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

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
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 19:01:35 GMT 2023
Edited
by admin
on Fri Dec 15 19:01:35 GMT 2023
Record UNII
5K4B6994FB
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SEZOLAMIDE HYDROCHLORIDE
USAN   WHO-DD  
USAN  
Official 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
MK-417
Code English
Classification Tree Code System Code
NCI_THESAURUS C29577
Created by admin on Fri Dec 15 19:01:35 GMT 2023 , Edited by admin on Fri Dec 15 19:01:35 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL417975
Created by admin on Fri Dec 15 19:01:35 GMT 2023 , Edited by admin on Fri Dec 15 19:01:35 GMT 2023
PRIMARY
EPA CompTox
DTXSID60152377
Created by admin on Fri Dec 15 19:01:35 GMT 2023 , Edited by admin on Fri Dec 15 19:01:35 GMT 2023
PRIMARY
FDA UNII
5K4B6994FB
Created by admin on Fri Dec 15 19:01:35 GMT 2023 , Edited by admin on Fri Dec 15 19:01:35 GMT 2023
PRIMARY
USAN
AA-70
Created by admin on Fri Dec 15 19:01:35 GMT 2023 , Edited by admin on Fri Dec 15 19:01:35 GMT 2023
PRIMARY
NCI_THESAURUS
C96538
Created by admin on Fri Dec 15 19:01:35 GMT 2023 , Edited by admin on Fri Dec 15 19:01:35 GMT 2023
PRIMARY
CAS
119271-78-2
Created by admin on Fri Dec 15 19:01:35 GMT 2023 , Edited by admin on Fri Dec 15 19:01:35 GMT 2023
PRIMARY
PUBCHEM
60692
Created by admin on Fri Dec 15 19:01:35 GMT 2023 , Edited by admin on Fri Dec 15 19:01:35 GMT 2023
PRIMARY
Related Record Type Details
SOLVATE->ANHYDROUS
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY