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MedKoo Cat#: 318200 | Name: Methazolamide
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Methazolamide 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.

Chemical Structure

Methazolamide
Methazolamide
CAS#554-57-4

Theoretical Analysis

MedKoo Cat#: 318200

Name: Methazolamide

CAS#: 554-57-4

Chemical Formula: C5H8N4O3S2

Exact Mass: 236.0038

Molecular Weight: 236.26

Elemental Analysis: C, 25.42; H, 3.41; N, 23.71; O, 20.31; S, 27.14

Price and Availability

Size Price Availability Quantity
5g USD 350.00 2 Weeks
10g USD 550.00 2 Weeks
25g USD 950.00 2 Weeks
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Synonym
Methazolamide; Neptazane; Methenamide; Neptazaneat; Naptazane; N Methylacetazolamide;N-Methylacetazolamide;
IUPAC/Chemical Name
N-(3-methyl-5-sulfamoyl-1,3,4-thiadiazol-2-ylidene)acetamide
InChi Key
FLOSMHQXBMRNHR-QPJJXVBHSA-N
InChi Code
InChI=1S/C5H8N4O3S2/c1-3(10)7-4-9(2)8-5(13-4)14(6,11)12/h1-2H3,(H2,6,11,12)/b7-4+
SMILES Code
CC(=O)N=C1N(N=C(S1)S(=O)(=O)N)C
Appearance
White to off-white crystalline powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Methazolamide (L584601) is a sulfonamide derivative used as a carbonic anhydrase inhibitor with a Ki of 14 nM for human carbonic anhydrase II.
In vitro activity:
MTZ prevented DNA fragmentation, CytC release and activation of caspase 9 and caspase 3 induced by Aβ in neuronal and glial cells in culture through the inhibition of mitochondrial hydrogen peroxide production. Reference: Neurobiol Dis. 2016 Feb;86:29-40. https://pubmed.ncbi.nlm.nih.gov/26581638/
In vivo activity:
In anesthetized spontaneously breathing rabbits (n = 7), this study measured simultaneously the CO(2) responses of tidal phrenic nerve activity, tidal transpulmonary pressure changes, and tidal volume before and after intravenous application of methazolamide at two mean (+/- SE) cumulative doses of 3.5 +/- 0.1 and 20.8 +/- 0.4 mg/kg. Similar to acetazolamide, low- and high-dose methazolamide enhanced baseline ventilation by 52 +/- 10% and 166 +/- 30%, respectively (P < 0.01) and lowered the base excess in a dose-dependent manner by up to 8.3 +/- 0.9 mmol/l (P < 0.001). Reference: Am J Physiol Regul Integr Comp Physiol. 2009 Sep;297(3):R648-54. https://pubmed.ncbi.nlm.nih.gov/19553495/
Solvent mg/mL mM comments
Solubility
DMSO 32.5 137.56
DMSO:PBS (pH 7.2) (1:3) 0.3 1.06
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 236.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Fossati S, Giannoni P, Solesio ME, Cocklin SL, Cabrera E, Ghiso J, Rostagno A. 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. Neurobiol Dis. 2016 Feb;86:29-40. doi: 10.1016/j.nbd.2015.11.006. Epub 2015 Nov 12. PMID: 26581638; PMCID: PMC4713307. 2. Chen X, Li Y, Yuan X, Yuan W, Li C, Zeng Y, Lian Y, Qiu X, Qin Y, Zhang G, Liu X, Luo C, Luo JD, Hou N. Methazolamide Attenuates the Development of Diabetic Cardiomyopathy by Promoting β-Catenin Degradation in Type 1 Diabetic Mice. Diabetes. 2022 Apr 1;71(4):795-811. doi: 10.2337/db21-0506. PMID: 35043173. 3. Kiwull-Schöne HF, Li Y, Kiwull PJ, Teppema LJ. Methazolamide does not impair respiratory work performance in anesthetized rabbits. Am J Physiol Regul Integr Comp Physiol. 2009 Sep;297(3):R648-54. doi: 10.1152/ajpregu.00134.2009. Epub 2009 Jun 24. PMID: 19553495.
In vitro protocol:
1. Fossati S, Giannoni P, Solesio ME, Cocklin SL, Cabrera E, Ghiso J, Rostagno A. 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. Neurobiol Dis. 2016 Feb;86:29-40. doi: 10.1016/j.nbd.2015.11.006. Epub 2015 Nov 12. PMID: 26581638; PMCID: PMC4713307.
In vivo protocol:
1. Chen X, Li Y, Yuan X, Yuan W, Li C, Zeng Y, Lian Y, Qiu X, Qin Y, Zhang G, Liu X, Luo C, Luo JD, Hou N. Methazolamide Attenuates the Development of Diabetic Cardiomyopathy by Promoting β-Catenin Degradation in Type 1 Diabetic Mice. Diabetes. 2022 Apr 1;71(4):795-811. doi: 10.2337/db21-0506. PMID: 35043173. 2. Kiwull-Schöne HF, Li Y, Kiwull PJ, Teppema LJ. Methazolamide does not impair respiratory work performance in anesthetized rabbits. Am J Physiol Regul Integr Comp Physiol. 2009 Sep;297(3):R648-54. doi: 10.1152/ajpregu.00134.2009. Epub 2009 Jun 24. PMID: 19553495.
1: Yang F, Xuan J, Chen J, Zhong H, Luo H, Zhou P, Sun X, He L, Chen S, Cao Z, Luo X, Xing Q. HLA-B*59:01: a marker for Stevens-Johnson syndrome/toxic epidermal necrolysis caused by methazolamide in Han Chinese. Pharmacogenomics J. 2016 Feb;16(1):83-7. doi: 10.1038/tpj.2015.25. Epub 2015 Apr 28. PubMed PMID: 25918017. 2: Fossati S, Giannoni P, Solesio ME, Cocklin SL, Cabrera E, Ghiso J, Rostagno A. 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. Neurobiol Dis. 2016 Feb;86:29-40. doi: 10.1016/j.nbd.2015.11.006. Epub 2015 Nov 12. PubMed PMID: 26581638; PubMed Central PMCID: PMC4713307. 3: Shu C, Shu D, Tie D, Yu M, Zhang R, Wang T, Dong Q, Sun Q, Mao X, Yan Y. Toxic epidermal necrolysis induced by methazolamide in a Chinese-Korean man carrying HLA-B*59:01. Int J Dermatol. 2015 Nov;54(11):1242-5. doi: 10.1111/ijd.12651. Epub 2015 May 13. PubMed PMID: 25970075. 4: 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. Methazolamide Plus Aminophylline Abrogates Hypoxia-Mediated Endurance Exercise Impairment. High Alt Med Biol. 2015 Dec;16(4):331-42. doi: 10.1089/ham.2015.0066. PubMed PMID: 26680684. 5: Xu Y, Wu M, Sheng F, Sun Q. Methazolamide-induced toxic epidermal necrolysis in a Chinese woman with HLA-B5901. Indian J Ophthalmol. 2015 Jul;63(7):623-4. doi: 10.4103/0301-4738.167105. PubMed PMID: 26458485; PubMed Central PMCID: PMC4652259. 6: 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. Efficacy and safety of oral methazolamide in patients with type 2 diabetes: a 24-week, placebo-controlled, double-blind study. Diabetes Care. 2014 Nov;37(11):3121-3. doi: 10.2337/dc14-1038. Epub 2014 Aug 14. PubMed PMID: 25125506. 7: Wang F, Chen L, Zhang D, Jiang S, Shi K, Huang Y, Li R, Xu Q. Methazolamide-loaded solid lipid nanoparticles modified with low-molecular weight chitosan for the treatment of glaucoma: vitro and vivo study. J Drug Target. 2014 Nov;22(9):849-58. doi: 10.3109/1061186X.2014.939983. Epub 2014 Jul 21. PubMed PMID: 25045926. 8: Wang F, Chen L, Jiang S, He J, Zhang X, Peng J, Xu Q, Li R. Optimization of methazolamide-loaded solid lipid nanoparticles for ophthalmic delivery using Box-Behnken design. J Liposome Res. 2014 Sep;24(3):171-81. doi: 10.3109/08982104.2014.891231. Epub 2014 Mar 10. Review. PubMed PMID: 24611687. 9: Jiang S, Wang F, Zhu S, Zhang X, Guo Z, Li R, Xu Q. Preformulation study of methazolamide for topical ophthalmic delivery: physicochemical properties and degradation kinetics in aqueous solutions. Int J Pharm. 2013 May 20;448(2):390-3. doi: 10.1016/j.ijpharm.2013.03.018. Epub 2013 Mar 29. PubMed PMID: 23541985. 10: Aref AA, Sayyad FE, Ayres B, Lee RK. Acute bilateral angle closure glaucoma induced by methazolamide. Clin Ophthalmol. 2013;7:279-82. doi: 10.2147/OPTH.S41540. Epub 2013 Feb 11. PubMed PMID: 23430961; PubMed Central PMCID: PMC3573826. 11: Koo NK, Kim YC. A case of paclitaxel-induced maculopathy treated with methazolamide. Korean J Ophthalmol. 2012 Oct;26(5):394-7. doi: 10.3341/kjo.2012.26.5.394. Epub 2012 Sep 24. PubMed PMID: 23060729; PubMed Central PMCID: PMC3464326. 12: Kwon SJ, Park DH, Shin JP. Bilateral transient myopia, angle-closure glaucoma, and choroidal detachment induced by methazolamide. Jpn J Ophthalmol. 2012 Sep;56(5):515-7. doi: 10.1007/s10384-012-0159-y. Epub 2012 Jul 12. PubMed PMID: 22782646. 13: Konstantopoulos N, Molero JC, McGee SL, Spolding B, Connor T, de Vries M, Wanyonyi S, Fahey R, Morrison S, Swinton C, Jones S, Cooper A, Garcia-Guerra L, Foletta VC, Krippner G, Andrikopoulos S, Walder KR. Methazolamide is a new hepatic insulin sensitizer that lowers blood glucose in vivo. Diabetes. 2012 Aug;61(8):2146-54. doi: 10.2337/db11-0578. Epub 2012 May 14. PubMed PMID: 22586591; PubMed Central PMCID: PMC3402314. 14: Hassan MG, Emara KM, Mohamed HA, Abdel-Wadood HM, Ikeda R, Wada M, Kuroda N, Nakashima K. Determination of memantine in rat plasma by HPLC-fluorescence method and its application to study of the pharmacokinetic interaction between memantine and methazolamide. Biomed Chromatogr. 2012 Feb;26(2):214-9. doi: 10.1002/bmc.1648. Epub 2011 May 19. PubMed PMID: 21594878. 15: Youshia J, Kamel AO, El Shamy A, Mansour S. Design of cationic nanostructured heterolipid matrices for ocular delivery of methazolamide. Int J Nanomedicine. 2012;7:2483-96. doi: 10.2147/IJN.S28307. Epub 2012 May 17. PubMed PMID: 22679362; PubMed Central PMCID: PMC3367493. 16: Li R, Jiang S, Liu D, Bi X, Wang F, Zhang Q, Xu Q. A potential new therapeutic system for glaucoma: solid lipid nanoparticles containing methazolamide. J Microencapsul. 2011;28(2):134-41. doi: 10.3109/02652048.2010.539304. Epub 2010 Dec 10. PubMed PMID: 21142697. 17: Chang X, Yan X, Zhang Y. Treat ankylosing spondylitis with methazolamide. Int J Med Sci. 2011;8(5):413-9. Epub 2011 Jul 1. PubMed PMID: 21750646; PubMed Central PMCID: PMC3133847. 18: Kishida K, Yamamura N, Iwai Y, Sakamoto Y, Kuhara M, Sasabe T. The metabolism of methazolamide - identification of metabolites in guinea pig urine. Drug Metab Lett. 2011 Jan;5(1):45-54. PubMed PMID: 21198437. 19: Qian Y, Wang F, Li R, Zhang Q, Xu Q. Preparation and evaluation of in situ gelling ophthalmic drug delivery system for methazolamide. Drug Dev Ind Pharm. 2010 Nov;36(11):1340-7. doi: 10.3109/03639041003801893. PubMed PMID: 20849349. 20: Kim SH, Kim M, Lee KW, Kim SH, Kang HR, Park HW, Jee YK. HLA-B*5901 is strongly associated with methazolamide-induced Stevens-Johnson syndrome/toxic epidermal necrolysis. Pharmacogenomics. 2010 Jun;11(6):879-84. doi: 10.2217/pgs.10.54. PubMed PMID: 20504258.