Methazolamide

Methazolamide
Clinical data
Other names	N-(3-Methyl-5-sulfamoyl-3H-1,3,4-thiadiazol-2-ylidene) ethanamide
AHFS/Drugs.com	Monograph
MedlinePlus	a601233
Routes of; administration	Oral
ATC code	S01EC05 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Protein binding	~55%
Elimination half-life	~14 hours
Identifiers
	IUPAC name N-[5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide;
CAS Number	554-57-4 ;
PubChem CID	4100;
IUPHAR/BPS	6828;
DrugBank	DB00703 ;
ChemSpider	3958 ;
UNII	W733B0S9SD;
KEGG	D00655 ;
ChEMBL	ChEMBL19 ;
CompTox Dashboard (EPA)	DTXSID1023281 ;
ECHA InfoCard	100.008.243
Chemical and physical data
Formula	C5H8N4O3S2
Molar mass	236.26 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=S(=O)(C\1=N\N(C(=N/C(=O)C)/S/1)C)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)/b7-4- ; Key:FLOSMHQXBMRNHR-DAXSKMNVSA-N ;
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Methazolamide (trade name Neptazane) is a potent carbonic anhydrase inhibitor. It is indicated in the treatment of increased intraocular pressure (IOP) in chronic open-angle glaucoma and secondary glaucoma. Also it is used preoperatively in acute angle-closure (narrow-angle) glaucoma where lowering the IOP is desired before surgery.

This drug has displayed teratogenic effects in rats. Compared to another drug in the same class, acetazolamide, methazolamide requires a lower dose when administered to patients.

Recently, research has also uncovered a potential new role for this drug, addressing tau toxicity, a theorized cause for diseases such as Alzheimer’s. ^[1]

^ Lopez A, Siddiqi FH, Villeneuve J, Ureshino RP, Jeon HY, Koulousakis P, et al. (October 2024). "Carbonic anhydrase inhibition ameliorates tau toxicity via enhanced tau secretion". Nature Chemical Biology. 21 (4): 577–587. doi:10.1038/s41589-024-01762-7. PMC 11949835. PMID 39482469.

[1] Lopez A, Siddiqi FH, Villeneuve J, Ureshino RP, Jeon HY, Koulousakis P, et al. (October 2024). "Carbonic anhydrase inhibition ameliorates tau toxicity via enhanced tau secretion". Nature Chemical Biology. 21 (4): 577–587. doi:10.1038/s41589-024-01762-7. PMC 11949835. PMID 39482469.

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