Methyprylon: Difference between revisions
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Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'StdInChI', 'StdInChIKey', 'DrugBank', 'ChEMBL', 'KEGG'). |
+ Legal status in Brazil |
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{{Short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
| Verifiedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 457635672 |
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| IUPAC_name = (''RS'')-3,3-diethyl-5-methylpiperidine-2,4-dione |
| IUPAC_name = (''RS'')-3,3-diethyl-5-methylpiperidine-2,4-dione |
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| image = |
| image = Methyprylon structure.svg |
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| width = |
| width = 150 |
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| |
| chirality = [[Racemic mixture]] |
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| |
| image2 = Methyprylon ball-and-stick.png |
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| width2 = 200 |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = Dimerin, Methyprylone, Noctan, Noludar |
| tradename = Dimerin, Methyprylone, Noctan, Noludar |
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| Drugs.com = |
| Drugs.com = |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = <!-- A / B / C / D / X --> |
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| pregnancy_category = |
| pregnancy_category = |
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| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> |
| legal_AU = <!-- Unscheduled / S2 / S4 / S8 --> |
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| legal_BR = B1 |
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| legal_UK = <!-- GSL / P / POM / CD --> |
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| legal_BR_comment = <ref>{{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=[[Diário Oficial da União]] |language=pt-BR |publication-date=2023-04-04}}</ref> |
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| legal_CA = Schedule IV |
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| legal_UK = Class C |
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| legal_US = Schedule III<!-- OTC / Rx-only --> |
| legal_US = Schedule III<!-- OTC / Rx-only --> |
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| legal_DE = Anlage II |
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| routes_of_administration = |
| routes_of_administration = [[Oral administration|By mouth]] |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = |
| bioavailability = |
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| elimination_half-life = 6-16 hours |
| elimination_half-life = 6-16 hours |
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| excretion = |
| excretion = |
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<!--Identifiers--> |
<!--Identifiers--> |
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| IUPHAR_ligand = 7238 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 125-64-4 |
| CAS_number = 125-64-4 |
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| ATC_suffix = CE02 |
| ATC_suffix = CE02 |
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| ATC_supplemental = |
| ATC_supplemental = |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C10H17NO2/c1-4-10(5-2)8(12)7(3)6-11-9(10)13/h7H,4-6H2,1-3H3,(H,11,13) |
| StdInChI = 1S/C10H17NO2/c1-4-10(5-2)8(12)7(3)6-11-9(10)13/h7H,4-6H2,1-3H3,(H,11,13) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = SIDLZWOQUZRBRU-UHFFFAOYSA-N |
| StdInChIKey = SIDLZWOQUZRBRU-UHFFFAOYSA-N |
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| PubChem = 4162 |
| PubChem = 4162 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB01107 |
| DrugBank = DB01107 |
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| ChemSpiderID_Ref = {{chemspidercite| |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 4018 |
| ChemSpiderID = 4018 |
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| UNII_Ref = {{fdacite| |
| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = CUT48I42ON |
| UNII = CUT48I42ON |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
| KEGG_Ref = {{keggcite|changed|kegg}} |
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| KEGG = |
| KEGG = D01150 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = |
| ChEMBL = 1200790 |
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<!--Chemical data--> |
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| C=10 | H=17 | N=1 | O=2 |
| C=10 | H=17 | N=1 | O=2 |
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| molecular_weight = 183.248 g/mol |
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| smiles = CCC1(CC)C(=O)NCC(C)C1=O |
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}} |
}} |
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'''Methyprylon''' |
'''Methyprylon''', or '''Noludar''', is a [[sedative]] of the [[piperidinedione]] derivative family first developed by Hoffmann-La Roche.<ref>{{ cite patent | country = US | status = granted | number = 2680116 | title = Piperidiones and Process for the Manufacture thereof | gdate = 1954-06-01 | inventor = Frick H, Lutz AH | assign1 = Hoffmann-La Roche }}</ref> |
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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]].<ref>{{cite journal | vauthors = Lomen P, Linet OI | title = Hypnotic efficacy of triazolam and methyprylon ininsomniac in-patients | journal = The Journal of International Medical Research | volume = 4 | issue = 1 | pages = 55–8 | year = 1976 | pmid = 16792 | doi = 10.1177/030006057600400108 | s2cid = 12500779 }}</ref> |
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{{ cite patent |
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| country = US |
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| status = patent |
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Some other trade names are Noctan and Dimerin. |
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| number = 2680116 |
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| title = Piperidiones and Process for the Manufacture thereof |
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| gdate = 1954-06-01 |
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| invent1 = Frick,H. |
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| invent2 = Lutz,A.H. |
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| assign1 = Hoffmann-La Roche Inc. |
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}}</ref>. |
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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]].<ref>{{ cite pmid | 16792 }}</ref> |
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==Adverse effects== |
==Adverse effects== |
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Side effects can include |
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.{{Citation needed|date=October 2011}} |
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==Pharmacokinetics== |
==Pharmacokinetics== |
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A study of single oral doses of 300 |
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.<ref>{{cite journal | vauthors = Gwilt PR, Pankaskie MC, Thornburg JE, Zustiak R, Shoenthal DR | title = Pharmacokinetics of methyprylon following a single oral dose | journal = Journal of Pharmaceutical Sciences | volume = 74 | issue = 9 | pages = 1001–3 | date = September 1985 | pmid = 2866242 | doi = 10.1002/jps.2600740920 }}</ref> |
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A case report found the pharmacokinetics of methyprylon |
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.<ref>{{cite journal | vauthors = Contos DA, Dixon KF, Guthrie RM, Gerber N, Mays DC | title = Nonlinear elimination of methyprylon (noludar) in an overdosed patient: correlation of clinical effects with plasma concentration | journal = Journal of Pharmaceutical Sciences | volume = 80 | issue = 8 | pages = 768–71 | date = August 1991 | pmid = 1686463 | doi = 10.1002/jps.2600800813 }}</ref> |
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== |
== See also == |
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{{div col|colwidth=30em}} |
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Methyprylon may be synthesized starting from an aldol condensation of ethyl 2,2-diethyl-3-oxobutanoate with ethyl formate. The resulting enol is converted to the [[lactam]] [[pyrithyldione]] by treating with ammonia and heating. The lactam is [[formylation reaction|formylated]] at postion-5 and reduced to yield methyprylon.<ref>{{ cite pmid | 13161893 }}</ref> |
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[[File:Methyprylon synth.tif|400px]] |
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==See also== |
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*[[Pyrithyldione]] |
*[[Pyrithyldione]] |
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*[[Piperidione]] |
*[[Piperidione]] |
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*[[Bemegride]] |
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*[[Thalidomide]] |
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*[[Glutethimide]] |
*[[Glutethimide]] |
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*[[Phenglutarimide]] |
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*[[Ethchlorvynol]] |
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{{div col end}} |
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==References== |
== References == |
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{{reflist}} |
{{reflist}} |
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{{Sedatives}} |
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{{GABAAR PAMs}} |
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[[Category:Ketones]] |
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[[de:Methyprylon]] |
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[[fi:Metypryloni]] |
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[[Category:GABAA receptor positive allosteric modulators]] |
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[[sv:Metyprylon]] |