CAS 125-64-4|Methyprylone [INN-French]|Metiprilona [INN-Spanish]|3,3-diethyl-5-methylpiperidine-2,4-dione|Dea No. 2575|Noctan|Dimerin|Nodular|Methyprylon|dimerin|Metiprilon|Methprylon|Methyprylonum ...

General Information

Structure

Molecular Formula

C₁₀H₁₇NO₂

Molecular Mass

183.24748

Exact Mass

183.12592879

Charge

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

Canonic Smiles

CCC1(CC)C(=O)NCC(C1=O)C

Isomeric Smiles

O=C1C(CC)(CC)C(=O)NCC1C

Calculated Properties

JChem

Acid pKa

14.534169

H Acceptors

H Donor

LogD (pH = 5.5)

1.8847077

LogD (pH = 7.4)

1.8847076

Log P

1.8847077

Molar Refractivity

50.2501

Polarizability

19.710049

Polar Surface Area

46.17

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

0.94

LOG S

-1.21

Solubility (Water)

1.13e+01 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

Methyprylone [INN-French]Metiprilona [INN-Spanish]Dea No. 2575MethyprylonMetiprilonMethprylonMethyprylonum [INN-Latin]MetipriloneMethyprolonMethyprylon [INN]

IUPAC name

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

Brand Name

NoctanDimerinNodularNoludar

IUPAC Traditional name

dimerin

Names and Identifiers

Registration numbers

PubChem CID

4162

PubChem SID

16096444146506891

CAS Number

125-64-4

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

1.2

Solubility

1.15E+004 mg/L

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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illicit; approved; withdrawn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 This medicine was used for treating insomnia, but is now rarely used as it has been replaced by newer drugs with less side effects, such as benzodiazepines. Methyprylon was withdrawn from the US market in June 1965 and the Canadian market in September 1990.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]

Molecule Details

References

PubChem Literature

From Data Sources

• Lomen P, Linet OI: Hypnotic efficacy of triazolam and methyprylon ininsomniac in-patients. J Int Med Res. 1976;4(1):55-8. 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

References

Bioactivity

PubChem BioAssay

Bioactivity

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General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data