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

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

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

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^Y
PubChem CID	24812758
IUPHAR/BPS	4582
DrugBank	DB08907^N
ChemSpider	26333259^N
UNII	6S49DGR869
KEGG	D09592
ChEBI	CHEBI:73274^N
ChEMBL	ChEMBL2103841^N
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^N Key:XTNGUQKDFGDXSJ-ZXGKGEBGSA-N^N
^NY (what is this?) (verify)