp) Reference Standard

151. Nitrazepam, European Pharmacopoeia (ep) Reference Standard

152. (z)-7-nitro-5-phenyl-1h-benzo[e][1,4]diazepin-2(3h)-one

153. 1,3-dihydro-7-nitro-5-phenyl-2h-1,4-benzodiazepine-2-one

154. 7-nitro-5-phenyl-1,3-dihydro-2h-1,4-benzodiazepin-2-one #

155. Nitrazepam Solution, 1.0 Mg/ml In Acetonitrile, Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₁N₃O₃
Molecular Weight	281.27 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	1
Exact Mass	281.08004122 g/mol
Monoisotopic Mass	281.08004122 g/mol
Topological Polar Surface Area	87.3 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	452
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

Used to treat short-term sleeping problems (insomnia), such as difficulty falling asleep, frequent awakenings during the night, and early-morning awakening.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Nitrazepam is a type of benzodiazepine drug. It is a powerful hypnotic drug which possesses strong sedative, anxiolytic, amnestic, anticonvulsant, and skeletal muscle relaxant properties. Nitrazepam shortens the time required to fall asleep and lengthens the duration of sleep. It is also useful for the management of myoclonic seizures.

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.)

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.)

Hypnotics and Sedatives

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)

Anticonvulsants

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

5.3 ATC Code

N05CD02

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

N05C - Hypnotics and sedatives

N05CD - Benzodiazepine derivatives

N05CD02 - Nitrazepam

5.4 Absorption, Distribution and Excretion

Absorption

Bioavailability is 53-94% following oral administration.

5.5 Biological Half-Life

15-38 hours (mean elimination half life 26 hours).

5.6 Mechanism of Action

Nitrazepam belongs to a group of medicines called benzodiazepines. This drug affects central benzodiazepine receptors, which are associated with inhibitory GABA (gamma amino butyric acid)receptors, leading to enhanced GABA binding activity. GABA is a major neurotransmitter in the brain, which causes somnolence, relaxation of muscles, a decrease in anxiety and general central nervous system depression. Nitrazepam has anticonvulsant properties that may be attributed to its ability to bind to voltage-dependent sodium channels. Sustained repetitive firing seems to be limited by benzodiazepines effect of slowing recovery of sodium channels from inactivation.

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