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    Synopsis

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    Chemistry

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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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Curiel, 34 - 20067 Paullo MISDNF Italy","customerAddress":"564\/A\/22, ROAD NO.92"}]
    04-Jan-2021
    22-Nov-2024
    KGS
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    Average Price (USD/KGS)

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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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