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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H18N2O4S3.ClH
Molecular Weight 374.928
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SEZOLAMIDE HYDROCHLORIDE

SMILES

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

InChI

InChIKey=VYZDSLFBCSLIEA-FVGYRXGTSA-N
InChI=1S/C11H18N2O4S3.ClH/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);1H/t9-;/m0./s1

HIDE SMILES / InChI

Molecular Formula C11H18N2O4S3
Molecular Weight 338.467
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
Substance Class Chemical
Created
by admin
on Mon Mar 31 19:30:27 GMT 2025
Edited
by admin
on Mon Mar 31 19:30:27 GMT 2025
Record UNII
5K4B6994FB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SEZOLAMIDE HYDROCHLORIDE
USAN   WHO-DD  
USAN  
Official Name English
MK-417
Preferred Name English
Sezolamide hydrochloride [WHO-DD]
Common Name English
4H-THIENO(2,3-B)THIOPYRAN-2-SULFONAMIDE, 5,6-DIHYDRO-4-((2-METHYLPROPYL)AMINO)-, 7,7-DIOXIDE, MONOHYDROCHLORIDE, (S)-
Common Name English
SEZOLAMIDE HYDROCHLORIDE [USAN]
Common Name English
4H-THIENO(2,3-B)THIOPYRAN-2-SULFONAMIDE, 5,6-DIHYDRO-4-((2-METHYLPROPYL)AMINO)-, 7,7-DIOXIDE, HYDROCHLORIDE (1:1), (4S)-
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29577
Created by admin on Mon Mar 31 19:30:27 GMT 2025 , Edited by admin on Mon Mar 31 19:30:27 GMT 2025
Code System Code Type Description
ChEMBL
CHEMBL417975
Created by admin on Mon Mar 31 19:30:27 GMT 2025 , Edited by admin on Mon Mar 31 19:30:27 GMT 2025
PRIMARY
SMS_ID
300000055197
Created by admin on Mon Mar 31 19:30:27 GMT 2025 , Edited by admin on Mon Mar 31 19:30:27 GMT 2025
PRIMARY
EPA CompTox
DTXSID60152377
Created by admin on Mon Mar 31 19:30:27 GMT 2025 , Edited by admin on Mon Mar 31 19:30:27 GMT 2025
PRIMARY
FDA UNII
5K4B6994FB
Created by admin on Mon Mar 31 19:30:27 GMT 2025 , Edited by admin on Mon Mar 31 19:30:27 GMT 2025
PRIMARY
USAN
AA-70
Created by admin on Mon Mar 31 19:30:27 GMT 2025 , Edited by admin on Mon Mar 31 19:30:27 GMT 2025
PRIMARY
NCI_THESAURUS
C96538
Created by admin on Mon Mar 31 19:30:27 GMT 2025 , Edited by admin on Mon Mar 31 19:30:27 GMT 2025
PRIMARY
CAS
119271-78-2
Created by admin on Mon Mar 31 19:30:27 GMT 2025 , Edited by admin on Mon Mar 31 19:30:27 GMT 2025
PRIMARY
PUBCHEM
60692
Created by admin on Mon Mar 31 19:30:27 GMT 2025 , Edited by admin on Mon Mar 31 19:30:27 GMT 2025
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY