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Methyprylon

Clinical data
Trade names	Dimerin, Methyprylone, Noctan, Noludar
Routes of administration	By mouth
ATC code	N05CE02 (WHO)
Legal status
Legal status	BR: Class B1 (Psychoactive drugs) 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
PubChem CID	4162
IUPHAR/BPS	7238
DrugBank	DB01107
ChemSpider	4018
UNII	CUT48I42ON
KEGG	D01150
ChEMBL	ChEMBL1200790
CompTox Dashboard (EPA)	DTXSID7023306
ECHA InfoCard	100.004.315
Chemical and physical data
Formula	C10H17NO2
Molar mass	183.251 g·mol
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) Key:SIDLZWOQUZRBRU-UHFFFAOYSA-N
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Methyprylon, or Noludar, is a sedative of the piperidinedione derivative family first developed by Hoffmann-La Roche. This medicine was used for treating insomnia, but is now rarely used as it has been replaced by newer drugs with fewer side effects, such as benzodiazepines.

Methyprylon was withdrawn from the US market in June 1975 and the Canadian market in September 1990.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, confusion, fast heartbeat, respiratory depression, swelling of feet or lower legs, dizziness, drowsiness, headache, double vision, clumsiness, constipation, diarrhea, nausea, vomiting, unusual weakness.

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.

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.

See also

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

References

1. Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
2. US granted 2680116, Frick H, Lutz AH, "Piperidiones and Process for the Manufacture thereof", issued 1954-06-01, assigned to Hoffmann-La Roche 
3. Lomen P, Linet OI (1976). "Hypnotic efficacy of triazolam and methyprylon ininsomniac in-patients". The Journal of International Medical Research. 4 (1): 55–8. doi:10.1177/030006057600400108. PMID 16792. S2CID 12500779.
4. Gwilt PR, Pankaskie MC, Thornburg JE, Zustiak R, Shoenthal DR (September 1985). "Pharmacokinetics of methyprylon following a single oral dose". Journal of Pharmaceutical Sciences. 74 (9): 1001–3. doi:10.1002/jps.2600740920. PMID 2866242.
5. Contos DA, Dixon KF, Guthrie RM, Gerber N, Mays DC (August 1991). "Nonlinear elimination of methyprylon (noludar) in an overdosed patient: correlation of clinical effects with plasma concentration". Journal of Pharmaceutical Sciences. 80 (8): 768–71. doi:10.1002/jps.2600800813. PMID 1686463.

• 2-Piperidinones
• 4-Piperidinones
• GABAA receptor positive allosteric modulators