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Encyclopedia > Levomethadyl Acetate
Levomethadyl Acetate
Systematic (IUPAC) name
(6-dimethylamino-4,4-diphenyl-heptan-3-yl) acetate
Identifiers
CAS number 509-74-0
ATC code  ?
PubChem 15130
DrugBank APRD00745
Chemical data
Formula C23H31NO2 
Mol. mass 353.50
Pharmacokinetic data
Bioavailability  ?
Protein binding ~80%
Metabolism CYP3A4
Half life 2.6 days
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? Image File history File links No higher resolution available. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... This article does not cite its references or sources. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... A drugs efficacy may be affected by the degree to which it binds to the proteins within blood plasma. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status

?(AU) Schedule I(CA) ?(UK) Schedule II(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... Anthem Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official languages English (de facto 1) Government Federal constitutional monarchy and parliamentary democracy  -  Queen Elizabeth II  -  Governor-General Michael Jeffery  -  Prime Minister John Howard Independence from the United Kingdom   -  Constitution 1 January 1901   -  Statute of... The Controlled Drugs and Substances Act is Canadas federal drug control statute. ... Motto (Latin for From Sea to Sea) Anthem O Canada Royal anthem: God Save the Queen Capital Ottawa Largest city Toronto Official languages English, French Government Parliamentary democracy and federal constitutional monarchy  -  Monarch Queen Elizabeth II  -  Governor General Michaëlle Jean  -  Prime Minister Stephen Harper Establishment  -  Act of Union February... The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Routes Oral

Levomethadyl acetate, also known as levo-α-acetylmethadol (LAAM) is a synthetic opioid similar in structure to methadone. It has a long duration of action due to its active metabolites. It was approved in 1993 by the U.S. Food and Drug Administration for use in the treatment of opioid dependence. In 2001, the product ORLAAM was removed from the European market due to reports of severe cardiac-related adverse events. In 2003, Roxane Laboratories, Inc. discontinued ORLAAM in the US.[1] In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Look up oral in Wiktionary, the free dictionary. ... An opioid is a chemical substance that has a morphine-like action in the body. ... Methadone is a synthetic opioid, used medically as an analgesic and in the treatment of narcotic addiction. ... The United States Food and Drug Administration is the government agency responsible for regulating food, dietary supplements, drugs, cosmetics, medical devices, biologics and blood products in the United States. ... Drug addiction, or dependency is the compulsive use of drugs, to the point where the user has no effective choice but to continue use. ...

Contents

Indications

LAAM is indicated as a second-line treatment for the treatment and management of opioid dependence if patients fail to respond to drugs like methadone or buprenorphine. LAAM is not approved for use in Canada. Drug addiction, or dependency is the compulsive use of drugs, to the point where the user has no effective choice but to continue use. ... Methadone is a synthetic opioid, used medically as an analgesic and in the treatment of narcotic addiction. ... Buprenorphine, also colloquially referred to as bupe or subbies, is an opioid drug with partial agonist and antagonist actions. ...


Chemistry and Pharmacology

Levomethadyl acetate is the levo isomer of α-methadyl acetate. The dextro isomer is more potent but shorter acting. The levo isomer is also less toxic with an LD50 in mice of 110mg/kg s.c. and 172.8mg/kg orally as opposed to LD50s of 61mg/kg s.c. and 118.3mg/kg orally for dl-α-methadyl acetate. It has a melting point of 215°C and a molecular weight of 353.50. β-methadyl acetate also exists, however it is more toxic and less active than α-methadyl acetate and has no current medical use. An LD50 test being administered In toxicology, the LD50 or colloquially semilethal dose of a particular substance is a measure of how much constitutes a lethal dose. ... An LD50 test being administered In toxicology, the LD50 or colloquially semilethal dose of a particular substance is a measure of how much constitutes a lethal dose. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... The molecular mass of a substance (less accurately called molecular weight and abbreviated as MW) is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... Toxic redirects here, but this is also the name of a song by Britney Spears; see Toxic (song) Look up toxic and toxicity in Wiktionary, the free dictionary. ...


Levomethadyl acetate undergoes extensive first-pass metabolism to the active demethylated metabolite nor-LAAM, which is further demethylated to a second active metabolite, dinor-LAAM. These metabolites are more potent than the parent drug. A few of the metabolic pathways in a cell. ... Metabolites are the intermediates and products of metabolism. ...


Dosing

LAAM is used as an oral solution of levomethadyl acetate hydrochloride at a concentration of 10mg/mL in bottles of 120 and 500 mL under the brand name ORLAAM. The first dose of LAAM for patients who have not started treatment with methadone is 20-40mg. The first dose for patients who have been receiving methadone will be a little higher than the amount of methadone that was being taken every day, but not more than 120 mg. Afterwords, the dosage may be adjusted as needed. Unlike methadone, which requires daily administration, LAAM is administered three times a week. Look up oral in Wiktionary, the free dictionary. ... Dissolving table salt (NaCl) in water This article is about a chemical solution; for other uses of the term solution, see solution (disambiguation). ... In chemistry, hydrochlorides are salts resulting, or regarded as resulting, from the reaction of hydrochloric acid with an organic base (mostly amines). ... Methadone is a synthetic opioid, used medically as an analgesic and in the treatment of narcotic addiction. ... Methadone is a synthetic opioid, used medically as an analgesic and in the treatment of narcotic addiction. ...


References

  1. ^ http://www.fda.gov/cder/drug/shortages/orlaam.htm

External links

  • LAAM Drug Information
  • RxList Monograph for Orlaam
  • DrugBank: Levomethadyl Acetate
  • http://cat.inist.fr/?aModele=afficheN&cpsidt=2706063
  • http://cat.inist.fr/?aModele=afficheN&cpsidt=2390242
  • Links to external chemical sources

 
 

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