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- a toxic anticonvulsant drug (trade name Mesantoin) used in the treatment of epilepsy when less toxic anticonvulsants have been ineffective (同)Mesantoin
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2016/07/20 22:29:18」(JST)
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Mephenytoin
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Systematic (IUPAC) name |
5-ethyl-3-methyl-5-phenyl-imidazolidine-2,4-dione
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Clinical data |
AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
MedlinePlus |
a611020 |
Pregnancy
category |
- US: C (Risk not ruled out)
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Routes of
administration |
Oral |
Pharmacokinetic data |
Biological half-life |
7 hours |
Identifiers |
CAS Number |
50-12-4 Y |
ATC code |
N03AB04 (WHO) |
PubChem |
CID 4060 |
IUPHAR/BPS |
7223 |
DrugBank |
DB00532 Y |
ChemSpider |
3920 Y |
UNII |
R420KW629U Y |
KEGG |
D00375 Y |
ChEMBL |
CHEMBL861 Y |
Chemical data |
Formula |
C12H14N2O2 |
Molar mass |
218.252 |
SMILES
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O=C2N(C(=O)NC2(c1ccccc1)CC)C
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InChI
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InChI=1S/C12H14N2O2/c1-3-12(9-7-5-4-6-8-9)10(15)14(2)11(16)13-12/h4-8H,3H2,1-2H3,(H,13,16) Y
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Key:GMHKMTDVRCWUDX-UHFFFAOYSA-N Y
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(verify) |
Mephenytoin (marketed as Mesantoin by Novartis) is a hydantoin, used as an anticonvulsant. It was introduced approximately 10 years after phenytoin, in the late 1940s. The significant metabolite of mephenytoin is nirvanol (5-ethyl-5-phenylhydantoin), which was the first hydantoin (briefly used as a hypnotic). However, nirvanol is quite toxic and mephenytoin was only considered after other less toxic anticonvulsants had failed. It can cause potentially fatal blood dyscrasia in 1% of patients.
Mephenytoin is no longer available in the US or the UK. It is still studied largely because of its interesting hydroxylation polymorphism.
References
- The Treatment of Epilepsy edited by S. D. Shorvon, David R. Fish, Emilio Perucca, W. Edwin Dodson. Blackwell Publishing. 2004. ISBN 0-632-06046-8
- The Medical Treatment of Epilepsy by Stanley R Resor. Published by Marcel Dekker (1991). ISBN 0-8247-8549-5.
- The Comparative Toxicogenomics Database: Mephenytoin
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
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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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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
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Calcium blockers |
- Oxazolidinediones: Ethadione
- Paramethadione
- Trimethadione; Succinimides: Ethosuximide#
- Mesuximide
- Phensuximide; Gabapentinoids: Gabapentin
- Pregabalin; Others: Lamotrigine
- Topiramate
- Zonisamide
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Potassium openers |
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Others |
CA inhibitors |
- Sulfonamides: Acetazolamide
- Ethoxzolamide
- Sultiame
- Topiramate
- Zonisamide
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Others |
- Beclamide
- Brivaracetam
- Levetiracetam
- Perampanel
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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UpToDate Contents
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English Journal
- Cytochrome P450 metabolic activities in the small intestine of cynomolgus macaques bred in Cambodia, China, and Indonesia.
- Nakanishi Y, Yamashita H, Yoshikawa T, Tominaga T, Nojiri K, Sunaga Y, Muneoka A, Iwasaki K, Utoh M, Nakamura C, Yamazaki H, Uno Y.SourcePharmacokinetics and Bioanalysis Center, Shin Nippon Biomedical Laboratories, Ltd.
- Drug metabolism and pharmacokinetics.Drug Metab Pharmacokinet.2013 May 7. [Epub ahead of print]
- Cynomolgus macaques, used in drug metabolism studies due to their evolutionary closeness to humans, are mainly bred in Asian countries, including Cambodia, China, and Indonesia. Cytochromes P450 (P450s) are important drug-metabolizing enzymes, present in liver and small intestine, major drug met
- PMID 23648676
- Predicted metabolic drug clearance with increasing adult age.
- Polasek TM, Patel F, Jensen BP, Sorich MJ, Wiese MD, Doogue MP.SourceDepartment of Clinical Pharmacology, Flinders University and Flinders Medical Centre, Adelaide, SA, Australia. tom.polasek@flinders.edu.au
- British journal of clinical pharmacology.Br J Clin Pharmacol.2013 Apr;75(4):1019-28. doi: 10.1111/j.1365-2125.2012.04446.x.
- AIM: To determine the effect of increasing adult age on predicted metabolic drug clearance.METHOD: Predicted metabolic drug clearances (CLPT ) were determined using in vitro-in vivo extrapolation coupled with physiological-based pharmacokinetic modelling and simulation (IVIVE-PBPK) in Simcyp®. Simu
- PMID 22924488
- In vitro metabolism of obovatol and its effect on cytochrome P450 enzyme activities in human liver microsomes.
- Joo J, Lee D, Wu Z, Shin JH, Lee HS, Kwon BM, Huh TL, Kim YW, Lee SJ, Kim TW, Lee T, Liu KH.SourceCollege of Pharmacy and Research Institute of Pharmaceutical Sciences, Kyungpook National University, Daegu, Korea.
- Biopharmaceutics & drug disposition.Biopharm Drug Dispos.2013 Feb 28. doi: 10.1002/bdd.1837. [Epub ahead of print]
- Obovatol, a major constituent of the leaves of Magnolia obovata Thunb, is known to inhibit nuclear factor-κB activity and arachidonic acid-induced platelet aggregation. This study was performed to identify the metabolites of obovatol in human liver microsomes. Human liver microsomes incubated with
- PMID 23446989
Japanese Journal
- Identification and Characterization of CYP2C18 in Cynomolgus Macaque (Macaca fascicularis)
- UNO Yasuhiro,MATSUNO Kiyomi,NAKAMURA Chika,UTOH Masahiro,YAMAZAKI Hiroshi
- Journal of Veterinary Medical Science advpub(0), 0911170038, 2010
- … Moreover, the metabolic assay using cynomolgus CYP2C18 protein heterologously expressed in Escherichia coli revealed its activity toward S-mephenytoin 4’-hydroxylation. …
- NAID 130000134522
- Effect of Cyclosporine and Tacrolimus on Cytochrome P450 Activities in Human Liver Microsomes
- 丹羽 俊朗,山本 幸子,斎藤 美穂,白神 歳文,高木 明
- 藥學雜誌 127(1), 209-216, 2007-01-01
- … The effects of cyclosporine and tacrolimus on cytochrome P450 (CYP) 1A2-mediated 7-ethoxyresorufin O-deethylation, CYP2C9-mediated tolbutamide hydroxylation, CYP2C19-mediated S-mephenytoin 4'-hydroxylation, CYP2D6-mediated debrisoquine 4-hydroxylation, CYP2E1-mediated chlorzoxazone 6-hydroxylation, CYP3A4-mediated nifedipine oxidation, and CYP3A4-mediated testosterone 6β-hydroxylation activities in human liver microsomes were compared. …
- NAID 110006155027
Related Links
- Read more about the pharmacogenomics of mephenytoin on PharmGKB. ... The table below contains information about pharmacogenomic variants on PharmGKB. Please follow the link in the "Variant" column for more ...
- Thesaurus Antonyms Related Words Synonyms Legend: Noun 1. mephenytoin - a toxic anticonvulsant drug (trade name Mesantoin) used in the treatment of epilepsy when less toxic anticonvulsants have been ineffective Mesantoin ...
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