Page last updated: 2024-11-06

sezolamide

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Sezolamide is a carbonic anhydrase inhibitor used in the treatment of open-angle glaucoma and ocular hypertension. It is structurally similar to acetazolamide and methazolamide. It is available as an ophthalmic solution for topical use. Sezolamide acts by inhibiting the enzyme carbonic anhydrase, which is found in the ciliary body of the eye. Carbonic anhydrase is involved in the production of aqueous humor, the fluid that fills the front part of the eye. By inhibiting carbonic anhydrase, sezolamide reduces the production of aqueous humor, which lowers intraocular pressure (IOP). Sezolamide is studied to understand its effectiveness in treating glaucoma and its potential side effects. Researchers are also investigating the use of sezolamide in combination with other glaucoma medications.'

sezolamide: decreases intraocular pressure, topically in vivo; inhibits carbonic anhydrase; RN given refers to parent cpd without isomeric designation [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID60693
CHEMBL ID417975
SCHEMBL ID637480
MeSH IDM0161824

Synonyms (15)

Synonym
bdbm50041029
4-isopropylamino-7,7-dioxo-4,5,6,7-tetrahydro-7lambda*6*-thieno[2,3-b]thiopyran-2-sulfonic acid amide
sezolamide
(4s)-4-(2-methylpropylamino)-7,7-dioxo-5,6-dihydro-4h-thieno[2,3-b]thiopyran-2-sulfonamide
CHEMBL417975 ,
unii-fc9c0xb7d4
fc9c0xb7d4 ,
sezolamide [inn]
123308-22-5
sezolamide [who-dd]
4h-thieno(2,3-b)thiopyran-2-sulfonamide, 5,6-dihydro-4-((2-methylpropyl)amino)-, 7,7-dioxide, (4s)-
SCHEMBL637480
JFLUCCKXAYBETQ-VIFPVBQESA-N
Q27277920
[s,(+)]-4beta-(isobutylamino)-5,6-dihydro-4h-thieno[2,3-b]thiopyran-2-sulfonamide 7,7-dioxide.hydrochlo

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" In this longest chronic administration study to date, MK-927 did not cause adverse ocular or systemic side effects."( Six week safety study of 2% MK-927 administered twice daily to ocular hypertensive volunteers.
Camras, CB; Deasy, D; Framm, L; Lippa, EA; Lustgarten, J; Payne, JE; Podos, SM; Serle, JB, 1992
)
0.28

Pharmacokinetics

ExcerptReferenceRelevance
"1 mg/kg), the pharmacokinetic parameters for MK-417 remained unchanged and there were no significant differences in the pharmacokinetic parameters among the anemic, polycythemic, and normal rats."( Dose-dependent pharmacokinetics of MK-417, a potent carbonic anhydrase inhibitor, in experimental polycythemic and anemic rats.
Chen, IW; deLuna, FA; Lin, JH, 1991
)
0.28
" administration, both total blood clearance and apparent volume of distribution for MK-417 increased disproportionately between the low and high dose, while the half-life of the drug appeared to be independent of dose."( Dose-dependent pharmacokinetics of MK-417, a potent carbonic anhydrase inhibitor, in rabbits following single and multiple doses.
Chen, IW; Duggan, DE; Gehret, JR; Lin, JH; Ulm, EH,
)
0.13

Bioavailability

ExcerptReferenceRelevance
"05 mg/kg, the bioavailability varied from 58% to 98."( Dose-dependent pharmacokinetics of MK-417, a potent carbonic anhydrase inhibitor, in rabbits following single and multiple doses.
Chen, IW; Duggan, DE; Gehret, JR; Lin, JH; Ulm, EH,
)
0.13

Dosage Studied

ExcerptRelevanceReference
"We investigated the dose-response and reproducibility of the intraocular pressure-lowering effect of MK-927 in ocular hypertensive patients."( MK-927, a topical carbonic anhydrase inhibitor. Dose response and reproducibility.
Camras, CB; Lippa, EA; Lustgarten, JS; Panebianco, DL; Podos, SM; Serle, JB, 1990
)
0.28
" The 1% concentration was chosen as the basis for comparison, as preliminary data indicated that the concentration would fall relatively steeply on the dose-response curve."( [Stereospecificity of lowering intraocular pressure using a locally administered carbonic anhydrase inhibitor].
Bechetoille, A; Brunner-Ferber, F; Diestelhorst, M; Krieglstein, GK; Lippa, E, 1990
)
0.28
"8 mmHg by 2 min) and aqueous flow (33% and 40% by 5 min) following intravenous dosing with either methazolamide or ethoxzolamide."( A comparison between the effect of topical and systemic carbonic anhydrase inhibitors on aqueous humor secretion.
Brechue, WF; Maren, TH, 1993
)
0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Carbonic anhydrase 2Homo sapiens (human)IC50 (µMol)0.00160.00021.10608.3000AID47728; AID47729; AID47739; AID47743; AID47744; AID47750
Carbonic anhydrase 2Homo sapiens (human)Ki0.00060.00000.72369.9200AID47906; AID47917; AID47925; AID48098
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (12)

Processvia Protein(s)Taxonomy
morphogenesis of an epitheliumCarbonic anhydrase 2Homo sapiens (human)
positive regulation of synaptic transmission, GABAergicCarbonic anhydrase 2Homo sapiens (human)
positive regulation of cellular pH reductionCarbonic anhydrase 2Homo sapiens (human)
angiotensin-activated signaling pathwayCarbonic anhydrase 2Homo sapiens (human)
regulation of monoatomic anion transportCarbonic anhydrase 2Homo sapiens (human)
secretionCarbonic anhydrase 2Homo sapiens (human)
regulation of intracellular pHCarbonic anhydrase 2Homo sapiens (human)
neuron cellular homeostasisCarbonic anhydrase 2Homo sapiens (human)
positive regulation of dipeptide transmembrane transportCarbonic anhydrase 2Homo sapiens (human)
regulation of chloride transportCarbonic anhydrase 2Homo sapiens (human)
carbon dioxide transportCarbonic anhydrase 2Homo sapiens (human)
one-carbon metabolic processCarbonic anhydrase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
arylesterase activityCarbonic anhydrase 2Homo sapiens (human)
carbonate dehydratase activityCarbonic anhydrase 2Homo sapiens (human)
protein bindingCarbonic anhydrase 2Homo sapiens (human)
zinc ion bindingCarbonic anhydrase 2Homo sapiens (human)
cyanamide hydratase activityCarbonic anhydrase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
cytosolCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
myelin sheathCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
extracellular exosomeCarbonic anhydrase 2Homo sapiens (human)
cytoplasmCarbonic anhydrase 2Homo sapiens (human)
plasma membraneCarbonic anhydrase 2Homo sapiens (human)
apical part of cellCarbonic anhydrase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID48109Ex vivo inhibition of carbonic anhydrase II in iris - ciliary body of an albino rabbit at a concentration of 0.1%1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
3-substituted thieno[2,3-b][1,4]thiazine-6-sulfonamides. A novel class of topically active carbonic anhydrase inhibitors.
AID166195Change in intraocular pressure (IOP) was measured in the normotensive pigmented rabbit in presence of MK-9271994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
3-substituted thieno[2,3-b][1,4]thiazine-6-sulfonamides. A novel class of topically active carbonic anhydrase inhibitors.
AID47743Activity against human carbonic anhydrase II1994Journal of medicinal chemistry, May-27, Volume: 37, Issue:11
Synthesis and carbonic anhydrase inhibitory activity of 4-substituted 2-thiophenesulfonamides.
AID166337Reduction of the elevated intraocular pressure (IOP) in alpha-chymotrypsin treated albino rabbit1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
3-substituted thieno[2,3-b][1,4]thiazine-6-sulfonamides. A novel class of topically active carbonic anhydrase inhibitors.
AID48110Ex vivo inhibition of carbonic anhydrase II in iris - ciliary body of an albino rabbit at a concentration of 0.5%1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
3-substituted thieno[2,3-b][1,4]thiazine-6-sulfonamides. A novel class of topically active carbonic anhydrase inhibitors.
AID27788Calculated partition coefficient (clogP) (MlogP)2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
Successful virtual screening for novel inhibitors of human carbonic anhydrase: strategy and experimental confirmation.
AID47750Inhibitory activity against carbonic anhydrase II2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
Successful virtual screening for novel inhibitors of human carbonic anhydrase: strategy and experimental confirmation.
AID47906Tested for ability to compete with dansylamide for binding to human erythrocyte carbonic-anhydrase-II (HCA-II)1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
3-substituted thieno[2,3-b][1,4]thiazine-6-sulfonamides. A novel class of topically active carbonic anhydrase inhibitors.
AID26233The aqueous solubility in 2% solution was determined; soluble1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Thienothiopyran-2-sulfonamides: novel topically active carbonic anhydrase inhibitors for the treatment of glaucoma.
AID4772950% inhibitory concentration against human carbonic anhydrase II (HCA II) after pre-incubation for 4 min at 37 degree C1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Thienothiopyran-2-sulfonamides: novel topically active carbonic anhydrase inhibitors for the treatment of glaucoma.
AID21493Solubility in pH 5.2 buffer1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
3-substituted thieno[2,3-b][1,4]thiazine-6-sulfonamides. A novel class of topically active carbonic anhydrase inhibitors.
AID166194Change in intraocular pressure (IOP) was measured in the normotensive pigmented rabbit1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
3-substituted thieno[2,3-b][1,4]thiazine-6-sulfonamides. A novel class of topically active carbonic anhydrase inhibitors.
AID48108Ex vivo inhibition of carbonic anhydrase II in iris - ciliary body of an albino rabbit at a concentration of 0.02%1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
3-substituted thieno[2,3-b][1,4]thiazine-6-sulfonamides. A novel class of topically active carbonic anhydrase inhibitors.
AID47739Tested for ability to inhibit human erythrocyte carbonic-anhydrase-II- (HCA II) catalyzed carbon dioxide hydration1994Journal of medicinal chemistry, Jan-21, Volume: 37, Issue:2
3-substituted thieno[2,3-b][1,4]thiazine-6-sulfonamides. A novel class of topically active carbonic anhydrase inhibitors.
AID228500Ocular sensitization assay as susceptibility to nucleophilic attack by cysteine1994Journal of medicinal chemistry, May-27, Volume: 37, Issue:11
Synthesis and carbonic anhydrase inhibitory activity of 4-substituted 2-thiophenesulfonamides.
AID48106Ex Vivo evaluation of the ability to penetrate the rabbit eye and inhibit carbonic anhydrase in a homogenate of the iris ciliary body1994Journal of medicinal chemistry, May-27, Volume: 37, Issue:11
Synthesis and carbonic anhydrase inhibitory activity of 4-substituted 2-thiophenesulfonamides.
AID48098The equilibrium dissociation constant of the inhibitor-enzyme complex of human carbonic anhydrase1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Thienothiopyran-2-sulfonamides: novel topically active carbonic anhydrase inhibitors for the treatment of glaucoma.
AID48111Inhibition of carbonic anhydrase after topical administration of compound (50 uL) at 0.5% in iris-ciliary body from albino rabbit1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Thienothiopyran-2-sulfonamides: novel topically active carbonic anhydrase inhibitors for the treatment of glaucoma.
AID4772850% inhibitory concentration against human carbonic anhydrase II (HCA II) after pre-incubation at 3 degree C1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Thienothiopyran-2-sulfonamides: novel topically active carbonic anhydrase inhibitors for the treatment of glaucoma.
AID47925Dissociation constant was reported against Carbonic anhydrase II2002Journal of medicinal chemistry, Aug-15, Volume: 45, Issue:17
Successful virtual screening for novel inhibitors of human carbonic anhydrase: strategy and experimental confirmation.
AID167786Maximum fall in ocular hypertension in the right eye of albino rabbits1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Thienothiopyran-2-sulfonamides: novel topically active carbonic anhydrase inhibitors for the treatment of glaucoma.
AID47917Compound was evaluated for the affinity towards Human Carbonic anhydrase II (HCA II)1994Journal of medicinal chemistry, Apr-15, Volume: 37, Issue:8
Application of the three-dimensional structures of protein target molecules in structure-based drug design.
AID47744Compound was evaluated for the inhibitory activity against Human Carbonic anhydrase II (HCA II)1994Journal of medicinal chemistry, Apr-15, Volume: 37, Issue:8
Application of the three-dimensional structures of protein target molecules in structure-based drug design.
AID145917Binding of 10 phosphate buffer1989Journal of medicinal chemistry, Dec, Volume: 32, Issue:12
Thienothiopyran-2-sulfonamides: novel topically active carbonic anhydrase inhibitors for the treatment of glaucoma.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (44)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (9.09)18.7374
1990's38 (86.36)18.2507
2000's2 (4.55)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 16.26

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index16.26 (24.57)
Research Supply Index4.19 (2.92)
Research Growth Index5.27 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (16.26)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials18 (38.30%)5.53%
Reviews2 (4.26%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other27 (57.45%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]