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

General Information of Drug (ID: DR0412)
Drug Name
Dapagliflozin
Synonyms
Dapagliflozin S-propylene glycol monohydrate; Dapagliflozin mixture with propylene glycol, hydrate; Dapagliflozin propanediol; Dapagliflozin propanediol [USAN]; Dapagliflozin propanediol hydrate; Dapagliflozin propylene glycol hydrate; Dapagliflozin propylene glycolate hydrate; UNII-887K2391VH; Dapagliflozin (S)-propylene glycol hydrate; Dapagliflozin propanediol monohydrate; Dapagliflozin; Forxiga; Forxiga (TN); UNII-1ULL0QJ8UC; (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol; (2S,3R,4R,5S,6R)-2-(4-Chloro-3-(4-ethoxybenzyl)phenyl)-6- (hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; (2S,3R,4R,5S,6R)-2-(4-chloro-3-(4-ethoxybenzyl)phenyl)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol; 1ULL0QJ8UC; 461432-26-8; BMS 512148; BMS-512148; BMS512148; CHEBI:85078; CHEMBL3125458; CHEMBL429910; 887K2391VH; 960404-48-2; AK322430; BMS-512148-05; CHEBI:85079; Dapagliflozin ((2S)-1,2-propanediol, hydrate)
Indication Diabetes mellitus [ICD11: 5A10] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 408.9 Topological Polar Surface Area 99.4
Heavy Atom Count 28 Rotatable Bond Count 6
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
9887712
PubChem SID
14855234 ; 15451267 ; 24173975 ; 45634651 ; 49688954 ; 57304407 ; 57373691 ; 76500746 ; 96025580 ; 103578280 ; 104253204 ; 109692963 ; 123051086 ; 124757330 ; 124772065 ; 125164134 ; 126667088 ; 126731318 ; 134338792 ; 134358357 ; 136348250 ; 136367545 ; 136367974 ; 137261282 ; 140046947 ; 143499356 ; 144115882 ; 152234916 ; 152258220 ; 160647056 ; 162011553 ; 162037657 ; 162172238 ; 164838825 ; 165245557 ; 170497930 ; 174529446 ; 175427068 ; 178101315 ; 185978787 ; 194946819 ; 198934677 ; 198991956 ; 210024059 ; 211535346 ; 221678783 ; 223471387 ; 223554897 ; 223670709 ; 223701082
ChEBI ID
CHEBI:61397
CAS Number
461432-26-8
TTD Drug ID
D01TNW
Formula
C21H25ClO6
Canonical SMILES
CCOC1=CC=C(C=C1)CC2=C(C=CC(=C2)C3C(C(C(C(O3)CO)O)O)O)Cl
InChI
1S/C21H25ClO6/c1-2-27-15-6-3-12(4-7-15)9-14-10-13(5-8-16(14)22)21-20(26)19(25)18(24)17(11-23)28-21/h3-8,10,17-21,23-26H,2,9,11H2,1H3/t17-,18-,19+,20-,21+/m1/s1
InChIKey
JVHXJTBJCFBINQ-ADAARDCZSA-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
Dapagliflozin 3-O-glucuronide metabolite DM001878
91617971
Conjugation - Glucuronidation 1 [3]
Dapagliflozin BMS-511926 DM001879
44580555
Oxidation - O-Deethylation 1 [4]
Dapagliflozin BMS-639432 DM001880
59235375
Oxidation - Hydroxylation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002838 Dapagliflozin Dapagliflozin 3-O-glucuronide metabolite Conjugation - Glucuronidation UGT1A9 [3]
MR002839 Dapagliflozin Dapagliflozin BMS-511926 Oxidation - O-Deethylation CYP3A4 ... [4]
MR002840 Dapagliflozin Dapagliflozin BMS-639432 Oxidation - Hydroxylation CYP3A4 ... [4]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2A6 (CYP2A6) DME0005 Homo sapiens
CP2A6_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
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 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
⏷ Show the Full List of 7  DME(s)
References
1 Dapagliflozin Propanediol was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Clinical pharmacokinetics and pharmacodynamics of dapagliflozin, a selective inhibitor of sodium-glucose co-transporter type 2. Clin Pharmacokinet. 2014 Jan;53(1):17-27.
3 Pharmacokinetics and pharmacodynamics of dapagliflozin, a novel selective inhibitor of sodium-glucose co-transporter type 2, in Japanese subjects without and with type 2 diabetes mellitus
4 In vitro characterization and pharmacokinetics of dapagliflozin (BMS-512148), a potent sodium-glucose cotransporter type II inhibitor, in animals and humans Drug Metab Dispos. 2010 Mar;38(3):405-14. doi: 10.1124/dmd.109.029165.

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