Dapagliflozin

Dapagliflozin
Haworth projection (bottom)
Clinical data
Pronunciation/ˌdæpəɡlɪˈfloʊzɪn/ DAP-ə-glif-LOH-zin
Trade namesFarxiga, Forxiga, others
Other namesBMS-512148; (1S)-1,5-anhydro-1-C-{4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl}-D-glucitol
AHFS/Drugs.comMonograph
MedlinePlusa614015
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%)[6]
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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.167.331
Chemical and physical data
FormulaC21H25ClO6
Molar mass408.88 g·mol−1
3D model (JSmol)
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.[6][7][10] It is also used to treat adults with heart failure and chronic kidney disease.[11][12][7] 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.[13]

Common side effects include hypoglycaemia (low blood sugar), urinary tract infections, genital infections, and volume depletion (reduced amount of water in the body).[14] Diabetic ketoacidosis is a common side effect in people with type 1 diabetes.[15] Serious but rare side effects include Fournier gangrene.[16]

It was developed by Bristol-Myers Squibb in partnership with AstraZeneca. It is on the World Health Organization's List of Essential Medicines.[17] In 2022, it was the 115th most commonly prescribed medication in the United States, with more than 5 million prescriptions.[18][19] Dapagliflozin is available as a generic medication.[20]

  1. ^ "Dapagliflozin (Farxiga) Use During Pregnancy". Drugs.com. 30 August 2018. Archived from the original on 17 April 2021. Retrieved 5 May 2020.
  2. ^ "Forxiga dapagliflozin (as propanediol monohydrate) 10 mg film-coated tablet blister pack (180147)". Therapeutic Goods Administration (TGA). 27 May 2022. Retrieved 20 April 2024.
  3. ^ "AusPAR: Dapagliflozin". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 20 April 2024.
  4. ^ "AusPAR: Dapagliflozin (as propanediol monohydrate)". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 20 April 2024.
  5. ^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 1 April 2024.
  6. ^ a b c "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.
  7. ^ a b c Cite error: The named reference Forxiga EPAR was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference Dapagliflozin Viatris EPAR was invoked but never defined (see the help page).
  9. ^ "Edistride EPAR". European Medicines Agency (EMA). 9 November 2015. Retrieved 26 September 2024.
  10. ^ "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.
  11. ^ "FDA approves new treatment for a type of heart failure". U.S. Food and Drug Administration (FDA) (Press release). 5 May 2020. Archived from the original on 6 May 2020. Retrieved 5 May 2020. This article incorporates text from this source, which is in the public domain.
  12. ^ National Institute for Health and Care Excellence (24 February 2021). "Dapagliflozin for treating chronic heart failure with reduced ejection fraction". NICE Technology Appraisal Guidance [TA679]. NICE. Archived from the original on 9 May 2021. Retrieved 9 May 2021.
  13. ^ "BNF: Dapagliflozin". NICE. Retrieved 2 February 2024.
  14. ^ 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.
  15. ^ 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.
  16. ^ Hu Y, Bai Z, Tang Y, Liu R, Zhao B, Gong J, et al. (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.
  17. ^ World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  18. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  19. ^ "Dapagliflozin Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  20. ^ "Generic Farxiga Availability". Drugs.com. 6 November 2024. Retrieved 30 November 2024.
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