Methimazole

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Methimazole
Systematic (IUPAC) name
1-methyl-3H-imidazole-2-thione
Clinical data
AHFS/Drugs.commonograph
MedlinePlusa682464
Pregnancy cat.D (US)
Legal statusPrescription Only (S4) (AU) -only (US)
RoutesOral
Pharmacokinetic data
Bioavailability93%
Protein bindingNone
MetabolismHepatic
Half-life5-6 hours
ExcretionRenal
Identifiers
CAS number60-56-0 YesY
ATC codeH03BB02
PubChemCID 1349907
DrugBankDB00763
ChemSpider1131173 YesY
UNII554Z48XN5E YesY
KEGGD00401 YesY
ChEBICHEBI:50673 YesY
ChEMBLCHEMBL1515 YesY
Chemical data
FormulaC4H6N2S 
Mol. mass114.17 g/mol
Physical data
Melt. point146 °C (295 °F)
Solubility in water275[1] mg/mL (20 °C)
 YesY (what is this?)  (verify)
 
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Methimazole
Systematic (IUPAC) name
1-methyl-3H-imidazole-2-thione
Clinical data
AHFS/Drugs.commonograph
MedlinePlusa682464
Pregnancy cat.D (US)
Legal statusPrescription Only (S4) (AU) -only (US)
RoutesOral
Pharmacokinetic data
Bioavailability93%
Protein bindingNone
MetabolismHepatic
Half-life5-6 hours
ExcretionRenal
Identifiers
CAS number60-56-0 YesY
ATC codeH03BB02
PubChemCID 1349907
DrugBankDB00763
ChemSpider1131173 YesY
UNII554Z48XN5E YesY
KEGGD00401 YesY
ChEBICHEBI:50673 YesY
ChEMBLCHEMBL1515 YesY
Chemical data
FormulaC4H6N2S 
Mol. mass114.17 g/mol
Physical data
Melt. point146 °C (295 °F)
Solubility in water275[1] mg/mL (20 °C)
 YesY (what is this?)  (verify)

Methimazole (also known as Tapazole or Thiamazole or MMI) is an antithyroid drug,[2] and part of the thioamide group. Like its counterpart propylthiouracil, a major side effect of treatment is agranulocytosis.

Indications[edit]

Methimazole is a drug used to treat hyperthyroidism, a condition that occurs when the thyroid gland begins to produce an excess of thyroid hormone. The drug may also be taken before thyroid surgery to lower thyroid hormone levels and minimize the effects of thyroid manipulation. Additionally, Methimazole is used in the veterinary setting to treat hyperthyroidism in cats.

Mechanism of action[edit]

Methimazole inhibits the enzyme thyroperoxidase, which normally acts in thyroid hormone synthesis by oxidizing the anion iodide (I-) to iodine (I0), facilitating iodine's addition to tyrosine residues on the hormone precursor thyroglobulin, a necessary step in the synthesis of triiodothyronine (T3) and thyroxine (T4).

It does not inhibit the action of the sodium-dependent iodide transporter located on follicular cells' basolateral membranes. Inhibition of this step requires competitive inhibitors such as perchlorate and thiocyanate.

It acts at CXCL10.[3]

Adverse effects[edit]

It is important to monitor any symptoms of fever or sore throat while taking methimazole; this could indicate the development of agranulocytosis, an uncommon but severe side effect resulting from a drop in the white blood cell count (to be specific, neutropenia, a deficiency of neutrophils). A complete blood count (CBC) with differential is performed to confirm the suspicion, in which case the drug is discontinued. Administration of recombinant human granulocyte colony-stimulating factor (rhG-CSF) may increase recovery.

Other known side effects include:

Drug interactions[edit]

Adverse effects may occur for individuals who:

See also[edit]

References[edit]

  1. ^ http://www.drugbank.ca/drugs/DB00763
  2. ^ Nakamura H, Noh JY, Itoh K, Fukata S, Miyauchi A, Hamada N (June 2007). "Comparison of methimazole and propylthiouracil in patients with hyperthyroidism caused by Graves' disease". The Journal of Clinical Endocrinology and Metabolism 92 (6): 2157–62. doi:10.1210/jc.2006-2135. PMID 17389704. 
  3. ^ Crescioli C, Cosmi L, Borgogni E, et al. (October 2007). "Methimazole inhibits CXC chemokine ligand 10 secretion in human thyrocytes". J. Endocrinol. 195 (1): 145–55. doi:10.1677/JOE-07-0240. PMID 17911406.