Peringatan Keamanan

The oral LD50 of methimazole in rats is 2250 mg/kg.L8333 Signs and symptoms of methimazole overdose may include gastrointestinal distress, headache, fever, joint pain, pruritus, and edema. More serious adverse effects, such as aplastic anemia or agranulocytosis, may manifest within hours to days.L8336,L8339 Hepatitis, nephrotic syndrome, exfoliative dermatitis, and CNS effects such as neuropathy or CNS depression/stimulation are also potential, albeit less frequent, results of overdose.L8336,L8339

Management of overdose involves supportive treatment as dictated by the patient's status.L8336,L8339 This may involve monitoring of the patient's vital signs, blood gases, serum electrolytes, or bone marrow function as indicated.L8339

Methimazole

DB00763

small molecule approved

Deskripsi

Methimazole is a thionamide antithyroid agent that inhibits the synthesis of thyroid hormones.A184559,A184733,A184694 It was first introduced as an antithyroid agent in 1949A184502 and is now commonly used in the management of hyperthyroidism, particularly in those for whom more aggressive options such as surgery or radioactive iodine therapy are inappropriate.L8336,L8339

On a weight basis, methimazole is 10 times more potent than the other major antithyroid thionamide used in North America, propylthiouracil,L8339 and is the active metabolite of the pro-drug carbimazole, which is an antithyroid medication used in the United Kingdom and parts of the former British Commonwealth.A184733 Traditionally, methimazole has been preferentially used over propylthiouracil due to the risk of fulminant hepatotoxicity carried by the latter,A184757 with propylthiouracil being preferred in pregnancy due to a perceived lower risk of teratogenic effects. Despite documented teratogenic effects in its published labels,L8336,L8339 the true teratogenicity of methimazole appears to be unclearA184643,A184757,A184763 and its place in therapy may change in the future.

Struktur Molekul 2D

Berat 114.169
Wujud solid

Peta Jejaring Molekuler
Legenda: Obat • Target • Gen • Enzim • (Panah → menunjukkan arah efek / relasi) • Transporter • Carrier

Profil Farmakokinetik

Waktu Paruh (Half-Life) Following a single intravenous bolus injection of 10mg of methimazole, the t<sub>1/2</sub> of the distribution phase was 0.17 hours and the t<sub>1/2</sub> of the elimination phase was 5.3 hours.[A184499] Methimazole's primary active metabolite, 3-methyl-2-thiohydantoin, has a half-life approximately 3 times longer than its parent drug.[A184541] Renal impairment does not appear to alter the half-life of methimazole, but patients with hepatic impairment showed an increase in half-life roughly proportional to the severity of their impairment - moderate insufficiency resulted in a elimination t<sub>1/2</sub> of 7.1 hours, while severe insufficiency resulted in an elimination t<sub>1/2</sub> of 22.1 hours.[A184499] There does not appear to be any significant differences in half-life based on thyroid status (i.e. no difference between euthyroid and hyperthyroid patients).[A184499,A184502,A184514]
Volume Distribusi The apparent volume of distribution of methimazole has been reported as roughly 20 L.[A184541] Following oral administration, methimazole is highly concentrated in the thyroid gland - intrathyroidal methimazole levels are approximately 2 to 5 times higher than peak plasma levels, and remain high for 20 hours after ingestion.[A184559]
Klirens (Clearance) Following a single intravenous bolus injection of 10mg of methimazole, clearance was found to be 5.70 L/h.[A184499] Renal impairment does not appear to alter clearance of methimazole, but patients with hepatic impairment showed a reduction in clearance roughly proportional to the severity of their impairment - moderate insufficiency resulted in a clearance of 3.49 L/h, while severe insufficiency resulted in a clearance of 0.83 L/h.[A184499] There does not appear to be any significant differences in clearance based on thyroid status (i.e. no difference between euthyroid and hyperthyroid patients).[A184499,A184502,A184514]

Absorpsi

Absorption of methimazole after oral administration is rapid and extensive,A184514,A184541,A184499 with an absolute bioavailability of approximately 0.93A184499 and a Tmax ranging from 0.25 to 4.0 hours.A184514,A184499 Cmax is slightly, but not significantly, higher in hyperthyroid patients, and both Cmax and AUC are significantly affected by the oral dose administered.A184514

Metabolisme

Methimazole is rapidly and extensively metabolized by the liver, mainly via the CYP450 and FMO enzyme systems.A184571,A184574 Several metabolites have been identified, though the specific enzyme isoforms responsible for their formation are not entirely clear. One of the first methimazole metabolites identified, 3-methyl-2-thiohydantoin, may contribute to antithyroid activity - its antithyroid activity has been demonstrated in rats and may explain the prolonged duration of iodination inhibition following administration despite methimazole's relatively short half-life.A184541 A number of metabolites have been investigated as being the culprits behind methimazole-induced hepatotoxicity. Both glyoxal and N-methylthiourea have established cytotoxicity and are known metabolic products of methimazole's dihydrodiol intermediate. Sulfenic and sulfinic acid derivatives of methimazole are thought to be the ultimate toxicants responsible for hepatotoxicity, though their origin is unclear - they may arise from direct oxidation of methimazole via FMO, or from oxidation of N-methylthiourea further downstream in the metabolic process.A184571,A184574

Rute Eliminasi

Urinary excretion of unchanged methimazole has been reported to be between 7% and 12%. Elimination via feces appears to be limited, with a cumulative fecal excretion of 3% after administration of methimazole.A184514 Enterohepatic circulation also appears to play a role in the elimination of methimazole and its metabolites, as significant amounts of these substances are found in the bile post-administration.A184643

Interaksi Obat

1949 Data
Denosumab The risk or severity of adverse effects can be increased when Denosumab is combined with Methimazole.
Etanercept The risk or severity of adverse effects can be increased when Etanercept is combined with Methimazole.
Peginterferon alfa-2a The risk or severity of adverse effects can be increased when Peginterferon alfa-2a is combined with Methimazole.
Interferon alfa-n1 The risk or severity of adverse effects can be increased when Interferon alfa-n1 is combined with Methimazole.
Interferon alfa-n3 The risk or severity of adverse effects can be increased when Interferon alfa-n3 is combined with Methimazole.
Peginterferon alfa-2b The risk or severity of adverse effects can be increased when Peginterferon alfa-2b is combined with Methimazole.
Anakinra The risk or severity of adverse effects can be increased when Anakinra is combined with Methimazole.
Interferon gamma-1b The risk or severity of adverse effects can be increased when Interferon gamma-1b is combined with Methimazole.
Interferon alfa-2a The risk or severity of adverse effects can be increased when Interferon alfa-2a is combined with Methimazole.
Adalimumab The risk or severity of adverse effects can be increased when Adalimumab is combined with Methimazole.
Gemtuzumab ozogamicin The risk or severity of adverse effects can be increased when Gemtuzumab ozogamicin is combined with Methimazole.
Pegaspargase The risk or severity of adverse effects can be increased when Pegaspargase is combined with Methimazole.
Infliximab The risk or severity of adverse effects can be increased when Infliximab is combined with Methimazole.
Interferon beta-1b The risk or severity of adverse effects can be increased when Interferon beta-1b is combined with Methimazole.
Interferon alfacon-1 The risk or severity of adverse effects can be increased when Interferon alfacon-1 is combined with Methimazole.
Rituximab The risk or severity of adverse effects can be increased when Rituximab is combined with Methimazole.
Basiliximab The risk or severity of adverse effects can be increased when Basiliximab is combined with Methimazole.
Muromonab The risk or severity of adverse effects can be increased when Muromonab is combined with Methimazole.
Ibritumomab tiuxetan The risk or severity of adverse effects can be increased when Ibritumomab tiuxetan is combined with Methimazole.
Tositumomab The risk or severity of adverse effects can be increased when Tositumomab is combined with Methimazole.
Alemtuzumab The risk or severity of adverse effects can be increased when Alemtuzumab is combined with Methimazole.
Alefacept The risk or severity of adverse effects can be increased when Alefacept is combined with Methimazole.
Efalizumab The risk or severity of adverse effects can be increased when Efalizumab is combined with Methimazole.
Antithymocyte immunoglobulin (rabbit) The risk or severity of adverse effects can be increased when Antithymocyte immunoglobulin (rabbit) is combined with Methimazole.
Interferon alfa-2b The risk or severity of adverse effects can be increased when Interferon alfa-2b is combined with Methimazole.
Daclizumab The risk or severity of adverse effects can be increased when Daclizumab is combined with Methimazole.
Phenylalanine The risk or severity of adverse effects can be increased when Phenylalanine is combined with Methimazole.
Cladribine Methimazole may increase the immunosuppressive activities of Cladribine.
Carmustine The risk or severity of adverse effects can be increased when Carmustine is combined with Methimazole.
Amsacrine The risk or severity of adverse effects can be increased when Amsacrine is combined with Methimazole.
Bleomycin The risk or severity of adverse effects can be increased when Bleomycin is combined with Methimazole.
Chlorambucil The risk or severity of adverse effects can be increased when Chlorambucil is combined with Methimazole.
Raltitrexed The risk or severity of adverse effects can be increased when Raltitrexed is combined with Methimazole.
Mitomycin The risk or severity of adverse effects can be increased when Mitomycin is combined with Methimazole.
Floxuridine The risk or severity of adverse effects can be increased when Floxuridine is combined with Methimazole.
Indomethacin The risk or severity of adverse effects can be increased when Indomethacin is combined with Methimazole.
Tioguanine The risk or severity of adverse effects can be increased when Tioguanine is combined with Methimazole.
Dexrazoxane The risk or severity of adverse effects can be increased when Dexrazoxane is combined with Methimazole.
Streptozocin The risk or severity of adverse effects can be increased when Streptozocin is combined with Methimazole.
Trifluridine The risk or severity of adverse effects can be increased when Trifluridine is combined with Methimazole.
Gemcitabine The risk or severity of adverse effects can be increased when Gemcitabine is combined with Methimazole.
Epirubicin The risk or severity of adverse effects can be increased when Epirubicin is combined with Methimazole.
Chloramphenicol The risk or severity of adverse effects can be increased when Chloramphenicol is combined with Methimazole.
Lenalidomide The risk or severity of adverse effects can be increased when Lenalidomide is combined with Methimazole.
Altretamine The risk or severity of adverse effects can be increased when Altretamine is combined with Methimazole.
Cisplatin The risk or severity of adverse effects can be increased when Cisplatin is combined with Methimazole.
Oxaliplatin The risk or severity of adverse effects can be increased when Oxaliplatin is combined with Methimazole.
Propylthiouracil The risk or severity of adverse effects can be increased when Propylthiouracil is combined with Methimazole.
Pentostatin The risk or severity of adverse effects can be increased when Pentostatin is combined with Methimazole.
Linezolid The risk or severity of adverse effects can be increased when Linezolid is combined with Methimazole.
Clofarabine The risk or severity of adverse effects can be increased when Clofarabine is combined with Methimazole.
Pemetrexed The risk or severity of adverse effects can be increased when Pemetrexed is combined with Methimazole.
Sulfasalazine The risk or severity of adverse effects can be increased when Methimazole is combined with Sulfasalazine.
Dacarbazine The risk or severity of adverse effects can be increased when Methimazole is combined with Dacarbazine.
Temozolomide The risk or severity of adverse effects can be increased when Methimazole is combined with Temozolomide.
Penicillamine The risk or severity of adverse effects can be increased when Methimazole is combined with Penicillamine.
Mechlorethamine The risk or severity of adverse effects can be increased when Methimazole is combined with Mechlorethamine.
Azacitidine The risk or severity of adverse effects can be increased when Methimazole is combined with Azacitidine.
Carboplatin The risk or severity of adverse effects can be increased when Methimazole is combined with Carboplatin.
Dactinomycin The risk or severity of adverse effects can be increased when Methimazole is combined with Dactinomycin.
Azathioprine The risk or severity of adverse effects can be increased when Methimazole is combined with Azathioprine.
Hydroxyurea The risk or severity of adverse effects can be increased when Methimazole is combined with Hydroxyurea.
Mycophenolic acid The risk or severity of adverse effects can be increased when Methimazole is combined with Mycophenolic acid.
Topotecan The risk or severity of adverse effects can be increased when Methimazole is combined with Topotecan.
Thalidomide The metabolism of Thalidomide can be decreased when combined with Methimazole.
Melphalan The risk or severity of adverse effects can be increased when Methimazole is combined with Melphalan.
Fludarabine The risk or severity of adverse effects can be increased when Methimazole is combined with Fludarabine.
Flucytosine The risk or severity of adverse effects can be increased when Methimazole is combined with Flucytosine.
Procarbazine The risk or severity of adverse effects can be increased when Methimazole is combined with Procarbazine.
Arsenic trioxide The risk or severity of adverse effects can be increased when Methimazole is combined with Arsenic trioxide.
Idarubicin The risk or severity of adverse effects can be increased when Methimazole is combined with Idarubicin.
Mitoxantrone The risk or severity of adverse effects can be increased when Methimazole is combined with Mitoxantrone.
Lomustine The risk or severity of adverse effects can be increased when Methimazole is combined with Lomustine.
Eculizumab The risk or severity of adverse effects can be increased when Methimazole is combined with Eculizumab.
Decitabine The risk or severity of adverse effects can be increased when Methimazole is combined with Decitabine.
Nelarabine The risk or severity of adverse effects can be increased when Methimazole is combined with Nelarabine.
Abatacept The risk or severity of adverse effects can be increased when Methimazole is combined with Abatacept.
Stepronin The risk or severity of adverse effects can be increased when Methimazole is combined with Stepronin.
Castanospermine The risk or severity of adverse effects can be increased when Methimazole is combined with Castanospermine.
Vorinostat The risk or severity of adverse effects can be increased when Methimazole is combined with Vorinostat.
2-Methoxyethanol The risk or severity of adverse effects can be increased when Methimazole is combined with 2-Methoxyethanol.
Brequinar The risk or severity of adverse effects can be increased when Methimazole is combined with Brequinar.
Pirfenidone The risk or severity of adverse effects can be increased when Methimazole is combined with Pirfenidone.
Afelimomab The risk or severity of adverse effects can be increased when Methimazole is combined with Afelimomab.
Glatiramer The risk or severity of adverse effects can be increased when Methimazole is combined with Glatiramer.
Briakinumab The risk or severity of adverse effects can be increased when Methimazole is combined with Briakinumab.
Human interferon omega-1 The risk or severity of adverse effects can be increased when Methimazole is combined with Human interferon omega-1.
Canakinumab The risk or severity of adverse effects can be increased when Methimazole is combined with Canakinumab.
Tocilizumab The risk or severity of adverse effects can be increased when Methimazole is combined with Tocilizumab.
Rilonacept The risk or severity of adverse effects can be increased when Methimazole is combined with Rilonacept.
Mepolizumab The risk or severity of adverse effects can be increased when Methimazole is combined with Mepolizumab.
Abetimus The risk or severity of adverse effects can be increased when Methimazole is combined with Abetimus.
Golimumab The risk or severity of adverse effects can be increased when Methimazole is combined with Golimumab.
Belatacept The risk or severity of adverse effects can be increased when Methimazole is combined with Belatacept.
Bendamustine The risk or severity of adverse effects can be increased when Methimazole is combined with Bendamustine.
Pralatrexate The risk or severity of adverse effects can be increased when Methimazole is combined with Pralatrexate.
Wortmannin The risk or severity of adverse effects can be increased when Methimazole is combined with Wortmannin.
Eribulin The risk or severity of adverse effects can be increased when Methimazole is combined with Eribulin.
Belimumab The risk or severity of adverse effects can be increased when Methimazole is combined with Belimumab.
Teriflunomide The risk or severity of adverse effects can be increased when Methimazole is combined with Teriflunomide.

Target Protein

Thyroid peroxidase TPO

Referensi & Sumber

Synthesis reference: ?????????, "Methimazole synthesizing and purifying method." Chinese Patent CN107162983A, published September, 2017.
Artikel (PubMed)
  • PMID: 4042519
    Jansson R, Lindstrom B, Dahlberg PA: Pharmacokinetic properties and bioavailability of methimazole. Clin Pharmacokinet. 1985 Sep-Oct;10(5):443-50. doi: 10.2165/00003088-198510050-00006.
  • PMID: 6546390
    Cooper DS, Bode HH, Nath B, Saxe V, Maloof F, Ridgway EC: Methimazole pharmacology in man: studies using a newly developed radioimmunoassay for methimazole. J Clin Endocrinol Metab. 1984 Mar;58(3):473-9. doi: 10.1210/jcem-58-3-473.
  • PMID: 3830069
    Okamura Y, Shigemasa C, Tatsuhara T: Pharmacokinetics of methimazole in normal subjects and hyperthyroid patients. Endocrinol Jpn. 1986 Oct;33(5):605-15. doi: 10.1507/endocrj1954.33.605.
  • PMID: 27615550
    Okosieme OE, Lazarus JH: Current trends in antithyroid drug treatment of Graves' disease. Expert Opin Pharmacother. 2016 Oct;17(15):2005-17. doi: 10.1080/14656566.2016.1232388. Epub 2016 Sep 14.
  • PMID: 7356900
    Skellern GG, Knight BI, Low CK, Alexander WD, McLarty DG, Kalk WJ: The pharmacokinetics of methimazole after oral administration of carbimazole and methimazole, in hyperthyroid patients. Br J Clin Pharmacol. 1980 Feb;9(2):137-43. doi: 10.1111/j.1365-2125.1980.tb05823.x.
  • PMID: 30320502
    Burch HB, Cooper DS: ANNIVERSARY REVIEW: Antithyroid drug therapy: 70 years later Eur J Endocrinol. 2018 Oct 12;179(5):R261-R274. doi: 10.1530/EJE-18-0678.
  • PMID: 25789213
    Heidari R, Niknahad H, Jamshidzadeh A, Eghbal MA, Abdoli N: An overview on the proposed mechanisms of antithyroid drugs-induced liver injury. Adv Pharm Bull. 2015 Mar;5(1):1-11. doi: 10.5681/apb.2015.001. Epub 2015 Mar 5.
  • PMID: 10725113
    Mizutani T, Yoshida K, Murakami M, Shirai M, Kawazoe S: Evidence for the involvement of N-methylthiourea, a ring cleavage metabolite, in the hepatotoxicity of methimazole in glutathione-depleted mice: structure-toxicity and metabolic studies. Chem Res Toxicol. 2000 Mar;13(3):170-6.
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Contoh Produk & Brand

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