Aprobarbital |
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| Trade names | Oramon, Somnifane, Allonal |
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| Other names | aprobarbitone, allylpropymal, Alurate, 5-isopropyl- 5-allylbarbituric acid |
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| AHFS/Drugs.com | International Drug Names |
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| Drug class | Barbiturate |
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| ATC code | |
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| Legal status |
- BR: Class B1 (Psychoactive drugs)[1]
- CA: Schedule IV
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5-propan-2-yl-5-prop-2-enyl-1,3-diazinane-2,4,6-trione
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| CAS Number | |
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| PubChem CID | |
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| DrugBank | |
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| ChemSpider | |
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| UNII | |
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| KEGG | |
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| ChEMBL | |
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| CompTox Dashboard (EPA) | |
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| ECHA InfoCard | 100.000.908 |
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| Formula | C10H14N2O3 |
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| Molar mass | 210.233 g·mol−1 |
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| 3D model (JSmol) | |
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O=C1NC(=O)NC(=O)C1(C(C)C)C\C=C
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InChI=1S/C10H14N2O3/c1-4-5-10(6(2)3)7(13)11-9(15)12-8(10)14/h4,6H,1,5H2,2-3H3,(H2,11,12,13,14,15) YKey:UORJNBVJVRLXMQ-UHFFFAOYSA-N Y
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Aprobarbital (or aprobarbitone), sold under the brand names Oramon, Somnifaine, and Allonal, is a barbiturate derivative invented in the 1920s by Ernst Preiswerk. It has sedative, hypnotic, and anticonvulsant properties, and was used primarily for the treatment of insomnia.[2] Aprobarbital was never as widely used as more common barbiturate derivatives such as phenobarbital and is now rarely prescribed. It has been largely replaced by newer drugs with a better safety margin.
See also
References
GABAA receptor positive modulators |
|---|
| Alcohols | |
|---|
| Barbiturates | |
|---|
| Benzodiazepines | |
|---|
| Carbamates |
- Carisbamate
- Carisoprodol
- Clocental
- Cyclarbamate
- Difebarbamate
- Emylcamate
- Ethinamate
- Febarbamate
- Felbamate
- Hexapropymate
- Hydroxyphenamate
- Lorbamate
- Mebutamate
- Meprobamate
- Nisobamate
- Pentabamate
- Phenprobamate
- Procymate
- Styramate
- Tetrabamate
- Tybamate
|
|---|
| Flavonoids | |
|---|
| Imidazoles |
- Etomidate
- Metomidate
- Methoxyetomidate
- Propoxate
- Isopropoxate
- Butomidate
- Iso-butomidate
- Sec-butomidate
- CF2-Etomidate
- CF3-Etomidate
- CF3-Propoxate
- Flutomidate
- 2,6-Dichloro-3-fluoroetomidate
|
|---|
| 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 | |
|---|
| Nonbenzodiazepines |
- Imidazopyridines: Alpidem
- DS-1
- Necopidem
- Saripidem
- Zolpidem
- Pyrazolopyrimidines: Divaplon
- Fasiplon
- Indiplon
- Lorediplon
- Ocinaplon
- Panadiplon
- Taniplon
- Zaleplon
- Others: Adipiplon
- AXS-17 (BAER-101, AZD-7325)
- 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)
- Miltirone (rosmariquinone)
- 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 | |
|---|
| Piperidinediones | |
|---|
| Pyrazolopyridines |
- Cartazolate
- Etazolate
- ICI-190,622
- Tracazolate
|
|---|
| Quinazolinones |
- Afloqualone
- Cloroqualone
- Diproqualone
- Etaqualone
- Mebroqualone
- Mecloqualone
- Methaqualone
- Methylmethaqualone
- Nitromethaqualone
- SL-164
|
|---|
| Volatiles/gases | |
|---|
| Others/unsorted |
- 3-Hydroxybutanal
- α-EMTBL
- AA-29504
- Alogabat
- Avermectins (e.g., ivermectin)
- Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide)
- Carbamazepine
- Chloralose
- Chlormezanone
- Clomethiazole
- Darigabat
- DEABL
- Deuterated etifoxine
- 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
- KRM-II-81
- Lanthanum
- Lavender oil
- Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol)
- Loreclezole
- Menthyl isovalerate (validolum)
- Monastrol
- Nicotinic acid
- Nicotinamide
- 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 |
Hypnotics/sedatives (N05C) |
|---|
| GABAA | | Alcohols | |
|---|
| Barbiturates | |
|---|
| Benzodiazepines | |
|---|
| Carbamates | |
|---|
| Imidazoles | |
|---|
| Monoureides |
- Acecarbromal
- Apronal (apronalide)
- Bromisoval
- Capuride
- Carbromal
- Ectylurea
|
|---|
| Neurosteroids | |
|---|
| Nonbenzodiazepines | |
|---|
| Phenols |
- Cipepofol (ciprofol)
- Fospropofol
- Propofol
- Propofol hemisuccinate
|
|---|
| Piperidinediones | |
|---|
| Quinazolinones |
- Afloqualone
- Cloroqualone
- Diproqualone
- Etaqualone
- Mebroqualone
- Mecloqualone
- Methaqualone
- Methylmethaqualone
- Nitromethaqualone
- SL-164
|
|---|
| Others | |
|---|
|
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| GABAB | |
|---|
| H1 | | Antihistamines | |
|---|
| Antidepressants |
- Serotonin antagonists and reuptake inhibitors
- Tricyclic antidepressants
- Tetracyclic antidepressants
|
|---|
| Antipsychotics |
- Typical antipsychotics
- Atypical antipsychotics
|
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|
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| α2-Adrenergic | |
|---|
| 5-HT2A | | Antidepressants |
- Trazodone
- Tricyclic antidepressants
- Tetracyclic antidepressants
|
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| Antipsychotics |
- Typical antipsychotics
- Atypical antipsychotics
|
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| Others | |
|---|
|
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| Melatonin | |
|---|
| Orexin |
- Daridorexant
- Lemborexant
- Suvorexant
|
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| α2δ VDCC | |
|---|
| Others | |
|---|
GABAA receptor positive modulators |
|---|
| Alcohols | |
|---|
| Barbiturates | |
|---|
| Benzodiazepines | |
|---|
| Carbamates |
- Carisbamate
- Carisoprodol
- Clocental
- Cyclarbamate
- Difebarbamate
- Emylcamate
- Ethinamate
- Febarbamate
- Felbamate
- Hexapropymate
- Hydroxyphenamate
- Lorbamate
- Mebutamate
- Meprobamate
- Nisobamate
- Pentabamate
- Phenprobamate
- Procymate
- Styramate
- Tetrabamate
- Tybamate
|
|---|
| Flavonoids | |
|---|
| Imidazoles |
- Etomidate
- Metomidate
- Methoxyetomidate
- Propoxate
- Isopropoxate
- Butomidate
- Iso-butomidate
- Sec-butomidate
- CF2-Etomidate
- CF3-Etomidate
- CF3-Propoxate
- Flutomidate
- 2,6-Dichloro-3-fluoroetomidate
|
|---|
| 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 | |
|---|
| Nonbenzodiazepines |
- Imidazopyridines: Alpidem
- DS-1
- Necopidem
- Saripidem
- Zolpidem
- Pyrazolopyrimidines: Divaplon
- Fasiplon
- Indiplon
- Lorediplon
- Ocinaplon
- Panadiplon
- Taniplon
- Zaleplon
- Others: Adipiplon
- AXS-17 (BAER-101, AZD-7325)
- 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)
- Miltirone (rosmariquinone)
- 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 | |
|---|
| Piperidinediones | |
|---|
| Pyrazolopyridines |
- Cartazolate
- Etazolate
- ICI-190,622
- Tracazolate
|
|---|
| Quinazolinones |
- Afloqualone
- Cloroqualone
- Diproqualone
- Etaqualone
- Mebroqualone
- Mecloqualone
- Methaqualone
- Methylmethaqualone
- Nitromethaqualone
- SL-164
|
|---|
| Volatiles/gases | |
|---|
| Others/unsorted |
- 3-Hydroxybutanal
- α-EMTBL
- AA-29504
- Alogabat
- Avermectins (e.g., ivermectin)
- Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide)
- Carbamazepine
- Chloralose
- Chlormezanone
- Clomethiazole
- Darigabat
- DEABL
- Deuterated etifoxine
- 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
- KRM-II-81
- Lanthanum
- Lavender oil
- Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol)
- Loreclezole
- Menthyl isovalerate (validolum)
- Monastrol
- Nicotinic acid
- Nicotinamide
- 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 |