Metaclazepam

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Metaclazepam
Systematic (IUPAC) name
7-bromo-5-(2-chlorophenyl)-2-(methoxymethyl)-1-methyl-2,3-dihydro-1H-1,4-benzodiazepine
Clinical data
Legal status ?
Identifiers
CAS number 84031-17-4 YesY
ATC code None
PubChem CID 71272
ChemSpider 64398 YesY
UNII C2N2B1303L YesY
Chemical data
Formula C18H18BrClN2O 
Mol. mass 393.705
 YesY (what is this?)  (verify)

Metaclazepam[1] (marketed under the brand name Talis) is a drug which is a benzodiazepine derivative.[2][3] It is a relatively selective anxiolytic with less sedative or muscle relaxant properties than other benzodiazepines such as diazepam or bromazepam.[4] It has an active metabolite N-desmethylmetaclazepam, which is the main metabolite of metaclazepam.[5] There is no significant difference in metabolism between younger and older individuals.[6]

Metaclazepam is slightly more effective as an anxiolytic than bromazepam,[7] or diazepam,[8] with a 15 mg dose of metaclazepam equivalent to 4 mg of bromazepam.[9] Metaclazepam can interact with alcohol producing additive sedative-hypnotic effects.[10][11] Fatigue is a common side effect from metaclazepam at high doses.[12] Small amounts of metaclazepam as well as its metabolites enter into human breast milk.[13]

See also


References

  1. ↑ US Patent 4098786
  2. ↑ Borchers, F.; Achtert, G.; Hausleiter, HJ.; Zeugner, H. "Metabolism and pharmacokinetics of metaclazepam (Talis), Part III: Determination of the chemical structure of metabolites in dogs, rabbits and men.". Eur J Drug Metab Pharmacokinet 9 (4): 325–46. PMID 6532806. 
  3. ↑ Althaus, W.; Block, J.; Förster, A.; Kühnhold, M.; Meister, D.; Wischniewski, M. (Sep 1986). "Analytical profile of metaclazepam.". Arzneimittelforschung 36 (9): 1302–6. PMID 3790179. 
  4. ↑ Buschmann, G.; Kühl, UG.; Rohte, O. (1985). "General pharmacology of the anxiolytic compound metaclazepam in comparison to other benzodiazepines.". Arzneimittelforschung 35 (11): 1643–55. PMID 2868732. 
  5. ↑ Gielsdorf, W.; Molz, KH.; Hausleiter, HJ.; Achtert, G.; Philipp, P. "Pharmacokinetic profile of metaclazepam (Talis), a new 1.4-benzodiazepine. Influence of different dosage regimens on the pharmacokinetic profile of metaclazepam and its main metabolite under steady-state conditions.". Eur J Drug Metab Pharmacokinet 11 (3): 205–10. PMID 3816876. 
  6. ↑ Molz, KH.; Gielsdorf, W.; Rasper, J.; Jaeger, H.; Hausleiter, HJ.; Achtert, G.; Philipp, P. (1985). "Comparison of the pharmacokinetic profile of metaclazepam in old and young volunteers.". Eur J Clin Pharmacol 29 (2): 247–9. PMID 4076323. 
  7. ↑ Bilone, F.; Roncari, R. (1988). "A double-blind comparison of the anxiolytic activity of two benzodiazepines, metaclazepam and bromazepam, in anxiety neurosis.". Curr Med Res Opin 11 (1): 45–7. doi:10.1185/03007998809111130. PMID 2898321. 
  8. ↑ Laakmann, G.; Blaschke, D.; Hippius, H.; Schewe, S. (May 1989). "Double-blind study of metaclazepam versus diazepam treatment of outpatients with anxiety syndrome.". Pharmacopsychiatry 22 (3): 120–5. doi:10.1055/s-2007-1014593. PMID 2568645. 
  9. ↑ Marano, P.; Patti, F.; Nicoletti, F. (1988). "Controlled study on the anxiolytic activity of a newly developed benzodiazepine, metaclazepam.". Curr Med Res Opin 11 (1): 41–4. doi:10.1185/03007998809111129. PMID 2898320. 
  10. ↑ Molz, KH.; Gielsdorf, W.; Rasper, J.; Jaeger, H.; Hausleiter, HJ.; Achtert, G.; Philipp, P. (1985). "Comparison of the pharmacokinetic profile of metaclazepam in old and young volunteers.". Eur J Clin Pharmacol 29 (2): 247–9. PMID 4076323. 
  11. ↑ Schmidt, V. (1983). "[Experimental studies on the interaction of alcohol and metaclazepam]". Beitr Gerichtl Med 41: 413–7. PMID 6639614. 
  12. ↑ Laakmann, G.; Blaschke, D.; Hippius, H.; Schewe, S. (May 1988). "Double-blind randomized trial of the benzodiazepine derivative metaclazepam as compared with placebo treatment of outpatients with anxiety syndromes.". Pharmacopsychiatry 21 (3): 136–43. doi:10.1055/s-2007-1014665. PMID 2900514. 
  13. ↑ Schotter, A.; Müller, R.; Günther, C.; Hausleiter, HJ.; Achtert, G. (Nov 1989). "Transfer of metaclazepam and its metabolites into breast milk.". Arzneimittelforschung 39 (11): 1468–70. PMID 2575907. 
Benzodiazepine derivatives
1,4-Benzodiazepines
1,5-Benzodiazepines
2,3-Benzodiazepines *
Triazolobenzodiazepines
Imidazobenzodiazepines
Oxazolobenzodiazepines
Thienodiazepines
Pyridodiazepines
Pyrazolodiazepines
Pyrrolodiazepines
Tetrahydroisoquinobenzodiazepines
Benzodiazepine prodrugs
* atypical activity profile (not GABAA receptor ligands)
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