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
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
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4979 Sources: http://www.lexpharma.com/pipeline/sotagliflozin |
36.0 nM [IC50] | ||
Target ID: CHEMBL3884 Sources: http://www.lexpharma.com/pipeline/sotagliflozin |
1.8 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | SOTAGLIFLOZIN Approved UseUnknown |
|||
Primary | SOTAGLIFLOZIN Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
274 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22739142/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22739142/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2879 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22739142/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22739142/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
18.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/ |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25529979/ |
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 |
PubMed
Title | Date | PubMed |
---|---|---|
LX4211, a dual SGLT1/SGLT2 inhibitor, improved glycemic control in patients with type 2 diabetes in a randomized, placebo-controlled trial. | 2012 Aug |
|
Sotagliflozin as a potential treatment for type 2 diabetes mellitus. | 2015 |
|
LX4211 therapy reduces postprandial glucose levels in patients with type 2 diabetes mellitus and renal impairment despite low urinary glucose excretion. | 2015 Jan 1 |
|
Sotagliflozin, a Dual SGLT1 and SGLT2 Inhibitor, as Adjunct Therapy to Insulin in Type 1 Diabetes. | 2015 Jul |
|
Development of sotagliflozin, a dual sodium-dependent glucose transporter 1/2 inhibitor. | 2015 Mar |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25529979
Sotagliflozin (LX4211) at 400 mg once daily for 7 days.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25690134
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
Edited
Sat Dec 16 01:31:17 GMT 2023
by
admin
on
Sat Dec 16 01:31:17 GMT 2023
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Record UNII |
6B4ZBS263Y
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Record Status |
Validated (UNII)
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Record Version |
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C98083
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Related Record | Type | Details | ||
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TARGET -> INHIBITOR |
HEK293 cells overexpressing human SGLT2
IC50
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TARGET -> INHIBITOR |
HEK293 cells overexpressing human SGLT1
IC50
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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