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=CC([C@@H]3S[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)=C(OC)C=C2C)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

Molecular Formula	C23H30O6S
Molecular Weight	434.546
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 8504		2.26 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Type 2 diabetes mellitus 262 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24848756	Primary		Approved 8583	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 2014

C_max

Value	Dose	Analyte	Population
38.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
187 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
721 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
205 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
248 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	5 mg 1 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Analyte	Population
337 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1830 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
8510 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1930 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1980 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	5 mg 1 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Analyte	Population
10.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
9.72 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
12.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
10.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	5 mg single, oral dose: 5 mg route of administration: Oral experiment type: SINGLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
10.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/24535625/	5 mg 1 times / day multiple, oral dose: 5 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LUSEOGLIFLOZIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
10 mg 1 times / day multiple, oral Highest studied dose Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/	Other AEs: Diarrhoea, Occult blood positive... Other AEs: Diarrhoea (grade 1, 12.5%) Occult blood positive (grade 1, 12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/
25 mg single, oral Highest studied dose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/	Other AEs: Diarrhoea, Urethritis... Other AEs: Diarrhoea (grade 1, 12.5%) Urethritis (grade 1, 12.5%) Occult blood positive (grade 1, 12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/

AEs

AE	Significance	Dose	Population
Diarrhoea	grade 1, 12.5%	10 mg 1 times / day multiple, oral Highest studied dose Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/
Occult blood positive	grade 1, 12.5%	10 mg 1 times / day multiple, oral Highest studied dose Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/
Diarrhoea	grade 1, 12.5%	25 mg single, oral Highest studied dose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/
Occult blood positive	grade 1, 12.5%	25 mg single, oral Highest studied dose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/
Urethritis	grade 1, 12.5%	25 mg single, oral Highest studied dose Dose: 25 mg Route: oral Route: single Dose: 25 mg Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/24535625/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inducer 1087 inhibitor 2252 substrate 1946	inhibitor 2438 substrate 1193	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 910 OATP1B3 961 CYP2E1 1060 CYP1A2 2153 CYP2C8 1057 CYP2C19 2057 CYP2B6 926 CYP2A6 879 P-gp 1741 OATP1B1 1079 OAT1 725 OAT3 747 OCT2 779	BCRP 697 P-gp 2052 OAT1 395 OATP1B1 503 OATP1B3 435 OAT3 391 OCT2 434 UGT1A3 470 CYP4F3A 3 UGT1A7 249 CYP1B1 104 CYP2A6 626 CYP1A1 389 CYP4A11 137 CYP4F3B 7 CYP2J2 71 CYP2C19 1119 CYP4F12 10 CYP2B6 776 UGT2B17 237 UGT1A6 343 CYP4F2 11 UGT2B7 456 UGT2B4 278 CYP2C8 810 CYP2E1 729 UGT1A4 399 CYP3A5 446 UGT1A8 323 CYP1A2 1197 UGT1A1 479 UGT1A9 423 UGT1A10 331	CYP1A2 832 CYP2B6 669

Drug as perpetrator

Target	Modality	Activity
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no [IC50 >100 uM]
CYP2A6 911	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no [IC50 >100 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no [IC50 >100 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no [IC50 >100 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no [IC50 >100 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no [IC50 >100 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no [IC50 >100 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no [IC50 >100 uM]
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no [IC50 >100 uM]
BCRP 985	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
CYP1A2 2333	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
CYP2B6 1160	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
OCT2 782	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	weak [IC50 93.1 uM]
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	weak
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	yes [IC50 58.3 uM]
CYP3A4 2633	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	yes

Drug as victim

Target	Modality	Activity
CYP3A4 1946	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	major
CYP3A5 446	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	major
UGT1A1 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	major
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	no
CYP2A6 626	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	no
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	no
OAT1 395	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
OAT3 391	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
OATP1B1 503	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
OATP1B3 435	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
OCT2 434	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	no
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	no
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	no
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	no
UGT2B17 237	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	no
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	no
UGT2B7 456	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	no
CYP1B1 104	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP2C8 810	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP2J2 71	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP4A11 137	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP4F12 10	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP4F2 11	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP4F3A 3	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP4F3B 7	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
UGT1A4 399	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
UGT1A8 323	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	weak
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27347703/	yes
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27324291/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.pmda.go.jp/drugs/2014/P201400033/400059000_22600AMX00540_A100_1.pdf Page: 13.0

PubMed

Title	Date	PubMed
In vitro evaluation of potential drug interactions mediated by cytochrome P450 and transporters for luseogliflozin, an SGLT2 inhibitor.	2017-04	27324291
Effects of diuretics on sodium-dependent glucose cotransporter 2 inhibitor-induced changes in blood pressure in obese rats suffering from the metabolic syndrome.	2016-05	26982381
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.	2016-04	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.	2016-04	27021608
Characterization and comparison of sodium-glucose cotransporter 2 inhibitors in pharmacokinetics, pharmacodynamics, and pharmacologic effects.	2016-03	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.	2016-03	26846284
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.	2016-01-29	26826156
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.	2016-01-01	26718606
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
Luseogliflozin: first global approval.	2014-06	24848756
(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.	2010-04-22	20302302

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:43:23 GMT 2025` Edited by `admin` on `Mon Mar 31 19:43:23 GMT 2025`
Record UNII	C596HWF74Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

luseogliflozin [INN]

Preferred Name

English

LUSEOGLIFLOZIN

Official Name

English

TS071

Code

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