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

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

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

Công ty : Physicians Total Care Inc.

Website : http://www.physicianstotalcare.com

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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