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

General Information of Drug (ID: DR0591)
Drug Name
Epirubicin
Synonyms
Ellence; Epi-DX; Epiadriamycin; Epidoxorubicin; Epirubicin; Epirubicin [INN:BAN]; Epirubicina; Epirubicina [INN-Spanish]; Epirubicina [Spanish]; Epirubicine; Epirubicine [French]; Epirubicine [INN-French]; Epirubicinum; Epirubicinum [INN-Latin]; Epirubicinum [Latin]; Farmorubicin; IMI 28; Pidorubicin; Pidorubicina; Pidorubicina [INN-Spanish]; Pidorubicine; Pidorubicine [INN-French]; Pidorubicinum; Pidorubicinum [INN-Latin]; Ridorubicin; WP 697; 4'-Epiadriamycin; 4'-epi-Doxorubicin; 4'-epidoxorubicin; 4-Epidoxorubicin; 56420-45-2
Indication Breast cancer [ICD11: 2C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 543.5 Topological Polar Surface Area 206
Heavy Atom Count 39 Rotatable Bond Count 5
Hydrogen Bond Donor Count 6 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
41867
PubChem SID
13409 ; 793944 ; 8177324 ; 14716206 ; 14812446 ; 14837077 ; 24769893 ; 26704252 ; 26710264 ; 34707467 ; 46507282 ; 46530809 ; 48415946 ; 49995002 ; 50070726 ; 53787927 ; 56311421 ; 56313206 ; 56313988 ; 57288587 ; 57288773 ; 57312617 ; 77126435 ; 96024597 ; 103164726 ; 104338146 ; 117597720 ; 123080197 ; 126686290 ; 127301368 ; 127301369 ; 127301370 ; 127301371 ; 127301372 ; 127301373 ; 127301374 ; 127301375 ; 127301376 ; 127301377 ; 127301378 ; 127301379 ; 127301380 ; 127301381 ; 127301382 ; 127301383 ; 127301384 ; 127301385 ; 127301386 ; 127301387 ; 127301388
ChEBI ID
ChEBI:47898
CAS Number
56420-45-2
TTD Drug ID
D0C9XJ
Formula
C27H29NO11
Canonical SMILES
CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O
InChI
1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22-,27-/m0/s1
InChIKey
AOJJSUZBOXZQNB-VTZDEGQISA-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
7-deoxydoxorubicinane DM001983
83958
Unclear - Unclear 1 [3]
Epirubicin-glucuronide DM001980
156028101
Unclear - Unclear 1 [4] , [2]
Epirubicinol DM001979
127118
Unclear - Unclear 1 [4]
7-deoxydaxorubicinol DM001715
45038813
Unclear - Unclear 2 [3]
Epirubicinol-glucuronide DM018098 N. A. Unclear - Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR009952 Epirubicin Epirubicinol Unclear - Unclear Unclear [4]
MR009954 Epirubicin Epirubicin-glucuronide Unclear - Unclear UGT2B7 [4], [2]
MR009956 Epirubicin 7-deoxydoxorubicinane Unclear - Unclear Unclear [3]
MR009957 7-deoxydoxorubicinane 7-deoxydaxorubicinol Unclear - Unclear Unclear [3]
MR009955 Epirubicin-glucuronide Epirubicinol-glucuronide Unclear - Unclear Unclear [3]
MR009953 Epirubicinol Epirubicinol-glucuronide Unclear - Unclear Unclear [3]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
References
1 Epirubicin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Epirubicin glucuronidation and UGT2B7 developmental expression. Drug Metab Dispos. 2006 Dec;34(12):2097-101.
3 Comparative effects of paclitaxel and docetaxel on the metabolism and pharmacokinetics of epirubicin in breast cancer patients
4 Pharmacokinetics of epirubicin after intravenous administration: experimental and clinical aspects

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