Mr. Ibrahem/Dapagliflozin
Haworth projection (bottom)
Clinical data
Pronunciation/ˌdæpəɡlɪˈflzɪn/ 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 (tablets)
Drug classSodium-glucose co-transporter 2 (SGLT2) inhibitor
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
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%)[2]
Identifiers
  • (2S,3R,4R,5S,6R)-2-[4-Chloro-3-(4-ethoxybenzyl)phenyl]-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
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
 ☒NcheckY (what is this?)  (verify)

Dapagliflozin, sold under the brand name Farxiga among others, is a medication used to treat type 2 diabetes.[2] It is also used in heart failure with reduced ejection fraction.[3] In type 1 diabetes, it may be used together with insulin.[4] It is taken by mouth once a day.[2]

Common side effect include urinary tract infections, fungal infections of the groin, increased urination, nausea, and constipation.[2] Other side effects may include low blood sugar, especially when used with other diabetic medications, low blood pressure, Fournier gangrene, allergic reactions, and diabetic ketoacidosis.[2] Use is not recommended in pregnancy or breastfeeding.[4] It is of the gliflozin (SGLT2 inhibitor) class.[2]

Dapagliflozin was approved for medical use in the United States in 2014.[2] It was originally brought to market by AstraZeneca.[2] In the United States it costs about 500 USD per month as of 2020.[5] This amount costs the NHS in the United Kingdom about 40 pounds.[4] In 2017, it was the 259th most commonly prescribed medication in the United States, with more than one million prescriptions.[6][7]

References edit

  1. ^ a b "Dapagliflozin (Farxiga) Use During Pregnancy". Drugs.com. 30 August 2018. Retrieved 5 May 2020.
  2. ^ a b c d e f g h "Dapagliflozin Propanediol Monograph for Professionals". Drugs.com. Retrieved 3 December 2020.
  3. ^ "FDA approves new treatment for a type of heart failure". U.S. Food and Drug Administration (FDA) (Press release). 5 May 2020. Retrieved 5 May 2020.   This article incorporates text from this source, which is in the public domain.
  4. ^ a b c BNF 79. London: Pharmaceutical Press. March 2020. p. 725. ISBN 978-0857113658.
  5. ^ "Dapagliflozin Prices, Coupons & Savings Tips". GoodRx. Retrieved 3 December 2020.
  6. ^ "The Top 300 of 2020". ClinCalc. Retrieved 11 April 2020.
  7. ^ "Dapagliflozin - Drug Usage Statistics". ClinCalc. Retrieved 11 April 2020.