U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H25ClO5S
Molecular Weight 424.938
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SOTAGLIFLOZIN

SMILES

CCOC1=CC=C(CC2=C(Cl)C=CC(=C2)[C@@H]3O[C@H](SC)[C@@H](O)[C@H](O)[C@H]3O)C=C1

InChI

InChIKey=QKDRXGFQVGOQKS-CRSSMBPESA-N
InChI=1S/C21H25ClO5S/c1-3-26-15-7-4-12(5-8-15)10-14-11-13(6-9-16(14)22)20-18(24)17(23)19(25)21(27-20)28-2/h4-9,11,17-21,23-25H,3,10H2,1-2H3/t17-,18-,19+,20+,21-/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H25ClO5S
Molecular Weight 424.938
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Sotagliflozin (LX4211) is an orally-delivered small molecule compound that is currently in development for the treatment of type 1 and type 2 diabetes mellitus. Sotagliflozin (LX4211) inhibits both sodium-glucose cotransporter type 2, or SGLT2, a transporter responsible for most of the glucose reabsorption performed by the kidney, and sodium-glucose cotransporter type 1, or SGLT1, a transporter responsible for glucose and galactose absorption in the gastrointestinal tract, and to a lesser extent than SGLT2, glucose reabsorption in the kidney. Combining SGLT1 and SGLT2 inhibition in a single molecule would provide complementary insulin-independent mechanisms to treat diabetes.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
36.0 nM [IC50]
1.8 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SOTAGLIFLOZIN

Approved Use

Unknown
Primary
SOTAGLIFLOZIN

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
274 ng/mL
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SOTAGLIFLOZIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
180 ng/mL
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SOTAGLIFLOZIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
291 ng/mL
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SOTAGLIFLOZIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
113 ng/mL
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SOTAGLIFLOZIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2879 ng × h/mL
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SOTAGLIFLOZIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2213 ng × h/mL
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SOTAGLIFLOZIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1752 ng × h/mL
300 mg 1 times / day steady-state, oral
dose: 300 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SOTAGLIFLOZIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
732 ng × h/mL
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
SOTAGLIFLOZIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
18.1 h
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SOTAGLIFLOZIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
16.6 h
400 mg 1 times / day multiple, oral
dose: 400 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
SOTAGLIFLOZIN plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
LX4211 therapy reduces postprandial glucose levels in patients with type 2 diabetes mellitus and renal impairment despite low urinary glucose excretion.
2015 Jan 1
Patents

Sample Use Guides

Sotagliflozin (LX4211) at 400 mg once daily for 7 days.
Route of Administration: Oral
The ability of sotagliflozin in vitro to inhibit sodium-dependent glucose transporters 1 and 2 (SGLT1 and SGLT2) was established. Sotagliflozin inhibited SGLT2 with an IC50 of 0.0018 uΜ, and it inhibited SGLT1 with an IC50 of 0.036 uM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:31:17 GMT 2023
Edited
by admin
on Sat Dec 16 01:31:17 GMT 2023
Record UNII
6B4ZBS263Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SOTAGLIFLOZIN
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
SOTAGLIFLOZIN [MI]
Common Name English
LP-802034
Code English
LX-4211
Code English
INPEFA
Brand Name English
Sotagliflozin [WHO-DD]
Common Name English
SAR-439954
Common Name English
sotagliflozin [INN]
Common Name English
METHYL (5S)-5-C-(4-CHLORO-3-((4-ETHOXYPHENYL)METHYL)PHENYL)-1-THIO-.BETA.-L-XYLOPYRANOSIDE
Systematic Name English
SAR439954
Common Name English
.BETA.-L-XYLOPYRANOSIDE, METHYL 5-C-(4-CHLORO-3-((4-ETHOXYPHENYL)METHYL)PHENYL)-1-THIO-, (5S)-
Common Name English
LX4211
Code English
SOTAGLIFLOZIN [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C98083
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
Code System Code Type Description
USAN
ZZ-95
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
WIKIPEDIA
Sotagliflozin
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
DRUG CENTRAL
5339
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
NCI_THESAURUS
C119623
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
INN
9824
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
PUBCHEM
24831714
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL3039507
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
SMS_ID
100000164728
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
CAS
1018899-04-1
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID20144314
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
FDA UNII
6B4ZBS263Y
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
DRUG BANK
DB12713
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
MERCK INDEX
m12141
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
EVMPD
SUB179285
Created by admin on Sat Dec 16 01:31:17 GMT 2023 , Edited by admin on Sat Dec 16 01:31:17 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
HEK293 cells overexpressing human SGLT2
IC50
TARGET -> INHIBITOR
HEK293 cells overexpressing human SGLT1
IC50
Related Record Type Details
ACTIVE MOIETY