Remogliflozin etabonate | CAS#442201-24-3 | SGLT2 inhibitor

MedKoo Cat#: 319897 | Name: Remogliflozin etabonate

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Description:

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

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

Remogliflozin etabonate

CAS#442201-24-3

Theoretical Analysis

MedKoo Cat#: 319897

Name: Remogliflozin etabonate

CAS#: 442201-24-3

Chemical Formula: C26H38N2O9

Exact Mass: 522.2577

Molecular Weight: 522.60

Elemental Analysis: C, 59.76; H, 7.33; N, 5.36; O, 27.55

Price and Availability

Size	Price	Availability	Quantity
1mg	USD 295.00	2 Weeks
5mg	USD 950.00	2 Weeks

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Related CAS #

No Data

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

Product Data

Instruction

View handling instruction

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/

	Solvent	mg/mL	mM
Solubility
	DMSO	2.0	3.83

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 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.

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: Patel R, Kotadiya R. Stability-indicating green HPLC method for fixed-dose tablets containing remogliflozin etabonate and teneligliptin: an AQbD approach. Drug Dev Ind Pharm. 2024 Sep 11:1-13. doi: 10.1080/03639045.2024.2400199. Epub ahead of print. PMID: 39226128. 2: Acharya H, Kotadiya R. Stability-indicating HPLC for remogliflozin, vildagliptin, and metformin: Method development, validation, and greenness. Ann Pharm Fr. 2024 Jun 28:S0003-4509(24)00099-3. doi: 10.1016/j.pharma.2024.06.006. Epub ahead of print. PMID: 38945392. 3: Sharma V, Chawla S, Garg S, Singh B. Efficacy and Safety of Vildagliptin and Remogliflozin as Add-on Therapy to Metformin in Patients of Type 2 Diabetes Mellitus: An open-label comparative study. Sultan Qaboos Univ Med J. 2024 May;24(2):243-249. doi: 10.18295/squmj.1.2024.006. Epub 2024 May 27. PMID: 38828248; PMCID: PMC11139359. 4: Muruganathan G, Thangavel M, Kochupapy RT. Stability-Indicating HPTLC Method for Determination of Remogliflozin Etabonate and Vildagliptin in Tablets. J Chromatogr Sci. 2023 Dec 30;62(1):27-34. doi: 10.1093/chromsci/bmad001. PMID: 36670546. 5: Prajapati P, Prajapati B, Pulusu VS, Shah S. Multivariate Analysis and Response Surface Modeling to Green Analytical Chemistry-Based RP-HPLC-PDA Method for Chromatographic Analysis of Vildagliptin and Remogliflozin Etabonate. J AOAC Int. 2023 May 3;106(3):601-612. doi: 10.1093/jaoacint/qsad013. PMID: 36651669. 6: Prajapati P, Ahir H, Prajapati B, Shah S. Chemometric-Based AQbD and Green Chemistry Approaches to Chromatographic Analysis of Remogliflozin Etabonate and Vildagliptin. J AOAC Int. 2022 Dec 22;106(1):239-249. doi: 10.1093/jaoacint/qsac084. PMID: 35822588. 7: Attimarad M, Venugopala KN, Chohan MS, David M, Molina EIP, Sreeharsha N, Nair AB, Tratrat C, Altaysan AI, Balgoname AA. An Experimental Design Approach to Quantitative Expression for Quality Control of a Multicomponent Antidiabetic Formulation by the HILIC Method. Molecules. 2022 May 13;27(10):3135. doi: 10.3390/molecules27103135. PMID: 35630608; PMCID: PMC9148089. 8: Itigimatha N, Chadchan KS, Yallur BC, Hadagali MD. Simple and Sensitive RP- HPLC and UV Spectroscopic Methods for the Determination of Remogliflozin Etabonate in Pure and Pharmaceutical Formulations. Turk J Pharm Sci. 2022 Apr 29;19(2):213-219. doi: 10.4274/tjps.galenos.2021.55381. PMID: 35510349; PMCID: PMC9083516. 9: Khaladkar K, Mohan B, Khaladkar K, Suryawanshi S, Barkatestrong/Strong H. Efficacy and Safety of a Fixed Dose Combination of Remogliflozin Etabonate and Vildagliptin in Patients with Type-2 Diabetes Mellitus: A Randomized, Active- Controlled, Double-Blind, Phase III Study. J Assoc Physicians India. 2022 Apr;70(4):11-12. PMID: 35443373. 10: Dutta D, Jindal R, Mehta D, Khandelwal D, Sharma M. Efficacy and safety of novel sodium glucose cotransporter-2 inhibitor remogliflozin in the management of type 2 diabetes mellitus: A systematic review and meta-analysis. Diabetes Metab Syndr. 2021 Nov-Dec;15(6):102315. doi: 10.1016/j.dsx.2021.102315. Epub 2021 Oct 22. PMID: 34700292. 11: Attimarad M, Venugopala KN, Al-Dhubiab BE, Elgorashe REE, Shafi S. Development of Ecofriendly Derivative Spectrophotometric Methods for the Simultaneous Quantitative Analysis of Remogliflozin and Vildagliptin from Formulation. Molecules. 2021 Oct 12;26(20):6160. doi: 10.3390/molecules26206160. PMID: 34684741; PMCID: PMC8537597. 12: Suryavanshi VD, Sharma S, Sahu JK. Review on Characteristics and Analytical Methods of Remogliflozin Etabonate: An Update. Mini Rev Med Chem. 2022;22(9):1341-1350. doi: 10.2174/1389557521666211007115611. PMID: 34620050. 13: Dobbins R, Hussey EK, O'Connor-Semmes R, Andrews S, Tao W, Wilkison WO, Cheatham B, Sagar K, Hanmant B. Assessment of safety and tolerability of remogliflozin etabonate (GSK189075) when administered with total daily dose of 2000 mg of metformin. BMC Pharmacol Toxicol. 2021 Jun 13;22(1):34. doi: 10.1186/s40360-021-00502-0. PMID: 34120651; PMCID: PMC8201735. 14: Shimizu K, Fujikura H, Fushimi N, Nishimura T, Tatani K, Katsuno K, Fujimori Y, Watanabe S, Hiratochi M, Nakabayashi T, Kamada N, Arakawa K, Hikawa H, Azumaya I, Isaji M. Discovery of remogliflozin etabonate: A potent and highly selective SGLT2 inhibitor. Bioorg Med Chem. 2021 Mar 15;34:116033. doi: 10.1016/j.bmc.2021.116033. Epub 2021 Jan 22. PMID: 33581390. 15: Attimarad M, Nair AB, Sreeharsha N, Al-Dhubiab BE, Venugopala KN, Shinu P. Development and Validation of Green UV Derivative Spectrophotometric Methods for Simultaneous Determination Metformin and Remogliflozin from Formulation: Evaluation of Greenness. Int J Environ Res Public Health. 2021 Jan 8;18(2):448. doi: 10.3390/ijerph18020448. PMID: 33429964; PMCID: PMC7827813. 16: Bhattacharya S, Rathore A, Parwani D, Mallick C, Asati V, Agarwal S, Rajoriya V, Das R, Kashaw SK. An exhaustive perspective on structural insights of SGLT2 inhibitors: A novel class of antidiabetic agent. Eur J Med Chem. 2020 Oct 15;204:112523. doi: 10.1016/j.ejmech.2020.112523. Epub 2020 Jul 19. PMID: 32717480. 17: Mohan V, Mithal A, Joshi SR, Aravind SR, Chowdhury S. Remogliflozin Etabonate in the Treatment of Type 2 Diabetes: Design, Development, and Place in Therapy. Drug Des Devel Ther. 2020 Jun 24;14:2487-2501. doi: 10.2147/DDDT.S221093. PMID: 32612352; PMCID: PMC7322139. 18: Dharmalingam M, Aravind SR, Thacker H, Paramesh S, Mohan B, Chawla M, Asirvatham A, Goyal R, Shembalkar J, Balamurugan R, Kadam P, Alva H, Kodgule R, Tandon M, Vaidyanathan S, Pendse A, Gaikwad R, Katare S, Suryawanshi S, Barkate H. 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. Drugs. 2020 Apr;80(6):587-600. doi: 10.1007/s40265-020-01285-0. PMID: 32162274; PMCID: PMC7165159. 19: Joshi S, Gudi G, Menon VCA, Tandon M, Joshi V, Suryawanshi S, Barkate H, Sawant N, Katare S, Siddique W. An Open-Label, Single-Period, Two-Stage, Single Oral Dose Pharmacokinetic Study of Remogliflozin Etabonate Tablet 100 and 250 mg in Healthy Asian Indian Male Subjects Under Fasting and Fed Conditions. Clin Pharmacokinet. 2020 Mar;59(3):349-357. doi: 10.1007/s40262-019-00819-4. PMID: 31583610. 20: Markham A. Remogliflozin Etabonate: First Global Approval. Drugs. 2019 Jul;79(10):1157-1161. doi: 10.1007/s40265-019-01150-9. PMID: 31201711.