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MedKoo Cat#: 464488 | Name: Methazolamide-d6
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Description:

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

Methazolamide-d6 is intended for use as an internal standard for the quantification of methazolamide by GC- or LC-MS. Methazolamide is a carbonic anhydrase inhibitor. It reduces intraocular pressure and cerebrospinal fluid flow in a rat model of glaucoma. Methazolamide reduces electroshock-induced seizures in rats with an ED50 value of 19.2 mg/kg. It also inhibits production of reactive oxygen species (ROS) in a primary cortical neuron (PCN) cellular model of subarachnoid hemorrhage (SAH) and reduces cerebral edema in a mouse model of SAH.3 Methazolamide is larvicidal, with a 50% larvicidal concentration (LC50) value of 724 ppm, but has no activity when administered in the diet to adult A. aegypti. Formulations containing methazolamide have been used in the treatment of glaucoma.

Chemical Structure

Methazolamide-d6
Methazolamide-d6
CAS#1795142-30-1

Theoretical Analysis

MedKoo Cat#: 464488

Name: Methazolamide-d6

CAS#: 1795142-30-1

Chemical Formula: C5H2D6N4O3S2

Exact Mass: 242.0414

Molecular Weight: 242.30

Elemental Analysis: C, 24.79; H, 5.82; N, 23.12; O, 19.81; S, 26.46

Price and Availability

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1mg USD 450.00 2 Weeks
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Synonym
Methazolamide-d6; Methazolamide d6;
IUPAC/Chemical Name
(Z)-N-(3-(methyl-d3)-5-sulfamoyl-1,3,4-thiadiazol-2(3H)-ylidene)acetamide-d3
InChi Key
FLOSMHQXBMRNHR-OXIQCEOHSA-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-/i1D3,2D3
SMILES Code
O=C(C([2H])([2H])[2H])/N=C1SC(S(N)(=O)=O)=NN\1C([2H])([2H])[2H]
Appearance
Solid powder
Purity
>99% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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-d6 (L584601-d6) is the deuterium labeled Methazolamide. 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/

Preparing Stock Solutions

The following data is based on the product molecular weight 242.30 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: Drugs and Lactation Database (LactMed) [Internet]. Bethesda (MD): National Library of Medicine (US); 2006–. Methazolamide. 2020 Aug 17. PMID: 30000740. 2: Lu H, Zhang H, Jiang Y. Methazolamide in high-altitude illnesses. Eur J Pharm Sci. 2020 May 30;148:105326. doi: 10.1016/j.ejps.2020.105326. Epub 2020 Apr 3. PMID: 32251722. 3: Supuran CT. An update on drug interaction considerations in the therapeutic use of carbonic anhydrase inhibitors. Expert Opin Drug Metab Toxicol. 2020 Apr;16(4):297-307. doi: 10.1080/17425255.2020.1743679. Epub 2020 Mar 21. PMID: 32172611. 4: Ghorai S, Pulya S, Ghosh K, Panda P, Ghosh B, Gayen S. Structure-activity relationship of human carbonic anhydrase-II inhibitors: Detailed insight for future development as anti-glaucoma agents. Bioorg Chem. 2020 Jan;95:103557. doi: 10.1016/j.bioorg.2019.103557. Epub 2019 Dec 27. PMID: 31911296. 5: Popovic M, Chan C, Lattanzio N, El-Defrawy S, Schlenker MB. Comparative cost evaluation of brand name and generic ophthalmology medications in Ontario. Can J Ophthalmol. 2018 Apr;53(2):173-187. doi: 10.1016/j.jcjo.2017.08.003. Epub 2017 Sep 27. PMID: 29631831. 6: Linkuvienė V, Zubrienė A, Manakova E, Petrauskas V, Baranauskienė L, Zakšauskas A, Smirnov A, Gražulis S, Ladbury JE, Matulis D. Thermodynamic, kinetic, and structural parameterization of human carbonic anhydrase interactions toward enhanced inhibitor design. Q Rev Biophys. 2018 Jan;51:e10. doi: 10.1017/S0033583518000082. PMID: 30912486. 7: Bakthavatchalam M, Lai FHP, Rong SS, Ng DS, Brelen ME. Treatment of cystoid macular edema secondary to retinitis pigmentosa: a systematic review. Surv Ophthalmol. 2018 May-Jun;63(3):329-339. doi: 10.1016/j.survophthal.2017.09.009. Epub 2017 Oct 5. PMID: 28987613. 8: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Diuretics. 2017 Oct 2. PMID: 31644115. 9: LiverTox: Clinical and Research Information on Drug-Induced Liver Injury [Internet]. Bethesda (MD): National Institute of Diabetes and Digestive and Kidney Diseases; 2012–. Carbonic Anhydrase Inhibitors. 2017 Oct 2. PMID: 31643975. 10: Supuran CT. Legionella pneumophila Carbonic Anhydrases: Underexplored Antibacterial Drug Targets. Pathogens. 2016 Jun 16;5(2):44. doi: 10.3390/pathogens5020044. PMID: 27322334; PMCID: PMC4931395. 11: Supuran CT. Drug interaction considerations in the therapeutic use of carbonic anhydrase inhibitors. Expert Opin Drug Metab Toxicol. 2016;12(4):423-31. doi: 10.1517/17425255.2016.1154534. Epub 2016 Mar 3. PMID: 26878088. 12: Supuran CT. Acetazolamide for the treatment of idiopathic intracranial hypertension. Expert Rev Neurother. 2015;15(8):851-6. doi: 10.1586/14737175.2015.1066675. Epub 2015 Jul 7. PMID: 26154918. 13: Murphy RM, Bakir B, O'Brien C, Wiggs JL, Pasquale LR. Drug-induced Bilateral Secondary Angle-Closure Glaucoma: A Literature Synthesis. J Glaucoma. 2016 Feb;25(2):e99-105. doi: 10.1097/IJG.0000000000000270. PMID: 25943730. 14: 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. PMID: 24611687. 15: Scozzafava A, Supuran CT. Glaucoma and the applications of carbonic anhydrase inhibitors. Subcell Biochem. 2014;75:349-59. doi: 10.1007/978-94-007-7359-2_17. PMID: 24146387. 16: Masini E, Carta F, Scozzafava A, Supuran CT. Antiglaucoma carbonic anhydrase inhibitors: a patent review. Expert Opin Ther Pat. 2013;23(6):705-16. doi: 10.1517/13543776.2013.794788. Epub 2013 Apr 30. PMID: 23627893. 17: Aggarwal M, Kondeti B, McKenna R. Anticonvulsant/antiepileptic carbonic anhydrase inhibitors: a patent review. Expert Opin Ther Pat. 2013;23(6):717-24. doi: 10.1517/13543776.2013.782394. Epub 2013 Mar 21. PMID: 23514045. 18: Isik S, Guler OO, Kockar F, Aydin M, Arslan O, Supuran CT. Saccharomyces cerevisiae β-carbonic anhydrase: inhibition and activation studies. Curr Pharm Des. 2010;16(29):3327-36. doi: 10.2174/138161210793429878. PMID: 20819061. 19: Mincione F, Scozzafava A, Supuran CT. The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. doi: 10.2174/138161208783877866. PMID: 18336310. 20: Nishimori I, Onishi S, Takeuchi H, Supuran CT. The alpha and beta classes carbonic anhydrases from Helicobacter pylori as novel drug targets. Curr Pharm Des. 2008;14(7):622-30. doi: 10.2174/138161208783877875. PMID: 18336307.

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SR-302

SR-302