Methyprylon

Methyprylon, or Noludar, is a sedative/tranquilizer and hypnotic central nervous system depressant of the piperidinedione derivative chemical class, first developed in the 1940s by Hoffmann-La Roche.^[2] This medicine was used for treating insomnia, but is now rarely used as it has been replaced by newer drugs with fewer side effects, such as benzodiazepines.^[3]

Methyprylon

Clinical data
Trade names	Noludar, Dimerin, Noctan, Methyprylone, Noctan
Routes of administration	By mouth
ATC code	N05CE02 (WHO)
Legal status
Legal status	BR: Class B1 (Psychoactive drugs)[1] CA: Schedule IV DE: Anlage II (Authorized trade only, not prescriptible) UK: Class C US: Schedule III
Pharmacokinetic data
Protein binding	60%
Elimination half-life	6-16 hours
Identifiers
IUPAC name (RS)-3,3-diethyl-5-methylpiperidine-2,4-dione
CAS Number	125-64-4 Y
PubChem CID	4162
IUPHAR/BPS	7238
DrugBank	DB01107 Y
ChemSpider	4018 Y
UNII	CUT48I42ON
KEGG	D01150 N
ChEMBL	ChEMBL1200790 N
CompTox Dashboard (EPA)	DTXSID7023306
ECHA InfoCard	100.004.315
Chemical and physical data
Formula	C10H17NO2
Molar mass	183.251 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic mixture
SMILES CCC1(CC)C(=O)NCC(C)C1=O
InChI InChI=1S/C10H17NO2/c1-4-10(5-2)8(12)7(3)6-11-9(10)13/h7H,4-6H2,1-3H3,(H,11,13) Y Key:SIDLZWOQUZRBRU-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Methyprylon was withdrawn from the US market in June 1975 and the Canadian market in September 1990. Some other trade names are Noctan and Dimerin.

Adverse effects

Side effects can include

• skin rash
• fever
• depression
• ulcers or sores in mouth or throat
• unusual bleeding or bruising
• fast heartbeat
• CNS depressant effects, including mental depression and confusion, clumsiness, lack of coordination, respiratory depression, confusion, drowsiness, lethargy, swelling of feet or lower legs, dizziness
• headache
• double vision
• constipation, diarrhea,
• nausea and/or vomiting
• ataxia, unusual weakness, clumsiness

Pharmacokinetics

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.^[4]

A case report found that the pharmacokinetics of methyprylon were not 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.^[5]

See also

• Pyrithyldione
• Piperidione
• Bemegride
• Thalidomide
• Glutethimide
• Phenglutarimide
• Ethchlorvynol
• Ethinamate