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

General Information of Drug (ID: DR0604)
Drug Name
Ertugliflozin
Synonyms
Ertugliflozin; Ertugliflozin (PF 04971729); Ertugliflozin [USAN:INN]; MK-8835; PF 04971729; PF-04971729; PF04971729; Steglatro; (1S,2S,3S,4R,5S)-5-(4-chloro-3-(4-ethoxybenzyl)phenyl)-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol; (1S,2S,3S,4R,5S)-5-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-1-(hydroxymethyl)-6,8-dioxabicyclo[3.2.1]octane-2,3,4-triol; 1,6-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-5-C-(hydroxymethyl)-beta-L-idopyranose; 1210344-57-2; 6C282481IP; CHEMBL1770248; UNII-6C282481IP
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 436.9 Topological Polar Surface Area 109
Heavy Atom Count 30 Rotatable Bond Count 6
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
44814423
PubChem SID
89442948 ; 120130619 ; 131281547 ; 131345821 ; 140604034 ; 162011560 ; 162108670 ; 162205143 ; 163312343 ; 174526435 ; 185978788 ; 198984080 ; 210024075 ; 223404370 ; 223471394 ; 224604107 ; 226541727 ; 243511761 ; 252109952 ; 252166588 ; 252448906
CAS Number
1210344-57-2
TTD Drug ID
D0Q3VE
Formula
C22H25ClO7
Canonical SMILES
CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C34C(C(C(C(O3)(CO4)CO)O)O)O)Cl
InChI
1S/C22H25ClO7/c1-2-28-16-6-3-13(4-7-16)9-14-10-15(5-8-17(14)23)22-20(27)18(25)19(26)21(11-24,30-22)12-29-22/h3-8,10,18-20,24-27H,2,9,11-12H2,1H3/t18-,19-,20+,21-,22-/m0/s1
InChIKey
MCIACXAZCBVDEE-CUUWFGFTSA-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
Ertugliflozin metabolite M1a DM002001
52931638
Oxidation - Hydroxylation 1 [3] , [4]
Ertugliflozin metabolite M1b DM002002
67153944
Oxidation - Hydroxylation 1 [3] , [4]
Ertugliflozin metabolite M2 DM001998 N. A. Conjugation - Glucuronidation 1 [3] , [4]
Ertugliflozin metabolite M3 DM002003 N. A. Conjugation - Glucuronidation 1 [3] , [4]
Ertugliflozin metabolite M4a DM002004 N. A. Conjugation - Glucuronidation 1 [4]
Ertugliflozin metabolite M4b DM002005 N. A. Conjugation - Glucuronidation 1 [4]
Ertugliflozin metabolite M4c DM002006 N. A. Conjugation - Glucuronidation 1 [4]
Ertugliflozin metabolite M5a DM001999
118753360
Unclear 2 [4]
Ertugliflozin metabolite M5c DM002000
118752988
Unclear 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000932 Ertugliflozin Ertugliflozin metabolite M2 Conjugation - Glucuronidation CYP3A4 ... [3], [4]
MR000933 Ertugliflozin Ertugliflozin metabolite M1a Oxidation - Hydroxylation CYP3A4 ... [3], [4]
MR000934 Ertugliflozin Ertugliflozin metabolite M1b Oxidation - Hydroxylation CYP3A4 ... [3], [4]
MR000935 Ertugliflozin Ertugliflozin metabolite M3 Conjugation - Glucuronidation CYP3A4 ... [3], [4]
MR000936 Ertugliflozin Ertugliflozin metabolite M4a Conjugation - Glucuronidation UGT1A9 ... [4]
MR000937 Ertugliflozin Ertugliflozin metabolite M4b Conjugation - Glucuronidation UGT1A9 ... [4]
MR000938 Ertugliflozin Ertugliflozin metabolite M4c Conjugation - Glucuronidation UGT1A9 ... [4]
MR000930 Ertugliflozin metabolite M2 Ertugliflozin metabolite M5a Unclear UGT1A9 ... [4]
MR000931 Ertugliflozin metabolite M2 Ertugliflozin metabolite M5c Unclear UGT1A9 ... [4]
⏷ Show the Full List of 9 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A9 (UGT1A9) DME0042 Homo sapiens
UD19_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
References
1 Ertugliflozin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The effect of renal impairment on the pharmacokinetics and pharmacodynamics of ertugliflozin in subjects with type 2 diabetes mellitus. J Clin Pharmacol. 2017 Nov;57(11):1432-1443.
3 In Vitro Characterization of Ertugliflozin Metabolism by UDP-Glucuronosyltransferase and Cytochrome P450 Enzymes Drug Metab Dispos. 2020 Dec;48(12):1350-1363. doi: 10.1124/dmd.120.000171.
4 Pharmacokinetics, metabolism, and excretion of the antidiabetic agent ertugliflozin (PF-04971729) in healthy male subjects Drug Metab Dispos. 2013 Feb;41(2):445-56. doi: 10.1124/dmd.112.049551.

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