2D 3D
	ID	DDInter636
	Drug Type	small molecule
	Molecular Formula	C23H27ClO7
	Molecular Weight	450.910
	CAS Number	864070-44-0
	Description	Empagliflozin is an inhibitor of sodium-glucose co-transporter-2 (SGLT2), the transporters primarily responsible for the reabsorption of glucose in the kidney.[A203453] It is used clinically as an adjunct to diet and exercise, often in combination with other drug therapies,[L13673,L13679,L11479] for the management of type 2 diabetes mellitus.[L13688] The first known inhibitor of SGLTs, phlorizin, was isolated from the bark of apple trees in 1835 and researched extensively into the 20th century, but was ultimately deemed inappropriate for clinical use given its lack of specificity and significant gastrointestinal side effects.[A203501] Attempts at overcoming these limitations first saw the development of O-glucoside analogs of phlorizin (e.g. [remogliflozin etabonate]), but these molecules proved relatively pharmacokinetically unstable. The development of C-glucoside phlorizin analogs remedied the issues observed in the previous generation, and led to the FDA approval of [canagliflozin] in 2013 and both [dapagliflozin] and empagliflozin in 2014.[A203501] As the most recently approved of the "flozin" drugs, empagliflozin carries the highest selectivity for SGLT2 over SGLT1 (approximately 2700-fold). Empagliflozin was further approved by the EMA in March 2022 and Health Canada in April 2022, making it the first and only approved treatment in Europe and Canada for adults with symptomatic chronic heart failure regardless of ejection fraction.[L40783,L13916]
	ATC Classification	A10BD19 A10BD20 A10BK03 A10BD27
IUPAC Name	(2S,3R,4R,5S,6R)-2-[4-chloro-3-({4-[(3S)-oxolan-3-yloxy]phenyl}methyl)phenyl]-6-(hydroxymethyl)oxane-3,4,5-triol
InChI	OBWASQILIWPZMG-QZMOQZSNSA-N
Canonical SMILES	OC[C@H]1O[C@H]([C@H](O)[C@@H](O)[C@@H]1O)C1=CC=C(Cl)C(CC2=CC=C(O[C@H]3CCOC3)C=C2)=C1
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