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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

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

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 Jan
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 Fri Dec 15 18:52:02 GMT 2023
Edited
by admin
on Fri Dec 15 18:52:02 GMT 2023
Record UNII
FC9C0XB7D4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SEZOLAMIDE
INN   WHO-DD  
INN  
Official Name English
4H-THIENO(2,3-B)THIOPYRAN-2-SULFONAMIDE, 5,6-DIHYDRO-4-((2-METHYLPROPYL)AMINO)-, 7,7-DIOXIDE, (4S)-
Systematic 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 Fri Dec 15 18:52:02 GMT 2023 , Edited by admin on Fri Dec 15 18:52:02 GMT 2023
Code System Code Type Description
SMS_ID
100000084325
Created by admin on Fri Dec 15 18:52:02 GMT 2023 , Edited by admin on Fri Dec 15 18:52:02 GMT 2023
PRIMARY
MESH
C057921
Created by admin on Fri Dec 15 18:52:02 GMT 2023 , Edited by admin on Fri Dec 15 18:52:02 GMT 2023
PRIMARY
ChEMBL
CHEMBL417975
Created by admin on Fri Dec 15 18:52:02 GMT 2023 , Edited by admin on Fri Dec 15 18:52:02 GMT 2023
PRIMARY
NCI_THESAURUS
C96536
Created by admin on Fri Dec 15 18:52:02 GMT 2023 , Edited by admin on Fri Dec 15 18:52:02 GMT 2023
PRIMARY
INN
6540
Created by admin on Fri Dec 15 18:52:02 GMT 2023 , Edited by admin on Fri Dec 15 18:52:02 GMT 2023
PRIMARY
PUBCHEM
60693
Created by admin on Fri Dec 15 18:52:02 GMT 2023 , Edited by admin on Fri Dec 15 18:52:02 GMT 2023
PRIMARY
CAS
123308-22-5
Created by admin on Fri Dec 15 18:52:02 GMT 2023 , Edited by admin on Fri Dec 15 18:52:02 GMT 2023
PRIMARY
EVMPD
SUB10508MIG
Created by admin on Fri Dec 15 18:52:02 GMT 2023 , Edited by admin on Fri Dec 15 18:52:02 GMT 2023
PRIMARY
FDA UNII
FC9C0XB7D4
Created by admin on Fri Dec 15 18:52:02 GMT 2023 , Edited by admin on Fri Dec 15 18:52:02 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY