Remogliflozin etabonate
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MedKoo CAT#: 319897

CAS#: 442201-24-3

Description: Remogliflozin etabonate, also known as GSK 189075A or GSK 189075, is a SGLT2 inhibitor under development for the treatment of type 2 diabetes. Remogliflozin etabonate is a pro-drug of remogliflozin. Remogliflozin inhibits the sodium-glucose transport proteins (SGLT), which are responsible for glucose reabsorption in the kidney. Blocking this transporter causes blood glucose to be eliminated through the urine. Remogliflozin is selective for SGLT2.


Chemical Structure

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Remogliflozin etabonate
CAS# 442201-24-3

Theoretical Analysis

MedKoo Cat#: 319897
Name: Remogliflozin etabonate
CAS#: 442201-24-3
Chemical Formula: C26H38N2O9
Exact Mass: 522.26
Molecular Weight: 522.600
Elemental Analysis: C, 59.76; H, 7.33; N, 5.36; O, 27.55

Price and Availability

Size Price Availability Quantity
1mg USD 295 2 Weeks
5mg USD 950 2 Weeks
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Synonym: GSK189075A; GSK-189075A; GSK 189075A; GSK189075; GSK-189075; GSK 189075; Remogliflozin etabonate.

IUPAC/Chemical Name: 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

InChi Key: UAOCLDQAQNNEAX-ABMICEGHSA-N

InChi Code: InChI=1S/C26H38N2O9/c1-7-33-26(32)34-13-20-21(29)22(30)23(31)25(36-20)37-24-19(16(6)28(27-24)14(2)3)12-17-8-10-18(11-9-17)35-15(4)5/h8-11,14-15,20-23,25,29-31H,7,12-13H2,1-6H3/t20-,21-,22+,23-,25+/m1/s1

SMILES Code: O[C@H]([C@H]([C@@H]([C@@H](COC(OCC)=O)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:
Biological target: Remogliflozin etabonate is a prodrug form of the sodium-glucose transporter 2 (SGLT2) inhibitor remogliflozin A. Remogliflozin etabonate inhibits human SGLT2 and SGLT1 (Kis = 1.95 and 43.1 μM, respectively). It inhibits increases in plasma glucose levels in a glucose tolerance test in a rat model of diabetes induced by streptozotocin. Remogliflozin etabonate (10 and 30 mg/kg twice per day for 6 weeks) also increases fasting plasma insulin levels and reduces fasting plasma glucose and triglyceride levels, as well as urinary glucose excretion, in a db/db mouse model of diabetes with hyperinsulinemia and obesity.
In vitro activity: To be determined
In vivo activity: In high-fat diet-fed Goto-Kakizaki rats, remogliflozin etabonate improved hyperglycemia, hyperinsulinemia, hypertriglyceridemia, and insulin resistance. Remogliflozin etabonate treatment exhibits antidiabetic efficacy in several rodent models. These findings suggest that remogliflozin etabonate may be a new and useful drug for the treatment of diabetes. Reference: J Pharmacol Exp Ther. 2008 Oct;327(1):268-76. https://pubmed.ncbi.nlm.nih.gov/18583547/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 2.0 3.83

Preparing Stock Solutions

The following data is based on the product molecular weight 522.60 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.

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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. PubMed PMID: 26628836; PubMed Central PMCID: PMC4632078.

2: 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. PubMed PMID: 26288025.

3: 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.

4: 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.

5: 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.

6: 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.

7: 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.

8: 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.

9: 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.

10: 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.

11: 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.

12: 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.

13: 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.

14: 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.

15: 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. PubMed PMID: 18583547.