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MedKoo Cat#: 330131 | Name: Remogliflozin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Remogliflozin, also known as Remogliflozin A and GSK189074, is a potent inhibitor of sodium-glucose transporter 2 (SGLT2; Kis = 12.4 and 26 nM for human and rat SGLT2, respectively). Remogliflozin has applications in treating type II diabetes, most commonly as Remogliflozin Etabonate.

Chemical Structure

Remogliflozin
Remogliflozin
CAS#329045-45-6

Theoretical Analysis

MedKoo Cat#: 330131

Name: Remogliflozin

CAS#: 329045-45-6

Chemical Formula: C23H34N2O7

Exact Mass: 450.2366

Molecular Weight: 450.53

Elemental Analysis: C, 61.32; H, 7.61; N, 6.22; O, 24.86

Price and Availability

Size Price Availability Quantity
5mg USD 485.00
10mg USD 850.00
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Related CAS #
No Data
Synonym
Remogliflozin A; GSK189074; GSK-189074; GSK 189074.
IUPAC/Chemical Name
beta-D-Glucopyranoside, 5-methyl-4-((4-(1-methylethoxy)phenyl)methyl)-1-(1-methylethyl)-1H-pyrazol-3-yl
InChi Key
GSINGUMRKGRYJP-VZWAGXQNSA-N
InChi Code
InChI=1S/C23H34N2O7/c1-12(2)25-14(5)17(10-15-6-8-16(9-7-15)30-13(3)4)22(24-25)32-23-21(29)20(28)19(27)18(11-26)31-23/h6-9,12-13,18-21,23,26-29H,10-11H2,1-5H3/t18-,19-,20+,21-,23+/m1/s1
SMILES Code
O[C@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)[C@@H]1OC2=NN(C(C)C)C(C)=C2CC3=CC=C(OC(C)C)C=C3
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#A20M04C20
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Remogliflozin A is a potent inhibitor of sodium-glucose transporter 2 (SGLT2; Kis = 12.4 and 26 nM for human and rat SGLT2, respectively). It is selective for SGLT2 over SGLT1 (Kis = 4,520 and 997 nM for human and rat SGLT1, respectively). Remogliflozin etabonate is rapidly converted to remogliflozin A in vivo; rat urinary glucose excretion increases and plasma glucose and insulin concentrations decrease.
In vitro activity:
To be determined
In vivo activity:
Remogliflozin etabonate significantly improved markers associated with non-alcoholic fatty liver disease in this study’s murine model, and may be an effective compound for the treatment of non-alcoholic steatohepatitis and non-alcoholic fatty liver disease due to its insulin-sensitizing and antioxidant properties. Reference: J Clin Exp Hepatol. 2015 Sep;5(3):190-8. https://pubmed.ncbi.nlm.nih.gov/26628836/
Solvent mg/mL mM
Solubility
DMSO 30.0 66.59
DMF 30.0 66.59
Ethanol 30.0 66.59
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 450.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Nakano S, Katsuno K, Isaji M, Nagasawa T, Buehrer B, Walker S, Wilkison WO, Cheatham B. Remogliflozin Etabonate Improves Fatty Liver Disease in Diet-Induced Obese Male Mice. J Clin Exp Hepatol. 2015 Sep;5(3):190-8. doi: 10.1016/j.jceh.2015.02.005. Epub 2015 Apr 28. PMID: 26628836; PMCID: PMC4632078. 2. Fujimori Y, Katsuno K, Nakashima I, Ishikawa-Takemura Y, Fujikura H, Isaji M. Remogliflozin etabonate, in a novel category of selective low-affinity sodium glucose cotransporter (SGLT2) inhibitors, exhibits antidiabetic efficacy in rodent models. J Pharmacol Exp Ther. 2008 Oct;327(1):268-76. doi: 10.1124/jpet.108.140210. Epub 2008 Jun 26. PMID: 18583547.
In vitro protocol:
To be determined
In vivo protocol:
1. Nakano S, Katsuno K, Isaji M, Nagasawa T, Buehrer B, Walker S, Wilkison WO, Cheatham B. Remogliflozin Etabonate Improves Fatty Liver Disease in Diet-Induced Obese Male Mice. J Clin Exp Hepatol. 2015 Sep;5(3):190-8. doi: 10.1016/j.jceh.2015.02.005. Epub 2015 Apr 28. PMID: 26628836; PMCID: PMC4632078. 2. Fujimori Y, Katsuno K, Nakashima I, Ishikawa-Takemura Y, Fujikura H, Isaji M. Remogliflozin etabonate, in a novel category of selective low-affinity sodium glucose cotransporter (SGLT2) inhibitors, exhibits antidiabetic efficacy in rodent models. J Pharmacol Exp Ther. 2008 Oct;327(1):268-76. doi: 10.1124/jpet.108.140210. Epub 2008 Jun 26. PMID: 18583547.
1: Sadurní A, Kehr G, Ahlqvist M, Wernevik J, Sjögren HP, Kankkonen C, Knerr L, Gilmour R. Fluorine-Directed Glycosylation Enables the Stereocontrolled Synthesis of Selective SGLT2 Inhibitors for Type II Diabetes. Chemistry. 2018 Feb 26;24(12):2832-2836. doi: 10.1002/chem.201705373. Epub 2017 Dec 20. PubMed PMID: 29211300. 2: Dash RP, Babu RJ, Srinivas NR. Comparative pharmacokinetics of three SGLT-2 inhibitors sergliflozin, remogliflozin and ertugliflozin: an overview. Xenobiotica. 2017 Nov;47(11):1015-1026. doi: 10.1080/00498254.2016.1247219. Epub 2016 Oct 28. Review. PubMed PMID: 27718782. 3: Madaan T, Akhtar M, Najmi AK. Sodium glucose CoTransporter 2 (SGLT2) inhibitors: Current status and future perspective. Eur J Pharm Sci. 2016 Oct 10;93:244-52. doi: 10.1016/j.ejps.2016.08.025. Epub 2016 Aug 12. Review. PubMed PMID: 27531551. 4: Kobayashi M, Isawa H, Sonehara J, Kubota M, Ozawa T. O-Glycosylation of 4-(Substituted benzyl)-1,2-dihydro-3H-pyrazol-3-one Derivatives with 2,3,4,6-Tetra-O-acyl-α-D-glucopyranosyl Bromide via N1-Acetylation of the Pyrazole Ring. Chem Pharm Bull (Tokyo). 2016;64(7):1009-18. doi: 10.1248/cpb.c15-00982. PubMed PMID: 27373664. 5: Nakano S, Katsuno K, Isaji M, Nagasawa T, Buehrer B, Walker S, Wilkison WO, Cheatham B. Remogliflozin Etabonate Improves Fatty Liver Disease in Diet-Induced Obese Male Mice. J Clin Exp Hepatol. 2015 Sep;5(3):190-8. doi: 10.1016/j.jceh.2015.02.005. Epub 2015 Apr 28. PubMed PMID: 26628836; PubMed Central PMCID: PMC4632078. 6: Mikhail N. Remogliflozin etabonate: a novel SGLT2 inhibitor for treatment of diabetes mellitus. Expert Opin Investig Drugs. 2015;24(10):1381-7. doi: 10.1517/13543784.2015.1061501. Epub 2015 Aug 14. Review. PubMed PMID: 26288025. 7: Mikhail N. Remogliflozin etabonate : a novel SGLT2 inhibitor for treatment of diabetes mellitus. Expert Opin Investig Drugs. 2015 Aug 14:1-7. [Epub ahead of print] PubMed PMID: 26271274. 8: O'Connor-Semmes R, Walker S, Kapur A, Hussey EK, Ye J, Wang-Smith L, Tao W, Dobbins RL, Cheatham B, Wilkison WO. Pharmacokinetics and Pharmacodynamics of the SGLT2 Inhibitor Remogliflozin Etabonate in Subjects with Mild and Moderate Renal Impairment. Drug Metab Dispos. 2015 Jul;43(7):1077-83. doi: 10.1124/dmd.114.062828. Epub 2015 May 1. PubMed PMID: 25934577. 9: Sykes AP, Kemp GL, Dobbins R, O'Connor-Semmes R, Almond SR, Wilkison WO, Walker S, Kler L. Randomized efficacy and safety trial of once-daily remogliflozin etabonate for the treatment of type 2 diabetes. Diabetes Obes Metab. 2015 Jan;17(1):98-101. doi: 10.1111/dom.12393. Epub 2014 Nov 3. PubMed PMID: 25238025. 10: Sykes AP, O'Connor-Semmes R, Dobbins R, Dorey DJ, Lorimer JD, Walker S, Wilkison WO, Kler L. Randomized trial showing efficacy and safety of twice-daily remogliflozin etabonate for the treatment of type 2 diabetes. Diabetes Obes Metab. 2015 Jan;17(1):94-7. doi: 10.1111/dom.12391. Epub 2014 Nov 3. PubMed PMID: 25223369. 11: Jackson VM, Price DA, Carpino PA. Investigational drugs in Phase II clinical trials for the treatment of obesity: implications for future development of novel therapies. Expert Opin Investig Drugs. 2014 Aug;23(8):1055-66. doi: 10.1517/13543784.2014.918952. Epub 2014 Jul 7. Review. PubMed PMID: 25000213. 12: Napolitano A, Miller S, Murgatroyd PR, Hussey E, Dobbins RL, Bullmore ET, Nunez DJR. Exploring glycosuria as a mechanism for weight and fat mass reduction. A pilot study with remogliflozin etabonate and sergliflozin etabonate in healthy obese subjects. J Clin Transl Endocrinol. 2013 Dec 11;1(1):e3-e8. doi: 10.1016/j.jcte.2013.12.001. eCollection 2014 Mar. PubMed PMID: 29235586; PubMed Central PMCID: PMC5685025. 13: Kapur A, O'Connor-Semmes R, Hussey EK, Dobbins RL, Tao W, Hompesch M, Smith GA, Polli JW, James CD Jr, Mikoshiba I, Nunez DJ. First human dose-escalation study with remogliflozin etabonate, a selective inhibitor of the sodium-glucose transporter 2 (SGLT2), in healthy subjects and in subjects with type 2 diabetes mellitus. BMC Pharmacol Toxicol. 2013 May 13;14:26. doi: 10.1186/2050-6511-14-26. PubMed PMID: 23668634; PubMed Central PMCID: PMC3700763. 14: Hussey EK, Kapur A, O'Connor-Semmes R, Tao W, Rafferty B, Polli JW, James CD Jr, Dobbins RL. Safety, pharmacokinetics and pharmacodynamics of remogliflozin etabonate, a novel SGLT2 inhibitor, and metformin when co-administered in subjects with type 2 diabetes mellitus. BMC Pharmacol Toxicol. 2013 Apr 30;14:25. doi: 10.1186/2050-6511-14-25. PubMed PMID: 23631443; PubMed Central PMCID: PMC3682882. 15: O'Connor-Semmes RL, Sandefer EP, Hussey EK, Tao W, Doll WJ, Page RC, Dobbins R. Regional gastrointestinal delivery of remogliflozin etabonate in humans. Biopharm Drug Dispos. 2013 Mar;34(2):79-86. doi: 10.1002/bdd.1824. Epub 2013 Jan 7. PubMed PMID: 23111980. 16: Mudaliar S, Armstrong DA, Mavian AA, O'Connor-Semmes R, Mydlow PK, Ye J, Hussey EK, Nunez DJ, Henry RR, Dobbins RL. Remogliflozin etabonate, a selective inhibitor of the sodium-glucose transporter 2, improves serum glucose profiles in type 1 diabetes. Diabetes Care. 2012 Nov;35(11):2198-200. doi: 10.2337/dc12-0508. Epub 2012 Sep 25. PubMed PMID: 23011728; PubMed Central PMCID: PMC3476920. 17: Sigafoos JF, Bowers GD, Castellino S, Culp AG, Wagner DS, Reese MJ, Humphreys JE, Hussey EK, O'Connor Semmes RL, Kapur A, Tao W, Dobbins RL, Polli JW. Assessment of the drug interaction risk for remogliflozin etabonate, a sodium-dependent glucose cotransporter-2 inhibitor: evidence from in vitro, human mass balance, and ketoconazole interaction studies. Drug Metab Dispos. 2012 Nov;40(11):2090-101. doi: 10.1124/dmd.112.047258. Epub 2012 Jul 30. PubMed PMID: 22851617. 18: Papazafiropoulou AK, Kardara MS, Pappas SI. Challenges for the treatment of diabetes mellitus. Recent Pat Endocr Metab Immune Drug Discov. 2011 Sep;5(3):203-9. Review. PubMed PMID: 21913881. 19: Dobbins RL, O'Connor-Semmes R, Kapur A, Kapitza C, Golor G, Mikoshiba I, Tao W, Hussey EK. Remogliflozin etabonate, a selective inhibitor of the sodium-dependent transporter 2 reduces serum glucose in type 2 diabetes mellitus patients. Diabetes Obes Metab. 2012 Jan;14(1):15-22. doi: 10.1111/j.1463-1326.2011.01462.x. Epub 2011 Oct 30. PubMed PMID: 21733056. 20: Ghosh RK, Ghosh SM, Chawla S, Jasdanwala SA. SGLT2 inhibitors: a new emerging therapeutic class in the treatment of type 2 diabetes mellitus. J Clin Pharmacol. 2012 Apr;52(4):457-63. doi: 10.1177/0091270011400604. Epub 2011 May 4. Review. PubMed PMID: 21543663.