Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0262)
Drug Name
Canagliflozin
Synonyms
Canagliflozin; Canagliflozin anhydrous; Canagliflozin hydrate; Invokana; JNJ 24831754ZAE; JNJ 28431754; JNJ-28431754; TA 7284; TA-7284; canagliflozin hemihydrate; (1S)-1,5-anhydro-1-(3-{[5-(4-fluorophenyl)-2-thienyl]methyl}-4-methylphenyl)-D-glucitol; (2S,3R,4R,5S,6R)-2-(3-((5-(4-FLUOROPHENYL)THIOPHEN-2-YL)METHYL)-4-METHYLPHENYL)-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-3,4,5-TRIOL; 1-(Glucopyranosyl)-4-methyl-3-(5-(4-fluorophenyl)-2-thienylmethyl)benzene; 6S49DGR869; 842133-18-0; 928672-86-0; CHEBI:73274; UNII-6S49DGR869
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 444.5 Topological Polar Surface Area 118
Heavy Atom Count 31 Rotatable Bond Count 5
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
24812758
PubChem SID
49811874 ; 57127075 ; 125299338 ; 134358471 ; 135267033 ; 136023439 ; 136340353 ; 136367529 ; 136368011 ; 141631822 ; 144115779 ; 144224573 ; 152159581 ; 152258221 ; 160647057 ; 160695863 ; 160865968 ; 162011557 ; 162169318 ; 162205127 ; 164837687 ; 170500828 ; 172918748 ; 174530759 ; 175266021 ; 175427146 ; 178101303 ; 185964359 ; 196373210 ; 198993774 ; 202567714 ; 211535181 ; 223258907 ; 223471388 ; 223617458 ; 223705166 ; 224378424 ; 226521104 ; 248537044 ; 249737173 ; 250163176 ; 252109951 ; 252215091
ChEBI ID
CHEBI:73274
CAS Number
842133-18-0
TTD Drug ID
D08DFX
Formula
C24H25FO5S
Canonical SMILES
CC1=C(C=C(C=C1)C2C(C(C(C(O2)CO)O)O)O)CC3=CC=C(S3)C4=CC=C(C=C4)F
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
InChIKey
XTNGUQKDFGDXSJ-ZXGKGEBGSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Canagliflozin metabolite M5 DM000536
156596667
Conjugation - O-Glucuronidation 1 [4]
Canagliflozin metabolite M7 DM000535
156596691
Conjugation - O-Glucuronidation 1 [4]
Canagliflozin metabolite M9 DM000537
121428312
Oxidation - Hydroxylation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000548 Canagliflozin Canagliflozin metabolite M7 Conjugation - O-Glucuronidation UGT1A9 ... [4]
MR000549 Canagliflozin Canagliflozin metabolite M5 Conjugation - O-Glucuronidation UGT1A9 ... [4]
MR000550 Canagliflozin Canagliflozin metabolite M9 Oxidation - Hydroxylation CYP3A4 [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 2B4 (UGT2B4) DME0047 Homo sapiens
UD2B4_HUMAN
2.4.1.17
[3]
References
1 Canagliflozin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Sodium-glucose linked transporter 2 (SGLT2) inhibitors in the management of type-2 diabetes: a drug class overview. P T. 2015 Jul;40(7):451-62.
3 Effects of rifampin, cyclosporine A, and probenecid on the pharmacokinetic profile of canagliflozin, a sodium glucose co-transporter 2 inhibitor, in healthy participants. Int J Clin Pharmacol Ther. 2015 Feb;53(2):115-28.
4 Clinical Pharmacokinetic, Pharmacodynamic, and Drug-Drug Interaction Profile of Canagliflozin, a Sodium-Glucose Co-transporter 2 Inhibitor Clin Pharmacokinet. 2015 Oct;54(10):1027-41. doi: 10.1007/s40262-015-0285-z.

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