Diclazepam

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Diclazepam
Chlorodiazepam.png
Systematic (IUPAC) name
7-chloro-5-(2-chlorophenyl)-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
Clinical data
Legal status
  • UK: Unscheduled
  • US: Legal
Routes Oral, likely sublingual.
Pharmacokinetic data
Bioavailability ?
Metabolism Hepatic
Half-life ~42h[1]
Excretion Renal
Identifiers
CAS number 2894-68-0 YesY
ATC code ?
PubChem CID 76168
Chemical data
Formula C16H12Cl2N2O 
Mol. mass 319.185 g/mol
 N (what is this?)  (verify)

Diclazepam (Ro5-3448), also known as Chlorodiazepam and 2'-chloro-diazepam, is a benzodiazepine drug and analogue of diazepam. It was first synthesized by Leo Sternbach and his team at Hoffman-La Roche in 1960.[2] Its effects are similar to diazepam, possessing anxiolytic, anticonvulsant, hypnotic, sedative, skeletal muscle relaxant, and amnestic properties[3] in animal models with a potency of approximately x10 that of diazepam. It is not currently marketed as a medication but rather sold as a Research chemical. Potency has not been systematically tested in humans, but its closest relatives and two main metabolites are lormetazepam[4] with a potency value of x10-12 diazepam and delorazepam[5] which is roughly x10 the potency of diazepam.[6]

Metabolism[edit]

Metabolism of this compound has been recently assessed,[1] revealing diclazepam has an approximate elimination half-life of 42 h and undergoes N-demethylation to delorazepam, as expected, which can be detected in urine for 6 days following administration of the parent compound.[7] Other metabolites detected were lorazepam and lormetazepam which were detectable in urine for 19 and 11 days, respectively, indicating hydroxylation by P450 enzymes occurring concurrently with N-demethylation.

References[edit]

  1. ^ a b "Characterization of the designer benzodiazepine diclazepam and preliminary data on its metabolism and pharmacokinetics". Drug Testing and Analysis 6 (7-8): 757–763. July–August 2014. doi:10.1002/dta.1628. PMID 24604775. 
  2. ^ US Patent 3136815 - Amino substituted benzophenone oximes and derivatives thereof
  3. ^ Yakubovs'ka et al. - Dopovidi Akademii Nauk Ukrains'koi RSR, Seriya B: Geologichni, Khimichni ta Biologichni Nauki,1977,page 819
  4. ^ http://www.benzo.org.uk/manual/bzcha01.htm#4
  5. ^ http://www.drugbank.ca/drugs/DB01511
  6. ^ http://drugable.com/drug/Delorazepam
  7. ^ European Journal of Clinical Pharmacology 1988, Volume 34, Issue 1, pp 109-112 'Pharmacokinetics and bioavailability of intravenous and oral chlordesmethyldiazepam in humans' S.R.Bareggi, G.Truci, S.Leva, L.Zecca, R.Pirola, S.Smirne

See also[edit]