Systematic (IUPAC) name | |
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(RS)-3,3-diethyl-5-methylpiperidine-2,4-dione | |
Clinical data | |
Trade names | Dimerin, Methyprylone, Noctan, Noludar |
Pregnancy cat. | ? |
Legal status | Schedule III (US) |
Routes | oral |
Pharmacokinetic data | |
Protein binding | 60% |
Half-life | 6-16 hours |
Identifiers | |
CAS number | 125-64-4 |
ATC code | N05CE02 |
PubChem | CID 4162 |
DrugBank | APRD00734 |
ChemSpider | 4018 |
UNII | CUT48I42ON |
KEGG | D01150 |
ChEMBL | CHEMBL1200790 |
Chemical data | |
Formula | C10H17NO2 |
Mol. mass | 183.248 g/mol |
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Methyprylon (Noludar) is a sedative of the piperidinedione derivative family developed by Hoffmann-La Roche.[1] This medicine was used for treating insomnia, but is now rarely used as it has been replaced by newer drugs with fewer side effects, such as benzodiazepines.[2] Methyprylon was withdrawn from the US market in June 1989 and the Canadian market in September 1990.
Contents |
Side effects can include: Skin rash, fever, depression, ulcers or sores in mouth or throat, unusual bleeding or bruising, confusion, fast heartbeat, respiratory depression, swelling of feet or lower legs, dizziness, drowsiness, headache, double vision, clumsiness, constipation, diarrhea, nausea, vomiting, unusual weakness.
A study of single oral doses of 300 mg in healthy volunteers found that the zero-order absorption model fit the data best. Mean (+/- SD) values for the half-life (9.2 +/- 2.2 h), apparent clearance, (11.91 +/- 4.42 mL/h/kg) and apparent steady-state volume of distribution, (0.97 +/- 0.33 L/kg) were found.[3]
A case report found the pharmacokinetics of methyprylon nonlinear (concentration dependent) in an overdose case; explanations included saturation or inhibition of metabolic pathways. The generally accepted half-life for a therapeutic dose was not found appropriate in intoxicated patients and would underestimate the time required to reach a safe concentration of the drug.[4]
Methyprylon may be synthesized starting from an aldol condensation of ethyl 2,2-diethyl-3-oxobutanoate with ethyl formate. The resulting enol is converted to the lactam pyrithyldione by treating with ammonia and heating. The lactam is formylated at postion-5 and reduced to yield methyprylon.[5]