Skip to main content

Diazepam

  • Reference work entry
Atlas of Epilepsies

Chemical Structure and When it was Licensed

Diazepam (7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one; C16H13ClN2O; molecular weight 284.75; pK a 3.2) is a 1,4 benzodiazepine (Clonazepam, Lorazepam, Midazolam) that was first synthesized in 1959 in the laboratory of Dr. Louis Sternbach at the Hoffman-La Roche facility in Nutley, New Jersey. It was trademarked as Valium in 1961 and a US patent was granted in 1968. Its chemical structure is displayed in Fig. 263-1 .

Figure 263-1
figure 1_263 figure 1_263

The chemical structure of diazepam and its metabolites. Temazepam and oxazepam undergo glucornidation prior to renal excretion

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 599.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 899.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Abbreviations

AAP:

American Academy of Pediatrics

References

  • Alldredge BK, Gelb AM, Isaacs SM, Corry MD, Allen F, Ulrich S, Gottwald MD, O’Neil N, Neuhaus JM, Segal MR, Lowenstein DH (2001) A comparison of lorazepam, diazepam, and placebo for the treatment of out-of-hospital status epilepticus. New Engl J Med 345:631–637

    Article  CAS  PubMed  Google Scholar 

  • Alldredge BK, Venteicher R, Calderwood TS (2002) Stability of diazepam rectal gel in ambulance-like environments. Am J Emerg Med 20:88–91

    Article  PubMed  Google Scholar 

  • Appleton R, Sweeney A, Choonara I, Robson J, Molyneux E (1995) Lorazepam versus diazepam in the acute treatment of epileptic seizures and status epilepticus. Dev Med Child Neurol 37:682–688

    Article  CAS  PubMed  Google Scholar 

  • Dolovich LR, Addis A, Vaillancourt JM, Power JD, Koren G, Einarson TR (1998) Benzodiazepine use in pregnancy and major malformations or oral cleft: meta-analysis of cohort and case-control studies. BMJ 317:839–843

    CAS  PubMed  Google Scholar 

  • Dreifuss FE, Rosman NP, Cloyd JC, Pellock JM, Kuzniecky RI, Lo WD, Matsuo F, Sharp GB, Conry JA, Bergen DC, Bell WE (1998) A comparison of rectal diazepam gel and placebo for acute repetitive seizures. New Engl J Med 338:1869–1875

    Article  CAS  PubMed  Google Scholar 

  • Goodkin HP, Kapur J (2009) The impact of diazepam’s discovery on the treatment and understanding of status epilepticus. Epilepsia 50:2011–2018

    Article  CAS  PubMed  Google Scholar 

  • Knudsen FU (1985) Effective short-term diazepam prophylaxis in febrile convulsions. J Pediatr 106:487–490

    Article  CAS  PubMed  Google Scholar 

  • Leppik IE, Derivan AT, Homan RW, Walker J, Ramsay RE, Patrick B (1983) Double-blind study of lorazepam and diazepam in status epilepticus. JAMA 249:1452–1454

    Article  CAS  PubMed  Google Scholar 

  • Lowenstein DH, Alldredge BK (1998) Status epilepticus. New Engl J Med 338:970–976

    Article  CAS  PubMed  Google Scholar 

  • Naquet R, Soulayrol R, Dolce G, Tassinari C, Broughton R, Loeb H (1965) First attempt at treatment of experimental status epiletpicus in animals and spontaneous status epilepticus in man with diazepam. Electroencephalogr Clin Neurophysiol 18:427

    Article  Google Scholar 

  • Prasad K, Al-Roomi K, Krishnan PR, Sequeira R (2005) Anticonvulsant therapy for status epilepticus. Cochrane Database Syst Rev CD003723.2005

    Google Scholar 

  • Pritchett DB, Sontheimer H, Shivers BD, Ymer S, Kettenmann H, Schofield PR, Seeburg PH (1989) Importance of a novel GABAA receptor subunit for benzodiazepine pharmacology. Nature 338:582–585

    Article  CAS  PubMed  Google Scholar 

  • Riss J, Cloyd J, Gates J, Collins S (2008) Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand 118:69–86

    Article  CAS  PubMed  Google Scholar 

  • Rogers CJ, Twyman RE, Macdonald RL (1994) Benzodiazepine and beta-carboline regulation of single GABAA receptor channels of mouse spinal neurones in culture. J Physiol 475:69–82

    CAS  PubMed  Google Scholar 

  • Rosman NP, Colton T, Labazzo J, Gilbert PL, Gardella NB, Kaye EM, Van Bennekom C, Winter MR (1993) A controlled trial of diazepam administered during febrile illnesses to prevent recurrence of febrile seizures. New Engl J Med 329:79–84

    Article  CAS  PubMed  Google Scholar 

  • Schmidt D (1995) Benzodiazepines: diazepam. In: Levy R et al. (eds) Antiepileptic drugs. Raven Press, New York, pp 705–724

    Google Scholar 

  • Schmidt D, Wilensky AJ (2008) Benzodiazepines. In: Engel JE Jr, Pedley TA (eds) Epilepsy: a comprehensive textbook. Lipponcott Williams & Wilkins, Philadelphia, pp 1531–1541

    Google Scholar 

  • Steering Committee on Quality Improvements and Management (2008) Febrile seizures: clinical practice guideline for the long-term management of the child with simple febrile seizures. Pediatrics 121:1281–1286

    Article  Google Scholar 

  • Tanaka E (1999) Clinically significant pharmacokinetic drug interactions with benzodiazepines. J Clin Pharm Ther 24:347–355

    Article  CAS  PubMed  Google Scholar 

  • Treiman DM, Meyers PD, Walton NY, Collins JF, Colling C, Rowan AJ, Handforth A, Faught E, Calabrese VP, Uthman BM, Ramsay RE, Mamdani MB, Veterans Affairs Status Epilepticus Cooperative Study Group (1998) A comparison of four treatments for generalized convulsive status epilepticus. New Engl J Med 339:792–798

    Article  CAS  PubMed  Google Scholar 

  • Verrotti A, Latini G, di Corcia G, Giannuzzi R, Salladini C, Trotta D, Chiarelli F (2004) Intermittent oral diazepam prophylaxis in febrile convulsions: its effectiveness for febrile seizure recurrence. Eur J Paediatr Neurol 8:131–134

    Article  PubMed  Google Scholar 

  • Wesson DR, Camber S, Harkey M, Smith DE (1985) Diazepam and desmethyldiazepam in breast milk. J Psychoactive Drugs 17:55–56

    CAS  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer-Verlag London Limited

About this entry

Cite this entry

Goodkin, H.P. (2010). Diazepam. In: Panayiotopoulos, C.P. (eds) Atlas of Epilepsies. Springer, London. https://doi.org/10.1007/978-1-84882-128-6_263

Download citation

  • DOI: https://doi.org/10.1007/978-1-84882-128-6_263

  • Publisher Name: Springer, London

  • Print ISBN: 978-1-84882-127-9

  • Online ISBN: 978-1-84882-128-6

  • eBook Packages: MedicineReference Module Medicine

Publish with us

Policies and ethics