Empagliflozin

Systematic (IUPAC) name
(2S,3R,4R,5S,6R)-2-[4-chloro-3-[[4-[(3S)-oxolan-3-yl]oxyphenyl]methyl]phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
Clinical data
Trade names	Jardiance
AHFS/Drugs.com	entry
Pregnancy category	US: C (Risk not ruled out)
Legal status	℞ (Prescription only)
Routes of administration	Oral
Identifiers
CAS Number	864070-44-0
ATC code	A10BX12 (WHO)
PubChem	CID: 11949646
IUPHAR/BPS	4754
ChemSpider	10123957
UNII	HDC1R2M35U
ChEBI	CHEBI:82720 Y
Chemical data
Formula	C23H27ClO7
Molecular mass	450.91 g/mol
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
InChI InChI=1S/C23H27ClO7/c24-18-6-3-14(23-22(28)21(27)20(26)19(11-25)31-23)10-15(18)9-13-1-4-16(5-2-13)30-17-7-8-29-12-17/h1-6,10,17,19-23,25-28H,7-9,11-12H2/t17-,19+,20+,21-,22+,23-/m0/s1 Key:OBWASQILIWPZMG-QZMOQZSNSA-N

Empagliflozin (trade name Jardiance) is a drug of the gliflozin class, approved for the treatment of type 2 diabetes in adults in 2014. It was developed by Boehringer Ingelheim and Eli Lilly and Company.

Empagliflozin 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.

Side effects

When taken in dosages of 10 or 25 mg once a day, the incidence of adverse events was similar to placebo. However, there was a higher frequency of urinary tract infections.

There are concerns it may increase the risk of diabetic ketoacidosis.

Post-Market Studies

In August 2015, release of the post-marketing clinical trial EMPA-REG OUTCOME addressed the addition of empagliflozin to the standard of care for preventing myocardial infarction, stroke, and cardiovascular death.

Mode of action

Empagliflozin is an inhibitor of the sodium glucose co-transporter-2 (SGLT-2), which is found almost exclusively in the proximal tubules of nephronic components in the kidneys. SGLT-2 accounts for about 90 percent of glucose reabsorption into the blood. Blocking SGLT-2 reduces blood glucose by blocking glucose reabsorption in the kidney and thereby excreting glucose (i.e., blood sugar) via the urine.

Regulatory status

As of May 2013, Boehringer and Lilly had submitted applications for marketing approval to the European Medicines Agency and the U.S. Food and Drug Administration (FDA). The drug was approved in Europe in May 2014 and was approved by the FDA in August 2014. The FDA required four postmarketing studies: a cardiovascular outcomes trial, and two studies in children, and a toxicity study in animals related to the pediatric trials.

See also

• Empagliflozin/linagliptin (Glyxambi)