メチルフェノバルビタール
- 関
- mephobarbital
WordNet
- a long-acting crystalline barbiturate (trade name Mebaral) used as a sedative and as an anticonvulsant in the treatment of epilepsy (同)Mebaral
Wikipedia preview
出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/05/02 21:01:46」(JST)
[Wiki en表示]
Methylphenobarbital
|
| Systematic (IUPAC) name |
|
5-phenyl-5-ethyl-
1-methylbarbituric acid
|
| Clinical data |
| AHFS/Drugs.com |
International Drug Names |
| MedlinePlus |
a605022 |
Pregnancy
category |
|
Routes of
administration |
? |
| Legal status |
| Legal status |
- CA: Schedule IV
- DE: Anlage III (Prescription only)
- UK: Class B
- US: Schedule IV
|
| Pharmacokinetic data |
| Bioavailability |
? |
| Protein binding |
70-76% |
| Metabolism |
Hepatic |
| Biological half-life |
34 hours |
| Excretion |
? |
| Identifiers |
| CAS Number |
115-38-8 Y |
| ATC code |
N03AA01 (WHO) |
| PubChem |
CID 8271 |
| DrugBank |
DB00849 Y |
| ChemSpider |
7972 Y |
| UNII |
5NC67NU76B Y |
| KEGG |
D00700 Y |
| ChEBI |
CHEBI:6758 Y |
| ChEMBL |
CHEMBL45029 Y |
| Chemical data |
| Formula |
C13H14N2O3 |
| Molar mass |
246.3 g/mol |
SMILES
-
O=C1N(C(=O)NC(=O)C1(c2ccccc2)CC)C
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InChI
-
InChI=1S/C13H14N2O3/c1-3-13(9-7-5-4-6-8-9)10(16)14-12(18)15(2)11(13)17/h4-8H,3H2,1-2H3,(H,14,16,18) Y
-
Key:ALARQZQTBTVLJV-UHFFFAOYSA-N Y
|
| (verify) |
Methylphenobarbital (INN), also known as mephobarbital (USAN, JAN) and mephobarbitone (BAN), marketed under brand names such as Mebaral, Mephyltaletten, Phemiton, and Prominal, is a drug which is a barbiturate derivative and is used primarily as an anticonvulsant,[1] but also as a sedative and anxiolytic. It is the N-methylated analogue of phenobarbital and has similar indications, therapeutic value, and tolerability.
Contents
- 1 Approval history
- 2 Overdose
- 3 See also
- 4 References
Approval history
- 1935 – Mebaral was introduced by Winthrop Pharmaceuticals.
- 2001 – Methylphenobarbital discontinued in the UK.
- 2003 – Mebaral was acquired by Ovation Pharmaceuticals (a specialty pharmaceutical company that acquired under-promoted branded pharmaceutical products).
- 2009 – Ovation was acquired by Lundbeck, which now markets Mebaral.
- 2012 – Lundbeck announced that they were abandoning the product in the US as of January 6, 2012. The stated reason was because "the company thoroughly evaluated all avenues for keeping MEBARAL TABLETS available to patients, but ultimately concluded that no matter what steps they [i.e. Lundbeck] took, patients would be forced to transition to a new therapy."
The company further stated in a letter on its website [2] that under the FDA's Unapproved Drugs Initiative, FDA is no longer willing to allow the drug to be grandfathered. A new drug application would have needed to have been submitted to gain marketing approval, which would have taken an estimated five years, during which time patients would be required to change their therapies in any case. The last available tablets bore an expiration date of March 31, 2012, and the drug will no longer be available in the US when supplies are depleted.
Overdose
Symptoms of overdose of mephobarbital include confusion, decrease in or loss of reflexes, somnolence, fever, irritability, hypothermia, poor judgment, shortness of breath or slow/troubled breathing, slow heartbeat, slurred speech, staggering, trouble in sleeping, unusual movements of the eyes, weakness.
See also
- Barbiturate
- Hexobarbital
- Metharbital
References
- ^ S. D. Shorvon, David R. Fish, Emilio Perucca, W. Edwin Dodson, ed. (2004). The Treatment of Epilepsy (2nd ed.). Blackwell. ISBN 0-632-06046-8.
- ^ Letter from Lundbeck to prescribers
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Anticonvulsants (N03)
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| GABAergics |
| GABAAR PAMs |
- Barbiturates: Barbexaclone
- Metharbital
- Methylphenobarbital
- Pentobarbital
- Phenobarbital#
- Primidone; Carbamates: Felbamate; Benzodiazepines: Clobazam
- Clonazepam
- Clorazepate
- Diazepam#
- Lorazepam#
- Midazolam
- Nimetazepam
- Nitrazepam
- Temazepam; Others: Bromide (potassium bromide, sodium bromide)
- Paraldehyde
- Stiripentol
|
|
| GABA-T inhibitors |
- Fatty acids: Valproate
- Valpromide
- Valproate pivoxil; Others: Ethanolamine-O-sulfate
- Vigabatrin
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|
| Others |
- GABAR agonists: Progabide; GAT-1 inhibitors: Tiagabine
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|
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| Channelergics |
| Sodium blockers |
- Hydantoins: Ethotoin
- Fosphenytoin
- Mephenytoin
- Phenytoin#; Ureides: Acetylpheneturide
- Chlorphenacemide
- Phenacemide‡
- Pheneturide; Fatty acids: Valproate
- Valpromide
- Valproate pivoxil; Carboxamides: Carbamazepine#
- Eslicarbazepine acetate
- Oxcarbazepine; Others: Lacosamide
- Lamotrigine
- Rufinamide
- Topiramate
- Zonisamide
|
|
| Calcium blockers |
- Oxazolidinediones: Ethadione
- Paramethadione
- Trimethadione; Succinimides: Ethosuximide#
- Mesuximide
- Phensuximide; Gabapentinoids: Gabapentin
- Pregabalin; Others: Lamotrigine
- Topiramate
- Zonisamide
|
|
| Potassium openers |
|
|
|
| Others |
| CA inhibitors |
- Sulfonamides: Acetazolamide
- Ethoxzolamide
- Sultiame
- Topiramate
- Zonisamide
|
|
| Others |
- Beclamide
- Brivaracetam
- Levetiracetam
- Perampanel
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|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
|
|
GABAA receptor positive allosteric modulators
|
|
| Alcohols |
- Brometone
- Butanol
- Chloralodol
- Chlorobutanol (cloretone)
- Ethanol (drinking alcohol)
- 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
- CP-1414S
- 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
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|
| Benzodiazepines |
|
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| Carbamates |
- Carisbamate
- Carisoprodol
- Clocental
- Cyclarbamate
- Difebarbamate
- Emylcamate
- Ethinamate
- Febarbamate
- Felbamate
- Hexapropymate
- Lorbamate
- Mebutamate
- Meprobamate
- Nisobamate
- Pentabamate
- Phenprobamate
- Procymate
- Styramate
- Tetrabamate
- Tybamate
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| Flavonoids |
- 6-Methylapigenin
- Ampelopsin (dihydromyricetin)
- Apigenin
- Baicalein
- Baicalin
- Catechin
- EGC
- EGCG
- Hispidulin
- Linarin
- Luteolin
- Rc-OMe
- Skullcap constituents (e.g., baicalin)
- Wogonin
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|
| 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
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|
| Monoureides |
- Acecarbromal
- Apronal (apronalide)
- Bromisoval
- Carbromal
- Capuride
- Ectylurea
|
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| Neuroactive steroids |
- Acebrochol
- Allopregnanolone
- Alfadolone
- Alfaxalone
- 3α-Androstanediol
- Androstenol
- Androsterone
- Cholesterol
- DHDOC
- 3α-DHP
- 5α-DHP
- 5β-DHP
- Etiocholanolone
- Ganaxolone
- Hydroxydione
- Minaxolone
- Org 20599
- Org 21465
- Pregnanolone (eltanolone)
- Progesterone
- Renanolone
- SAGE-217
- SAGE-689
- THDOC
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|
| Nonbenzodiazepines |
- β-Carbolines: Abecarnil
- Gedocarnil
- Harmane
- SL-651,498
- ZK-93423; 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
- 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
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|
| 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
- SAGE-547
- 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 PAMs: MRK-409 (MK-0343)
- TCS-1105
- TCS-1205
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|
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See also: GABAergics
|
|
English Journal
- How did phenobarbital's chemical structure affect the development of subsequent antiepileptic drugs (AEDs)?
- Bialer M.SourceSchool of Pharmacy, Institute for Drug Research, Faculty of Medicine, and David R. Bloom Center for Pharmacy, Faculty of Medicine, The Hebrew University of Jerusalem, Jerusalem, Israel. bialer@md.huji.ac.il
- Epilepsia.Epilepsia.2012 Dec;53 Suppl 8:3-11. doi: 10.1111/epi.12024.
- Phenobarbital has been in clinical use as an antiepileptic drug (AED) since 1912. The initial clinical success of phenobarbital and other barbiturates affected the design of subsequent AEDs (e.g., phenytoin, primidone, ethosuximide), developed between 1938 and 1962, the chemical structures of which
- PMID 23205958
- Allyl m-trifluoromethyldiazirine mephobarbital: an unusually potent enantioselective and photoreactive barbiturate general anesthetic.
- Savechenkov PY, Zhang X, Chiara DC, Stewart DS, Ge R, Zhou X, Raines DE, Cohen JB, Forman SA, Miller KW, Bruzik KS.SourceDepartment of Anesthesia, Critical Care and Pain Medicine, Massachusetts General Hospital, 32 Fruit Street, Boston, MA 02114, USA.
- Journal of medicinal chemistry.J Med Chem.2012 Jul 26;55(14):6554-65. doi: 10.1021/jm300631e. Epub 2012 Jul 17.
- We synthesized 5-allyl-1-methyl-5-(m-trifluoromethyl-diazirynylphenyl)barbituric acid (14), a trifluoromethyldiazirine-containing derivative of general anesthetic mephobarbital, separated the racemic mixture into enantiomers by chiral chromatography, and determined the configuration of the (+)-enant
- PMID 22734650
- The antiepileptic drug mephobarbital is not transported by P-glycoprotein or multidrug resistance protein 1 at the blood-brain barrier: a positron emission tomography study.
- Mairinger S, Bankstahl JP, Kuntner C, Römermann K, Bankstahl M, Wanek T, Stanek J, Löscher W, Müller M, Erker T, Langer O.SourceHealth & Environment Department, Molecular Medicine, AIT Austrian Institute of Technology GmbH, Seibersdorf, Austria.
- Epilepsy research.Epilepsy Res.2012 Jun;100(1-2):93-103. doi: 10.1016/j.eplepsyres.2012.01.012. Epub 2012 Feb 17.
- Aim of this study was to determine whether the carbon-11-labeled antiepileptic drug [(11)C]mephobarbital is a substrate of P-glycoprotein (Pgp) and can be used to assess Pgp function at the blood-brain barrier (BBB) with positron emission tomography (PET). We performed paired PET scans in rats, wild
- PMID 22342565
Japanese Journal
- Congenital Anomalies in the Offspring of Epileptic Mothers
- IE-16 Methylphenobarbital発売中止によるてんかん治療への影響 その2 : 薬物代謝の観点より
- IE-15 Methylphenobarbital発売中止によるてんかん治療への影響 その1 : 発作頻度と副作用について
Related Links
- Read more about the pharmacogenomics of methylphenobarbital on PharmGKB. ... Methylphenobarbital, a barbiturate, is used in combination with acetaminophen or aspirin and caffeine for its sedative and relaxant effects in the ...
- Methylphenobarbital - Get up-to-date information on Methylphenobarbital side effects, uses, dosage, overdose, pregnancy, alcohol and more. Learn more about Methylphenobarbital ... Tell your doctor about all the medicines you take ...
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