Page last updated: 2024-11-11

sergliflozin etabonate

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

Description

sergliflozin: a hypoglycemic agent that inhibits SGLT2 sodium-glucose transporter; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID9824918
CHEMBL ID450044
CHEBI ID188680
SCHEMBL ID621807
MeSH IDM0542259

Synonyms (35)

Synonym
D06641
sergliflozin etabonate (usan)
408504-26-7
sergliflozin
gw869682x
gw-869682x
gw-869683x
CHEMBL450044 ,
CHEBI:188680
ethyl [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[2-[(4-methoxyphenyl)methyl]phenoxy]oxan-2-yl]methyl carbonate
sergliflozin etabonate
beta-d-glucopyranoside, 2-((4-methoxyphenyl)methyl)phenyl, 6-(ethyl carbonate)
4hy3523466 ,
2-(4-methoxybenzyl)phenyl 6-o-(ethoxycarbonyl)-beta-d-glucopyranoside
sergliflozin etabonate [usan:inn]
unii-4hy3523466
sergliflozin etabonate [inn]
sergliflozin etabonate [usan]
.beta.-d-glucopyranoside, 2-((4-methoxyphenyl)methyl)phenyl 6-o-(ethoxycarbonyl)-
sergliflozin etabonate [who-dd]
ethyl [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{2-[(4-methoxyphenyl)methyl]phenoxy}oxan-2-yl]methyl carbonate
gtpl4587
SCHEMBL621807
2-(4-methoxybenzyl)phenyl 6-o-ethoxycarbonyl-beta-d-glucopyranoside
QLXKHBNJTPICNF-QMCAAQAGSA-N
2-[(4-methoxyphenyl)methyl]phenyl-beta-d-glucopyranoside-6-(ethyl carbonate)
gsk-869682
ethyl (((2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(2-(4-methoxybenzyl)phenoxy)tetrahydro-2h-pyran-2-yl)methyl) carbonate
Q7454518
gw 869682x
2-(4-methoxybenzyl)phenyl6-o-(ethoxycarbonyl)-beta-d-glucopyranoside
DTXSID20961265
CS-0012078
HY-12611
AKOS040749484

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" At the doses tested, sergliflozin showed less than dose-proportional pharmacokinetic characteristics."( Multiple-dose pharmacokinetics and pharmacodynamics of sergliflozin etabonate, a novel inhibitor of glucose reabsorption, in healthy overweight and obese subjects: a randomized double-blind study.
Dobbins, RL; Hussey, EK; Kapur, A; Layko, D; Murray, SC; Nunez, DJ; O'Connor-Semmes, RL; Stockman, NL; Stoltz, RR, 2010
)
0.61
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
glycosideA glycosyl compound resulting from the attachment of a glycosyl group to a non-acyl group RO-, RS-, RSe-, etc. The bond between the glycosyl group and the non-acyl group is called a glycosidic bond. By extension, the terms N-glycosides and C-glycosides are used as class names for glycosylamines and for compounds having a glycosyl group attached to a hydrocarbyl group respectively. These terms are misnomers and should not be used. The preferred terms are glycosylamines and C-glycosyl compounds, respectively.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sodium/glucose cotransporter 1Homo sapiens (human)IC50 (µMol)22.00000.06071.61058.4440AID614607; AID670284
Sodium/glucose cotransporter 1Homo sapiens (human)Ki7.54000.18003.86007.5400AID1874420
Sodium/glucose cotransporter 2Homo sapiens (human)IC50 (µMol)0.26000.00050.16534.1000AID670283
Sodium/glucose cotransporter 2Homo sapiens (human)Ki0.15100.01860.08480.1510AID1874421
Solute carrier family 5 member 4Homo sapiens (human)IC50 (µMol)0.26000.00090.06960.2600AID614606
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (20)

Processvia Protein(s)Taxonomy
chloride transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
glucose transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
alpha-glucoside transportSodium/glucose cotransporter 1Homo sapiens (human)
intestinal D-glucose absorptionSodium/glucose cotransporter 1Homo sapiens (human)
response to inorganic substanceSodium/glucose cotransporter 1Homo sapiens (human)
pentose transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
fucose transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
galactose transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
myo-inositol transportSodium/glucose cotransporter 1Homo sapiens (human)
transepithelial water transportSodium/glucose cotransporter 1Homo sapiens (human)
renal glucose absorptionSodium/glucose cotransporter 1Homo sapiens (human)
glucose import across plasma membraneSodium/glucose cotransporter 1Homo sapiens (human)
sodium ion import across plasma membraneSodium/glucose cotransporter 1Homo sapiens (human)
intestinal hexose absorptionSodium/glucose cotransporter 1Homo sapiens (human)
transport across blood-brain barrierSodium/glucose cotransporter 1Homo sapiens (human)
glucose transmembrane transportSodium/glucose cotransporter 1Homo sapiens (human)
sodium ion transportSodium/glucose cotransporter 1Homo sapiens (human)
alpha-glucoside transportSodium/glucose cotransporter 2Homo sapiens (human)
carbohydrate metabolic processSodium/glucose cotransporter 2Homo sapiens (human)
hexose transmembrane transportSodium/glucose cotransporter 2Homo sapiens (human)
renal glucose absorptionSodium/glucose cotransporter 2Homo sapiens (human)
glucose import across plasma membraneSodium/glucose cotransporter 2Homo sapiens (human)
sodium ion import across plasma membraneSodium/glucose cotransporter 2Homo sapiens (human)
sodium ion transportSodium/glucose cotransporter 2Homo sapiens (human)
sodium ion transmembrane transportSolute carrier family 5 member 4Homo sapiens (human)
proton transmembrane transportSolute carrier family 5 member 4Homo sapiens (human)
sodium ion transportSolute carrier family 5 member 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (13)

Processvia Protein(s)Taxonomy
galactose transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
glucose transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
myo-inositol:sodium symporter activitySodium/glucose cotransporter 1Homo sapiens (human)
water transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
glucose:sodium symporter activitySodium/glucose cotransporter 1Homo sapiens (human)
protein bindingSodium/glucose cotransporter 1Homo sapiens (human)
pentose transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
fucose transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
alpha-glucoside transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
galactose:sodium symporter activitySodium/glucose cotransporter 1Homo sapiens (human)
D-glucose transmembrane transporter activitySodium/glucose cotransporter 1Homo sapiens (human)
low-affinity glucose:sodium symporter activitySodium/glucose cotransporter 2Homo sapiens (human)
glucose:sodium symporter activitySodium/glucose cotransporter 2Homo sapiens (human)
protein bindingSodium/glucose cotransporter 2Homo sapiens (human)
alpha-glucoside transmembrane transporter activitySodium/glucose cotransporter 2Homo sapiens (human)
D-glucose transmembrane transporter activitySodium/glucose cotransporter 2Homo sapiens (human)
glucose:sodium symporter activitySolute carrier family 5 member 4Homo sapiens (human)
protein bindingSolute carrier family 5 member 4Homo sapiens (human)
proton transmembrane transporter activitySolute carrier family 5 member 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
early endosomeSodium/glucose cotransporter 1Homo sapiens (human)
plasma membraneSodium/glucose cotransporter 1Homo sapiens (human)
apical plasma membraneSodium/glucose cotransporter 1Homo sapiens (human)
brush border membraneSodium/glucose cotransporter 1Homo sapiens (human)
intracellular organelleSodium/glucose cotransporter 1Homo sapiens (human)
perinuclear region of cytoplasmSodium/glucose cotransporter 1Homo sapiens (human)
extracellular exosomeSodium/glucose cotransporter 1Homo sapiens (human)
intracellular vesicleSodium/glucose cotransporter 1Homo sapiens (human)
plasma membraneSodium/glucose cotransporter 1Homo sapiens (human)
plasma membraneSodium/glucose cotransporter 2Homo sapiens (human)
membraneSodium/glucose cotransporter 2Homo sapiens (human)
apical plasma membraneSodium/glucose cotransporter 2Homo sapiens (human)
extracellular exosomeSodium/glucose cotransporter 2Homo sapiens (human)
plasma membraneSodium/glucose cotransporter 2Homo sapiens (human)
plasma membraneSolute carrier family 5 member 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID670294Half life in db/db mouse at 10 mg/kg, po administered as single dose by LC-MS/MS system method2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID614606Inhibition of human SGLT2 expressed in CHO cells assessed as [14C]AMG uptake after 45 mins2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
5a-Carba-β-D-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID670288Potency index, ratio of IC50 for CYP3A4 (unknown origin) using BFC substrate in which compound added to reaction mixture simultaneously with BFC substrate to IC50 for CYP3A4 using BFC substrate in which compound added to reaction mixture before addition o2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID614610Apparent oral clearance in db/db mouse at 10 mg/kg, po by LC-MS/MS analysis2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
5a-Carba-β-D-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID670291Hypoglycemic effect in db/db mouse assessed as reduction in glucose level at 30 mg/kg, po measured 8 hrs post dose administered as single dose by hexokinase method2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID418946Antidiabetic activity in normal Sprague-Dawley rat assessed as urinary glucose excretion at 30 mg/kg, po after 24 hrs2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.
AID670298Apparent volume of distribution during terminal phase in db/db mouse at 10 mg/kg, po administered as single dose by LC-MS/MS system method2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID614611Apparent volume of distribution during terminal phase in db/db mouse at 10 mg/kg, po by LC-MS/MS analysis2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
5a-Carba-β-D-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID614609Cmax in db/db mouse at 10 mg/kg, po by LC-MS/MS analysis2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
5a-Carba-β-D-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID670285Selectivity index, ratio of IC50 for human SGLT1 to IC50 for human SGLT22012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID670297AUC (infinity) in db/db mouse at 10 mg/kg, po administered as single dose by LC-MS/MS system method2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID418944Antidiabetic activity in normal Sprague-Dawley rat assessed as urinary glucose excretion at 3 mg/kg, po after 24 hrs2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.
AID418982Antidiabetic activity in normal human assessed as reduction urinary glucose excretion at 500 mg, po after 24 hrs2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.
AID670290Hypoglycemic effect in db/db mouse assessed as reduction in glucose level at 30 mg/kg, po measured 4 hrs post dose administered as single dose by hexokinase method2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID670296Cmax in db/db mouse at 10 mg/kg, po administered as single dose by LC-MS/MS system method2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID418945Antidiabetic activity in normal Sprague-Dawley rat assessed as urinary glucose excretion at 10 mg/kg, po after 24 hrs2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.
AID670287Inhibition of CYP3A4 using BFC substrate in which compound added to reaction mixture before addition of BFC substrate by fluorometric assay2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID614613Antidiabetic activity in db/db mouse assessed as reduction of blood glucose level at 100 mg/kg, po after 8 hrs by hexokinase method2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
5a-Carba-β-D-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID695405Toxicity in Wistar rat assessed as overnight urinary glucose excretion at 10 mg/kg, po2012Bioorganic & medicinal chemistry, Nov-15, Volume: 20, Issue:22
Structure-activity relationship studies of 4-benzyl-1H-pyrazol-3-yl β-d-glucopyranoside derivatives as potent and selective sodium glucose co-transporter 1 (SGLT1) inhibitors with therapeutic activity on postprandial hyperglycemia.
AID418980Antidiabetic activity in over-weight subject assessed as reduction of body weight at 500 to 1000 mg/kg, po tid for 2 weeks2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.
AID418979Antidiabetic activity in normal human assessed as plasma glucose level at 500 mg, po after 4 hrs by OGTT2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.
AID1874420Inhibition of human SGLT1 expressed in CHO-K1 cells2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Sodium-Glucose Cotransporter Inhibitors as Antidiabetic Drugs: Current Development and Future Perspectives.
AID614607Inhibition of human SGLT1 expressed in CHO cells assessed as [14C]AMG uptake after 45 mins2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
5a-Carba-β-D-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID614608Selectivity ratio of IC50 for human SGLT1 to IC50 for human SGLT22011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
5a-Carba-β-D-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID670283Inhibition of human SGLT2 expressed in CHO-K1 cells by [14C]AMG uptake assay2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID670295Tmax in db/db mouse at 10 mg/kg, po administered as single dose by LC-MS/MS system method2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID614612Half life in db/db mouse at 10 mg/kg, po by LC-MS/MS analysis2011Bioorganic & medicinal chemistry, Sep-15, Volume: 19, Issue:18
5a-Carba-β-D-glucopyranose derivatives as novel sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID670284Inhibition of human SGLT1 expressed in CHO-K1 cells by [14C]AMG uptake assay2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID1874421Inhibition of human SGLT2 expressed in CHO-K1 cells2022Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16
Sodium-Glucose Cotransporter Inhibitors as Antidiabetic Drugs: Current Development and Future Perspectives.
AID670299Apparent oral clearance in db/db mouse at 10 mg/kg, po administered as single dose by LC-MS/MS system method2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID418981Antidiabetic activity in normal human assessed as reduction urinary glucose excretion at 200 mg, po after 24 hrs2009Journal of medicinal chemistry, Apr-09, Volume: 52, Issue:7
Development of the renal glucose reabsorption inhibitors: a new mechanism for the pharmacotherapy of diabetes mellitus type 2.
AID670286Inhibition of CYP3A4 using BFC substrate in which compound added to reaction mixture simultaneously with BFC substrate by fluorometric assay2012Bioorganic & medicinal chemistry, Jul-01, Volume: 20, Issue:13
C-Aryl 5a-carba-β-d-glucopyranosides as novel sodium glucose cotransporter 2 (SGLT2) inhibitors for the treatment of type 2 diabetes.
AID1346965Human Sodium/glucose cotransporter 2 (Hexose transporter family)2007The Journal of pharmacology and experimental therapeutics, Jan, Volume: 320, Issue:1
Sergliflozin, a novel selective inhibitor of low-affinity sodium glucose cotransporter (SGLT2), validates the critical role of SGLT2 in renal glucose reabsorption and modulates plasma glucose level.
AID1346950Human Sodium/glucose cotransporter 1 (Hexose transporter family)2007The Journal of pharmacology and experimental therapeutics, Jan, Volume: 320, Issue:1
Sergliflozin, a novel selective inhibitor of low-affinity sodium glucose cotransporter (SGLT2), validates the critical role of SGLT2 in renal glucose reabsorption and modulates plasma glucose level.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's6 (40.00)29.6817
2010's8 (53.33)24.3611
2020's1 (6.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.57

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index11.57 (24.57)
Research Supply Index2.89 (2.92)
Research Growth Index4.46 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.57)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (13.33%)5.53%
Reviews6 (40.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (46.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]