ChemicalBook Product Catalog API Inhibitors ReMogliflozin etabonate

ReMogliflozin etabonate

Product NameReMogliflozin etabonate
CAS442201-24-3
MFC26H38N2O9
MW522.6
EINECS
MOL File442201-24-3.mol

Chemical Properties

Boiling point	661.3±55.0 °C(Predicted)
Density	1.31±0.1 g/cm3(Predicted)
storage temp.	Store at -20°C
solubility	DMSO: Soluble; Methanol: Soluble
form	A solid
pka	12.58±0.70(Predicted)
color	White to off-white
InChIKey	UAOCLDQAQNNEAX-JJJFNNNPNA-N
SMILES	O([C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](COC(=O)OCC)O1)O)C1=NN(C(C)C)C(C)=C1CC1C=CC(OC(C)C)=CC=1 \|&1:1,2,3,5,7,r\|

Usage And Synthesis

Uses

Remogliflozin etabonate (GSK189075) is an orally active, selective and low-affinity sodium glucose cotransporter (SGLT2) inhibitor with Ki values of 1.95 μM, 2.14 μM, 43.1 μM, 8.57 μM for hSGLT2, rSGLT2, hSGLT1, rSGLT1, respectively. Remogliflozin etabonate is a proagent based on benzylpyrazole glucoside and is metabolized to its active form, Remogliflozin, in the body. Remogliflozin etabonate exhibits antidiabetic efficacy in rodent models[1].

Definition

ChEBI: Remogliflozin etabonate is a glycoside.

Synthesis

Synthesis of ReMogliflozin etabonate
ReMogliflozin etabonate synthesis

in vivo

Remogliflozin etabonate (GSK189075; 10 or 30 mg/kg; orally; twice daily for 6 weeks) significantly reduced both the FPG and GHb levels in a dosedependent manner^[1].
Remogliflozin etabonate (3, 10, 30 mg/kg; orally) increases urinary glucose excretion in a dose-dependent manner. Remogliflozin etabonate dose-dependently inhibits the increase in plasma glucose after glucose loading and decreases the plasma insulin in normal rats^[1].
Remogliflozin etabonate (1-10 mg/kg; orally) decreases the blood glucose and reduces the AUC_{0–6 h} for blood glucose in a dose-dependent manner^[1].
Remogliflozin etabonate (high-fat diet containing 0.01, 0.03, or 0.1% remogliflozin etabonate for 8 weeks) reduces the levels of plasma glucose, plasma insulin, and GHb in a dose-dependent manner, and it suppresses the development of hypertriglyceridemia in male GK rats (6 weeks of age)^[1].

Animal Model:	db/db mice at the age of 8 weeks^[1]
Dosage:	10 or 30 mg/kg
Administration:	Orally; twice daily for 6 weeks
Result:	Significantly reduced both the fasting plasma glucose (FPG) and glycated hemoglobin (GHb) levels in a dosedependent manner. Reduced both urine volume and urinary glucose excretion with ameliorated the hyperglycemia.

IC 50

hSGLT2: 1.95 μM (Ki); rSGLT2: 2.14 μM (Ki); hSGLT1: 43.1 μM (Ki); rSGLT1: 8.57 μM (Ki)

References

[1] Yoshikazu Fujimori, et al. 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