| Version |
2.5 |
| Creation Date |
2005-06-13 13:24:05 |
| Update Date |
2009-06-23 18:05:57 |
| Primary Accession Number |
DB01107 |
| Secondary Accession Number |
|
| Name |
Methyprylon |
| Drug Type |
- Approved
- Illicit
- Small Molecule
- Withdrawn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 This medicine was used for treating insomnia, but is now rarely used as it has been replaced by newer drugs with less side effects, such as benzodiazepines. Methyprylon was withdrawn from the US market in June 1965 and the Canadian market in September 1990.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] |
| Synonyms |
- Dea No. 2575
- Methprylon
- Methyprolon
- Methyprylon [INN]
- Methyprylone [INN-French]
- Methyprylonum [INN-Latin]
- Metiprilon
- Metiprilona [INN-Spanish]
- Metiprilone
|
| Brand Names |
- Dimerin
- Noctan
- Nodular
- Noludar
|
| Brand Mixtures |
Not Available |
| Chemical IUPAC Name |
3,3-diethyl-5-methylpiperidine-2,4-dione |
| Chemical Formula |
C10H17NO2 |
| Chemical Structure |
 |
| CAS Registry Number |
125-64-4 |
| InChI Identifier |
InChI=1/C10H17NO2/c1-4-10(5-2)8(12)7(3)6-11-9(10)13/h7H,4-6H2,1-3H3,(H,11,13)/f/h11H |
| InChI Key |
SIDLZWOQUZRBRU-WXRBYKJCCA |
| KEGG Drug |
D01150  |
| KEGG Compound |
Not Available |
| PubChem Compound |
4162  |
| PubChem Substance |
582940  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA450470  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
Not Available |
| RxList Link |
Not Available |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Methyprylon  |
| FDA Label |
Not Available |
| Material Safety Data Sheet (MSDS) |
Not Available |
| Synthesis Reference |
Not Available |
| Average Molecular Weight |
183.2475 |
| Monoisotopic Molecular Weight |
183.1259 |
| State |
Solid |
| Melting Point |
Not Available |
| Experimental Water Solubility |
1.15E+004 mg/L
Source: PhysProp
|
| Predicted Water Solubility |
1.13e+01 mg/mL
Calculated using ALOGPS
|
| Experimental LogP/Hydrophobicity |
1.2
Source: PhysProp
|
| Predicted LogP |
0.94
Calculated using ALOGPS
|
| Experimental LogS |
Not Available |
| Predicted LogS |
-1.21
Calculated using ALOGPS
|
| Experimental Caco2 Permeability |
Not Available |
| pKa/Isoelectric Point |
Not Available |
| Mass Spectrum |
Not Available
|
| MOL File |
Show | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
Not Available |
| Isomeric SMILES |
CCC1(CC)C(=O)NC[C@H](C)C1=O |
| Canonical SMILES |
CCC1(CC)C(=O)NCC(C)C1=O |
| Drug Category |
|
| ATC Codes |
|
| AHFS Codes |
Not Available |
| 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. |
| 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 |
| Toxicity |
Symptoms of overdose include excitation and convulsions. |
| Protein Binding |
60% |
| Biotransformation |
Hepatic. Methyprylon is almost completely metabolized. |
| Half Life |
6-16 hours |
| Dosage Forms |
Not Available
|
| Patient Information |
Not Available |
| Contraindications |
Show  |
| Interactions |
Show  |
| Drug Interactions |
Not Available
|
| Food Interactions |
- Take without regard to meals.
|
| Pathways |
Not Available
|
| General References |
- Lomen P, Linet OI: Hypnotic efficacy of triazolam and methyprylon ininsomniac in-patients. J Int Med Res. 1976;4(1):55-8. [PubMed
]
- 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
]
- Drugs.com

- Wikipedia

|
| Organisms Affected |
|
| Targets |
- Gamma-aminobutyric-acid receptor subunit alpha-1
|
|
Drug Target 1
[top]
|
| Target 1 ID |
872 |
| Target 1 Name |
Gamma-aminobutyric-acid receptor subunit alpha-1 |
| Target 1 Synonyms |
- Gamma-aminobutyric-acid receptor subunit alpha-1 precursor
|
| Target 1 Gene Name |
GABRA1 |
| Target 1 Protein Sequence |
>Gamma-aminobutyric-acid receptor subunit alpha-1 precursor
MRKSPGLSDCLWAWILLLSTLTGRSYGQPSLQDELKDNTTVFTRILDRLLDGYDNRLRPG
LGERVTEVKTDIFVTSFGPVSDHDMEYTIDVFFRQSWKDERLKFKGPMTVLRLNNLMASK
IWTPDTFFHNGKKSVAHNMTMPNKLLRITEDGTLLYTMRLTVRAECPMHLEDFPMDAHAC
PLKFGSYAYTRAEVVYEWTREPARSVVVAEDGSRLNQYDLLGQTVDSGIVQSSTGEYVVM
TTHFHLKRKIGYFVIQTYLPCIMTVILSQVSFWLNRESVPARTVFGVTTVLTMTTLSISA
RNSLPKVAYATAMDWFIAVCYAFVFSALIEFATVNYFTKRGYAWDGKSVVPEKPKKVKDP
LIKKNNTYAPTATSYTPNLARGDPGLATIAKSATIEPKEVKPETKPPEPKKTFNSVSKID
RLSRIAFPLLFGIFNLVYWATYLNREPQLKAPTPHQ
|
| Target 1 Number of Residues |
463 |
| Target 1 Molecular Weight |
51802 |
| Target 1 Theoretical pI |
9.61 |
| Target 1 GO Classification |
|
Function
|
neurotransmitter receptor activity
transporter activity
ion transporter activity
ion channel activity
ligand-gated ion channel activity
extracellular ligand-gated ion channel activity
signal transducer activity
receptor activity
transmembrane receptor activity
GABA receptor activity
GABA-A receptor activity |
|
Process
|
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
gamma-aminobutyric acid signaling pathway
anion transport
inorganic anion transport
chloride transport
physiological process
cellular physiological process
transport
ion transport |
|
Component
|
postsynaptic membrane
cell
membrane
intrinsic to membrane
integral to membrane |
|
| Target 1 General Function |
Involved in GABA-A receptor activity |
| Target 1 Specific Function |
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 |
| Target 1 Pathways |
Not Available
|
| Target 1 Reactions |
Not Available |
| Target 1 Pfam Domain Function |
|
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
- 252-273
- 279-300
- 313-334
- 422-443
|
| Target 1 Essentiality |
Non-Essential |
| Target 1 GenBank ID Protein |
31631  |
| Target 1 UniProtKB/Swiss-Prot ID |
P14867  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
GBRA1_HUMAN  |
| Target 1 PDB ID |
Not Available |
| Target 1 Cellular Location |
- Membrane
- multi-pass membrane protein
|
| Target 1 Gene Sequence |
>1371 bp
ATGAGGAAAAGTCCAGGTCTGTCTGACTGTCTTTGGGCCTGGATCCTCCTTCTGAGCACA
CTGACTGGAAGAAGCTATGGACAGCCGTCATTACAAGATGAACTTAAAGACAATACCACT
GTCTTCACCAGGATTTTGGACAGACTCCTAGATGGTTATGACAATCGCCTGAGACCAGGA
TTGGGAGAGCGTGTAACCGAAGTGAAGACTGATATCTTCGTCACCAGTTTCGGACCCGTT
TCAGACCATGATATGGAATATACAATAGATGTATTTTTCCGTCAAAGCTGGAAGGATGAA
AGGTTAAAATTTAAAGGACCTATGACAGTCCTCCGGTTAAATAACCTAATGGCAAGTAAA
ATCTGGACTCCGGACACATTTTTCCACAATGGAAAGAAGTCAGTGGCCCACAACATGACC
ATGCCCAACAAACTCCTGCGGATCACAGAGGATGGCACCTTGCTGTACACCATGAGGCTG
ACAGTGAGAGCTGAATGTCCGATGCATTTGGAGGACTTCCCTATGGATGCCCATGCTTGC
CCACTAAAATTTGGAAGTTATGCTTATACAAGAGCAGAAGTTGTTTATGAATGGACCAGA
GAGCCAGCACGCTCAGTGGTTGTAGCAGAAGATGGATCACGTCTAAACCAGTATGACCTT
CTTGGACAAACAGTAGACTCTGGAATTGTCCAGTCAAGTACAGGAGAATATGTTGTTATG
ACCACTCATTTCCACTTGAAGAGAAAGATTGGCTACTTTGTTATTCAAACATACCTGCCA
TGCATAATGACAGTGATTCTCTCACAAGTCTCCTTCTGGCTCAACAGAGAGTCTGTACCA
GCAAGAACTGTCTTTGGAGTAACAACTGTGCTCACCATGACAACATTGAGCATCAGTGCC
AGAAACTCCCTCCCTAAGGTGGCTTATGCAACAGCTATGGATTGGTTTATTGCCGTGTGC
TATGCCTTTGTGTTCTCAGCTCTGATTGAGTTTGCCACAGTAAACTATTTCACTAAGAGA
GGTTATGCATGGGATGGCAAAAGTGTGGTTCCAGAAAAGCCAAAGAAAGTAAAGGATCCT
CTTATTAAGAAAAACAACACTTACGCTCCAACAGCAACCAGCTACACCCCTAATTTGGCC
AGGGGCGACCCGGGCTTAGCCACCATTGCTAAAAGTGCAACCATAGAACCTAAAGAGGTC
AAGCCCGAAACAAAACCACCAGAACCCAAGAAAACCTTTAACAGTGTCAGCAAAATTGAC
CGACTGTCAAGAATAGCCTTCCCGCTGCTATTTGGAATCTTTAACTTAGTCTACTGGGCT
ACGTATTTAAACAGAGAGCCTCAGCTAAAAGCCCCCACACCACATCAATAG
|
| Target 1 GenBank Gene ID |
|
| Target 1 GeneCard ID |
GABRA1  |
| Target 1 GenAtlas ID |
GABRA1  |
| Target 1 HGNC ID |
HGNC:4075  |
| Target 1 Chromosome Location |
5 |
| Target 1 Locus |
5q34-q35 |
| Target 1 SNPs |
SNPJam Report  |
| Target 1 General References |
- Cossette P, Liu L, Brisebois K, Dong H, Lortie A, Vanasse M, Saint-Hilaire JM, Carmant L, Verner A, Lu WY, Wang YT, Rouleau GA: Mutation of GABRA1 in an autosomal dominant form of juvenile myoclonic epilepsy. Nat Genet. 2002 Jun;31(2):184-9. Epub 2002 May 6. [PubMed
]
- Schofield PR, Pritchett DB, Sontheimer H, Kettenmann H, Seeburg PH: Sequence and expression of human GABAA receptor alpha 1 and beta 1 subunits. FEBS Lett. 1989 Feb 27;244(2):361-4. [PubMed
]
- Garrett KM, Duman RS, Saito N, Blume AJ, Vitek MP, Tallman JF: Isolation of a cDNA clone for the alpha subunit of the human GABA-A receptor. Biochem Biophys Res Commun. 1988 Oct 31;156(2):1039-45. [PubMed
]
|
| Target 1 Drug References |
- 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
]
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed
]
|