Metaclazepam

Metaclazepam

Clinical data
Trade names	Talis
ATC code	none
Identifiers
IUPAC name 7-bromo-5-(2-chlorophenyl)-2-(methoxymethyl)-1-methyl-2,3-dihydro-1,4-benzodiazepine
CAS Number	84031-17-4
PubChem (CID)	71272
ChemSpider	64398
UNII	C2N2B1303L
ChEMBL	CHEMBL1290783
Chemical and physical data
Formula	C18H18BrClN2O
Molar mass	393.705 g/mol
3D model (Jmol)	Interactive image
SMILES ClC1=CC=CC=C1C2=NCC(COC)N(C)C3=C2C=C(Br)C=C3
InChI 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 Key:WABYCCJHARSRBH-UHFFFAOYSA-N
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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.^[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 human breast milk.^[12]

See also

• Benzodiazepine

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. doi:10.1007/bf03189684. 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. doi:10.1007/bf03189848. 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. doi:10.1007/bf00547431. 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. Schmidt, V. (1983). "[Experimental studies on the interaction of alcohol and metaclazepam]". Beitr Gerichtl Med. 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. (Nov 1989). "Transfer of metaclazepam and its metabolites into breast milk.". Arzneimittelforschung. 39 (11): 1468–70. PMID 2575907.