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Methazolamide

Methazolamide

  • CAT Number: A000538
  • CAS Number: 554-57-4
  • Molecular Formula: C5H8N4O3S2
  • Molecular Weight: 236.27
  • Purity: ≥95%
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Methazolamide( CAS 554-57-4) is a carbonic anhydrase inhibitor that is used as a diuretic and in the treatment of glaucoma. Methazolamide inhibits tumor-associated carbonic anhydrase IX (CAIX), which may result in increased cell death in hypoxic tumors. As a hypoxia-inducible transmembrane glycoprotein, CAIX catalyzes the rapid interconversion of carbon dioxide and water into carbonic acid, protons, and bicarbonate ions, helping to maintain acidification of the tumor microenvironment and enhance resistance to cytotoxic therapy in some hypoxic tumors.

Catalog Number A000538
CAS Number 554-57-4
Molecular Formula

C5H8N4O3S2

Purity 95%
Target Carbonic Anhydrase Inhibitor
Storage 3 years -20C powder
Overview of Clinical Research

<p>
Methazolamide is a&nbsp;<span style="font-family:arial,helvetica,sans-serif;"><span style="font-size:12px;"><span style="font-variant-ligatures: normal; orphans: 2; widows: 2;">carbonic anhydrase IX inhibitor developed by Cipla. The&nbsp;</span><span style="orphans: 2; widows: 2;">Pharmacodynamics data from preclinical trials in Pancreatic cancer presented at the 110th Annual Meeting of the American Association for Cancer Research (AACR-2019)</span></span></span></p>
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IUPAC Name N-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)acetamide
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)
InChIKey FLOSMHQXBMRNHR-UHFFFAOYSA-N
SMILES CC(=O)N=C1N(N=C(S1)S(=O)(=O)N)C
Reference

<br />
1:Neutron structure of human carbonic anhydrase II in complex with methazolamide: mapping the solvent and hydrogen-bonding patterns of an effective clinical drug. Aggarwal M, Kovalevsky AY, Velazquez H, Fisher SZ, Smith JC, McKenna R.IUCrJ. 2016 Jul 22;3(Pt 5):319-325. doi: 10.1107/S2052252516010514. eCollection 2016 Sep 1. PMID: 28461893 Free PMC Article<br />
2:CD8<sup>+</sup> T-cell activation by methazolamide causes methazolamide-induced Stevens-Johnson syndrome and toxic epidermal necrolysis. Jee YK, Kim S, Lee JM, Park HS, Kim SH.Clin Exp Allergy. 2017 Mar 13. doi: 10.1111/cea.12919. [Epub ahead of print] No abstract available. PMID: 28295713<br />
3:The metabolism of methazolamide in immortalized human keratinocytes, HaCaT cells. Sasabe T, Maeda S, Kishida K, Yamano M, Miwa Y, Sugiyama T.Drug Metab Lett. 2017 Jan 27. [Epub ahead of print] PMID: 28137210<br />
4:Methazolamide improves neurological behavior by inhibition of neuron apoptosis in subarachnoid hemorrhage mice. Li M, Wang W, Mai H, Zhang X, Wang J, Gao Y, Wang Y, Deng G, Gao L, Zhou S, Chen Q, Wang X.Sci Rep. 2016 Oct 12;6:35055. doi: 10.1038/srep35055. PMID: 27731352 Free PMC Article<br />
5:Methazolamide Plus Aminophylline Abrogates Hypoxia-Mediated Endurance Exercise Impairment. Scalzo RL, Binns SE, Klochak AL, Giordano GR, Paris HL, Sevits KJ, Beals JW, Biela LM, Larson DG, Luckasen GJ, Irwin D, Schroeder T, Hamilton KL, Bell C.High Alt Med Biol. 2015 Dec;16(4):331-42. doi: 10.1089/ham.2015.0066. PMID: 26680684<br />
6:The carbonic anhydrase inhibitor methazolamide prevents amyloid beta-induced mitochondrial dysfunction and caspase activation protecting neuronal and glial cells in vitro and in the mouse brain. Fossati S, Giannoni P, Solesio ME, Cocklin SL, Cabrera E, Ghiso J, Rostagno A.Neurobiol Dis. 2016 Feb;86:29-40. doi: 10.1016/j.nbd.2015.11.006. Epub 2015 Nov 12. PMID: 26581638 Free PMC Article<br />
7:Methazolamide-induced toxic epidermal necrolysis in a Chinese woman with HLA-B5901. Xu Y, Wu M, Sheng F, Sun Q.Indian J Ophthalmol. 2015 Jul;63(7):623-4. doi: 10.4103/0301-4738.167105. No abstract available. PMID: 26458485 Free PMC Article<br />
8:Toxic epidermal necrolysis induced by methazolamide in a Chinese-Korean man carrying HLA-B*59:01. Shu C, Shu D, Tie D, Yu M, Zhang R, Wang T, Dong Q, Sun Q, Mao X, Yan Y.Int J Dermatol. 2015 Nov;54(11):1242-5. doi: 10.1111/ijd.12651. Epub 2015 May 13. PMID: 25970075<br />
9:HLA-B*59:01: a marker for Stevens-Johnson syndrome/toxic epidermal necrolysis caused by methazolamide in Han Chinese. Yang F, Xuan J, Chen J, Zhong H, Luo H, Zhou P, Sun X, He L, Chen S, Cao Z, Luo X, Xing Q.Pharmacogenomics J. 2016 Feb;16(1):83-7. doi: 10.1038/tpj.2015.25. Epub 2015 Apr 28. PMID: 25918017<br />
10:Efficacy and safety of oral methazolamide in patients with type 2 diabetes: a 24-week, placebo-controlled, double-blind study. Simpson RW, Nicholson GC, Proietto J, Sarah A, Sanders KM, Phillips G, Chambers J, MacGinley R, Orford N, Walder K, Krippner G, Skoff K, Wacher VJ.Diabetes Care. 2014 Nov;37(11):3121-3. doi: 10.2337/dc14-1038. Epub 2014 Aug 14. PMID: 25125506

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