Thiamazole

Thiamazole
Clinical data
Trade names Tapazole, others
Synonyms thiamazole (INN, BAN); methimazole (USAN); MMI
AHFS/Drugs.com Monograph
MedlinePlus a682464
Pregnancy
category
  • D (US)
Routes of
administration		 by mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 93%
Protein binding None
Metabolism Liver
Elimination half-life 5-6 hours
Excretion Kidney
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.000.439 Edit this at Wikidata
Chemical and physical data
Formula C4H6N2S
Molar mass 114.17 g/mol
3D model (JSmol)
Melting point 146 °C (295 °F)
Solubility in water 275[1] mg/mL (20 °C)
  (verify)

Thiamazole, also known as methimazole, is an antithyroid drug,[2] and part of the thioamide group. Like its counterpart propylthiouracil, possible major side effects of treatment include agranulocytosis and liver inflammation.

Medical uses

Thiamazole is a drug used to treat hyperthyroidism such as in Graves' disease, 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, thiamazole is used in the veterinary setting to treat hyperthyroidism in cats.

Adverse effects

It is important to monitor any symptoms of fever or sore throat while taking thiamazole; 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.[3] Administration of recombinant human granulocyte colony-stimulating factor (rhG-CSF) may increase recovery.

Other known side effects include:

Drug interactions

Adverse effects may occur for individuals who:

  • Take anticoagulants ('blood thinners') such as warfarin (Coumadin), diabetes medications, digoxin (Lanoxin), theophylline (Theobid, Theo-Dur), and vitamins
  • Have ever had any blood disease, such as decreased white blood cells (leukopenia), decreased platelets (thrombocytopenia) or aplastic anemia, or liver disease (hepatitis, jaundice)
  • Are pregnant, or going to become pregnant, or are breastfeeding.

Mechanism of action

Thiamazole inhibits the enzyme thyroperoxidase, which normally acts in thyroid hormone synthesis by oxidizing the anion iodide (I−) to iodine (I2), hypoiodous acid (HOI), enzyme linked hypoiodate (EOI) 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.[4]

References

  1. ↑ "DrugBank: Methimazole (DB00763)". drugbank.ca. Retrieved 21 July 2015.
  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. ↑ Fumarola, A; Di Fiore, A; Dainelli, M; Grani, G; Calvanese, A (Nov 2010). "Medical treatment of hyperthyroidism: state of the art". Experimental and Clinical Endocrinology & Diabetes. 118 (10): 678–84. doi:10.1055/s-0030-1253420. PMID 20496313.
  4. ↑ 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.


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