remogliflozin etabonate: orally administered hypoglycemic agent; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
ID Source | ID |
---|---|
PubMed CID | 9871420 |
CHEMBL ID | 2028665 |
CHEBI ID | 177541 |
SCHEMBL ID | 721678 |
MeSH ID | M0525700 |
Synonym |
---|
442201-24-3 |
ethyl [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[5-methyl-1-propan-2-yl-4-[(4-propan-2-yloxyphenyl)methyl]pyrazol-3-yl]oxyoxan-2-yl]methyl carbonate |
CHEBI:177541 |
gsk-189075 |
gsk-189075a |
remogliflozin etabonate |
kgt-1681 |
remogliflozin etabonate [inn] |
gsk 189075 |
beta-d-glucopyranoside, 5-methyl-4-((4-(1-methylethoxy)phenyl)methyl)-1-(1-methylethyl)-1h-pyrazol-3-yl, 6-(ethyl carbonate) |
gsk 189075a |
5-methyl-4-(4-(1-methylethoxy)benzyl)-1-(1-methylethyl)-1h-pyrazol-3-yl 6-o-(ethoxycarbonyl)-beta-d-glucopyranoside |
unii-tr0qt6qsul |
tr0qt6qsul , |
D10055 |
remogliflozin etabonate (usan/inn) |
5-methyl-4-(4-(1-methylethoxy)benzyl)-1-(1-methylethyl)-1h-pyrazol-3-yl 6-o- (ethoxycarbonyl)-.beta.-d-glucopyranoside |
remogliflozin etabonate [who-dd] |
beta-d-glucopyranoside, 5-methyl-4-[[4-(1-methylethoxy)phenyl]methyl]-1-(1-methylethyl)-1h-pyrazol-3-yl, 6-(ethyl carbonate) |
ethyl (((2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-((4-(4-isopropoxybenzyl)-1-isopropyl-5-methyl-1h-pyrazol-3-yl)oxy)tetrahydro-2h-pyran-2-yl)methyl) carbonate |
5-methyl-1-(propan-2-yl)-4-((4-((propan-2-yl)oxy)phenyl)methyl)-1h-pyrazol-3-yl 6-o-(ethoxycarbonyl)-.beta.-d-glucopyranoside |
remogliflozin etabonate [usan] |
bhv-091009 |
CHEMBL2028665 |
gsk189075 |
gsk189075a |
SCHEMBL721678 |
3-(6-o-ethoxycarbonyl-beta-d-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-1-isopropyl-5-methylpyrazole |
UAOCLDQAQNNEAX-ABMICEGHSA-N |
3-(6-o-ethoxycarbonyl-beta-d-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)-methyl]-1-isopropyl-5-methylpyrazole |
AKOS030528241 |
DB12935 |
bdbm50559516 |
HY-14945 |
S0993 |
Q7312052 |
CS-0003650 |
DTXSID50963191 |
MS-29684 |
remogliflozin etabonate (gsk189075) |
BR162756 |
Remogliflozin etabonate is a prodrug based on benzylpyrazole glucoside. It is metabolized to its active form, remogl iflozin, in the body.
Excerpt | Reference | Relevance |
---|---|---|
"Remogliflozin etabonate (RE) is a prodrug of remogliflozin, an SGLT2 inhibitor under development." | ( Remogliflozin etabonate: a novel SGLT2 inhibitor for treatment of diabetes mellitus. Mikhail, N, 2015) | 2.58 |
"Remogliflozin etabonate is a prodrug based on benzylpyrazole glucoside and is metabolized to its active form, remogliflozin, in the body." | ( Remogliflozin etabonate, in a novel category of selective low-affinity sodium glucose cotransporter (SGLT2) inhibitors, exhibits antidiabetic efficacy in rodent models. Fujikura, H; Fujimori, Y; Isaji, M; Ishikawa-Takemura, Y; Katsuno, K; Nakashima, I, 2008) | 2.51 |
Excerpt | Reference | Relevance |
---|---|---|
" The present study (Clintrials number NCT00519480) was conducted to evaluate the safety, tolerability, pharmacokinetics and pharmacodynamics of remogliflozinetabonate, an SGLT2 inhibitor, withdoses (500 mg and 750 mg BID) greater than the commercial dose (100 mg BID)in combination with metformin with minimum daily dose of 2000 mg given in two divided doses." | ( Assessment of safety and tolerability of remogliflozin etabonate (GSK189075) when administered with total daily dose of 2000 mg of metformin. Andrews, S; Cheatham, B; Dobbins, R; Hanmant, B; Hussey, EK; O'Connor-Semmes, R; Sagar, K; Tao, W; Wilkison, WO, 2021) | 0.89 |
" Cohort 2 subjects were administered with either remogliflozin etabonate 750 mg BID or placebo BID (2:1) in addition to metformin for 13 days." | ( Assessment of safety and tolerability of remogliflozin etabonate (GSK189075) when administered with total daily dose of 2000 mg of metformin. Andrews, S; Cheatham, B; Dobbins, R; Hanmant, B; Hussey, EK; O'Connor-Semmes, R; Sagar, K; Tao, W; Wilkison, WO, 2021) | 1.14 |
Excerpt | Reference | Relevance |
---|---|---|
" Oral administration of the IR tablet of RE showed similar bioavailability of R compared with small intestine delivery with both suspension and solution." | ( Regional gastrointestinal delivery of remogliflozin etabonate in humans. Dobbins, R; Doll, WJ; Hussey, EK; O'Connor-Semmes, RL; Page, RC; Sandefer, EP; Tao, W, 2013) | 0.66 |
" Remogliflozin etabonate, a novel agent, is an orally bioavailable prodrug of remogliflozin, which is a potent and selective sodium-glucose co-transporter-2 inhibitor." | ( Efficacy and Safety of Remogliflozin Etabonate, a New Sodium Glucose Co-Transporter-2 Inhibitor, in Patients with Type 2 Diabetes Mellitus: A 24-Week, Randomized, Double-Blind, Active-Controlled Trial. Alva, H; Aravind, SR; Asirvatham, A; Balamurugan, R; Barkate, H; Chawla, M; Dharmalingam, M; Gaikwad, R; Goyal, R; Kadam, P; Katare, S; Kodgule, R; Mohan, B; Paramesh, S; Pendse, A; Shembalkar, J; Suryawanshi, S; Tandon, M; Thacker, H; Vaidyanathan, S, 2020) | 1.78 |
Class | Description |
---|---|
glycoside | A 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 | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Sodium/glucose cotransporter 1 | Homo sapiens (human) | IC50 (µMol) | 100.0000 | 0.0607 | 1.6105 | 8.4440 | AID1719619; AID1874422 |
Sodium/glucose cotransporter 2 | Homo sapiens (human) | IC50 (µMol) | 2.5300 | 0.0005 | 0.1653 | 4.1000 | AID1719618; AID1874423 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID418704 | Antidiabetic activity in normal Sprague-Dawley rat assessed as urinary glucose excretion at 1 mg/kg, po after 24 hrs | 2009 | Journal 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. |
AID1719618 | Inhibition of human SGLT2 expressed in COS7 cells assessed as reduction in [14C]-AMG uptake | 2021 | Bioorganic & medicinal chemistry, 03-15, Volume: 34 | Discovery of remogliflozin etabonate: A potent and highly selective SGLT2 inhibitor. |
AID1874422 | Inhibition of human SGLT1 expressed in COS-7 cells | 2022 | Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16 | Sodium-Glucose Cotransporter Inhibitors as Antidiabetic Drugs: Current Development and Future Perspectives. |
AID1719619 | Inhibition of human SGLT1 expressed in COS7 cells assessed as reduction in [14C]-AMG uptake | 2021 | Bioorganic & medicinal chemistry, 03-15, Volume: 34 | Discovery of remogliflozin etabonate: A potent and highly selective SGLT2 inhibitor. |
AID1719628 | Oral bioavailability in rat assessed as ratio of AUC at 3 mg/kg up to 360 mins by LC-MS/MS analysis | 2021 | Bioorganic & medicinal chemistry, 03-15, Volume: 34 | Discovery of remogliflozin etabonate: A potent and highly selective SGLT2 inhibitor. |
AID1719623 | Apparent permeability of compound in human Caco-2 cells by LC-MS/MS analysis | 2021 | Bioorganic & medicinal chemistry, 03-15, Volume: 34 | Discovery of remogliflozin etabonate: A potent and highly selective SGLT2 inhibitor. |
AID418945 | Antidiabetic activity in normal Sprague-Dawley rat assessed as urinary glucose excretion at 10 mg/kg, po after 24 hrs | 2009 | Journal 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. |
AID418944 | Antidiabetic activity in normal Sprague-Dawley rat assessed as urinary glucose excretion at 3 mg/kg, po after 24 hrs | 2009 | Journal 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. |
AID1874423 | Inhibition of human SGLT2 expressed in COS-7 cells | 2022 | Journal of medicinal chemistry, 08-25, Volume: 65, Issue:16 | Sodium-Glucose Cotransporter Inhibitors as Antidiabetic Drugs: Current Development and Future Perspectives. |
AID1719621 | Intrinsic clearance in mouse intestinal S9 fraction at 10 uM up to 60 min in presence of NADPH by LC-MS/MS analysis | 2021 | Bioorganic & medicinal chemistry, 03-15, Volume: 34 | Discovery of remogliflozin etabonate: A potent and highly selective SGLT2 inhibitor. |
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 2 (7.69) | 29.6817 |
2010's | 14 (53.85) | 24.3611 |
2020's | 10 (38.46) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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 very strong demand-to-supply ratio for research on this compound.
| This Compound (55.91) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 12 (46.15%) | 5.53% |
Reviews | 8 (30.77%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 6 (23.08%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
Trial | Phase | Enrollment | Study Type | Start Date | Status | ||
---|---|---|---|---|---|---|---|
An Evaluation of the Safety, Tolerability, and Pharmacodynamic Effects of GSK189075 When Administered With Furosemide or Hydrochlorothiazide [NCT00671424] | Phase 1 | 48 participants (Anticipated) | Interventional | 2008-03-31 | Completed | ||
A 12-week Randomized, Double-blind, Parallel-group, Placebo-controlled Study to Determine the Efficacy and Safety of Biphasic Remogliflozin Etabonate When Administered to Subjects With Type 2 Diabetes Mellitus [NCT02537470] | Phase 2 | 191 participants (Actual) | Interventional | 2015-07-31 | Completed | ||
[information is prepared from clinicaltrials.gov, extracted Sep-2024] |