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 O=C1N/C=C\C(=O)C1(CC)CC
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 [edit]

^ 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 t e Hypnotics/sedatives (N05C)

GABA_A agonists/PAMs	Alcohols: 2M2B • Chloralodol • Ethanol (Alcohol) • Ethchlorvynol • Methylpentynol • Trichloroethanol Barbiturates: Allobarbital • Amobarbital • Aprobarbital • Barbital • Butabarbital • Butobarbital • Cyclobarbital • Ethallobarbital • Heptabarb • Hexobarbital • Mephobarbital • Methohexital • Pentobarbital • Phenallymal • Phenobarbital • Propylbarbital • Proxibarbal • Reposal • Secobarbital • Talbutal • Thiamylal • Thiopental • Vinbarbital • Vinylbital Benzodiazepines: Brotizolam • Clonazepam • Cinolazepam • Climazolam • Doxefazepam • Estazolam • Flunitrazepam • Flurazepam • Flutoprazepam • Haloxazolam • Loprazolam • Lorazepam •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 • SL-164 Volatiles/gases: • Acetophenone • Acetylglycinamide chloral hydrate • Centalun • Chloral hydrate • Paraldehyde Others: Bromide (Lithium bromide, Potassium bromide, Sodium bromide) • Chloralose • Clomethiazole • Dichloralphenazone • Etomidate • Gaboxadol • Loreclezole • 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) • UMB68 • 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: Alcohols (2M2B, Ethanol, Ethchlorvynol, Methylpentynol Barbiturates Benzodiazepines Carbamates Chlormezanone Clomethiazole 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) Note: See the GABA_A receptor PAMs navbox for a full list of GABA_A positive allosteric modulators. Antagonists: Main site: Bicuculline Gabazine Pitrazepin Quisqualamine; Negative allosteric modulators: 17-Phenylandrostenol (17-PA) α5IA Bilobalide Cicutoxin Cyclothiazide DMCM Flumazenil Flurothyl Furosemide Iomazenil (¹²³I) L-655,708 Oenanthotoxin Penicillin Pentylenetetrazol Picrotoxin PWZ-029 Radequinil Ro15-4513 Sarmazenil Suritozole Terbequinil Thujone 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 N⁴-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 Hopantenic acid Picamilon Pregabalin L-Theanine

v t e GABA_A receptor PAMs

Alcohols	2M2B Butanol Chloralodol Chlorobutanol Ethanol (drinking alcohol) Ethchlorvynol Menthol Methanol Methylpentynol Pentanol Propanol Trichloroethanol

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

Neuroactive steroids	Acebrochol Allopregnanolone Alphadolone Alphaxolone Eltanolone Ganaxolone Hydroxydione Minaxolone Org 20599 Org 21465 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 Stiripentol 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	Acetone Acetophenone Acetylglycinamide chloral hydrate Benzene Butane Butylene Centalun Chloral Chloral hydrate Chloroform Cyclopropane Desflurane Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Gasoline Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Paraldehyde Propane Propylene Sevoflurane Toluene Trichloroethylene Vinyl ether Xenon

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

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