Diclazepam

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Diclazepam
Chlorodiazepam.png
Diclazepam molecule ball.png
Systematic (IUPAC) name
7-Chloro-5-(2-chlorophenyl)-1-methyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one
Clinical data
  • UK: Unscheduled
  • US: Not FDA approved
Oral, likely sublingual
Pharmacokinetic data
Bioavailability ?
Metabolism Hepatic
Half-life ~42h[1]
Excretion Renal
Identifiers
2894-68-0 YesY
PubChem CID 76168
ChemSpider 68652
Chemical data
Formula C16H12Cl2N2O
319.185 g/mol
 N (what is this?)  (verify)

Diclazepam (Ro5-3448), also known as chlorodiazepam and 2'-chloro-diazepam, is a benzodiazepine designer drug and functional analog of diazepam. It was first synthesized by Leo Sternbach and his team at Hoffman-La Roche in 1960.[2] It is not currently approved for use as a medication, but rather sold as a designer drug and research chemical. Efficacy and safety have not been tested in humans.

In animal models, its effects are similar to diazepam, possessing anxiolytic, anticonvulsant, hypnotic, sedative, skeletal muscle relaxant, and amnestic properties with a potency of approximately ten times that of diazepam.[3][verification needed]

Metabolism[edit]

Metabolism of this compound has been assessed,[1] revealing diclazepam has an approximate elimination half-life of 42 hours and undergoes N-demethylation to delorazepam, which can be detected in urine for 6 days following administration of the parent compound.[4] Other metabolites detected were lorazepam and lormetazepam which were detectable in urine for 19 and 11 days, respectively, indicating hydroxylation by cytochrome P450 enzymes occurring concurrently with N-demethylation.

See also[edit]

References[edit]

  1. ^ a b Moosmann B, Bisel P, Auwärter V (2014). "Characterization of the designer benzodiazepine diclazepam and preliminary data on its metabolism and pharmacokinetics". Drug Testing and Analysis 6 (7-8): 757–63. doi:10.1002/dta.1628. PMID 24604775. 
  2. ^ US 3136815, "Amino substituted benzophenone oximes and derivatives thereof" 
  3. ^ Yakubovs'ka et al. (1977). Dopovidi Akademii Nauk Ukrains'koi RSR, Seriya B: Geologichni, Khimichni ta Biologichni Nauki: 819.  Missing or empty |title= (help)
  4. ^ Bareggi SR, Truci G, Leva S, Zecca L, Pirola R, Smirne S (1988). "Pharmacokinetics and bioavailability of intravenous and oral chlordesmethyldiazepam in humans". European Journal of Clinical Pharmacology 34 (1): 109–112. doi:10.1007/bf01061430. PMID 2896126.