Dapagliflozin

Dapagliflozin
	Haworth projection (bottom)
Clinical data
Pronunciation	/ˌdæpəɡlɪˈfloʊzɪn/ DAP-ə-glif-LOH-zin
Trade names	Forxiga, Farxiga, others
Other names	BMS-512148; (1S)-1,5-anhydro-1-C-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-D-glucitol
AHFS/Drugs.com	Monograph
MedlinePlus	a614015
License data	US DailyMed: Dapagliflozin;
Pregnancy; category	AU: D;
Routes of; administration	By mouth
Drug class	Sodium-glucose co-transporter 2 (SGLT2) inhibitor
ATC code	A10BK01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	78% (after 10 mg dose)
Protein binding	~91%
Metabolism	UGT1A9 (major), CYP (minor)
Metabolites	Dapagliflozin 3-O-glucuronide (inactive)
Elimination half-life	~12.9 hours
Excretion	Urine (75%), feces (21%)
Identifiers
	IUPAC name (2S,3R,4R,5S,6R)-2-[4-Chloro-3-(4-ethoxybenzyl)phenyl]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol;
CAS Number	461432-26-8;
PubChem CID	9887712;
IUPHAR/BPS	4594;
DrugBank	DB06292;
ChemSpider	8063384;
UNII	1ULL0QJ8UC;
KEGG	D08897; as salt: D09763;
ChEBI	CHEBI:85078;
ChEMBL	ChEMBL429910;
CompTox Dashboard (EPA)	DTXSID20905104 ;
ECHA InfoCard	100.167.331
Chemical and physical data
Formula	C21H25ClO6
Molar mass	408.88 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Clc1ccc(cc1Cc2ccc(OCC)cc2)[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O;
	InChI InChI=1S/C21H25ClO6/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21/h3-8,10,17-21,23-26H,2,9,11H2,1H3/t17-,18-,19+,20-,21+/m1/s1; Key:JVHXJTBJCFBINQ-ADAARDCZSA-N;

Dapagliflozin, sold under the brand names Farxiga (US) and Forxiga (EU) among others, is a medication used to treat type 2 diabetes. It is also used to treat adults with heart failure and chronic kidney disease. It reversibly inhibits sodium-glucose co-transporter 2 (SGLT-2) in the renal proximal convoluted tubule to reduce glucose reabsorption and increase urinary glucose excretion.

Common side effects include hypoglycaemia (low blood sugar), urinary tract infections, genital infections, and volume depletion (reduced amount of water in the body). Diabetic ketoacidosis is a common side effect in people with type 1 diabetes. Serious but rare side effects include Fournier gangrene.

It was developed by Bristol-Myers Squibb in partnership with AstraZeneca. It is on the World Health Organization's List of Essential Medicines. In 2021, it was the 187th most commonly prescribed medication in the United States, with more than 2 million prescriptions. Dapagliflozin is available as a generic medication.

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