Mexazolam (original) (raw)

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Benzodiazepam

Mexazolam
Clinical data
Trade names Melex, Sedoxil
Other names 13-chloro- 2-(2-chlorophenyl)- 5-methyl- 3-oxa- 6,9-diazatricyclo[8.4.0.02,6] tetradeca- 1(10),11,13-trien- 8-one
AHFS/Drugs.com International Drug Names
Routes of administration Oral
ATC code N05BA25 (WHO)
Legal status
Legal status CA: Schedule IV
Pharmacokinetic data
Metabolism Liver (CYP3A4)
Excretion Kidney
Identifiers
IUPAC name 10-chloro-11_b_-(2-chlorophenyl)-3-methyl-2,3,5,7-tetrahydro-[1,3]oxazolo[3,2-_d_][1,4]benzodiazepin-6-one
CAS Number 31868-18-5
PubChem CID 4177
ChemSpider 4033 checkY
UNII S5969B6237
KEGG D01316 checkY
CompTox Dashboard (EPA) DTXSID9057715 Edit this at Wikidata
Chemical and physical data
Formula C18H16Cl2N2O2
Molar mass 363.24 g·mol−1
3D model (JSmol) Interactive image
SMILES Clc1ccccc1C42OCC(N2CC(=O)Nc3c4cc(Cl)cc3)C
InChI InChI=1S/C18H16Cl2N2O2/c1-11-10-24-18(13-4-2-3-5-15(13)20)14-8-12(19)6-7-16(14)21-17(23)9-22(11)18/h2-8,11H,9-10H2,1H3,(H,21,23) checkYKey:ANUCDXCTICZJRH-UHFFFAOYSA-N checkY
(verify)

Mexazolam[1] (marketed under the trade names Melex and Sedoxil)[2] is a drug which is a benzodiazepine derivative.[3] Mexazolam has been trialed for anxiety and was found to be effective in alleviating anxiety at one week follow-up. Mexazolam is metabolised via the CYP3A4 pathway. HMG-CoA reductase inhibitors including simvastatin, simvastatin acid, lovastatin, fluvastatin, atorvastatin and cerivastatin inhibit the metabolism of mexazolam,[4] but not the HMG-CoA reductase inhibitor pravastatin.[5][6] Its principal active metabolites are chlorodesmethyldiazepam (also known as chloronordiazepam or delorazepam, trade name Dadumir) and chloroxazepam (also known as lorazepam, trade name Ativan).[7]

  1. ^ DE Patent 1954065
  2. ^ "Benzodiazepine Names". non-benzodiazepines.org.uk. Archived from the original on 2008-12-08. Retrieved 2009-04-05.
  3. ^ Kurono Y, Kamiya K, Kuwayama T, Jinno Y, Yashiro T, Ikeda K (September 1987). "Kinetics and mechanism of the acid-base equilibrium of mexazolam and comparison with those of other commercial benzodiazepinooxazole drugs". Chemical & Pharmaceutical Bulletin. 35 (9): 3831–3837. doi:10.1248/cpb.35.3831. PMID 2893667.
  4. ^ Mc Donnell CG, Harte S, O'Driscoll J, O'Loughlin C, Van Pelt FN, Shorten GD (September 2003). "The effects of concurrent atorvastatin therapy on the pharmacokinetics of intravenous midazolam". Anaesthesia. 58 (9): 899–904. doi:10.1046/j.1365-2044.2003.03339.x. PMID 12911366. S2CID 25382546.
  5. ^ Ishigami M, Takasaki W, Ikeda T, Komai T, Ito K, Sugiyama Y (August 2002). "Sex difference in inhibition of in vitro mexazolam metabolism by various 3-hydroxy-3-methylglutaryl-coenzyme a reductase inhibitors in rat liver microsomes". Drug Metabolism and Disposition. 30 (8): 904–910. doi:10.1124/dmd.30.8.904. PMID 12124308. S2CID 2620104.
  6. ^ Ishigami M, Honda T, Takasaki W, Ikeda T, Komai T, Ito K, Sugiyama Y (March 2001). "A comparison of the effects of 3-hydroxy-3-methylglutaryl-coenzyme a (HMG-CoA) reductase inhibitors on the CYP3A4-dependent oxidation of mexazolam in vitro". Drug Metabolism and Disposition. 29 (3): 282–288. PMID 11181496.
  7. ^ Fernandes H, Moreira R (June 2014). "Mexazolam: clinical efficacy and tolerability in the treatment of anxiety". Neurology and Therapy. 3 (1): 1–14. doi:10.1007/s40120-014-0016-7. PMC 4381915. PMID 26000220.