3,3-diethyl-5-methylpiperidine-2,4-dione

• ChemBase ID: 978
• Molecular Formular: C10H17NO2
• Molecular Mass: 183.24748
• Monoisotopic Mass: 183.12592879
• SMILES: O=C1C(CC)(CC)C(=O)NCC1C
• Canonical SMILES: CCC1(CC)C(=O)NCC(C1=O)C
• 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)
• InChIKey: SIDLZWOQUZRBRU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,3-diethyl-5-methylpiperidine-2,4-dione
• IUPAC Traditional name: dimerin
• Brand Name: Dimerin; Noctan; Nodular; Noludar
• Synonyms: Dea No. 2575; Methyprylon [INN]; Methyprylone [INN-French]; Methyprylonum [INN-Latin]; Methyprolon; Methprylon; Metiprilon; Metiprilona [INN-Spanish]; Metiprilone; Methyprylon

Database IDs

• CAS Number: 125-64-4
• PubChem SID: 160964441; 46506891
• PubChem CID: 4162

CALCULATED PROPERTIES

JChem

• Acid pKa: 14.534169
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 1.8847077
• LogD (pH = 7.4): 1.8847076
• Log P: 1.8847077
• Molar Refractivity: 50.2501 cm^3
• Polarizability: 19.710049 Å^3
• Polar Surface Area: 46.17 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.94
• LOG S: -1.21
• Solubility (Water): 1.13e+01 g/l

PROPERTIES

Physical Property

• Solubility: 1.15E+004 mg/L
• Hydrophobicity(logP): 1.2

DETAILS

DrugBank - DB01107

• Drug Groups: illicit; approved; withdrawn
• Description: Methyprylon is a sedative of the piperidinedione derivative family. This medicine was used for treating insomnia, but is now rarely used as it has been replaced by newer drugs with less side effects, such as benzodiazepines. Methyprylon was withdrawn from the US market in June 1965 and the Canadian market in September 1990. [Wikipedia]
• Indication: For the treatment of insomnia.
• Pharmacology: Methyprylon, a piperidinedione CNS depressant, is close to barbituric acid in structure, but different enough to be called a "non-barbiturate" sedative-hynotic. Methyprylon is used for insomnia and daytime tension. Methyprylon depresses the activity of muscle tissues, the heart, and the respiratory system.
• Toxicity: Symptoms of overdose include excitation and convulsions.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Methyprylon is almost completely metabolized.
• Half Life: 6-16 hours
• Protein Binding: 60%
• References: Contos DA, Dixon KF, Guthrie RM, Gerber N, Mays DC: Nonlinear elimination of methyprylon (noludar) in an overdosed patient: correlation of clinical effects with plasma concentration. J Pharm Sci. 1991 Aug;80(8):768-71. [Pubmed] ; Gwilt PR, Pankaskie MC, Thornburg JE, Zustiak R, Shoenthal DR: Pharmacokinetics of methyprylon following a single oral dose. J Pharm Sci. 1985 Sep;74(9):1001-3. [Pubmed] ; Lomen P, Linet OI: Hypnotic efficacy of triazolam and methyprylon ininsomniac in-patients. J Int Med Res. 1976;4(1):55-8. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Contos DA, Dixon KF, Guthrie RM, Gerber N, Mays DC: Nonlinear elimination of methyprylon (noludar) in an overdosed patient: correlation of clinical effects with plasma concentration. J Pharm Sci. 1991 Aug;80(8):768-71. Pubmed
• Gwilt PR, Pankaskie MC, Thornburg JE, Zustiak R, Shoenthal DR: Pharmacokinetics of methyprylon following a single oral dose. J Pharm Sci. 1985 Sep;74(9):1001-3. Pubmed
• Lomen P, Linet OI: Hypnotic efficacy of triazolam and methyprylon ininsomniac in-patients. J Int Med Res. 1976;4(1):55-8. Pubmed