Piperidione

Short description: Chemical compound

Piperidione

Clinical data
Trade names| Ascron, Dihyprylon, Dihyprylone, Sedulon, Tusseval
ATC code|

* R05DB23 (WHO)

Identifiers

IUPAC name

* 3,3-diethylpiperidine-2,4-dione

CAS Number|

* 77-03-2 N

PubChem CID|

* 6465

ChemSpider|

* 6222 Y

UNII|

* BZ6KL0Q8UD

Chemical and physical data
Formula| C9H15NO2
Molar mass| 169.224 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* O=C1C(C(=O)NCC1)(CC)CC

InChI

* InChI=1S/C9H15NO2/c1-3-9(4-2)7(11)5-6-10-8(9)12/h3-6H2,1-2H3,(H,10,12) Y

* Key:RGEVWUKXWFOAID-UHFFFAOYSA-N Y

NY (what is this?) (verify)

Piperidione (trade name Sedulon) is a sedative drug, structurally related to methyprylon and pyrithyldione. It used to be marketed by Roche as a cough medicine available in liquid form.[1][2][3] In the US, it was approved by the FDA on grounds of safety alone in 1947. After Roche failed to submit evidence of efficacy to the Drug Efficacy Study Implementation program in 1972, it was withdrawn from the US market.[4]

## See also

* Glutethimide

## References

1. ↑ "On pethidine and methadone derivatives". Bulletin of the World Health Organization 2 (2): 193–204. 1949. PMID 15409516.
2. ↑ "The use of piperidione as a cough sedative". Medical Times 76 (10): 445–7. October 1948. PMID 18102053.
3. ↑ "[Use of an antitussive drug in pulmonary pathology]". Bollettino Chimico Farmaceutico 124 (2): 1S–6S. February 1985. PMID 3839404.
4. ↑ "﻿Certain Preparations Containing Dihyprylone or Pipazethate Hydrochloride; Notice of Withdrawal of Approval of New-Drug Applications﻿". Federal Register 37 (152): 15887. August 5, 1972. FDC–D–458. https://www.govinfo.gov/content/pkg/FR-1972-08-05/pdf/FR-1972-08-05.pdf.

* v
* t
* e

Cough and cold preparations (R05)

Expectorants|

* Althea root
* Antimony pentasulfide
* Creosote
* Guaiacolsulfonate
* Guaifenesin (\+ oxomemazine)
* Ipecacuanha (Syrup of ipecac)
* Levoverbenone
* Potassium iodide
* Senega
* Tyloxapol
* Ammonium Chloride

Mucolytics|

* Acetylcysteine#
* Ambroxol
* Bromhexine
* Carbocisteine
* Domiodol
* Dornase alfa
* Eprazinone
* Erdosteine
* Letosteine
* Mannitol
* Mesna
* Neltenexine
* Sobrerol
* Stepronin
* Tiopronin

Cough suppressants|

| Opium alkaloids,
opioids,
and derivatives|

* Acetyldihydrocodeine
* Benzylmorphine
* Butorphanol
* Codeine#
* Dextromethorphan
* Dihydrocodeine
* Dimemorfan
* Droxypropine
* Ethylmorphine
* Heroin
* Hydrocodone
* Hydromorphone
* Isoaminile
* Laudanum
* Levomethadone
* Levopropoxyphene
* Methadone
* Nicocodeine
* Nicodicodeine
* Normethadone
* Noscapine
* Pholcodine
* Thebacon
* Tipepidine

|

Other|

* Benzonatate
* Benproperine
* Bibenzonium bromide
* Butamirate
* Clobutinol
* Clofedanol
* Cloperastine
* Diphenhydramine
* Dibunate
* Dimethoxanate
* Dropropizine
* Fedrilate
* Glaucine
* Levodropropizine
* Meprotixol
* Morclofone
* Nepinalone
* Oxolamine
* Oxeladin
* Pentoxyverine
* Pipazetate
* Prenoxdiazine
* Piperidione
* Zipeprol

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

* v
* t
* e

Hypnotics/sedatives (N05C)

GABAA|

| Alcohols|

* 2M2B
* Chloralodol
* Ethanol (alcohol)
* Ethchlorvynol
* Methylpentynol
* Trichloroethanol

|

Barbiturates|

* Allobarbital
* Amobarbital
* Aprobarbital
* Barbital
* Butabarbital
* Butobarbital
* Cyclobarbital
* Ethallobarbital
* Heptabarb
* Hexobarbital
* Mephobarbital
* Methohexital
* Narcobarbital
* Pentobarbital
* Phenallymal
* Phenobarbital
* Propylbarbital
* Proxibarbal
* Reposal
* Secobarbital
* Talbutal
* Thiamylal
* Thiopental
* Thiotetrabarbital
* Vinbarbital
* Vinylbital

Benzodiazepines|

* Brotizolam
* Cinolazepam
* Climazolam
* Doxefazepam
* Estazolam
* Flunitrazepam
* Flurazepam
* Flutoprazepam
* Lorazepam
* Loprazolam
* Lormetazepam
* Midazolam
* Nimetazepam
* Nitrazepam
* Phenazepam
* Quazepam
* Temazepam
* Triazolam

Carbamates|

* Carisoprodol
* Emylcamate
* Ethinamate
* Hexapropymate
* Meprobamate
* Methocarbamol
* Phenprobamate
* Procymate
* Tybamate

Imidazoles|

* Etomidate
* Metomidate
* Propoxate

Monoureides|

* Acecarbromal
* Apronal (apronalide)
* Bromisoval
* Capuride
* Carbromal
* Ectylurea

Neuroactive steroids|

* Acebrochol
* Allopregnanolone
* Alphadolone
* Alphaxolone
* Eltanolone
* Hydroxydione
* Minaxolone
* Progesterone

Nonbenzodiazepines|

* Eszopiclone
* Indiplon
* Lirequinil
* Necopidem
* Pazinaclone
* Saripidem
* Suproclone
* Suriclone
* Zaleplon
* Zolpidem
* Zopiclone

Phenols|

* Propofol

Piperidinediones|

* Glutethimide
* Methyprylon
* Pyrithyldione
* Piperidione

Quinazolinones|

* Afloqualone
* Cloroqualone
* Diproqualone
* Etaqualone
* Mebroqualone
* Mecloqualone
* Methaqualone
* Methylmethaqualone
* Nitromethaqualone

Others|

* Acetophenone
* Acetylglycinamide chloral hydrate
* Bromide compounds
* Lithium bromide
* Potassium bromide
* Sodium bromide
* Centalun
* Chloral betaine
* Chloral hydrate
* Chloralose
* Clomethiazole
* Dichloralphenazone
* Gaboxadol
* Kavalactones
* Loreclezole
* Paraldehyde
* Petrichloral
* Sulfonylalkanes
* Sulfonmethane (sulfonal)
* Tetronal
* Trional
* Triclofos
* Sesquiterpene
* Isovaleramide
* Isovaleric acid
* Valerenic acid

GABAB|

* 1,4-Butanediol
* 4-Fluorophenibut
* Aceburic acid
* Baclofen
* GABOB
* GHB (sodium oxybate)
* GBL
* GVL
* Phenibut
* Tolibut

H1|

| Antihistamines|

* Captodiame
* Cyproheptadine
* Diphenhydramine
* Doxylamine
* Hydroxyzine
* Methapyrilene
* Perlapine
* Pheniramine
* Promethazine
* Propiomazine

|

Antidepressants|

* Serotonin antagonists and reuptake inhibitors
* Etoperidone
* Nefazodone
* Trazodone
* Tricyclic antidepressants
* Amitriptyline
* Doxepin
* Trimipramine, etc.
* Tetracyclic antidepressants
* Mianserin
* Mirtazapine, etc.

Antipsychotics|

* Typical antipsychotics
* Chlorpromazine
* Thioridazine, etc.
* Atypical antipsychotics
* Olanzapine
* Quetiapine
* Risperidone, etc.

α2-Adrenergic|

* Clonidine
* Detomidine
* Dexmedetomidine
* Lofexidine
* Medetomidine
* Romifidine
* Tizanidine
* Xylazine

5-HT2A|

| Antidepressants|

* 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|

* Niaprazine

Melatonin|

* Agomelatine
* Melatonin
* Ramelteon
* Tasimelteon

Orexin|

* Almorexant
* Filorexant
* Suvorexant

α2δ VDCC|

* Gabapentin
* Gabapentin enacarbil
* Mirogabalin
* Phenibut
* Pregabalin

Others|

* Cannabidiol
* Cannabis
* Chlorophenylalkyldiols
* Fenpentadiol
* Metaglycodol
* Phenaglycodol
* Diethylpropanediol
* Evoxine
* Fenadiazole
* Guaifenesin-related muscle relaxants
* Chlorphenesin
* Mephenesin
* Mephenoxalone
* Metaxalone
* Methocarbamol
* Midaflur
* Opioids (e.g., morphine)
* Passion flower
* Scopolamine
* Trazodone
* UMB68
* Valnoctamide

* v
* t
* e

GABAA receptor positive modulators

Alcohols|

* Brometone
* Butanol
* Chloralodol
* Chlorobutanol (cloretone)
* Ethanol (alcohol) (alcoholic drink)
* Ethchlorvynol
* Isobutanol
* Isopropanol
* Menthol
* Methanol
* Methylpentynol
* Pentanol
* Petrichloral
* Propanol
* tert-Butanol (2M2P)
* tert-Pentanol (2M2B)
* Tribromoethanol
* Trichloroethanol
* Triclofos
* Trifluoroethanol

Barbiturates|

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

Benzodiazepines|

* 2-Oxoquazepam
* 3-Hydroxyphenazepam
* Adinazolam
* Alprazolam
* Arfendazam
* Avizafone
* Bentazepam
* Bretazenil
* Bromazepam
* Brotizolam
* Camazepam
* Carburazepam
* Chlordiazepoxide
* Ciclotizolam
* Cinazepam
* Cinolazepam
* Clazolam
* Climazolam
* Clobazam
* Clonazepam
* Clonazolam
* Cloniprazepam
* Clorazepate
* Clotiazepam
* Cloxazolam
* CP-1414S
* Cyprazepam
* Delorazepam
* Demoxepam
* Diazepam
* Diclazepam
* Doxefazepam
* Elfazepam
* Estazolam
* Ethyl carfluzepate
* Ethyl dirazepate
* Ethyl loflazepate
* Etizolam
* EVT-201
* FG-8205
* Fletazepam
* Flubromazepam
* Flubromazolam
* Fludiazepam
* Flunitrazepam
* Flunitrazolam
* Flurazepam
* Flutazolam
* Flutemazepam
* Flutoprazepam
* Fosazepam
* Gidazepam
* Halazepam
* Haloxazolam
* Iclazepam
* Imidazenil
* Irazepine
* Ketazolam
* Lofendazam
* Lopirazepam
* Loprazolam
* Lorazepam
* Lormetazepam
* Meclonazepam
* Medazepam
* Menitrazepam
* Metaclazepam
* Mexazolam
* Midazolam
* Motrazepam
* N-Desalkylflurazepam
* Nifoxipam
* Nimetazepam
* Nitrazepam
* Nitrazepate
* Nitrazolam
* Nordazepam
* Nortetrazepam
* Oxazepam
* Oxazolam
* Phenazepam
* Pinazepam
* Pivoxazepam
* Prazepam
* Premazepam
* Proflazepam
* Pyrazolam
* QH-II-66
* Quazepam
* Reclazepam
* Remimazolam
* Rilmazafone
* Ripazepam
* Ro48-6791
* Ro48-8684
* SH-053-R-CH3-2′F
* Sulazepam
* Temazepam
* Tetrazepam
* Tolufazepam
* Triazolam
* Triflubazam
* Triflunordazepam (Ro5-2904)
* Tuclazepam
* Uldazepam
* Zapizolam
* Zolazepam
* Zomebazam

Carbamates|

* Carisbamate
* Carisoprodol
* Clocental
* Cyclarbamate
* Difebarbamate
* Emylcamate
* Ethinamate
* Febarbamate
* Felbamate
* Hexapropymate
* Lorbamate
* Mebutamate
* Meprobamate
* Nisobamate
* Pentabamate
* Phenprobamate
* Procymate
* Styramate
* Tetrabamate
* Tybamate

Flavonoids|

* 6-Methylapigenin
* Ampelopsin (dihydromyricetin)
* Apigenin
* Baicalein
* Baicalin
* Catechin
* EGC
* EGCG
* Hispidulin
* Linarin
* Luteolin
* Rc-OMe
* Skullcap constituents (e.g., baicalin)
* Wogonin

Imidazoles|

* Etomidate
* Metomidate
* Propoxate

Kava constituents|

* 10-Methoxyyangonin
* 11-Methoxyyangonin
* 11-Hydroxyyangonin
* Desmethoxyyangonin
* 11-Methoxy-12-hydroxydehydrokavain
* 7,8-Dihydroyangonin
* Kavain
* 5-Hydroxykavain
* 5,6-Dihydroyangonin
* 7,8-Dihydrokavain
* 5,6,7,8-Tetrahydroyangonin
* 5,6-Dehydromethysticin
* Methysticin
* 7,8-Dihydromethysticin
* Yangonin

Monoureides|

* Acecarbromal
* Apronal (apronalide)
* Bromisoval
* Carbromal
* Capuride
* Ectylurea

Neuroactive steroids|

* Acebrochol
* Allopregnanolone (brexanolone)
* Alfadolone
* Alfaxalone
* 3α-Androstanediol
* Androstenol
* Androsterone
* Certain anabolic-androgenic steroids
* Cholesterol
* DHDOC
* 3α-DHP
* 5α-DHP
* 5β-DHP
* DHT
* Etiocholanolone
* Ganaxolone
* Hydroxydione
* Minaxolone
* ORG-20599
* ORG-21465
* P1-185
* Pregnanolone (eltanolone)
* Progesterone
* Renanolone
* SAGE-105
* SAGE-324
* SAGE-516
* SAGE-689
* SAGE-872
* Testosterone
* THDOC
* Zuranolone

Nonbenzodiazepines|

* Cyclopyrrolones: Eszopiclone
* Pagoclone
* Pazinaclone
* Suproclone
* Suriclone
* Zopiclone

* Imidazopyridines: Alpidem
* DS-1
* 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
* CTP-354
* ELB-139
* GBLD-345
* Imepitoin
* JM-1232
* L-838,417
* Lirequinil (Ro41-3696)
* NS-2664
* NS-2710
* NS-11394
* Pipequaline
* ROD-188
* RWJ-51204
* SB-205,384
* SX-3228
* TGSC01AA
* TP-003
* TPA-023
* TP-13
* U-89843A
* U-90042
* Viqualine
* 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
* Nitromethaqualone
* SL-164

Volatiles/gases|

* Acetone
* Acetophenone
* Acetylglycinamide chloral hydrate
* Aliflurane
* Benzene
* Butane
* Butylene
* Centalun
* Chloral
* Chloral betaine
* Chloral hydrate
* Chloroform
* Cryofluorane
* Desflurane
* Dichloralphenazone
* Dichloromethane
* Diethyl ether
* Enflurane
* Ethyl chloride
* Ethylene
* Fluroxene
* Gasoline
* Halopropane
* Halothane
* Isoflurane
* Kerosine
* Methoxyflurane
* Methoxypropane
* Nitric oxide
* Nitrogen
* Nitrous oxide
* Norflurane
* Paraldehyde
* Propane
* Propylene
* Roflurane
* Sevoflurane
* Synthane
* Teflurane
* Toluene
* Trichloroethane (methyl chloroform)
* Trichloroethylene
* Vinyl ether

Others/unsorted|

* 3-Hydroxybutanal
* α-EMTBL
* AA-29504
* Avermectins (e.g., ivermectin)
* Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide)
* Carbamazepine
* Chloralose
* Chlormezanone
* Clomethiazole
* DEABL
* Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine))
* DS2
* Efavirenz
* Etazepine
* Etifoxine
* Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid)
* Fluoxetine
* Flupirtine
* Hopantenic acid
* Lanthanum
* Lavender oil
* Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol)
* Loreclezole
* Menthyl isovalerate (validolum)
* Monastrol
* Niacin
* Nicotinamide (niacinamide)
* Org 25,435
* Phenytoin
* Propanidid
* Retigabine (ezogabine)
* Safranal
* Seproxetine
* Stiripentol
* Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional)
* Terpenoids (e.g., borneol)
* Topiramate
* Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol)

* Unsorted benzodiazepine site positive modulators: α-Pinene
* MRK-409 (MK-0343)
* TCS-1105
* TCS-1205

See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Piperidione&oldid=871743"
*[CID]: Compound ID
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*[α2δ]: alpha2delta subunit
*[VDCC]: voltage-gated calcium channel
*[GABAA]: γ-Aminobutyric acid A