Empagliflozin

Base Information

• Chemical Name: Empagliflozin
• CAS No.: 864070-44-0
• Deprecated CAS: 1240076-01-0,1314556-33-6
• Molecular Formula: C23H27ClO7
• Molecular Weight: 450.916
• European Community (EC) Number: 620-176-8
• UNII: HDC1R2M35U
• ChEMBL ID: CHEMBL2107830
• DSSTox Substance ID: DTXSID601026093
• Metabolomics Workbench ID: 152102
• NCI Thesaurus Code: C158136
• Nikkaji Number: J3.260.944I
• Pharos Ligand ID: QKPY8TZ7VLHD
• RXCUI: 1545653
• Wikidata: Q5373824
• Wikipedia: Empagliflozin
• Mol file: 864070-44-0.mol

Synonyms:1-chloro-4-(glucopyranos-1-yl)-2-(4-(tetrahydrofuran-3-yloxy)benzyl)benzene;BI 10773;BI-10773;BI10773;empagliflozin;Jardiance

Chemical Property of Empagliflozin

Chemical Property:

• Boiling Point: 665℃
• PKA: 13.23±0.70(Predicted)
• Flash Point: 356℃
• PSA: 108.61000
• Density: 1.398
• LogP: 1.61340
• Storage Temp.: 2-8°C
• Solubility.: insoluble in H2O; ≥20.75 mg/mL in DMSO; ≥7.06 mg/mL in EtOH with ultrasonic
• XLogP3: 2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 6
• Exact Mass: 450.1445309
• Heavy Atom Count: 31
• Complexity: 558

Purity/Quality:

99.0% ^*data from raw suppliers

Empagliflozin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1COCC1OC2=CC=C(C=C2)CC3=C(C=CC(=C3)C4C(C(C(C(O4)CO)O)O)O)Cl
• Isomeric SMILES: C1COC[C@H]1OC2=CC=C(C=C2)CC3=C(C=CC(=C3)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)Cl
• Recent ClinicalTrials: Impact of Empagliflozin on Functional Capacity in Heart Failure With Preserved Ejection Fraction
• Recent EU Clinical Trials: The impact of Empagliflozin on Left atrIal Volume and the feasibility of using Fitbit and mHealth to prescribe Exercise in non-diabetic Pre- Heart Failure (ELIVE pre-HF Study)
• Recent NIPH Clinical Trials: The effects of empagliflozin on ultrafiltration in patients with peritoneal dialysis
• Description: Empagliflozin(trade name Jardiance) is an inhibitor of the sodium glucose co-transporter-2 (SGLT-2), and causes sugar in the blood to be excreted by the kidneys and eliminated in urine. On August 1, 2014, the Food and Drug Administration (FDA) officially approved the drug for the treatment of type 2 diabetes, to improve and control blood glucose of adults. Empagliflozin is the third SGLT-2 inhibiting drugs approved by FDA. Another two SGLT-2 inhibitor drugs, canagliflozin and dapagliflozin, belonging to Johnson Pharmaceuticals, AstraZeneca and Bristol-Myers Squibb respectively, are approved by FDA in November 2013 and January 2014 respectively. The new drug Empagliflozin’s application to FDA can be described as twists and turns. In March 2014, due to a large particle contamination incident at the empagliflozin production plant in Boehringer, the application of new drug submitted by the Boehringer-Eli Lilly Alliance was rejected by FDA. In June 2014, after reviewing the summary and material submitted by Boehring in March, confirming that the quality management and compliance system of the Boehring drug production facility was acceptable, FDA withdrew the previously issued warning letter. The Boehringer-Eli Lilly Alliance also filed an application with the FDA on June 17th. Empagliflozin, a sodium-glucose co-transporter 2 (SGLT2) inhibitor, was originally discovered by Boehringer Ingelheim and codeveloped and co-marketed through research collaboration with Eli Lilly and Co. It was first approved by European Medicine Agency (EMA) in May 2014, followed by the approval of the US FDA in August 2014. SGLT2 inhibitors are anewclass of glucose-lowering agents developed for the treatment of type 2 diabetes mellitus, which have a mechanism of action that is independent of pancreatic b-cell function or the degree of insulin resistance. Consequently, SGLT2 inhibitors have the potential to be of use not only as standalone therapy but also in combination with any of the existing classes of glucose-lowering agents, including insulin. Empagliflozin selectively inhibits SGLT2, which in turn prevents glucose reabsorption by excreting excess glucose in the urine.
• Uses: Empagliflozin is a novel, potent and selective SGLT-2 inhibitor, improves glycaemic control and features of metabolic syndrome in diabetic rats.
• Drug interactions: Potentially hazardous interactions with other drugs None known

Technology Process of Empagliflozin

There total 116 articles about Empagliflozin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.8%

C29H32BrClO9 → empagliflozin (864070-44-0,1620758-33-9,864070-43-9)

Guidance literature:

With water; potassium hydroxide; In acetonitrile; at 50 - 60 ℃; Reagent/catalyst;

Reference yield: 93.7%

C51H49ClO7 → empagliflozin (864070-44-0,1620758-33-9,864070-43-9)

Guidance literature:

With hydrogen; In ethanol; at 75 - 80 ℃; for 20h; under 6000.6 - 6750.68 Torr; Solvent; Inert atmosphere; Autoclave;

Reference yield: 90.0%

C51H43ClO11 → empagliflozin (864070-44-0,1620758-33-9,864070-43-9)

Guidance literature:

With sodium methylate; In tetrahydrofuran; at 40 - 45 ℃;

upstream raw materials:

(2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-hydroxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

(R)-tetrahydrofuran-3-yl 4-methylbenzenesulfonate

methyl-1-C-(4-chloro-3-{4-[(3S)-tetrahydrofuran-3-yloxy]benzyl}phenyl)-D-glucopyranoside

(2S,3R,4S,5S,6R)-2-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)-6-(hydroxymethyl)-2-methoxytetrahydro-2H-pyran-3,4,5-triol

Downstream raw materials:

(2R,3R,4R,5S,6S)-2-(acetoxymethyl)-6-(4-chloro-3-(4-(((S)-tetrahydrofuran-3-yl)oxy)benzyl)phenyl)tetrahydro-2H-pyran-3,4,5-trityl triacetate

Refernces

• 1、 -. "Preparation method of SGLT-2 inhibitor and intermediate". Paragraph 0112-0118. . Retrieved 2021/05/19.
• 2、 -. "Synthetic method of empagliflozin". Paragraph 0029-0033. . Retrieved 2021/07/24.