Pyrithyldione

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Pyrithyldione

Systematic (IUPAC) name
3,3-diethylpyridine-2,4(1H,3H)-dione
Clinical data
Trade names	Benedorm, Didropyridine, Dihydroprylone, Persedon, Presidon, Pyridion, Pyridione, Pyrithyldion, Pyrithyldione, Tetridin, Tetridine
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	77-04-3^N
ATC code	N05CE03
PubChem	CID 4994
ChemSpider	4820^Y
UNII	8AB20823CK^Y
KEGG	D07329^Y
Chemical data
Formula	C₉H₁₃N O₂
Mol. mass	167.205 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C9H13NO2/c1-3-9(4-2)7(11)5-6-10-8(9)12/h5-6H,3-4H2,1-2H3,(H,10,12)^Y Key:NZASCBIBXNPDMH-UHFFFAOYSA-N^Y
N(what is this?) (verify)

Pyrithyldione (Presidon, Persedon) is a psychoactive drug invented in 1949.^[1] An improved method of manufacture was patented by Roche in 1959.^[2] It was used as a hypnotic or sedative and presumed to be less toxic than barbiturates.^[3] Today, this substance is no longer used. Agranulocytosis was sometimes reported as adverse effect.^[4]^[5]

References

^ Becker, E. L.; Fabing, H. D.; Hawkins, J. R. (1949). "Presidon; a new sedative-hypnotic". Christ Hospital medical bulletin 2 (4): 80–84. PMID 18144514. edit
^ US patent 3019230, Hinderling, R.; Lutz, A. H. & Schnider, O., "Method for the preparation of 2,4-dioxo-tetrahydropyridines", issued 1962-01-30, assigned to Hoffmann-La Roche
^ Pribilla, O. (1956). "Zur Toxikologie des Persedons". Archiv für Toxikologie 16 (1): 34–49. doi:10.1007/BF00577351. edit
^ Ibáñez, L.; Ballarín, E.; Pérez, E.; Vidal, X.; Capellà, D.; Laporte, J. R. (2000). "Agranulocytosis induced by pyrithyldione, a sedative hypnotic drug". European journal of clinical pharmacology 55 (10): 761–764. doi:10.1007/s002280050011. PMID 10663456. edit
^ Covner, A. H.; Halpern, S. L. (1950). "Fatal Agranulocytosis Following Therapy with Presidon (3,3-Diethyl-2,4-Dioxotetrahydropyridine), a New Sedative Hypnotic Agent". New England Journal of Medicine 242 (2): 49–52. doi:10.1056/NEJM195001122420203. PMID 15399031. edit

v d e Hypnotics/Sedatives (N05C)

GABA_A Agonists/PAMs	Barbiturates: Allobarbital • Amobarbital • Aprobarbital • Barbital • Butabarbital • Butobarbital • Cyclobarbital • Ethallobarbital • Heptabarb • Hexobarbital • Mephobarbital • Methohexital • Pentobarbital • Phenobarbital • Proxibarbal • Reposal • Secobarbital • Talbutal • Thiamylal • Thiopental • Vinbarbital • Vinylbital Benzodiazepines: Brotizolam • Clonazepam • Cinolazepam • Climazolam • Doxefazepam • Estazolam • Flunitrazepam • Flurazepam • Flutoprazepam • Haloxazolam • Loprazolam • Lormetazepam • Midazolam • Nimetazepam • Nitrazepam • Quazepam • Temazepam • Triazolam Carbamates: Carisoprodol • Ethinamate • Hexapropymate • Meprobamate • Methocarbamol • Procymate • Tybamate Neuroactive Steroids: Acebrochol • Allopregnanolone • Alphadolone • Alphaxolone • Eltanolone • Ganaxolone • Hydroxydione • Minaxolone • Org 20599 • Org 21465 • Tetrahydrodeoxycorticosterone Nonbenzodiazepines: CL-218,872 • Eszopiclone • Indiplon • JM-1232 • Lirequinil • Necopidem • Pazinaclone • ROD-188 • Saripidem • Suproclone • Suriclone • SX-3228 • U-89843A • U-90042 • Zaleplon • Zolpidem • Zopiclone Phenols: Fospropofol • Propofol Piperidinediones: Glutethimide • Methyprylon • Pyrithyldione • Piperidione Quinazolinones: Afloqualone • Cloroqualone • Diproqualone • Etaqualone • Mebroqualone • Mecloqualone • Methaqualone • Methylmethaqualone • Nitromethaqualone Volatiles/gases: 2-Methyl-2-butanol • Acetophenone • Acetylglycinamide chloral hydrate • Centalun • Chloral hydrate • Ethanol (Alcohol) • Paraldehyde • Trichloroethanol Others: Bromide (Lithium bromide, Potassium bromide, Sodium bromide) • Chloralose • Chloralodol • Clomethiazole • Dichloralphenazone • Ethchlorvynol • Etomidate • Gaboxadol • Loreclezole • Methylpentynol • Metomidate • Org 25435 • Petrichloral • Sulfonmethane • Triclofos • Valerenic acid (Valerian)

GABA_B Agonists	1,4-Butanediol • Aceburic acid • GABOB • GHB (Sodium oxybate) • GBL • GVL

H₁ Inverse agonists	Antihistamines: Captodiame • Cyproheptadine • Diphenhydramine • Doxylamine • Hydroxyzine • Methapyrilene • Pheniramine • Promethazine • Propiomazine Antidepressants: Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.)

α₁-Adrenergic Antagonists	Antidepressants: Serotonin antagonists and reuptake inhibitors (Trazodone) • Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.) Others: Niaprazine

α₂-Adrenergic Agonists	4-NEMD • Clonidine • Detomidine • Dexmedetomidine • Lofexidine • Medetomidine • Romifidine • Tizanidine • Xylazine

5-HT_2A Antagonists	Antidepressants: Serotonin antagonists and reuptake inhibitors (Trazodone) • Tricyclic antidepressants (Amitriptyline, Doxepin, Trimipramine, etc.) • Tetracyclic antidepressants (Mianserin, Mirtazapine, etc.) Antipsychotics: Typical antipsychotics (Chlorpromazine, Thioridazine, etc.) • Atypical antipsychotics (Olanzapine, Quetiapine, Risperidone, etc.) Others: Eplivanserin • Niaprazine • Pruvanserin • Volinanserin

Melatonin Agonists	Agomelatine • LY-156,735 • Melatonin • Ramelteon • Tasimelteon

Orexin Antagonists	Almorexant • SB-334,867 • SB-408,124 • SB-649,868 • Suvorexant • TCS-OX2-29

Others	Acecarbromal • Apronal • Bromisoval • Cannabidiol (Cannabis) • Carbromal • Embutramide • Evoxine • Fenadiazole • Gabapentin • Kavalactones (Kava) • Mephenoxalone • Opioids (Oxycodone, Morphine (Opium), etc.) • Passion flower • Scopolamine (Mandrake) • Valnoctamide

GABAergics

Receptor
ligands

GABA_A	Agonists: Main site: Bamaluzole • Gaboxadol • Ibotenic acid • Isoguvacine • Isonipecotic acid • Muscimol (Amanita Muscaria) • Progabide • SL 75102 • Thiomuscimol • Tolgabide; Positive allosteric modulators: Barbiturates • Benzodiazepines • Carbamates • Chlormezanone • Clomethiazole • Ethanol (Alcohol) • Etomidate • Kavalactones (Kava) • Loreclezole • Metomidate • Neuroactive steroids • Nonbenzodiazepines (β-Carbolines, Cyclopyrrolones, Imidazopyridines, Pyrazolopyrimidines, etc.) • Phenols • Piperidinediones • Propanidid • Pyrazolopyridines • Quinazolinones • ROD-188 • Skullcap • Stiripentol • Valerenic acid (Valerian) * See Template:GABAAergics for a full list of GABA_A positive allosteric modulators. Antagonists: Main site: Bicuculline • Gabazine • Pitrazepin • Quisqualamine; Negative allosteric modulators: α5IA • Bilobalide • Cicutoxin • Cyclothiazide • DMCM • Flumazenil • Flurothyl • Furosemide • L-655,708 • Oenanthotoxin • Penicillin • Pentylenetetrazol • Picrotoxin • PWZ-029 • Ro15-4513 • Sarmazenil • Suritozole • Thujone (Absinthe) • Thiocolchicoside • ZK-93426

GABA_B	Agonists: Main site: 1,4-Butanediol • Baclofen • GBL • GHB • GHV • GVL • Lesogaberan • Phenibut • Progabide • SKF-97,541 • Tolgabide; Positive allosteric modulators: BHF-177 • BHFF • BSPP • CGP-7930 • GS-39783 Antagonists: Main site: CGP-35348 • Phaclofen • Saclofen • SCH-50911

GABA_C	Agonists: Main site: CACA • CAMP • GABOB • N(4)-chloroacetylcytosine arabinoside • Progabide • Tolgabide Antagonists: Main site: Bilobalide • TPMPA

Reuptake
inhibitors

Plasmalemmal

GAT inhibitors	CI-966 • Deramciclane • EF-1502 • Gabaculine • Guvacine • Nipecotic acid • NNC 05-2090 • SKF-89976A • SNAP-5114 • Tiagabine

Enzyme
inhibitors

Anabolism

GAD inhibitors	Allylglycine

Catabolism

GABA-T inhibitors	3-Hydrazinopropionic acid • Aminooxyacetic acid • Gabaculine • Isoniazid • Phenelzine • Phenylethylidenehydrazine • Sodium valproate • Valnoctamide • Valproate pivoxil • Valproate semisodium (Divalproex sodium) • Valproic acid • Valpromide • Vigabatrin

Others

Precursors	Glutamate • Glutamine

Cofactors	Vitamin B6 (pyridoxine, pyridoxamine, pyridoxal phosphate)

Others	Gabapentin • L-Theanine • Picamilon • Pregabalin

v d e GABA_A receptor PAMs

Barbiturates	Allobarbital • Alphenal • Amobarbital • Aprobarbital • Barbexaclone • Barbital • Benzobarbital • Benzylbutylbarbiturate • Brallobarbital • Brophebarbital • Bucolome • Butabarbital • Butalbital • Butobarbital • Butallylonal • Carbubarb • Crotylbarbital • Cyclobarbital • Cyclopal • Difebarbamate • Enallylpropymal • Ethallobarbital • Febarbamate • Heptabarb • Heptobarbital • Hexethal • Hexobarbital • Metharbital • Methohexital • Methylphenobarbital • Narcobarbital • Nealbarbital • Pentobarbital • Phenobarbital • Phetharbital • Primidone • Prazitone • Probarbital • Propallylonal • Proxibarbal • Proxibarbital • Reposal • Secbutabarbital • Secobarbital • Sigmodal • Spirobarbital • Talbutal • Tetrabamate • Tetrabarbital • Thialbarbital • Thiamylal • Thiobarbital • Thiobutabarbital • Thiopental • Valofane • Vinbarbital • Vinylbital

Benzodiazepines	Adinazolam • Alprazolam • Arfendazam • Avizafone • Bentazepam • Bretazenil • Bromazepam • Brotizolam • Camazepam • Chlordiazepoxide • Ciclotizolam • Cinolazepam • Clazolam • Climazolam • Clobazam • Clonazepam • Clorazepate • Clotiazepam • Cloxazolam • Cyprazepam • Delorazepam • Diazepam • Doxefazepam • Elfazepam • Estazolam • Ethyl carfluzepate • Ethyl dirazepate • Ethyl loflazepate • Etizolam • Fletazepam • Fludiazepam • Flunitrazepam • Flurazepam • Flutazolam • Flutemazepam • Flutoprazepam • Fosazepam • Gidazepam • Girisopam • Halazepam • Haloxazolam • Iclazepam • Imidazenil • Ketazolam • Lofendazam • Lopirazepam • Lopirazepam • Loprazolam • Lorazepam • Lormetazepam • Meclonazepam • Medazepam • Menitrazepam • Metaclazepam • Mexazolam • Midazolam • Nerisopam • Nimetazepam • Nitrazepam • Nitrazepate • Nordazepam • Oxazepam • Oxazolam • Phenazepam • Pinazepam • Pivoxazepam • Prazepam • Premazepam • Proflazepam • QH-II-66 • Quazepam • Reclazepam • Remimazolam • Rilmazafone • Ripazepam • Ro48-6791 • SH-053-R-CH3-2′F • Sulazepam • Temazepam • Tetrazepam • Tofisopam • Triazolam • Triflubazam • Uldazepam • Zapizolam • Zolazepam • Zomebazam

Carbamates	Carisbamate • Carisoprodol • Cyclarbamate • Difebarbamate • Emylcamate • Ethinamate • Febarbamate • Felbamate • Hexapropymate • Lorbamate • Mebutamate • Meprobamate • Methocarbamol • Nisobamate • Pentabamate • Phenprobamate • Procymate • Styramate • Tetrabamate • Tybamate

Neuroactive steroids	Acebrochol • Allopregnanolone • Alphadolone • Alphaxolone • Ganaxolone • Hydroxydione • Minaxolone • Org 20599 • THDOC

Nonbenzodiazepines	β-Carbolines: Abecarnil • Gedocarnil • SL-651,498 • ZK-93423; Cyclopyrrolones: Eszopiclone • Pagoclone • Pazinaclone • Suproclone • Suriclone • Zopiclone; Imidazopyridines: Alpidem • Necopidem • Saripidem • Zolpidem; Pyrazolopyrimidines: Divaplon • Fasiplon • Indiplon • Lorediplon • Ocinaplon • Panadiplon • Taniplon • Zaleplon; Others: Adipiplon • CGS-8216 • CGS-9896 • CGS-13767 • CGS-20625 • CL-218,872 • CP-615,003 • ELB-139 • GBLD-345 • L-838,417 • NS-2664 • NS-2710 • NS-11394 • Pipequaline • ROD-188 • RWJ-51204 • SB-205,384 • SX-3228 • TP-003 • TPA-023 • TP-13 • U-89843A • U-90042 • Y-23684

Phenols	Fospropofol • Propofol • Thymol

Piperidinediones	Glutethimide • Methyprylon • Piperidione • Pyrithyldione

Pyrazolopyridines	Cartazolate • Etazolate • ICI-190,622 • Tracazolate

Quinazolinones	Afloqualone • Cloroqualone • Diproqualone • Etaqualone • Mebroqualone • Mecloqualone • Methaqualone • Methylmethaqualone

Volatiles/gases	2-Methyl-2-butanol • Acetone • Acetophenone • Acetylglycinamide chloral hydrate • Benzene • Butane • Butanol • Butylene • Centalun • Chloral • Chloral hydrate • Chlorobutanol • Chloroform • Cyclopropane • Desflurane • Dichloromethane • Diethyl ether • Enflurane • Ethanol (Alcohol) • Ethyl chloride • Ethylene • Gasoline • Halothane • Isoflurane • Kerosine • Menthol • Methanol • Methoxyflurane • Methoxypropane • Methylbutanol • Nitric oxide • Nitrogen • Nitrous oxide • Paraldehyde • Pentanol • Propane • Propanol • Propylene • Sevoflurane • Toluene • Trichloroethanol • Trichloroethylene • Vinyl ether • Xenon

Others	Bromide (Lithium bromide, Potassium bromide, Sodium bromide) • Chloralodol • Chloralose • Chlormezanone • Clomethiazole • DEABL • Etazepine • Ethchlorvynol • Etifoxine • Etomidate • GABA • Kavalactones (Kava) • Loreclezole • Methylpentynol • Metomidate • Org 25,435 • Petrichloral • Propanidid • Skullcap • Stiripentol • Sulfonmethane • Tetronal • Triclofos • Trional • Valeric acid, Valerenic acid (Valerian)

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Pyrithyldione

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Pyrithyldione

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Pyrithyldione

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