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targets (1) enzymes (1)
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Identification
Name Methyprylon
Accession Number DB01107 (APRD00734)
Type small molecule
Groups illicit, approved, withdrawn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 This medicine was used for treating insomnia, but is now rarely used as it has been replaced by newer drugs with less side effects, such as benzodiazepines. Methyprylon was withdrawn from the US market in June 1965 and the Canadian market in September 1990.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]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Dea No. 2575
Methprylon
Methyprolon
Methyprylon [INN]
Methyprylone [INN-French]
Methyprylonum [INN-Latin]
Metiprilon
Metiprilona [INN-Spanish]
Metiprilone
Salts Not Available
Brand names
Name Company
Dimerin
Noctan
Nodular
Noludar
Brand mixtures Not Available
Categories
  • Sedatives and Hypnotics
CAS number 125-64-4
Weight Average: 183.2475
Monoisotopic: 183.125928793
Chemical Formula C10H17NO2
InChI Key InChIKey=SIDLZWOQUZRBRU-UHFFFAOYSA-N
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)
Plain Text
IUPAC Name
3,3-diethyl-5-methylpiperidine-2,4-dione
SMILES
CCC1(CC)C(=O)NCC(C)C1=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Carbonyl Compounds
  • Delta Lactams
  • Piperidines
Substructures
  • Carbonyl Compounds
  • Delta Lactams
  • Amino Ketones
  • Carboxylic Acids and Derivatives
  • Heterocyclic compounds
  • Carboxamides and Derivatives
  • Lactams
  • Piperidines
  • Ketones
Pharmacology
Indication For the treatment of insomnia.
Pharmacodynamics 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.
Mechanism of action Methyprylon binds at a distinct binding site associated with a Cl- ionopore at the GABAA receptor, increasing the duration of time for which the Cl- ionopore is open. The post-synaptic inhibitory effect of GABA in the thalamus is, therefore, prolonged.
Absorption Not Available
Volume of distribution Not Available
Protein binding 60%
Metabolism
Hepatic. Methyprylon is almost completely metabolized.
Route of elimination Not Available
Half life 6-16 hours
Clearance Not Available
Toxicity Symptoms of overdose include excitation and convulsions.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Hoffmann la roche inc
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
water solubility 1.15E+004 mg/L Not Available
logP 0.78 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 1.13e+01 g/l ALOGPS
logP 0.94 ALOGPS
logP 1.88 ChemAxon
logS -1.2 ALOGPS
pKa (strongest acidic) 14.53 ChemAxon
pKa (strongest basic) -3.1 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 2 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 46.17 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 50.25 ChemAxon
polarizability 19.95 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. 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
  2. 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
  3. 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
Resource Link
KEGG Drug D01150 Link_out
PubChem Compound 4162 Link_out
PubChem Substance 46506891 Link_out
ChemSpider 4018 Link_out
Therapeutic Targets Database DAP000683 Link_out
PharmGKB PA164746748 Link_out
Wikipedia http://en.wikipedia.org/wiki/Methyprylon Link_out
ATC Codes
  • N05CE02
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions
  • Take without regard to meals.
Targets

1. Gamma-aminobutyric-acid receptor subunit alpha-1

Pharmacological action: yes
Actions: agonist

GABA, the major inhibitory neurotransmitter in the vertebrate brain, mediates neuronal inhibition by binding to the GABA/benzodiazepine receptor and opening an integral chloride channel

Organism class: human
UniProt ID: P14867 Link_out
Gene: GABRA1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. de Fiebre CM, Marley RJ, Miner LL, de Fiebre NE, Wehner JM, Collins AC: Classical genetic analyses of responses to sedative-hypnotic drugs in crosses derived from long-sleep and short-sleep mice. Alcohol Clin Exp Res. 1992 Jun;16(3):511-21. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. Cytochrome P450 2D6

Actions: substrate

Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants

UniProt ID: P10635 Link_out
Gene: CYP2D6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19