methazolamide   Click here for help

GtoPdb Ligand ID: 6828

Synonyms: methenamide | Neptazane®
Approved drug
methazolamide is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: Inhibits carbonic anhydrases. This compound is also represented on ChEMBL by the entry with ID CHEMBL19.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 2
Topological polar surface area 144.03
Molecular weight 236
XLogP -0.98
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES CC(=O)N=c1sc(nn1C)S(=O)(=O)N
Isomeric SMILES CC(=O)N=c1sc(nn1C)S(=O)(=O)N
InChI InChI=1S/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12)
InChI Key FLOSMHQXBMRNHR-UHFFFAOYSA-N
References
1. Nishimori I, Vullo D, Innocenti A, Scozzafava A, Mastrolorenzo A, Supuran CT. (2005)
Carbonic anhydrase inhibitors: inhibition of the transmembrane isozyme XIV with sulfonamides.
Bioorg. Med. Chem. Lett., 15 (17): 3828-33. [PMID:16039848]
2. Sethi KK, Vullo D, Verma SM, Tanç M, Carta F, Supuran CT. (2013)
Carbonic anhydrase inhibitors: synthesis and inhibition of the human carbonic anhydrase isoforms I, II, VII, IX and XII with benzene sulfonamides incorporating 4,5,6,7-tetrabromophthalimide moiety.
Bioorg. Med. Chem., 21 (19): 5973-82. [PMID:23965175]
3. Vullo D, Innocenti A, Nishimori I, Pastorek J, Scozzafava A, Pastoreková S, Supuran CT. (2005)
Carbonic anhydrase inhibitors. Inhibition of the transmembrane isozyme XII with sulfonamides-a new target for the design of antitumor and antiglaucoma drugs?.
Bioorg. Med. Chem. Lett., 15 (4): 963-9. [PMID:15686894]