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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 of LUSEOGLIFLOZIN

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

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.26 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
PubMed

PubMed

TitleDatePubMed
(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
Luseogliflozin: first global approval.
2014 Jun
Treatment with the SGLT2 inhibitor luseogliflozin improves nonalcoholic steatohepatitis in a rodent model with diabetes mellitus.
2015
Preclinical metabolism and disposition of luseogliflozin, a novel antihyperglycemic agent.
2015
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
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
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
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
Characterization and comparison of sodium-glucose cotransporter 2 inhibitors in pharmacokinetics, pharmacodynamics, and pharmacologic effects.
2016 Mar
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
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
Patents

Sample Use Guides

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
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 Fri Dec 15 19:19:43 GMT 2023
Edited
by admin
on Fri Dec 15 19:19:43 GMT 2023
Record UNII
C596HWF74Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LUSEOGLIFLOZIN
INN   WHO-DD  
INN  
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
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
NCI_THESAURUS
C174652
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
INN
9292
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
SMS_ID
100000155468
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
MERCK INDEX
m11866
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
EVMPD
SUB129554
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
DRUG BANK
DB12214
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
WIKIPEDIA
Luseogliflozin
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
FDA UNII
C596HWF74Z
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID10237921
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
CAS
898537-18-3
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
DRUG CENTRAL
4891
Created by admin on Fri Dec 15 19:19:43 GMT 2023 , Edited by admin on Fri Dec 15 19:19:43 GMT 2023
PRIMARY
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TARGET -> INHIBITOR
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ACTIVE MOIETY