Tìm theo
Mephenytoin
Thuốc chống co giật, chống động kinh
Thuốc Gốc
Small Molecule
CAS: 50-12-4
ĐG : Physicians Total Care Inc. , http://www.physicianstotalcare.com
CTHH: C12H14N2O2
PTK: 218.2518
Mephenytoin is used for the treatment of refractory partial epilepsy. Mephenytoin is a solid. This compound belongs to the phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. Mephenytoin is known to target sodium channel protein type 5 subunit alpha. Cytochrome P450 2C19, Cytochrome P450 2C8, Cytochrome P450 2C9, Cytochrome P450 2B6, Cytochrome P450 1A2, and Cytochrome P450 2D6 are known to metabolize mephenytoin. Mephenytoin is a hydantoin-derivative anticonvulsant used to control various partial seizures. Mephenytoin and oxazolidinedione derivatives are associated with higher incidences of blood dyscrasias compared to other anticonvulsants. It is still studied largely because of its interesting hydroxylation polymorphism.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C12H14N2O2
Phân tử khối
218.2518
Monoisotopic mass
218.105527702
InChI
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)
InChI Key
InChIKey=GMHKMTDVRCWUDX-UHFFFAOYSA-N
IUPAC Name
5-ethyl-3-methyl-5-phenylimidazolidine-2,4-dione
Traditional IUPAC Name
mephenytoin
SMILES
CCC1(NC(=O)N(C)C1=O)C1=CC=CC=C1
Độ tan chảy
135 °C
Độ hòa tan
1270 mg/L
logP
1.69
logS
-2.4
pKa (strongest acidic)
11.18
pKa (Strongest Basic)
-8.1
PSA
49.41 Å2
Refractivity
59.54 m3·mol-1
Polarizability
22.67 Å3
Rotatable Bond Count
2
H Bond Acceptor Count
2
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
2
Bioavailability
1
Rule of Five
true
Ghose Filter
true
pKa
8.51
Dược Lực Học : Mephenytoin is an antiepileptic drug which can be useful in the treatment of epilepsy. The primary site of action appears to be the motor cortex where spread of seizure activity is inhibited. Possibly by promoting sodium efflux from neurons, mephenytoin tends to stabilize the threshold against hyperexcitability caused by excessive stimulation or environmental changes capable of reducing membrane sodium gradient. This includes the reduction of posttetanic potentiation at synapses. Loss of posttetanic potentiation prevents cortical seizure foci from detonating adjacent cortical areas. Mephenytoin reduces the maximal activity of brain stem centers responsible for the tonic phase of tonic-clonic (grand mal) seizures.
Cơ Chế Tác Dụng : Mephenytoin is used for the treatment of refractory partial epilepsy. Mephenytoin is a solid. This compound belongs to the phenylhydantoins. These are heterocyclic aromatic compounds containing an imiazolidinedione moiety substituted by a phenyl group. Mephenytoin is known to target sodium channel protein type 5 subunit alpha. Cytochrome P450 2C19, Cytochrome P450 2C8, Cytochrome P450 2C9, Cytochrome P450 2B6, Cytochrome P450 1A2, and Cytochrome P450 2D6 are known to metabolize mephenytoin. Mephenytoin is a hydantoin-derivative anticonvulsant used to control various partial seizures. Mephenytoin and oxazolidinedione derivatives are associated with higher incidences of blood dyscrasias compared to other anticonvulsants. It is still studied largely because of its interesting hydroxylation polymorphism. The mechanism of action of mephenytoin is not definitely known, but extensive research strongly suggests that its main mechanism is to block frequency-, use- and voltage-dependent neuronal sodium channels, and therefore limit repetitive firing of action potentials.
Dược Động Học :

▧ Volume of Distribution :
* 1.4 L/kg
▧ Half Life :
Approximately 7 hours
Chỉ Định : For the treatment of refractory partial epilepsy.
Tương Tác Thuốc :
  • Alprazolam Mephenytoin may increase the metabolism of alprazolam via CYP3A4.
  • Aminophylline Decreased effect of both products
  • Amiodarone Increases the effect of hydantoin
  • Aprepitant The CYP3A4 inducer, mephenytoin, may decrease the effect of aprepitant.
  • Betamethasone The enzyme inducer, mephenytoin, may decrease the effect of the corticosteroid, betamethasone.
  • Capecitabine Capecitabine increases the effect of hydantoin
  • Chloramphenicol Increases phenytoin, modifies chloramphenicol
  • Chlordiazepoxide Mephenytoin may increase the metabolism of chlordiazepoxide via CYP3A4.
  • Chlorphenamine The antihistamine increases the effect of hydantoin
  • Cimetidine Increases the effect of hydantoin
  • Ciprofloxacin Decreases the hydantoin effect
  • Clomifene The enzyme inducer, mephenytoin, decreases the effect of the hormone agent, clomifene.
  • Clorazepate Mephenytoin may increase the metabolism of clorazepate via CYP3A4.
  • Clozapine Hydantoin decreases the effect of clozapine
  • Conjugated Estrogens The enzyme inducer, mephenytoin, decreases the effect of the hormone agent, conjugated estrogens.
  • Cyclosporine The hydantoin decreases the effect of cyclosporine
  • Dexamethasone The enzyme inducer, mephenytoin, may decrease the effect of the corticosteroid, dexamethasone.
  • Diazepam Mephenytoin may increase the metabolism of diazepam via CYP3A4.
  • Diethylstilbestrol The enzyme inducer, mephenytoin, decreases the effect of the hormone agent, diethylstilbestrol.
  • Disopyramide The hydantoin decreases the effect of disopyramide
  • Disulfiram Increases the effect of phenytoin
  • Doxycycline The anticonvulsant, mephenytoin, decreases the effect of doxycycline.
  • Estradiol The enzyme inducer, mephenytoin, decreases the effect of the hormone agent, estradiol.
  • Ethinyl Estradiol This product may cause a slight decrease of contraceptive effect
  • Felbamate Increased phenytoin levels and decreased felbamate levels
  • Felodipine The hydantoin decreases the effect of felodipine
  • Fluconazole Increases the effect of hydantoin
  • Fludrocortisone The enzyme inducer, mephenytoin, may decrease the effect of the corticosteroid, fludrocortisone.
  • Fluorouracil Fluorouracil increases the effect of hydantoin
  • Fluoxetine Fluoxetine increases the effect of phenytoin
  • Flurazepam Mephenytoin may increase the metabolism of flurazepam via CYP3A4.
  • Fluvoxamine Increases the effect of hydantoin
  • Folic Acid Folic acid decreases the levels of hydantoin
  • Furosemide The hydantoin decreases the effect of furosemide
  • Gabapentin Increases the effect of hydantoin
  • Gefitinib The CYP3A4 inducer, mephenytoin, may decrease the serum concentration and therapeutic effects of gefitinib.
  • Hydrocortisone The enzyme inducer, mephenytoin, may decrease the effect of the corticosteroid, hydrocortisone.
  • Imatinib The hydantoin decreases the levels of imatinib
  • Isoniazid Isoniazid increases the effect of phenytoin in 20% of patients
  • Itraconazole Phenytoin decreases the effect of itraconazole
  • Lamotrigine Phenytoin may reduce levels of lamotrigine
  • Levonorgestrel Phenytoin decreases the contraceptive effect
  • Mebendazole The hydantoin decreases the efficiency of mebendazole
  • Medroxyprogesterone Acetate The enzyme inducer, mephenytoin, decreases the effect of the hormone agent, medroxyprogesterone.
  • Megestrol acetate The enzyme inducer, mephenytoin, decreases the effect of the hormone agent, megestrol.
  • Methadone The hydantoin decreases the effect of methadone
  • Methotrexate The antineoplasic agent decreases the effect of hydantoin
  • Methoxsalen The hydantoin decreases the effect of psoralene
  • Mexiletine The hydantoin decreases the effect of mexiletine
  • Midazolam Mephenytoin may increase the metabolism of midazolam via CYP3A4.
  • Mirtazapine The hydantoins may reduce mirtazapine plasma concentrations and pharmacological effects
  • Norethindrone This product may cause a slight decrease of contraceptive effect
  • Omeprazole Omeprazole increases the effect of hydantoin
  • Oxcarbazepine Oxcarbazepine increases the effect of hydantoin
  • Oxtriphylline Decreased effect of both products
  • Oxyphenbutazone The NSAID, oxyphenbutazone, may increase the hydantoin effect of mephenytoin.
  • Phenylbutazone The NSAID, phenylbutazone, may increase the hydantoin effect of mephenytoin.
  • Prednisolone The enzyme inducer, mephenytoin, may decrease the effect of the corticosteroid, prednisolone.
  • Prednisone The enzyme inducer, mephenytoin, may decrease the effect of the corticosteroid, prednisone.
  • Quetiapine Phenytoin decreases the effect of quetiapine
  • Rifampicin Rifampin decreases the effect of the hydantoin
  • Theophylline Decreased effect of both products
  • Ticlopidine Ticlopidine increases the effect of hydantoin
  • Triamcinolone The enzyme inducer, mephenytoin, may decrease the effect of the corticosteroid, triamcinolone.
  • Triazolam Mephenytoin may increase the metabolism of triazolam via CYP3A4.
Dữ Kiện Thương Mại
Nhà Sản Xuất
  • Công ty : Novartis
    Sản phẩm biệt dược : Mesantoin
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00532
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=4060
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508677
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00375
ChemSpider
http://www.chemspider.com/Chemical-Structure.3920.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0078-0052-05
PharmGKB
http://www.pharmgkb.org/drug/PA450373
Wikipedia
http://en.wikipedia.org/wiki/Mephenytoin
Drugs.com
http://www.drugs.com/mtm/mephenytoin.html
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