methimazole   Click here for help

GtoPdb Ligand ID: 6649

Synonyms: Tapazole® | Thiamazole®
Approved drug PDB Ligand Immunopharmacology Ligand
methimazole is an approved drug (FDA (1950))
Compound class: Synthetic organic
Comment: Methimazole is a thioamide antithyroid drug which acts as a thyroperoxidase inhibitor and reduces serum CXCL10 (a chemokine that participates in the self-perpetuation of the inflammatory processes in patients with autoimmune thyroid disease) from thyrocytes [1].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 1
Hydrogen bond donors 0
Rotatable bonds 0
Topological polar surface area 56.62
Molecular weight 114.03
XLogP 0.65
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES Cn1ccnc1S
Isomeric SMILES Cn1ccnc1S
InChI InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
InChI Key PMRYVIKBURPHAH-UHFFFAOYSA-N
References
1. Crescioli C, Cosmi L, Borgogni E, Santarlasci V, Gelmini S, Sottili M, Sarchielli E, Mazzinghi B, Francalanci M, Pezzatini A et al.. (2007)
Methimazole inhibits CXC chemokine ligand 10 secretion in human thyrocytes.
J Endocrinol, 195 (1): 145-55. [PMID:17911406]
2. Nakashima T, Taurog A, Riesco G. (1978)
Mechanism of action of thioureylene antithyroid drugs: factors affecting intrathyroidal metabolism of propylthiouracil and methimazole in rats.
Endocrinology, 103 (6): 2187-97. [PMID:748042]