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Methazolamide

Summary

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.

Methazolamide
Ball-and-stick model of the methazolamide molecule
Clinical data
Other namesN-(3-Methyl-5-sulfamoyl-3H-1,3,4-thiadiazol-2-ylidene) ethanamide
AHFS/Drugs.comMonograph
MedlinePlusa601233
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding~55%
Elimination half-life~14 hours
Identifiers
  • N-[5-(aminosulfonyl)-3-methyl-1,3,4-thiadiazol-2(3H)-ylidene]acetamide
CAS Number
  • 554-57-4 checkY
PubChem CID
  • 4100
IUPHAR/BPS
  • 6828
DrugBank
  • DB00703 checkY
ChemSpider
  • 3958 checkY
UNII
  • W733B0S9SD
KEGG
  • D00655 ☒N
ChEMBL
  • ChEMBL19 ☒N
CompTox Dashboard (EPA)
  • DTXSID1023281 Edit this at Wikidata
ECHA InfoCard100.008.243 Edit this at Wikidata
Chemical and physical data
FormulaC5H8N4O3S2
Molar mass236.26 g·mol−1
3D model (JSmol)
  • Interactive image
  • O=S(=O)(C\1=N\N(C(=N/C(=O)C)/S/1)C)N
  • 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- checkY
  • Key:FLOSMHQXBMRNHR-DAXSKMNVSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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 edit

  • 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. S2CID 24294348.
  • 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.