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Metaclazepam

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Metaclazepam
Clinical data
Trade namesTalis
ATC code
  • none
Identifiers
  • 7-bromo-5-(2-chlorophenyl)-2-(methoxymethyl)-1-methyl-2,3-dihydro-1,4-benzodiazepine
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H18BrClN2O
Molar mass393.71 g·mol−1
3D model (JSmol)
  • ClC1=CC=CC=C1C2=NCC(COC)N(C)C3=C2C=C(Br)C=C3
  • InChI=1S/C18H18BrClN2O/c1-22-13(11-23-2)10-21-18(14-5-3-4-6-16(14)20)15-9-12(19)7-8-17(15)22/h3-9,13H,10-11H2,1-2H3 checkY
  • Key:WABYCCJHARSRBH-UHFFFAOYSA-N checkY
  (verify)

Metaclazepam[1] (marketed under the brand nameTalis) is a drug which is abenzodiazepine derivative.[2][3] It is a relatively selectiveanxiolytic with lesssedative ormuscle relaxant properties than other benzodiazepines such asdiazepam orbromazepam.[4] It has anactive metaboliteN-desmethylmetaclazepam, which is the mainmetabolite of metaclazepam.[5] There is no significant difference in metabolism between younger and older individuals.[6]

Metaclazepam is slightly more effective as an anxiolytic thanbromazepam,[7] ordiazepam,[8] with a 15 mg dose of metaclazepam equivalent to 4 mg of bromazepam.[9] Metaclazepam can interact withalcohol producing additive sedative-hypnotic effects.[6][10]Fatigue is a common side effect from metaclazepam at high doses.[11] Small amounts of metaclazepam as well as its metabolites enter into humanbreast milk.[12]

See also

[edit]

References

[edit]
  1. ^US 4098786 
  2. ^Borchers F, Achtert G, Hausleiter HJ, Zeugner H (1984). "Metabolism and pharmacokinetics of metaclazepam (Talis), Part III: Determination of the chemical structure of metabolites in dogs, rabbits and men".European Journal of Drug Metabolism and Pharmacokinetics.9 (4):325–46.doi:10.1007/bf03189684.PMID 6532806.S2CID 12290664.
  3. ^Althaus W, Block J, Förster A, Kühnhold M, Meister D, Wischniewski M (September 1986). "Analytical profile of metaclazepam".Arzneimittel-Forschung.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".Arzneimittel-Forschung.35 (11):1643–55.PMID 2868732.
  5. ^Gielsdorf W, Molz KH, Hausleiter HJ, Achtert G, Philipp P (1986). "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".European Journal of Drug Metabolism and Pharmacokinetics.11 (3):205–10.doi:10.1007/bf03189848.PMID 3816876.S2CID 8493668.
  6. ^abMolz 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".European Journal of Clinical Pharmacology.29 (2):247–9.doi:10.1007/bf00547431.PMID 4076323.S2CID 8017809.
  7. ^Bilone F, Roncari R (1988)."A double-blind comparison of the anxiolytic activity of two benzodiazepines, metaclazepam and bromazepam, in anxiety neurosis".Current Medical Research and Opinion.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".Current Medical Research and Opinion.11 (1):41–4.doi:10.1185/03007998809111129.PMID 2898320.
  10. ^Schmidt V (1983). "[Experimental studies on the interaction of alcohol and metaclazepam]".Beiträge zur Gerichtlichen Medizin.41:413–7.PMID 6639614.
  11. ^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.
  12. ^Schotter A, Müller R, Günther C, Hausleiter HJ, Achtert G (November 1989). "Transfer of metaclazepam and its metabolites into breast milk".Arzneimittel-Forschung.39 (11):1468–70.PMID 2575907.
1,4-Benzodiazepines
1,5-Benzodiazepines
2,3-Benzodiazepines*
Triazolobenzodiazepines
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* atypical activity profile (notGABAA receptor ligands)
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