LUSEOGLIFLOZIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H30O6S
Molecular Weight	434.546
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC1=CC=C(CC2=C(C)C=C(OC)C(=C2)[C@@H]3S[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)C=C1

InChI

InChIKey=WHSOLWOTCHFFBK-ZQGJOIPISA-N

InChI=1S/C23H30O6S/c1-4-29-16-7-5-14(6-8-16)10-15-11-17(18(28-3)9-13(15)2)23-22(27)21(26)20(25)19(12-24)30-23/h5-9,11,19-27H,4,10,12H2,1-3H3/t19-,20-,21+,22-,23+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20302302
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24848756

Luseogliflozin (TS-071), a derivative of a novel scaffold, C-phenyl 1-thio-D-glucitol, exhibited potent sodium-dependent glucose cotransporter (SGLT) 2 inhibition activity. Luseogliflozin exhibits a blood glucose lowering effect, excellent urinary glucose excretion properties, and promising pharmacokinetics profiles in animals. It showed good metabolic stability toward cryo-preserved human hepatic clearance, have acceptable human pharmacokinetics properties. Luseogliflozin [Lusefi(®) (Japan)] was developed by Taisho Pharmaceutical for the treatment of patients with type 2 diabetes mellitus. The drug has received its first global approval for this indication in Japan, either as monotherapy or in combination with other antihyperglycaemic agents.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium/glucose cotransporter 2 25 Target ID: CHEMBL3884 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20302302	Inhibitor 8297		2.26 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24848756	Primary		Approved 8429	LUSEFI Approved Use Lusefi tab. (2.5mg Luseogliflozin hydrate) inhibits glucose reabsorption in the renal proximal tubule and excretes excess glucose in urine to reduce blood sugar level. It is usually used to treat type 2 diabetic mellitus. Launch Date 1.39553276E12

PubMed

Title	Date	PubMed
(1S)-1,5-anhydro-1-[5-(4-ethoxybenzyl)-2-methoxy-4-methylphenyl]-1-thio-D-glucitol (TS-071) is a potent, selective sodium-dependent glucose cotransporter 2 (SGLT2) inhibitor for type 2 diabetes treatment.	2010 Apr 22	20302302
Luseogliflozin: first global approval.	2014 Jun	24848756
Treatment with the SGLT2 inhibitor luseogliflozin improves nonalcoholic steatohepatitis in a rodent model with diabetes mellitus.	2015	26594248
Preclinical metabolism and disposition of luseogliflozin, a novel antihyperglycemic agent.	2015	26489961
Evaluation of potential activity of luseogliflozin on vascular proliferation in the mesenteric lymph node with or without vascular tumors in Sprague-Dawley rats in a carcinogenicity study.	2016 Apr	27182112
Efficacy and Safety of the SGLT2 Inhibitor Luseogliflozin in Japanese Patients With Type 2 Diabetes Mellitus Stratified According to Baseline Body Mass Index: Pooled Analysis of Data From 52-Week Phase III Trials.	2016 Apr	27021608
Influence of Renal Function on the 52-Week Efficacy and Safety of the Sodium Glucose Cotransporter 2 Inhibitor Luseogliflozin in Japanese Patients with Type 2 Diabetes Mellitus.	2016 Jan 1	26718606
Comparative effectiveness of sodium-glucose co-transporter 2 inhibitors for controlling hyperglycaemia in patients with type 2 diabetes: protocol for a systematic review and network meta-analysis.	2016 Jan 29	26826156
Characterization and comparison of sodium-glucose cotransporter 2 inhibitors in pharmacokinetics, pharmacodynamics, and pharmacologic effects.	2016 Mar	26970780
Impact of Reduced Renal Function on the Glucose-Lowering Effects of Luseogliflozin, a Selective SGLT2 Inhibitor, Assessed by Continuous Glucose Monitoring in Japanese Patients with Type 2 Diabetes Mellitus.	2016 Mar	26846284
Effects of diuretics on sodium-dependent glucose cotransporter 2 inhibitor-induced changes in blood pressure in obese rats suffering from the metabolic syndrome.	2016 May	26982381
In vitro evaluation of potential drug interactions mediated by cytochrome P450 and transporters for luseogliflozin, an SGLT2 inhibitor.	2017 Apr	27324291

Patents

Sample Use Guides

In Vivo Use Guide

In general, for adults, take 1 tablet (2.5 mg of Luseogliflozin) at a time once a day before or after breakfast. The dosage may be increased to 2 tablets (5 mg) at a time once a day according to your symptoms.

Route of Administration: Oral

In Vitro Use Guide

The exposure of primary hepatocytes to luseogliflozin for 72 hrs weakly induced CYP3A4 at a concentration of 10 μM, whereas it did not induce CYP1A2 or CYP2B6 at concentrations of 0.1-10 μM.

Name

Type

Language

LUSEOGLIFLOZIN

Official Name

English

TS071

Code

English

luseogliflozin [INN]

Common Name

English

LUSEOGLIFLOZIN [MI]

Common Name

English

Luseogliflozin [WHO-DD]

Common Name

English

TS-71

Code

English

D-GLUCITOL, 1,5-DIDEOXY-1,5-EPITHIO-1-C-(5-((4-ETHOXYPHENYL)METHYL)-2-METHOXY-4-METHYLPHENYL)-, (1S)-

Common Name

English

TS-071

Code

English

(2S,3R,4R,5S,6R)-2-(5-((4-ETHOXYPHENYL)METHYL)-2-METHOXY-4-METHYLPHENYL)-6-(HYDROXYMETHYL)THIANE-3,4,5-TRIOL

Systematic Name

English

Code System Code Type Description

PUBCHEM

11988953