Canagliflozin

Canagliflozin
Clinical data
Pronunciation	/ˌkænəɡlɪˈfloʊzɪn/ KAN-ə-glif-LOH-zin
Trade names	Invokana, Sulisent, Prominad, others
Other names	JNJ-28431754; TA-7284; (1S)-1,5-anhydro-1-C-(3-{[5-(4-fluorophenyl)thiophen-2-yl]methyl]}-4-methylphenyl)-D-glucitol
AHFS/Drugs.com	Monograph
MedlinePlus	a613033
License data	US DailyMed: Canagliflozin;
Pregnancy; category	AU: C;
Routes of; administration	By mouth
Drug class	SGLT2 inhibitor
ATC code	A10BK02 (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	65%
Protein binding	99%
Metabolism	Liver glucuronidation
Elimination half-life	11.8 (10–13) hours
Excretion	53% faecal and 33% kidney
Identifiers
	IUPAC name (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	842133-18-0 ;
PubChem CID	24812758;
IUPHAR/BPS	4582;
DrugBank	DB08907 ;
ChemSpider	26333259 ;
UNII	6S49DGR869;
KEGG	D09592;
ChEBI	CHEBI:73274 ;
ChEMBL	ChEMBL2103841 ;
CompTox Dashboard (EPA)	DTXSID601004469 ;
ECHA InfoCard	100.223.671
Chemical and physical data
Formula	C24H25FO5S
Molar mass	444.52 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	98 °C (208 °F)
	SMILES Cc1ccc(cc1Cc2ccc(s2)c3ccc(cc3)F)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O;
	InChI 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 ; Key:XTNGUQKDFGDXSJ-ZXGKGEBGSA-N ;
	(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]

^ ^a ^b "Canagliflozin (Invokana) Use During Pregnancy". Drugs.com. Retrieved 6 April 2019.
^ "Invokana EPAR". European Medicines Agency. 15 November 2013. Retrieved 17 June 2024.
^ ^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.
^ Cite error: The named reference FDA approval was invoked but never defined (see the help page).
^ Cite error: The named reference Invokana EPAR was invoked but never defined (see the help page).
^ "Australian Public Assessment Report for Canagliflozin (as hemihydrate)" (PDF). Therapeutic Goods Administration (TGA). 31 March 2014. Retrieved 28 August 2020.
^ 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.

[Drugs.com_pregnancy-1] "Canagliflozin (Invokana) Use During Pregnancy". Drugs.com. Retrieved 6 April 2019.

[2] "Invokana EPAR". European Medicines Agency. 15 November 2013. Retrieved 17 June 2024.

[AHFS2019-3] ^ ^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.

[FDA_approval-4] Cite error: The named reference FDA approval was invoked but never defined (see the help page).

[Invokana_EPAR-5] Cite error: The named reference Invokana EPAR was invoked but never defined (see the help page).

[Canagliflozin_AusPAR-6] "Australian Public Assessment Report for Canagliflozin (as hemihydrate)" (PDF). Therapeutic Goods Administration (TGA). 31 March 2014. Retrieved 28 August 2020.

[WHO22nd-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.

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