Page last updated: 2024-11-13

deberza

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

Cross-References

ID SourceID
PubMed CID46908929
CHEMBL ID2110731
CHEBI ID136041
SCHEMBL ID903156
MeSH IDM000606730

Synonyms (30)

Synonym
CHEBI:136041
CHEMBL2110731
r-7201
csg-452
tofogliflozin anyhydrous
903565-83-3
ec 619-989-0
554245w62t ,
unii-554245w62t
spiro(isobenzofuran-1(3h),2'-(2h)pyran)-3',4',5'-triol,6-((4-ethylphenyl)methyl)-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)-,(1s,3'r,4's,5's,6'r)-
tofogliflozin [inn]
(1s,3'r,4's,5's,6'r)-6-((4-ethylphenyl)methyl)-3',4',5',6'-tetrahydro-6'-(hydroxymethyl)-spiro(isobenzofuran-1(3h), 2'-(2h)pyran)-3',4',5'-triol
bdbm50396779
(1s,3'r,4's,5's,6'r)-6-((4-ethylphenyl)methyl)-6'-(hydroxymethyl)-3',4',5',6'-tetrahydro-3h-spiro(2-benzofuran-1,2'-pyran)-3',4',5'-triol
tofogliflozin anhydrous
tofogliflozin [mi]
tofogliflozin [who-dd]
SCHEMBL903156
deberza
(3s,3'r,4's,5's,6'r)-5-[(4-ethylphenyl)methyl]-6'-(hydroxymethyl)spiro[1h-2-benzofuran-3,2'-oxane]-3',4',5'-triol
gtpl9395
compound 16d [pmid: 22889351]
AC-31468
DTXSID90238097
AKOS027250822
(1s,3'r,4's,5's,6'r)-6-(4-ethylbenzyl)-6'-(hydroxymethyl)-3',4',5',6'-tetrahydro-3h-spiro[isobenzofuran-1,2'-pyran]-3',4',5'-triol
NCGC00485920-01
DB11824
903565-83-3 (free)
Q27261271

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
2-benzofurans
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sodium/glucose cotransporter 1Homo sapiens (human)IC50 (µMol)8.44400.06071.61058.4440AID1546222; AID703959
Sodium/glucose cotransporter 2Homo sapiens (human)IC50 (µMol)0.00330.00050.16534.1000AID1396969; AID1546223; AID703960
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (18)

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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

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)
[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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (40)

Assay IDTitleYearJournalArticle
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346965Human Sodium/glucose cotransporter 2 (Hexose transporter family)2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID1346950Human Sodium/glucose cotransporter 1 (Hexose transporter family)2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703928AUC (infinity) in fasted cynomolgus monkey at 1.7 mg/kg, po2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703959Inhibition of human SGLT1 expressed in CHO cells assessed as inhibition of sodium-dependent [14C]methyl-alpha-D-glucopyranoside uptake after 45 mins2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703924Total clearance in fasted cynomolgus monkey at 1 mg/kg, iv2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703948AUC (infinity) in fasted Crlj:CD1(ICR) mouse at 2.8 mg/kg, po2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID1546232Selectivity ratio of IC50 for inhibition of human SGLT1 to IC50 for inhibition of human SGLT22019European journal of medicinal chemistry, Dec-15, Volume: 184Synthetic strategy and SAR studies of C-glucoside heteroaryls as SGLT2 inhibitor: A review.
AID703951Tmax in fasted Crlj:CD1(ICR) mouse at 2.8 mg/kg, po2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703958Selectivity ratio of IC50 for human SGLT1 to IC50 for human SGLT22012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703960Inhibition of human SGLT2 expressed in CHO cells assessed as inhibition of sodium-dependent [14C]methyl-alpha-D-glucopyranoside uptake after 45 mins2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703926AUC (infinity) in fasted cynomolgus monkey at 1 mg/kg, iv2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703923Ratio of renal clearance to total clearance in fasted cynomolgus monkey at 1 mg/kg, iv2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703953Induction of hypoglycemia in nonfasted db/db mouse at 1 to 10 mg/kg, po up to 6 hrs by hexokinase method2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703925Volume of distribution at steady state in fasted cynomolgus monkey at 1 mg/kg, iv2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703929Half life in fasted cynomolgus monkey at 1 mg/kg, iv2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID1546223Inhibition of human SGLT22019European journal of medicinal chemistry, Dec-15, Volume: 184Synthetic strategy and SAR studies of C-glucoside heteroaryls as SGLT2 inhibitor: A review.
AID703950Half life in fasted Crlj:CD1(ICR) mouse at 2.8 mg/kg, po2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID1546227Antidiabetic activity in human T2DM patients assessed as reduction in HbA1c level at 20 mg, po for 24 weeks relative to control2019European journal of medicinal chemistry, Dec-15, Volume: 184Synthetic strategy and SAR studies of C-glucoside heteroaryls as SGLT2 inhibitor: A review.
AID703943Ratio of renal clearance to total clearance in fasted Crlj:CD1(ICR) mouse at 2.9 mg/kg, iv2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703955Antidiabetic activity in nonfasted db/db mouse assessed as increase in renal glucose excretion at 3 and 10 mg/kg, po up to 6 hrs by hexokinase method2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703954Antidiabetic activity in po dosed nonfasted db/db mouse assessed as reduction in blood glucose level up to 6 hrs by hexokinase method2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID1546228Antidiabetic activity in human T2DM patients assessed as reduction in body weight at 20 mg, po for 24 weeks2019European journal of medicinal chemistry, Dec-15, Volume: 184Synthetic strategy and SAR studies of C-glucoside heteroaryls as SGLT2 inhibitor: A review.
AID1546229Toxicity in human T2DM patients assessed as reduction in blood pressure at 20 mg, po for 24 weeks2019European journal of medicinal chemistry, Dec-15, Volume: 184Synthetic strategy and SAR studies of C-glucoside heteroaryls as SGLT2 inhibitor: A review.
AID1396969Inhibition of SGLT2 (unknown origin)2018Bioorganic & medicinal chemistry, 08-07, Volume: 26, Issue:14
Design, synthesis and biological evaluation of nitric oxide releasing derivatives of dapagliflozin as potential anti-diabetic and anti-thrombotic agents.
AID703952Cmax in fasted Crlj:CD1(ICR) mouse at 2.8 mg/kg, po2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703949Half life in fasted Crlj:CD1(ICR) mouse at 2.9 mg/kg, iv2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703932Tmax in fasted cynomolgus monkey at 1.7 mg/kg, po2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703946Oral bioavailability in fasted Crlj:CD1(ICR) mouse at 2.8 mg/kg2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703947AUC (infinity) in fasted Crlj:CD1(ICR) mouse at 2.9 mg/kg, iv2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703927Oral bioavailability in fasted cynomolgus monkey at 1.7 mg/kg2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703931Cmax in fasted cynomolgus monkey at 1.7 mg/kg, po2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703930Half life in fasted cynomolgus monkey at 1.7 mg/kg, po2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703945Volume of distribution at steady state in fasted Crlj:CD1(ICR) mouse at 2.9 mg/kg, iv2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID703944Total clearance in fasted Crlj:CD1(ICR) mouse at 2.9 mg/kg, iv2012Journal of medicinal chemistry, Sep-13, Volume: 55, Issue:17
Discovery of tofogliflozin, a novel C-arylglucoside with an O-spiroketal ring system, as a highly selective sodium glucose cotransporter 2 (SGLT2) inhibitor for the treatment of type 2 diabetes.
AID1546222Inhibition of human SGLT12019European journal of medicinal chemistry, Dec-15, Volume: 184Synthetic strategy and SAR studies of C-glucoside heteroaryls as SGLT2 inhibitor: A review.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's0 (0.00)29.6817
2010's4 (66.67)24.3611
2020's2 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 23.15

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 Index23.15 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.51 (4.65)
Search Engine Demand Index21.17 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (23.15)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (16.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (83.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]