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Also known as: Valium, 439-14-5, Ansiolisina, Diazemuls, Apaurin, Faustan
Molecular Formula
C16H13ClN2O
Molecular Weight
284.74  g/mol
InChI Key
AAOVKJBEBIDNHE-UHFFFAOYSA-N
FDA UNII
Q3JTX2Q7TU

Diazepam
A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.
Diazepam is a Benzodiazepine.
1 2D Structure

Diazepam

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
7-chloro-1-methyl-5-phenyl-3H-1,4-benzodiazepin-2-one
2.1.2 InChI
InChI=1S/C16H13ClN2O/c1-19-14-8-7-12(17)9-13(14)16(18-10-15(19)20)11-5-3-2-4-6-11/h2-9H,10H2,1H3
2.1.3 InChI Key
AAOVKJBEBIDNHE-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1C(=O)CN=C(C2=C1C=CC(=C2)Cl)C3=CC=CC=C3
2.2 Other Identifiers
2.2.1 UNII
Q3JTX2Q7TU
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2h-1,4-benzodiazepin-2-one

2. Apaurin

3. Diazemuls

4. Faustan

5. Relanium

6. Seduxen

7. Sibazon

8. Stesolid

9. Valium

2.3.2 Depositor-Supplied Synonyms

1. Valium

2. 439-14-5

3. Ansiolisina

4. Diazemuls

5. Apaurin

6. Faustan

7. Relanium

8. Seduxen

9. Sibazon

10. Stesolid

11. Methyldiazepinone

12. Ansiolin

13. Apozepam

14. Atensine

15. Bensedin

16. Bialzepam

17. Calmocitene

18. Calmpose

19. Ceregulart

20. Condition

21. Diacepan

22. Diazepan

23. Diazetard

24. Dipezona

25. Domalium

26. Kiatrium

27. Liberetas

28. Neurolytril

29. Paranten

30. Quetinil

31. Quiatril

32. Quievita

33. Relaminal

34. Renborin

35. Ruhsitus

36. Seduksen

37. Serenack

38. Serenamin

39. Serenzin

40. Stesolin

41. Tensopam

42. Tranimul

43. Tranqdyn

44. Tranquirit

45. Unisedil

46. Valitran

47. Valrelease

48. Alboral

49. Aliseum

50. Amiprol

51. Armonil

52. Assival

53. Atilen

54. Cercine

55. Dialag

56. Diapam

57. Diastat

58. Dienpax

59. Duksen

60. Eridan

61. Eurosan

62. Freudal

63. Frustan

64. Gihitan

65. Lembrol

66. Levium

67. Morosan

68. Paxate

69. Plidan

70. Saromet

71. Sedipam

72. Setonil

73. Sonacon

74. Umbrium

75. Vatran

76. Velium

77. Duxen

78. Lamra

79. Paxel

80. Solis

81. Valeo

82. Vival

83. Vivol

84. Zipan

85. Noan

86. Usempax Ap

87. Methyl Diazepinone

88. Q-pam

89. Centrazepam

90. Kabivitrum

91. La-iii

92. Evacalm

93. Gewacalm

94. Horizon

95. Novazam

96. Tranquase

97. Valaxona

98. Valiquid

99. Dialar

100. Dipam

101. Dizac

102. Paceum

103. La Iii

104. An-ding

105. E-pam

106. Jinpanfan

107. Servizepam

108. Simasedan

109. Antenex

110. Arzepam

111. Diapax

112. Drenian

113. Ducene

114. Kratium

115. Nellium

116. Nerozen

117. Zepaxid

118. Doval

119. Paxum

120. Sipam

121. Vazen

122. Placidox 5

123. Ro 5-2807

124. Wy-3467

125. 7-chloro-1-methyl-5-phenyl-3h-1,4-benzodiazepin-2-one

126. 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2h-1,4-benzodiazepin-2-one

127. D-pam

128. Nsc-77518

129. 7-chloro-1-methyl-5-phenyl-1,3-dihydro-2h-1,4-benzodiazepin-2-one

130. Diacepin

131. Diazepam Civ

132. 2h-1,4-benzodiazepin-2-one, 7-chloro-1,3-dihydro-1-methyl-5-phenyl-

133. Faustan,

134. 7-chloro-1-methyl-5-phenyl-3h-1,4-benzodiazepin-2(1h)-one

135. 7-chloro-1-methyl-2-oxo-5-phenyl-3h-1,4-benzodiazepine

136. 7-chloro-1-methyl-5-phenyl-2h-1,4-benzodiazepin-2-one

137. Chembl12

138. Q3jtx2q7tu

139. Nsc-169897

140. 1-methyl-5-phenyl-7-chloro-1,3-dihydro-2h-1,4-benzodiazepin-2-one

141. Nrl-1

142. Ro-5-2807

143. Dzp

144. Methyldiazepinone, Pharmaceutical

145. Chebi:49575

146. Apo-diazepam

147. Wy 3467

148. Diazepam Intensol

149. La 111

150. Ro-52807

151. 7-chloro-1-methyl-5-3h-1,4-benzodiazepin-2(1h)-one

152. Ncgc00178168-02

153. Calmociteno

154. Alupram

155. Ansilive

156. Anxicalm

157. Anxionil

158. Benzopin

159. Betapam

160. Britazepam

161. Calmaven

162. Chuansuan

163. Desconet

164. Desloneg

165. Diaceplex

166. Diapine

167. Diaquel

168. Diatran

169. Diazepin

170. Disopam

171. Faustal

172. Gradual

173. Iazepam

174. Medipam

175. Mentalium

176. Metamidol

177. Nervium

178. Nivalen

179. Nixtensyn

180. Notense

181. Novodipam

182. Ortopsique

183. Paralium

184. Prozepam

185. Psychopax

186. Radizepam

187. Reliver

188. Sedapam

189. Trankinon

190. Trazepam

191. Valuzepam

192. Vanconin

193. Baogin

194. Calmod

195. Caudel

196. Diazem

197. Lovium

198. Mandro

199. Parzam

200. Dipaz

201. Dupin

202. Gubex

203. Lizan

204. Pomin

205. Winii

206. Diazepam Nordic

207. Diazepam-lipuro

208. Diazepan Leo

209. Diazepam Elmu

210. Diazepam Fabra

211. Diazepam Stada

212. Dsstox_cid_406

213. Metil Gobanal

214. Diazepam Dak

215. Tranquo-tablinen

216. Diazepam Desitin

217. Euphorin P

218. Mandro-zep

219. Sico Relax

220. Diazepam Rectubes

221. S.a. R.l.

222. Elcion Cr

223. Placidox 2

224. Kratium 2

225. Diazepam-ratiopharm

226. Dsstox_rid_75566

227. Dsstox_gsid_20406

228. Placidox 10

229. Diazepamu [polish]

230. Diazepam-eurogenerics

231. Diazepamum

232. Diazepamu

233. Mandrozep

234. Plumiaz

235. Tensium

236. Tranquo-puren

237. Diastat Acudial

238. Diazepamum [inn-latin]

239. 7-chloro-1-methyl-5-phenyl-1,3-dihydro-benzo[e][1,4]diazepin-2-one

240. 7-chloro-1-methyl-5-phenyl-2,3-dihydro-1h-1,4-benzodiazepin-2-one

241. Wln: T67 Gnv Jn Ihj Cg G1 Kr

242. Cas-439-14-5

243. Smr000058398

244. Ccris 6009

245. Best [pharaceutical]

246. Hsdb 3057

247. Methyldiazepinone (pharmaceutical)

248. 2h-1, 7-chloro-1,3-dihydro-1-methyl-5-phenyl-

249. Einecs 207-122-5

250. Unii-q3jtx2q7tu

251. La-111

252. 1-methyl-5-phenyl-7-chloro-1,4-benzodiazepin-2-one

253. 7-chloro-1-methyl-5-phenyl-1,4-benzodiazepin-2-one

254. Nsc 169897

255. Brn 0754371

256. Anlin

257. Dea No. 2765

258. Pro Pam

259. Diastat (tn)

260. Valium (tn)

261. Valtoco

262. Diazepam [usan:usp:inn:ban:jan]

263. Diazepam [hsdb]

264. Diazepam [iarc]

265. Diazepam [usan]

266. Diazepam [inn]

267. Diazepam [jan]

268. Diazepam [mi]

269. Diazepam [vandf]

270. Spectrum3_001780

271. Spectrum4_000576

272. Spectrum5_001890

273. Diazepam [mart.]

274. Diazepam [who-dd]

275. Bidd:pxr0158

276. Oprea1_126223

277. Schembl21442

278. Bspbio_003279

279. Kbiogr_001012

280. 5-24-04-00300 (beilstein Handbook Reference)

281. Mls000759402

282. Mls001424086

283. Bidd:gt0105

284. Diazepam [green Book]

285. Divk1c_000967

286. Diazepam (jp17/usp/inn)

287. Diazepam [orange Book]

288. Diazepam Civ [usp-rs]

289. Mono (2-ethylhexyl) Phthalate

290. Gtpl3364

291. S.a.r.l.

292. Zinc6427

293. Diazepam [ep Monograph]

294. Diazepam [usp Monograph]

295. Dtxsid4020406

296. Hms503a15

297. Kbio1_000967

298. Kbio3_002780

299. Diazepam 0.1 Mg/ml In Methanol

300. Diazepam 1.0 Mg/ml In Methanol

301. Ninds_000967

302. Hms2051n04

303. Hms3393n04

304. Bcp23002

305. Nsc77518

306. Tox21_113071

307. Tox21_202458

308. 7-chloro-1-methyl-5-phenyl-1h-benzo[e][1,4]diazepin-2(3h)-one

309. Bdbm50000766

310. Nsc169897

311. Stk735517

312. Akos003367969

313. Diazepam 1000 Microg/ml In Methanol

314. Tox21_113071_1

315. Ab02310

316. Bcp9000199

317. Ccg-100997

318. Cs-0653

319. Db00829

320. Nc00247

321. Ro 5-2805

322. Idi1_000967

323. Ncgc00178168-01

324. Ncgc00178168-03

325. Ncgc00178168-04

326. Ncgc00260007-01

327. Ac-10561

328. Hy-17027

329. Bcp0726000176

330. Db-051179

331. C06948

332. D00293

333. A826456

334. Q210402

335. Valium; Ansiolisina; Diazemuls; Apaurin; Faustan

336. Brd-k16508793-001-01-8

337. Diazepam, European Pharmacopoeia (ep) Reference Standard

338. 7-chloranyl-1-methyl-5-phenyl-3h-1,4-benzodiazepin-2-one

339. 7-chloro-1-methyl-5-phenyl-3h-1,4-benzodiazepin-2-one.

340. 7-chloro-1-methyl-5-phenyl-1h-1,4-benzodiazepine-2(3h)on

341. Diazepam, United States Pharmacopeia (usp) Reference Standard

342. 7-chloro-1-methyl-5-phenyl-1,3-dihydro-[1,4]benzodiazepin-2-one

343. 7 -chloro-1,3-dihydro-1-methyl-5-phenyl-2h-1,4-benzodiazepin-2-one

344. 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2h -1,4-benzodiazepin-2-one

345. 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2h-1,4-benzodiazepine-2-one

346. 7-chloro-1-methyl-1,3-dihydro-5-phenyl-2h-1,4-benzodiazepin-2-one

347. 7-chloro-1-methyl-5-phenyl-2-oxo-2,3-dihydro-1h-benzo[f]-1,4-diazepine

348. Diazepam For System Suitability, European Pharmacopoeia (ep) Reference Standard

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

350. Diazepam Solution, 1.0 Mg/ml In Methanol, Analytical Standard, For Drug Analysis

351. 11100-37-1

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 284.74 g/mol
Molecular Formula C16H13ClN2O
XLogP33
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass284.0716407 g/mol
Monoisotopic Mass284.0716407 g/mol
Topological Polar Surface Area32.7 Ų
Heavy Atom Count20
Formal Charge0
Complexity403
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 Information
1 of 10  
Drug NameDiastat
PubMed HealthDiazepam (Rectal)
Drug ClassesAnticonvulsant
Drug LabelDiazepam rectal gel rectal delivery system is a non-sterile diazepam gel provided in a prefilled, unit-dose, rectal delivery system. Diazepam rectal gel contains 5 mg/mL diazepam, propylene glycol, ethyl alcohol (10%), hydroxypropyl methylcellulose,...
Active IngredientDiazepam
Dosage FormGel
RouteRectal
Strength2.5mg/0.5ml (5mg/ml)
Market StatusPrescription
CompanyValeant

2 of 10  
Drug NameDiastat acudial
PubMed HealthDiazepam
Drug ClassesAntianxiety, Anticonvulsant, Skeletal Muscle Relaxant
Drug LabelDiazepam is a benzodiazepine derivative. The chemical name ofdiazepam is 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one. It is a colorless to light yellow crystalline compound, insoluble in water. The empirical formula is C16H13C...
Active IngredientDiazepam
Dosage FormGel
RouteRectal
Strength20mg/4ml (5mg/ml); 10mg/2ml (5mg/ml)
Market StatusPrescription
CompanyValeant

3 of 10  
Drug NameDiazepam
PubMed HealthDiazepam (By mouth)
Drug ClassesAntianxiety, Anticonvulsant, Skeletal Muscle Relaxant
Drug LabelEach 5 mL of Oral Solution contains:Diazepam........................................................... 5 mgEach mL of IntensolTM Oral Solution (Concentrate) contains:Diazepam............................................................ 5 mgAlcohol......
Active IngredientDiazepam
Dosage FormInjectable; Tablet; Concentrate; Solution
RouteInjection; Oral
Strength5mg; 5mg/ml; 2mg; 10mg; 5mg/5ml
Market StatusPrescription
CompanyLannett Holdings; Watson Labs; Vintage Pharms; Ivax Sub Teva Pharms; Hospira; Mylan; Roxane; Barr

4 of 10  
Drug NameDiazepam intensol
PubMed HealthDiazepam
Drug ClassesAntianxiety, Anticonvulsant, Skeletal Muscle Relaxant
Drug LabelValium (diazepam) is a benzodiazepine derivative. The chemical name of diazepam is 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one. It is a colorless to light yellow crystalline compound, insoluble in water. The empirical formula is...
Active IngredientDiazepam
Dosage FormConcentrate
RouteOral
Strength5mg/ml
Market StatusPrescription
CompanyRoxane

5 of 10  
Drug NameValium
Active IngredientDiazepam
Dosage FormTablet
RouteOral
Strength5mg; 2mg; 10mg
Market StatusPrescription
CompanyRoche

6 of 10  
Drug NameDiastat
PubMed HealthDiazepam (Rectal)
Drug ClassesAnticonvulsant
Drug LabelDiazepam rectal gel rectal delivery system is a non-sterile diazepam gel provided in a prefilled, unit-dose, rectal delivery system. Diazepam rectal gel contains 5 mg/mL diazepam, propylene glycol, ethyl alcohol (10%), hydroxypropyl methylcellulose,...
Active IngredientDiazepam
Dosage FormGel
RouteRectal
Strength2.5mg/0.5ml (5mg/ml)
Market StatusPrescription
CompanyValeant

7 of 10  
Drug NameDiastat acudial
PubMed HealthDiazepam
Drug ClassesAntianxiety, Anticonvulsant, Skeletal Muscle Relaxant
Drug LabelDiazepam is a benzodiazepine derivative. The chemical name ofdiazepam is 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one. It is a colorless to light yellow crystalline compound, insoluble in water. The empirical formula is C16H13C...
Active IngredientDiazepam
Dosage FormGel
RouteRectal
Strength20mg/4ml (5mg/ml); 10mg/2ml (5mg/ml)
Market StatusPrescription
CompanyValeant

8 of 10  
Drug NameDiazepam
PubMed HealthDiazepam (By mouth)
Drug ClassesAntianxiety, Anticonvulsant, Skeletal Muscle Relaxant
Drug LabelEach 5 mL of Oral Solution contains:Diazepam........................................................... 5 mgEach mL of IntensolTM Oral Solution (Concentrate) contains:Diazepam............................................................ 5 mgAlcohol......
Active IngredientDiazepam
Dosage FormInjectable; Tablet; Concentrate; Solution
RouteInjection; Oral
Strength5mg; 5mg/ml; 2mg; 10mg; 5mg/5ml
Market StatusPrescription
CompanyLannett Holdings; Watson Labs; Vintage Pharms; Ivax Sub Teva Pharms; Hospira; Mylan; Roxane; Barr

9 of 10  
Drug NameDiazepam intensol
PubMed HealthDiazepam
Drug ClassesAntianxiety, Anticonvulsant, Skeletal Muscle Relaxant
Drug LabelValium (diazepam) is a benzodiazepine derivative. The chemical name of diazepam is 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one. It is a colorless to light yellow crystalline compound, insoluble in water. The empirical formula is...
Active IngredientDiazepam
Dosage FormConcentrate
RouteOral
Strength5mg/ml
Market StatusPrescription
CompanyRoxane

10 of 10  
Drug NameValium
Active IngredientDiazepam
Dosage FormTablet
RouteOral
Strength5mg; 2mg; 10mg
Market StatusPrescription
CompanyRoche

4.2 Therapeutic Uses

Adjuvants, Anesthesia; Anesthetics, Intravenous; Anti-Anxiety Agents, Benzodiazepine; Anticonvulsants; Antiemetics; GABA Modulators; Muscle Relaxants, Central; Sedatives, Nonbarbiturate

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


Diazepam shares the actions of other benzodiazepines. The drug is used preoperatively to relieve anxiety and provide sedation, light anesthesia, and anterograde amnesia; as an adjunct during endoscopy to relieve anxiety and provide sedation, light anesthesia, and anterograde amnesia; for the management of agitation associated with acute alcohol withdrawal; as an adjunct for the relief of acute, painful musculoskeletal conditions; to manage skeletal muscle spasticity such as reflex spasm secondary to local pathology (e.g., trauma, inflammation), spasticity caused by upper motor neuron disorders (e.g., cerebral palsy, paraplegia), athetosis, stiff-man syndrome, or tetanus; and for the management of anxiety disorders or for the short-term relief of symptoms of anxiety. Anxiety or tension associated with the stress of everyday life usually does not require treatment with an anxiolytic. The efficacy of diazepam for long-term use (i.e., longer than 4 months) as an anxiolytic has not been evaluated. /Included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2576


Diazepam has been used orally to prevent night terrors. Although not recommended by the manufacturer, parenteral diazepam is used to reduce the requirements for opiate analgesics and produce anterograde amnesia during labor and delivery. The drug has been used parenterally to manage neonatal opiate withdrawal. /NOT included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2576


Diazepam is also used IV or rectally as an anticonvulsant, and IV diazepam or lorazepam generally are considered the drugs of choice for termination of status epilepticus. /Included in US product label/

American Society of Health System Pharmacists; AHFS Drug Information 2010. Bethesda, MD. (2010), p. 2576


For more Therapeutic Uses (Complete) data for DIAZEPAM (10 total), please visit the HSDB record page.


4.3 Drug Warning

Since Valium has a central nervous system depressant effect, patients should be advised against the simultaneous ingestion of alcohol and other CNS-depressant drugs during Valium therapy

US Natl Inst Health; DailyMed. Current Medication Information for VALIUM (diazepam) tablet (January 2008). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=18533


Diazepam is subject to Schedule IV control under the Controlled Substances Act of 1970. Abuse and dependence of benzodiazepines have been reported. Addiction-prone individuals (such as drug addicts or alcoholics) should be under careful surveillance when receiving diazepam or other psychotropic agents because of the predisposition of such patients to habituation and dependence. Once physical dependence to benzodiazepines have developed, termination of treatment will be accompanied by withdrawal symptoms. The risk is more pronounced in patients on long-term therapy.

US Natl Inst Health; DailyMed. Current Medication Information for VALIUM (diazepam) tablet (January 2008). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=18533


A transient syndrome whereby the symptoms that led to treatment with Valium recur in an enhanced form. This may occur upon discontinuation of treatment. It may be accompanied by other reactions including mood changes, anxiety, and restlessness. Since the risk of withdrawal phenomena and rebound phenomena is greater after abrupt discontinuation of treatment, it is recommended that the dosage be decreased gradually.

US Natl Inst Health; DailyMed. Current Medication Information for VALIUM (diazepam) tablet (January 2008). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=18533


Withdrawal symptoms, similar in character to those noted with barbiturates and alcohol have occurred following abrupt discontinuance of diazepam. These withdrawal symptoms may consist of tremor, abdominal and muscle cramps, vomiting, sweating, headache, muscle pain, extreme anxiety, tension, restlessness, confusion and irritability. In severe cases, the following symptoms may occur: derealization, depersonalization, hyperacusis, numbness and tingling of the extremities, hypersensitivity to light, noise and physical contact, hallucinations or epileptic seizures. The more severe withdrawal symptoms have usually been limited to those patients who had received excessive doses over an extended period of time. Generally milder withdrawal symptoms (e.g., dysphoria and insomnia) have been reported following abrupt discontinuance of benzodiazepines taken continuously at therapeutic levels for several months. Consequently, after extended therapy, abrupt discontinuation should generally be avoided and a gradual dosage tapering schedule followed. Chronic use (even at therapeutic doses) may lead to the development of physical dependence: discontinuation of the therapy may result in withdrawal or rebound phenomena.

US Natl Inst Health; DailyMed. Current Medication Information for VALIUM (diazepam) tablet (January 2008). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=18533


For more Drug Warnings (Complete) data for DIAZEPAM (24 total), please visit the HSDB record page.


4.4 Drug Indication

In general, diazepam is useful in the symptomatic management of mild to moderate degrees of anxiety in conditions dominated by tension, excitation, agitation, fear, or aggressiveness such as may occur in psychoneurosis, anxiety reactions due to stress conditions, and anxiety states with somatic expression. Moreover, in acute alcoholic withdrawal, diazepam may be useful in the symptomatic relief of acute agitation, tremor, and impending acute delirium tremens. Furthermore, diazepam is a useful adjunct for the relief of skeletal muscle spasm due to reflex spasm to local pathologies, such as inflammation of the muscle and joints or secondary to trauma; spasticity caused by upper motor neuron disorders, such as cerebral palsy and paraplegia; athetosis and the rare "stiff man syndrome". Particular label information from the United Kingdom also lists particular age-specific indications, including for adults: (1) The short-term relief (2-4 weeks) only, of anxiety which is severe, disabling, or subjecting the individual to unacceptable distress, occurring alone or in association with insomnia or short-term psychosomatic, organic or psychotic illness, (2) cerebral palsy, (3) muscle spasm, (4) as an adjunct to certain types of epilepsy (eg. myoclonus), (5) symptomatic treatment of acute alcohol withdrawal, (6) as oral premedication for the nervous dental patient, and (7) for premedication before surgery. In the same UK label information, diazepam is indicated in children for: (1) control of tension and irritability in cerebral spasticity in selected cases, (2) as an adjunct to the control of muscle spasm in tetanus, and for (3) oral premedication. A diazepam nasal spray is indicated in patients 6 years and older to treat intermittent, stereotypic episodes of frequent seizure activity that are different than the patient's usual seizure pattern.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Diazepam is a benzodiazepine that exerts anxiolytic, sedative, muscle- relaxant, anticonvulsant and amnestic effects. Most of these effects are thought to result from facilitation of the action of gamma aminobutyric acid (GABA), an inhibitory neurotransmitter in the central nervous system.


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.)


Adjuvants, Anesthesia

Agents that are administered in association with anesthetics to increase effectiveness, improve delivery, or decrease required dosage. (See all compounds classified as Adjuvants, Anesthesia.)


Anesthetics, Intravenous

Ultrashort-acting anesthetics that are used for induction. Loss of consciousness is rapid and induction is pleasant, but there is no muscle relaxation and reflexes frequently are not reduced adequately. Repeated administration results in accumulation and prolongs the recovery time. Since these agents have little if any analgesic activity, they are seldom used alone except in brief minor procedures. (From AMA Drug Evaluations Annual, 1994, p174) (See all compounds classified as Anesthetics, Intravenous.)


Antiemetics

Drugs used to prevent NAUSEA or VOMITING. (See all compounds classified as Antiemetics.)


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.)


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.)


Muscle Relaxants, Central

A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358) (See all compounds classified as Muscle Relaxants, Central.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
DIAZEPAM
5.3.2 FDA UNII
Q3JTX2Q7TU
5.3.3 Pharmacological Classes
Benzodiazepines [CS]; Benzodiazepine [EPC]
5.4 ATC Code

N05BA01

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


N05BA01

S66 | EAWAGTPS | Parent-Transformation Product Pairs from Eawag | DOI:10.5281/zenodo.3754448


N - Nervous system

N05 - Psycholeptics

N05B - Anxiolytics

N05BA - Benzodiazepine derivatives

N05BA01 - Diazepam


5.5 Absorption, Distribution and Excretion

Absorption

After oral administration, it is considered that diazepam is rapidly and completely absorbed from the gastrointestinal tract as >90% of diazepam is absorbed and the average time to achieve peak plasma concentrations is 1 1.5 hours with a range of 0.25 to 2.5 hours. Absorption is delayed and decreased when administered with a moderate fat meal. In the presence of food mean lag times are approximately 45 minutes as compared with 15 minutes when fasting. There is also an increase in the average time to achieve peak concentrations to about 2.5 hours in the presence of food as compared with 1.25 hours when fasting. This results in an average decrease in Cmax of 20% in addition to a 27% decrease in AUC (range 15% to 50%) when administered with food.


Route of Elimination

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


Volume of Distribution

In young healthy males, the volume of distribution at steady-state is 0.8 to 1.0 L/kg.


Clearance

The clearance of diazepam is 20 to 30 mL/min in young adults.


Diazepam rectal gel is well absorbed following rectal administration, reaching peak plasma concentrations in 1.5 hours. The absolute bioavailability of Diazepam rectal gel relative to Valium injectable is 90%. The volume of distribution of Diazepam rectal gel is calculated to be approximately 1 L/kg. ... Both diazepam and its major active metabolite desmethyldiazepam bind extensively to plasma proteins (95-98%).

US Natl Inst Health; DailyMed. Current Medication Information for diastat (diazepam) gel (October 2007). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5533


The concentration of diazepam in plasma and saliva and its binding to plasma protein was determined in normal subjects receiving 10 mg single oral dose over an 8 hr period. A linear relationship was found between diazepam concentration in plasma and that in both mixed and parotid saliva, over plasma concentrations ranging from 196-74.8 ug/mL. Results indicate that there is no significant difference between parotid saliva and mixed saliva concentrations over a period of 8 hr after a single oral dose of diazepam and that appearance of diazepam in saliva may provide an alternate, noninvasive method of determining plasma diazepam levels.

PMID:710030 DIGREGORIO GJ ET AL; CLIN PHARMACOL THER 24 (DEC): 720-5 (1978)


The rate of transplacental passage of diazepam was studied in 33 cases of cephalic presentation where operative forceps delivery was indicated by intrauterine hypoxia or by prolonged second stage of labor. Thirty mg of diazepam was injected iv immediately before delivery either during uterine contractions or in the relaxation period. It was concluded that transfer of diazepam from mother to fetus appears to be delayed when iv injection is given during uterine contractions.

PMID:699483 HARAM K ET AL; CLIN PHARMACOL THER 24 (NOV): 590-9 (1978)


Diazepam and its metabolites are highly bound to plasma proteins (diazepam 98%). Diazepam and its metabolites cross the blood-brain and placental barriers and are also found in breast milk in concentrations approximately one tenth of those in maternal plasma (days 3 to 9 post-partum).

US Natl Inst Health; DailyMed. Current Medication Information for VALIUM (diazepam) tablet (January 2008). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=18533


For more Absorption, Distribution and Excretion (Complete) data for DIAZEPAM (11 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Diazepam is N-demethylated by CYP3A4 and 2C19 to the active metabolite N-desmethyldiazepam, and is hydroxylated by CYP3A4 to the active metabolite temazepam. N-desmethyldiazepam and temazepam are both further metabolized to oxazepam. Temazepam and oxazepam are further largely eliminated by way of conjugation to glucuronic acid via glucuronidation. Furthermore, oxidation of diazepam is mediated by cytochrome P450 isozymes; formation of desmethyl-diazepam mainly by CYP2C19 and CYP3A and 3-hydroxy-diazepam (temazepam) and oxazepam by CYP3A. Because CYP2C19 is polymorphic, extensive metabolizers (EMs), and poor metabolizers (PMs) of diazepam can be distinguished. PMs of diazepam showed significantly lower clearance (12 vs 26 mL/min) and longer elimination half-life (88 vs 41 h) of diazepam than EMs after a single oral dose. Also, PMs had lower clearance, higher AUC and longer elimination half-life of desmethyl-diazepam.


Diazepam is N-demethylated by CYP3A4 and 2C19 to the active metabolite N-desmethyldiazepam, and is hydroxylated by CYP3A4 to the active metabolite temazepam. N-desmethyldiazepam and temazepam are both further metabolized to oxazepam. Temazepam and oxazepam are largely eliminated by glucuronidation.

US Natl Inst Health; DailyMed. Current Medication Information for VALIUM (diazepam) tablet (January 2008). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=18533


/Investigators/ observed variations in the metabolism of diazepam in Wistar rats. /The authors/ studied these variations carefully, and found that the variations are dimorphic and about 17% of male Wistar rats examined showed two times higher diazepam metabolic activities in their liver microsomes than the rest of animals at the substrate concentrations less than 5 uM. /They were/ classified as extensive metabolizer and poor metabolizer of diazepam. No sex difference was observed in the frequency of appearance of extensive metabolizer. Activities of the primary metabolic pathways of diazepam were examined to elucidate the cause of this polymorphism in male Wistar rats. No significant differences were observed in activities of neither diazepam 3-hydroxylation or N-desmethylation between extensive metabolizer and poor metabolizer rats, while activity of diazepam p-hydroxylation was markedly (more than 200 times) higher in extensive metabolizer rats, indicating that this reaction is responsible for the polymorphism of diazepam metabolism in Wistar rats. We examined the expression levels of CYP2D1, which was reported to catalyze diazepam p-hydroxylation in Wistar rats to find no differences in the expression levels of CYP2D1 between extensive metabolizer and PM rats. The kinetic study on diazepam metabolism in male Wistar rats revealed that extensive metabolizer rats had markedly higher V(max) and smaller K(m) in diazepam p-hydroxylation than those of poor metabolizer rats, indicating the presence of high affinity high capacity p-hydroxylase enzyme in extensive metabolizer rats. As a consequence, at low concentrations of diazepam, major pathways of diazepam metabolism were p-hydroxylation and 3-hydroxylation in male extensive metabolizer rats, while in male poor metabolizer rats, 3-hydroxylation followed by N-desmethylation. Due to this kinetic nature of p-hydroxylase activity, extensive metabolizer rats had markedly higher total CL(int) of diazepam than that of poor metabolizer rats. Polymorphism in diazepam metabolism in humans is well documented, but this is the first report revealing the presence of the polymorphism in diazepam metabolism in rats. The current results infer polymorphic expression of new diazepam p-hydroxylating enzyme with lower K(m) than CYP2D1 in extensive metabolizer Wistar rats.

PMID:15067703 Saito K et al; J Pharm Sci 93 (5): 1271-8 (2004)


Diazepam has known human metabolites that include Temazepam and nordiazepam.

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


5.7 Biological Half-Life

Diazepam has a biphasic half-life with an initial rapid distribution phase followed by a prolonged terminal elimination phase of 1 or 2 days; its action is further prolonged by the even longer half-life of 2-5 days of its principal active metabolite, desmethyldiazepam (nordiazepam), the relative proportion of which increases in the body on long-term administration. The plasma half-life of diazepam is prolonged in neonates, in the elderly, and in patients with kidney or liver disease.


... The distributive (alpha) half-life of diazepam is about 1 hr, while the elimination (beta) half-life is about 1.5 days initially and even longer after prolonged treatment.

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 423


In full term infants, elimination half-lives around 30 hours have been reported, with a longer average half-life of 54 hours reported in premature infants of 28 - 34 weeks gestational age and 8 - 81 days post-partum. In both premature and full term infants the active metabolite desmethyldiazepam shows evidence of continued accumulation compared to children. Longer half-lives in infants may be due to incomplete maturation of metabolic pathways

US Natl Inst Health; DailyMed. Current Medication Information for VALIUM (diazepam) tablet (January 2008). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=18533


Elimination half-life increases by approximately 1 hour for each year of age beginning with a half-life of 20 hours at 20 years of age.

US Natl Inst Health; DailyMed. Current Medication Information for VALIUM (diazepam) tablet (January 2008). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=18533


In mild and moderate cirrhosis, average half-life is increased. The average increase has been variously reported from 2-fold to 5-fold, with individual half-lives over 500 hours reported. ... Mean half-life is also prolonged with hepatic fibrosis to 90 hours (range 66 - 104 hours), with chronic active hepatitis to 60 hours (range 26 - 76 hours), and with acute viral hepatitis to 74 hours (range 49 - 129).

US Natl Inst Health; DailyMed. Current Medication Information for VALIUM (diazepam) tablet (January 2008). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=18533


For more Biological Half-Life (Complete) data for DIAZEPAM (7 total), please visit the HSDB record page.


5.8 Mechanism of Action

Diazepam is a benzodiazepine tranquilliser with anticonvulsant, sedative, muscle relaxant and amnesic properties. Benzodiazepines, such as diazepam, bind to receptors in various regions of the brain and spinal cord. This binding increases the inhibitory effects of gamma-aminobutyric acid (GABA). GABAs functions include CNS involvement in sleep induction. Also involved in the control of hypnosis, memory, anxiety, epilepsy and neuronal excitability.


Diazepam is a benzodiazepine that exerts anxiolytic, sedative, muscle-relaxant, anticonvulsant and amnestic effects. Most of these effects are thought to result from a facilitation of the action of gamma aminobutyric acid (GABA), an inhibitory neurotransmitter in the central nervous system.

US Natl Inst Health; DailyMed. Current Medication Information for VALIUM (diazepam) tablet (January 2008). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=18533


Benzodiazepines are widely used in clinical anesthesia as premedication, but also to induce general anesthesia. Recent in vitro studies suggest that gamma-aminobutyric acid type A receptors, harboring a classical high-affinity benzodiazepine binding site, possess another "nonclassical" binding site for benzodiazepines. At present, it is unclear if, and to what extent, this novel nonclassical binding site is of relevance for the actions of benzodiazepines in the central nervous system. Because neocortex is involved in mediating the sedative and hypnotic properties of general anesthetics, ... the actions of diazepam /were quantified/ over a wide range of concentrations (from 10 nM up to 100 uM) in organotypic slice cultures using extracellular multiunit recordings of spontaneous action potential activity. Up to a concentration of 6.25 uM, diazepam reduced the activity of neocortical neurons, approaching a maximum of approximately 20%. This action was nullified by the benzodiazepine antagonist flumazenil. At concentrations >12.5 uM, diazepam evoked a second concentration-dependent dampening of network activity. Unlike the low concentration effect, this high concentration component was resistant to flumazenil. Diazepam induced a biphasic attenuation of spontaneous action potential firing of neocortical neurons. Low to moderate concentrations caused a monotonic, mild depression that is mediated via the classical binding site as it is antagonized by flumazenil. However, the effects of diazepam observed at high concentrations were not affected by flumazenil. Hence, these findings support the concept of at least 2 different binding sites for benzodiazepines on gamma-aminobutyric acid type A receptors. Furthermore, /these/ results are consistent with the hypothesis that the classical high-affinity binding site mediates low-dose diazepam actions, such as amnesia, anxiolysis, and sedation, while a second, nonclassical and independent site contributes to the anesthetic effects of diazepam, such as hypnosis and immobility.

PMID:20889946 Drexler B et al; Anesth Analg 111 (6): 1394-9 (2010)


Benzodiazepine site agonists or inverse agonists enhance or reduce gamma-aminobutyric acid(A) (GABA(A)) receptor-mediated inhibition of neurons, respectively. Recently, it was demonstrated that the point mutation gamma 2F77I causes a drastic change in the affinity of a variety of benzodiazepine agonists or inverse agonists in receptor binding studies. Here we investigated the potency and efficacy of 10 benzodiazepine site ligands from 6 structural classes in wild-type and gamma 2F77I point mutated recombinant GABA(A) receptors composed of alpha 1 beta 3 gamma 2, alpha 2 beta 3 gamma 2, alpha 3 beta 3 gamma 2, alpha 4 beta 3 gamma 2, alpha 5 beta 3 gamma 2, and alpha 6 beta 3 gamma 2 subunits. Results indicate that the effects of the benzodiazepine site ligands zolpidem, zopiclone, Cl218872, L-655,708 and DMCM were nearly completely eliminated in all mutated receptors up to a 1 microM concentration. The effects of bretazenil, Ro15-1788 or abecarnil were eliminated in some, but not all mutated receptors, suggesting that the gamma 2F77I mutation differentially influences the actions of these ligands in different receptor subtypes. In addition, this point mutation also influences the efficacy of diazepam for enhancing GABA-induced chloride flux, suggesting that the amino acid residue gamma 2F77 might also be involved in the transduction of the effect of benzodiazepines from binding to gating.

PMID:20303942 Ramerstorfer J et al; Eur J Pharmacol 636 (1-3): 18-27 (2010)


Although the precise mechanism by which diazepam exerts its antiseizure effects is unknown, animal and in vitro studies suggest that diazepam acts to suppress seizures through an interaction with gamma-aminobutyric acid (GABA) receptors of the A-type (GABAA). GABA, the major inhibitory neurotransmitter in the central nervous system, acts at this receptor to open the membrane channel allowing chloride ions to flow into neurons. Entry of chloride ions causes an inhibitory potential that reduces the ability of neurons to depolarize to the threshold potential necessary to produce action potentials. Excessive depolarization of neurons is implicated in the generation and spread of seizures. It is believed that diazepam enhances the actions of GABA by causing GABA to bind more tightly to the GABAA receptor

US Natl Inst Health; DailyMed. Current Medication Information for diastat (diazepam) gel (October 2007). Available from, as of November 17, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=5533


For more Mechanism of Action (Complete) data for DIAZEPAM (8 total), please visit the HSDB record page.


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04-Jan-2021
07-Oct-2024
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INTERMEDIATES SUPPLIERS

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American Pharma Summit
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American Pharma Summit
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CAS Number : 719-59-5

End Use API : Diazepam

About The Company : LUNA Chemicals Co.,Ltd. markets and manufactures world-class quality Active Pharmaceutical Ingredients and intermediate chemicals for generic pharmaceutical com...

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - TABLET;ORAL - 10MG

USFDA APPLICATION NUMBER - 13263

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DOSAGE - TABLET;ORAL - 2MG

USFDA APPLICATION NUMBER - 13263

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DOSAGE - TABLET;ORAL - 5MG

USFDA APPLICATION NUMBER - 13263

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DOSAGE - GEL;RECTAL - 10MG/2ML (5MG/ML) **Fed...DOSAGE - GEL;RECTAL - 10MG/2ML (5MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20648

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DOSAGE - GEL;RECTAL - 15MG/3ML (5MG/ML) **Fed...DOSAGE - GEL;RECTAL - 15MG/3ML (5MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20648

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DOSAGE - GEL;RECTAL - 2.5MG/0.5ML (5MG/ML)

USFDA APPLICATION NUMBER - 20648

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DOSAGE - GEL;RECTAL - 20MG/4ML (5MG/ML) **Fed...DOSAGE - GEL;RECTAL - 20MG/4ML (5MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20648

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DOSAGE - GEL;RECTAL - 5MG/ML (5MG/ML) **Feder...DOSAGE - GEL;RECTAL - 5MG/ML (5MG/ML) **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20648

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