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Sotagliflozin

HCID 24831714
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Grundinformationen

CAS
1018899-04-1
Standard-SMILES
CCOc1ccc(Cc2cc([C@@H]3O[C@H](SC)[C@@H](O)[C@H](O)[C@H]3O)ccc2Cl)cc1
InChIKey
QKDRXGFQVGOQKS-CRSSMBPESA-N
Summenformel
C21H25ClO5S
Durchschnittliche Molmasse
424,9 g/mol
Monoisotopische Masse
424,1111228

Überblick

Sotagliflozin is an S-glycosyl compound that is 1-thio-beta-L-xylopyranose in which the anomeric hydroxy group is replaced by a 4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl group and the thiol is replaced by a methylsulfanediyl group. It is an inhibitor of SGLT1 and SGLT2 that is approved to reduce the risk of cardiovascular death, hospitalization for heart failure, and urgent heart failure visit in adults with heart failure or type 2 diabetes mellitus, chronic kidney disease, and other cardiovascular risk. It has a role as a sodium-glucose transport protein subtype 1 inhibitor, a hypoglycemic agent, an antihypertensive agent, a sodium-glucose transport protein subtype 2 inhibitor and a cardioprotective agent. It is a C-glycosyl compound, a S-glycosyl compound, an aromatic ether and a member of monochlorobenzenes.

Namen und Bezeichner

Bevorzugter Name
Sotagliflozin
IUPAC
(2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylsulfanyloxane-3,4,5-triol
Englischer Name
LX-4211
Summenformel
C21H25ClO5S
Molmasse
424.94

Namen und Synonyme

Sotagliflozin1018899-04-1LX-4211LX4211INPEFAsotagliflozinasotagliflozinesotagliflozinumLP-8020346B4ZBS263YSar439954LP 802034
Weitere Namen anzeigen
LX4211/Sotagliflozin-APIβ-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 802034LX421CS-1853SOTA-009EOS-61381
DTXSID20144314Sar-439954(2S,3R,4R,5S,6R)-2-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-6-methylsulfanyloxane-3,4,5-triolbeta-L-Xylopyranoside, methyl 5-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-thio-, (5S)-beta-l-Xylopyranoside, methyl 5-C-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-1-thio-, (5S)-(2S,3R,4R,5S,6R)-2-{4-CHLORO-3-[(4-ETHOXYPHENYL)METHYL]PHENYL}-6-(METHYLSULFANYL)OXANE-3,4,5-TRIOL(2S,3R,4R,5S,6R)-2-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-6-(methylsulfanyl)oxane-3,4,5-triol(2S,3R,4R,5S,6R)-2-(4-chloro-3-((4-ethoxyphenyl)methyl)phenyl)-6-methylsulfanyloxane-3,4,5-triol

Datenbank-Bezeichner

CAS
1018899-04-1

Eigenschaften

Berechnete Struktureigenschaften

XLogP
3,2
Polarare Oberfläche (TPSA)
104 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
6
Frei drehbare Bindungen
6
Schwere Atome
28
Formalladung
0
Komplexität
476

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15
Human Drugs · 3 Einträge

Breast Feeding; Lactation; Milk, Human; Hypoglycemic Agents; Sodium-Glucose Cotransporter 2 Inhibitors; SGLT2 Inhibitors

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Physikochemische Eigenschaften

Siedepunkt
607.9 · 607.9±55.0 °C(Predicted)
Dichte
1.37 · 1.37±0.1 g/cm3(Predicted)
storage temp.
-20 °C · Store at -20°C
Löslichkeit
84 · 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
12.87 · 12.87±0.70(Predicted)
Aggregatzustand
Powder
Farbe
White to off-white
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|

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 5 Einträge

This chemical does not meet GHS hazard criteria for 50% (2 of 4) of reports.

Warning

H302 (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.

Gefahrenhinweise

Hazard Classes and CategoriesAcute Tox. 4 (25%)

Toxikologische Informationen

Hepatotoxicity · 1 Eintrag

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 trial; 0.9% 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.

Chemie und Industrie

Pharmakologische Informationen

ATC Code · 2 Einträge

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Protein BindingBoth sotagliflozin and its major metabolite, M19, are extensively (~98%) protein-bound in plasma, although the specific protein(s) to which they bind have not been elucidated.
Pharmacodynamics · 1 Eintrag

Sotagliflozin exerts its pharmacologic effects by slowing glucose absorption in the gastrointestinal tract and increasing the excretion of glucose in the urine. It is administered by mouth once daily before the first meal of the day. The use of SGLT2 inhibitors, including sotagliflozin, can cause diabetic ketoacidosis (DKA). Patients, especially those with a higher baseline risk of DKA, should be instructed on how and when to monitor for ketoacidosis and what actions to take when DKA is suspected. SGLT2 inhibitors, including sotagliflozin, also increase the risk of genital infections. This is due to the increase in urinary glucose excretion, which provides a relatively glucose-rich environment in which infectious agents may establish themselves.

Mechanism of Action · 1 Eintrag

Sodium-glucose co-transporter types 1 and 2 (SGLT1 and SGLT2) are integral in the transport of glucose in the body. SGLT1 is the major transporter for glucose absorption in the gastrointestinal tract, while SGLT2 is the predominant transporter responsible for reabsorption of glucose in the glomerulus. Sotagliflozin is a dual inhibitor of both SGLT1 and SGLT2. Inhibition of SGLT1 results in a delay in glucose absorption and a blunting of postprandial hyperglycemia, while inhibition of SGLT2 reduces renal reabsorption of filtered glucose, thereby increasing urinary glucose excretion.

Biological Half-LifeThe mean terminal half-life of sotagliflozin ranged from 21 to 35 hours and from 19 to 26 hours for its M19 metabolite.
Metabolism/Metabolites · 1 Eintrag

The major metabolite of sotagliflozin is a 3-O-glucuronide (M19), which comprised ~94% of of the radioactivity in plasma following the oral administration of a radiolabeled dose of sotagliflozin. The M19 metabolite is effectively inactive, with >275-fold less activity at SGLT1 and SGLT2 compared to the parent drug. The primary route of metabolism is via glucuronidation by UGT1A9 (and both UGT1A1 and UGT2B7, to a lesser extent) as well as oxidation via CYP3A4.

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Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
PubChem CID
24831714
DTXSID
DTXSID20144314
ChEMBL
CHEMBL3039507
ChEBI
CHEBI:229226
UNII
6B4ZBS263Y
EC Number
805-113-6
Nikkaji
J3.750.394K
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation

Sicherheitsdaten

Alarmwort
Warnung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H351
FDA Pharmacological Classification · 6 Einträge

6B4ZBS263Y

SOTAGLIFLOZIN

Established Pharmacologic Class [EPC] - Sodium-Glucose Cotransporter 2 Inhibitor

Mechanisms of Action [MoA] - Sodium-Glucose Transporter 2 Inhibitors

Mechanisms of Action [MoA] - P-Glycoprotein Inhibitors

Sotagliflozin is a Sodium-Glucose Cotransporter 2 Inhibitor. The mechanism of action of sotagliflozin is as a Sodium-Glucose Transporter 2 Inhibitor and P-Glycoprotein Inhibitor.

MeSH Pharmacological ClassificationCompounds that inhibit SODIUM-GLUCOSE TRANSPORTER 2. They lower blood sugar by preventing the reabsorption of glucose by the kidney and are used in the treatment of TYPE 2 DIABETES MELLITUS.
Absorption, Distribution and Excretion · 4 Einträge

Following a single dose, the Tmax of sotagliflozin ranged from 1.25 to 3 hours. Following multiple doses, the Tmax ranged from 2.5 to 4 hours. The estimated oral bioavailability of sotagliflozin is 71%.

Sotagliflozin is primarily eliminated via the renal route, with 57% of administered drug material appearing in the urine and 37% appearing in the feces.

Sotagliflozin has a mean apparent volume of distribution of 9392 L.

In healthy volunteers, the mean apparent clearance of sotagliflozin ranged from 261 to 374 L/h. The mean apparent clearance estimated in a population of mostly type 1 diabetic patients was 239 L/h.

Anwendungen

VerwendenSotagliflozin is used for the treatment of patients with type 1 diabetes mellitus.

Anbieter100 Anbieter

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