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Details

Stereochemistry ABSOLUTE
Molecular Formula 2C11H18N2O4S3.2ClH.H2O
Molecular Weight 767.87
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SEZOLAMIDE HYDROCHLORIDE HEMIHYDRATE

SMILES

O.Cl.Cl.CC(C)CN[C@H]1CCS(=O)(=O)C2=C1C=C(S2)S(N)(=O)=O.CC(C)CN[C@H]3CCS(=O)(=O)C4=C3C=C(S4)S(N)(=O)=O

InChI

InChIKey=OMDSCSHWFCXOSL-UCJAQVTMSA-N
InChI=1S/2C11H18N2O4S3.2ClH.H2O/c2*1-7(2)6-13-9-3-4-19(14,15)11-8(9)5-10(18-11)20(12,16)17;;;/h2*5,7,9,13H,3-4,6H2,1-2H3,(H2,12,16,17);2*1H;1H2/t2*9-;;;/m00.../s1

HIDE SMILES / InChI

Molecular Formula H2O
Molecular Weight 18.0153
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

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 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 15:28:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:28:51 GMT 2023
Record UNII
03K812H9OC
Record Status Validated (UNII)
Record Version
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Name Type Language
SEZOLAMIDE HYDROCHLORIDE HEMIHYDRATE
Common Name English
Code System Code Type Description
FDA UNII
03K812H9OC
Created by admin on Fri Dec 15 15:28:51 GMT 2023 , Edited by admin on Fri Dec 15 15:28:51 GMT 2023
PRIMARY
PUBCHEM
76966756
Created by admin on Fri Dec 15 15:28:51 GMT 2023 , Edited by admin on Fri Dec 15 15:28:51 GMT 2023
PRIMARY
Related Record Type Details
ANHYDROUS->SOLVATE
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY