Back داباغليفلوزين Arabic Dapagliflozin German Δαπαγλιφλοζίνη Greek Dapagliflozina Spanish داپاگلیفلوزین FA Dapagliflotsiini Finnish Dapagliflozine French דאפאגליפלוזין HE Dapagliflozin Italian ダパグリフロジン Japanese

Dapagliflozin

Dapagliflozin
Haworth projection (bottom)
Clinical data
Pronunciation/ˌdæpəɡlɪˈfloʊzɪn/ DAP-ə-glif-LOH-zin
Trade namesForxiga, Farxiga, Edistride, others
Other namesBMS-512148; (1S)-1,5-anhydro-1-C-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-D-glucitol
AHFS/Drugs.comMonograph
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classSodium-glucose co-transporter 2 (SGLT2) inhibitor
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability78% (after 10 mg dose)
Protein binding~91%
MetabolismUGT1A9 (major), CYP (minor)
MetabolitesDapagliflozin 3-O-glucuronide (inactive)
Elimination half-life~12.9 hours
ExcretionUrine (75%), feces (21%)[3]
Identifiers
  • (2S,3R,4R,5S,6R)-2-[4-Chloro-3-(4-ethoxybenzyl)phenyl]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.167.331 Edit this at Wikidata
Chemical and physical data
FormulaC21H25ClO6
Molar mass408.88 g·mol−1
3D model (JSmol)
  • Clc1ccc(cc1Cc2ccc(OCC)cc2)[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O
  • 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 checkY
  • Key:JVHXJTBJCFBINQ-ADAARDCZSA-N checkY

Dapagliflozin, sold under the brand names Farxiga (US) and Forxiga (EU) among others, is a medication used to treat type 2 diabetes.[3][4][6] It is also used to treat adults with heart failure and chronic kidney disease.[7][8][4] It reversibly inhibits sodium-glucose co-transporter 2 (SGLT2) in the renal proximal convoluted tubule to reduce glucose reabsorption and increase urinary glucose excretion.[9]

Common side effects include hypoglycaemia (low blood sugar), urinary tract infections, genital infections, and volume depletion (reduced amount of water in the body).[10] Diabetic ketoacidosis is a common side effect in type 1 diabetic patients.[11] Serious but rare side effects include Fournier gangrene.[12] Dapagliflozin is a sodium-glucose co-transporter-2 (SGLT-2) inhibitor and works by removing sugar from the body with the urine.[3]

It was developed by Bristol-Myers Squibb in partnership with AstraZeneca. It is on the World Health Organization's List of Essential Medicines.[13] In 2021, it was the 187th most commonly prescribed medication in the United States, with more than 2 million prescriptions.[14][15] Dapagliflozin is available as a generic medication.

  1. ^ "Dapagliflozin (Farxiga) Use During Pregnancy". Drugs.com. 30 August 2018. Archived from the original on 17 April 2021. Retrieved 5 May 2020.
  2. ^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 1 April 2024.
  3. ^ a b c d "Farxiga- dapagliflozin tablet, film coated". DailyMed. National Institutes of Health, National Library of Medicine, U.S. Department of Health & Human Services. 3 February 2020. Archived from the original on 30 October 2020. Retrieved 5 May 2020.
  4. ^ a b c Cite error: The named reference Forxiga EPAR was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Dapagliflozin Viatris EPAR was invoked but never defined (see the help page).
  6. ^ "Forxiga (dapagliflozin) 5mg should no longer be used for the treatment of Type 1 Diabetes Mellitus". European Medicines Agency (EMA). 11 November 2021. Archived from the original on 11 November 2021. Retrieved 11 November 2021.
  7. ^ Cite error: The named reference FDA_PR_20200505 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference NICE_TA697 was invoked but never defined (see the help page).
  9. ^ "BNF: Dapagliflozin". NICE. Retrieved 2 February 2024.
  10. ^ Ptaszynska A, Johnsson KM, Parikh SJ, de Bruin TW, Apanovitch AM, List JF (October 2014). "Safety profile of dapagliflozin for type 2 diabetes: pooled analysis of clinical studies for overall safety and rare events". Drug Safety. 37 (10): 815–829. doi:10.1007/s40264-014-0213-4. PMID 25096959. S2CID 24064402.
  11. ^ Dandona P, Mathieu C, Phillip M, Hansen L, Tschöpe D, Thorén F, et al. (DEPICT-1 Investigators) (December 2018). "Efficacy and Safety of Dapagliflozin in Patients With Inadequately Controlled Type 1 Diabetes: The DEPICT-1 52-Week Study". Diabetes Care. 41 (12): 2552–2559. doi:10.2337/dc18-1087. PMID 30352894. S2CID 53027785.
  12. ^ Hu Y, Bai Z, Tang Y, Liu R, Zhao B, Gong J, Mei D (2020). "Fournier Gangrene Associated with Sodium-Glucose Cotransporter-2 Inhibitors: A Pharmacovigilance Study with Data from the U.S. FDA Adverse Event Reporting System". Journal of Diabetes Research. 2020: 3695101. doi:10.1155/2020/3695101. PMC 7368210. PMID 32695827.
  13. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  14. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  15. ^ "Dapagliflozin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.