Chemistry:Methazolamide

Short description: Chemical compound

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
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)

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.

References

• "In vitro characterization of the erythrocyte distribution of methazolamide: a model of erythrocyte transport and binding kinetics.". J Pharmacokinet Biopharm 27 (1): 45–66. 1999. doi:10.1023/A:1020630712388. PMID 10533697. 
• RxList. "Neptazane". http://www.rxlist.com/cgi/generic2/methaz.htm. Retrieved August 20, 2006. 
• "Stevens–Johnson syndrome induced by methazolamide treatment.". Arch Ophthalmol 115 (4): 550–3. 1997. doi:10.1001/archopht.1997.01100150552021. PMID 9109770. 
• "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. 2003. doi:10.2460/ajvr.2003.64.183. PMID 12602587.