Canagliflozin hydrateProduct ingredient for Canagliflozin

Name
Canagliflozin hydrate
Drug Entry
Canagliflozin

Canagliflozin, also known as Invokana, is a sodium-glucose cotransporter 2 (SGLT2) inhibitor used in the management of type 2 diabetes mellitus along with lifestyle changes including diet and exercise Label.

It was initially approved by the FDA in 2013 for the management of diabetes and later approved in 2018 for a second indication of reducing the risk of cardiovascular events in patients diagnosed with type 2 diabetes mellitus 8, Label.

Canagliflozin is the first oral antidiabetic drug approved for the prevention of cardiovascular events in patients with type 2 diabetes 8. Cardiovascular disease is the most common cause of death in these patients 4.

Accession Number
DBSALT001783
Structure
Synonyms
(1S)-1,5-Anhydro-1-(3-((5-(4-fluorophenyl)-2-thienyl)methyl)-4-methylphenyl)-D-glucitol hemihydrate / Canagliflozin hemihydrate
External IDs
JNJ-28431754 / TA-7284
UNII
0SAC974Z85
CAS Number
928672-86-0
Weight
Average: 907.05
Monoisotopic: 906.291911168
Chemical Formula
C48H52F2O11S2
InChI Key
VHOFTEAWFCUTOS-TUGBYPPCSA-N
InChI
InChI=1S/2C24H25FO5S.H2O/c2*1-13-2-3-15(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*2-10,19,21-24,26-29H,11-12H2,1H3;1H2/t2*19-,21-,22+,23-,24+;/m11./s1
IUPAC Name
bis((2S,3R,4R,5S,6R)-2-(3-{[5-(4-fluorophenyl)thiophen-2-yl]methyl}-4-methylphenyl)-6-(hydroxymethyl)oxane-3,4,5-triol) hydrate
SMILES
O.[H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=C(C)C(CC2=CC=C(S2)C2=CC=C(F)C=C2)=C1.[H][C@]1(O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C1=CC=C(C)C(CC2=CC=C(S2)C2=CC=C(F)C=C2)=C1
ChemSpider
28528041
ChEBI
73272
ChEMBL
CHEMBL2103841
Predicted Properties
PropertyValueSource
Water Solubility0.0045 mg/mLALOGPS
logP3.09ALOGPS
logP3.52Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)12.57Chemaxon
pKa (Strongest Basic)-3Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area90.15 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity116.14 m3·mol-1Chemaxon
Polarizability46.5 Å3Chemaxon
Number of Rings8Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon