Levacetylmethadol

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Structural formula
Structural formula of levacetylmethadol
General
Non-proprietary name Levacetylmethadol
other names
  • (3 S , 6 S ) -acetic acid-6-dimethylamino-4,4-diphenylheptan-3-yl ester ( IUPAC )
  • Levacetylmethadolum ( Latin )
  • Levo-α-acetylmethadol
  • Acetylmethadol
  • LAAM
  • Levomethadyl acetate ( USAN )
Molecular formula C 23 H 31 NO 2
External identifiers / databases
CAS number
  • 1477-40-3 [( S , S ) - (-) - acetylmethadol]
  • 43033-72-3 [( S , S ) - (-) - acetylmethadol · hydrochloride]
PubChem 15130
DrugBank DB01227
Wikidata Q411799
Drug information
ATC code

N07 BC03

Drug class

Opioid - analgesics

properties
Molar mass 353,50 g · mol -1
Physical state

firmly

Melting point

215 ° C (( S , S ) - (-) - acetylmethadol hydrochloride )

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 300-315-319-335-413
P: 261-264-301 + 310-305 + 351 + 338
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Levacetylmethadol , also levo-α-acetymethadol ( LAAM for short ) is an opioid that has not been marketed in the EU since 2003 due to rare side effects, although it has since been shown that methadone and buprenorphine are used in the treatment of opiate addiction ( drug substitution ) could be superior.

Since the duration of action or half-life is three times as long as that of methadone , it only needs to be taken three times a week. LAAM is metabolized in the liver to nor -LAAM and dinor-LAAM, both of which are also effective and contribute to the long duration of action. The substance is distributed in the USA by Roxane Laboratories in Columbus (Ohio) , a subsidiary of Boehringer Ingelheim . In 2003, the number of substituted patients in the US was estimated at 5,100.

FDA approval was granted on July 20, 1993. In 2001, the FDA issued a " black box warning " on the package insert due to the possibility of torsade de pointes - arrhythmias (10 episodes in a total of 33,000 treated patients) and in 2003 the Roxane Laboratories suspended marketing. The drug is still approved for the treatment of opioid addiction in the United States. Due to the possible cardiac side effects, the drug is currently not marketed in the EU . However, the authors of a European multicenter study come to the conclusion that a discussion should take place regarding the introduction of LAAM in the EU. A Cochrane study published in 2009 was unable to give an evaluation, as only two papers met the strict criteria required.

Web links

Individual evidence

  1. Entry on acetylmethadol. In: Römpp Online . Georg Thieme Verlag, accessed on June 15, 2012.
  2. a b LAAM hydrochloride data sheet from Sigma-Aldrich , accessed on April 7, 2011 ( PDF ).
  3. a b c Entry on levacetylmethadol in the ChemIDplus database of the United States National Library of Medicine (NLM) .
  4. ^ Richard P. Mattick et al .: Pharmacotherapies for the Treatment of Opioid Dependence: Efficacy, Cost-Effectiveness and Implementation Guidelines . Informa, 2009.
  5. Frank Vocci: Medications Development Update ; May 22, 2003. ( Memento of the original from March 13, 2013 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. ( MS Powerpoint ; 8.3 MB). @1@ 2Template: Webachiv / IABot / archives.drugabuse.gov
  6. ^ The FDA Safety Information and Adverse Event Reporting Program .
  7. ^ APA Practice Guidelines> Substance Use Disorders: Treatment of Patients With Substance Use Disorders. Second Edition DOI: 10.1176 / appi.books.9780890423363.141077 .
  8. NC Clark, N. Lintzeris, A. Gijsbers, G. Whelan, A. Dunlop, A. Ritter, WW Ling: A randomized, open-label trial comparing methadone and levo-alpha acetylmethadol (LAAM) in maintenance treatment of opioid addiction . In: Pharmacopsychiatry , 2009 Jan; 42 (1), pp. 1-8. Epub 2009 Jan 19, PMID 19153939 .
  9. ^ S. Minozzi, L. Amato, M. Davoli: Maintenance treatments for opiate dependent adolescent . Cochrane Database Syst Rev. 2009 Apr 15; (2): CD007210, PMID 19370679 .