HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sotagliflozin
Sotagliflozin · LX4211/Sotagliflozin-API · β-L-Xylopyranoside,methyl5-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-thio-,(5S)- · (5S)-Methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-thio-beta-L-xylopyranoside Sotagliflozin LP 802034 · LX421 · CS-1853 · LX-4211 · SOTA-009
Identifiers & Physical Properties
| CAS No. | 1018899-04-1 |
|---|---|
| Molecular formula | C21H25ClO5S |
| Average molar mass | 424.9 g/mol |
| Monoisotopic mass | 424.1111228 g/mol |
| SMILES | CCOc1ccc(Cc2cc([C@@H]3O[C@H](SC)[C@@H](O)[C@H](O)[C@H]3O)ccc2Cl)cc1 |
| InChIKey | QKDRXGFQVGOQKS-CRSSMBPESA-N |
| PubChem CID | 24831714 |
| ChEMBL | CHEMBL3039507 |
| ChEBI | CHEBI:229226 |
| EC No. | 805-113-6 |
| DTXSID | DTXSID20144314 |
Chemical & Physical Properties
| XLogP | 3.2 |
|---|---|
| Topological polar surface area | 104 |
| Hydrogen bond donors | 3 |
| Hydrogen bond acceptors | 6 |
| Rotatable bonds | 6 |
| Heavy atoms | 28 |
| Formal charge | 0 |
| Complexity | 476 |
| Drugs | Pharmaceuticals -> Listed in ZINC15 |
| Human Drugs | Breast FeedingLactationMilk, HumanHypoglycemic AgentsSodium-Glucose Cotransporter 2 InhibitorsSGLT2 InhibitorsFDA approved drugs -> Active ingredient |
| Boiling point | 607.9±55.0 °C(Predicted) |
| Density | 1.37±0.1 g/cm3(Predicted) |
| Storage conditions | Store at -20°C |
| Solubility | DMSO:84.0(Max Conc. mg/mL)197.67(Max Conc. mM)Ethanol:17.0(Max Conc. mg/mL)40.01(Max Conc. mM) |
| pKa (acidity coefficient) | 12.87±0.70(Predicted) |
| Physical state | Powder |
| Color | White to off-white |
| optical activity | 35.7°(C=0.01g/mL, CHCL3, 20°C, 589nm) |
| InChIKey | QKDRXGFQVGOQKS-WFCPIQDQNA-N |
| SMILES | [C@@H]1(C2=CC=C(Cl)C(CC3=CC=C(OCC)C=C3)=C2)O[C@H](SC)[C@@H](O)[C@H](O)[C@H]1O |&1:0,19,22,24,26,r| |
| FDA UNII | 6B4ZBS263Y |
| NCI Drug Dictionary | sotagliflozin |
| ATC code | A10BK06 |
| GHS pictogram | GHS08 |
| Signal word | Warning |
| GHS hazard statements | H351-H373 |
| GHS precautionary statements | P201-P202-P281-P308+P313-P405-P501-P260-P314-P501 |
Safety & Regulations
| GHS classification | This chemical does not meet GHS hazard criteria for 50% (2 of 4) of reports.WarningH302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 4 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (25%) |
| Hepatotoxicity | In two large pre-registration, placebo-controlled cardiovascular outcome trials that enrolled more than 11,000 patients, serum aminotransferase elevations were no more frequent with sotagliflozin than with placebo. Rates of ALT elevations above 3 times the upper limit of normal (ULN) were similar between treatment groups (2.0% vs 2.1% in the heart failure trial0.9% vs 0.9% in the diabetes and kidney disease trial), and mean aminotransferase levels did not change with treatment. Potential cases of drug-induced liver injury, adjudicated by a committee blinded to the treatment group, occurred at similarly low rates in the sotagliflozin and placebo patients [1.8% vs 2.3% and 0.7% vs 0.6%]. A single sotagliflozin-treated patient met laboratory criteria for clinically apparent liver injury with jaundice, but the event occurred months after stopping the drug and was judged to be due to biliary obstruction from gallstones. The product label does not list liver injury as an adverse reaction. Since its approval, there have been no published reports of clinically apparent liver injury attributed to sotagliflozin, but clinical experience with the drug has been limited. As with other agents in the SGLT2 inhibitor class, sotagliflozin appears to be an unlikely cause of liver injury. |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Signal word | Warning |
| GHS pictogram | GHS08 |
| GHS hazard statements | H351-H373 |
| GHS precautionary statements | P201-P202-P281-P308+P313-P405-P501-P260-P314-P501 |
Applications & Uses
Uses
Sotagliflozin is used for the treatment of patients with type 1 diabetes mellitus.