Methazolamide

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.

Not to be confused with methimazole, metamizole, or acetazolamide.

Methazolamide

Clinical data
Other names	N-(3-Methyl-5-sulfamoyl-3H-1,3,4-thiadiazol-2-ylidene) ethanamide
AHFS/Drugs.com	Monograph
MedlinePlus	a601233
Pregnancy category	US: C (Risk not ruled out)
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^Y
PubChem CID	4100
IUPHAR/BPS	6828
DrugBank	DB00703^Y
ChemSpider	3958^Y
UNII	W733B0S9SD
KEGG	D00655^N
ChEMBL	ChEMBL19^N
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-^Y Key:FLOSMHQXBMRNHR-DAXSKMNVSA-N^Y
^NY (what is this?)  (verify)

References

• Iyer G, Bellantone R, Taft D (1999). "In vitro characterization of the erythrocyte distribution of methazolamide: a model of erythrocyte transport and binding kinetics". J Pharmacokinet Biopharm. 27 (1): 45–66. doi:10.1023/A:1020630712388. PMID 10533697.
• RxList. "Neptazane". Archived from the original on August 12, 2006. Retrieved August 20, 2006.
• Shirato S, Kagaya F, Suzuki Y, Joukou S (1997). "Stevens–Johnson syndrome induced by methazolamide treatment". Arch Ophthalmol. 115 (4): 550–3. doi:10.1001/archopht.1997.01100150552021. PMID 9109770.
• Skorobohach B, Ward D, Hendrix D (2003). "Effects of oral administration of methazolamide on intraocular pressure and aqueous humor flow rate in clinically normal dogs". Am J Vet Res. 64 (2): 183–7. doi:10.2460/ajvr.2003.64.183. PMID 12602587.