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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H18N2O4S3
Molecular Weight 338.467
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SEZOLAMIDE

SMILES

CC(C)CN[C@H]1CCS(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O

InChI

InChIKey=JFLUCCKXAYBETQ-VIFPVBQESA-N
InChI=1S/C11H18N2O4S3/c1-7(2)6-13-9-3-4-19(14,15)11-8(9)5-10(18-11)20(12,16)17/h5,7,9,13H,3-4,6H2,1-2H3,(H2,12,16,17)/t9-/m0/s1

HIDE SMILES / InChI
Sezolamide (previously known as MK-417), a potent carbonic anhydrase inhibitor capable of reducing intraocular pressure after topical application, was under investigation for the treatment of glaucoma. . Sezolamide is the more potent of the two stereo isomers of MK-927 in inhibiting human carbonic anhydrase isoenzyme II, the isoenzyme found in ciliary processes. Sezolamide, the S-enantiomer of MK-927, has demonstrated activity in vitro approximately 80 times that of the R-enantiomer of MK-927 (concentrations of 0.54 nmolll and 44 nM, respectively, inhibiting activity of human carbonic anhydrase isoenzyme II by 50%). Clinically, sezolamide has also demonstrated greater activity than MK-927 both after single-dose and after twice daily administration in patients.

Approval Year

PubMed

PubMed

TitleDatePubMed
Urothelial hyperplasia induced by carbonic anhydrase inhibitors (CAIs) in animals and its relationship to urinary Na and pH.
1992-01
Patents

Sample Use Guides

A maximum intraocular pressure lowering activity from time-matched baseline diurnal curve values of about 20% was observed after multiple-dose twice daily administration of 1.8% sezolamide in patients with primary open angle glaucoma or ocular hypertension.
Route of Administration: Topical
Name Type Language
4H-THIENO(2,3-B)THIOPYRAN-2-SULFONAMIDE, 5,6-DIHYDRO-4-((2-METHYLPROPYL)AMINO)-, 7,7-DIOXIDE, (4S)-
Preferred Name English
SEZOLAMIDE
INN   WHO-DD  
INN  
Official Name English
Sezolamide [WHO-DD]
Common Name English
sezolamide [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29577
Created by admin on Mon Mar 31 19:23:16 GMT 2025 , Edited by admin on Mon Mar 31 19:23:16 GMT 2025
Code System Code Type Description
SMS_ID
100000084325
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MESH
C057921
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EPA CompTox
DTXSID30869687
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ChEMBL
CHEMBL417975
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NCI_THESAURUS
C96536
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INN
6540
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PUBCHEM
60693
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CAS
123308-22-5
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EVMPD
SUB10508MIG
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FDA UNII
FC9C0XB7D4
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