Canagliflozin

Canagliflozin
Clinical data
Pronunciation/ˌkænəɡlɪˈfloʊzɪn/ KAN-ə-glif-LOH-zin
Trade namesInvokana, Sulisent, Prominad, others
Other namesJNJ-28431754; TA-7284; (1S)-1,5-anhydro-1-C-(3-{[5-(4-fluorophenyl)thiophen-2-yl]methyl]}-4-methylphenyl)-D-glucitol
AHFS/Drugs.comMonograph
MedlinePlusa613033
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classSGLT2 inhibitor
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only[2]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability65%
Protein binding99%
MetabolismLiver glucuronidation
Elimination half-life11.8 (10–13) hours
Excretion53% faecal and 33% kidney
Identifiers
  • (2S,3R,4R,5S,6R)-2-{3-[5-[4-Fluoro-phenyl)-thiophen-2-ylmethyl]-4-methyl-phenyl}-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.223.671 Edit this at Wikidata
Chemical and physical data
FormulaC24H25FO5S
Molar mass444.52 g·mol−1
3D model (JSmol)
Melting point98 °C (208 °F)
  • Cc1ccc(cc1Cc2ccc(s2)c3ccc(cc3)F)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O
  • InChI=1S/C24H25FO5S/c1-13-2-3-15(24-23(29)22(28)21(27)19(12-26)30-24)10-16(13)11-18-8-9-20(31-18)14-4-6-17(25)7-5-14/h2-10,19,21-24,26-29H,11-12H2,1H3/t19-,21-,22+,23-,24+/m1/s1 ☒N
  • Key:XTNGUQKDFGDXSJ-ZXGKGEBGSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Canagliflozin, sold under the brand name Invokana among others, is a medication used to treat type 2 diabetes.[3] It is used together with exercise and diet.[3] It is not recommended in type 1 diabetes.[3] It is taken by mouth.[3]

Common side effects include vaginal yeast infections, nausea, constipation, and urinary tract infections.[3] Serious side effects may include low blood sugar, Fournier's gangrene, leg amputation, kidney problems, high blood potassium, and low blood pressure.[3] Diabetic ketoacidosis may occur despite nearly normal blood sugar levels.[3] Use in pregnancy and breastfeeding is not recommended.[1] Canagliflozin is a sodium-glucose cotransporter-2 (SGLT2) inhibitor.[3] It works by increasing the amount of glucose lost in the urine.[3]

Canagliflozin was approved for medical use in the United States, in the European Union, and in Australia in 2013.[3][4][5][6] It is on the World Health Organization's List of Essential Medicines.[7]

  1. ^ a b "Canagliflozin (Invokana) Use During Pregnancy". Drugs.com. Retrieved 6 April 2019.
  2. ^ "Invokana EPAR". European Medicines Agency. 15 November 2013. Retrieved 17 June 2024.
  3. ^ a b c d e f g h i j "Canagliflozin Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 6 April 2019.
  4. ^ Cite error: The named reference FDA approval was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Invokana EPAR was invoked but never defined (see the help page).
  6. ^ "Australian Public Assessment Report for Canagliflozin (as hemihydrate)" (PDF). Therapeutic Goods Administration (TGA). 31 March 2014. Retrieved 28 August 2020.
  7. ^ 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.