Drug Information

General Information
Drug ID
DR00170
Drug Name
Epirubicin
Synonyms
(1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside; (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside; (7S,9R)-7-[(2S,4S,5R,6S)-4-Amino-5-hydroxy-6-methyl-oxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione; 10-((3-amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-(8S-cis)-5,12-naphthacenedione; 4'-Epi-DXR; 4'-Epiadriamycin; 4'-epi-DX; 4'-epi-Doxorubicin; 4'-epidoxorubicin; 4-Epidoxorubicin; Ebewe (TN); Ellence; Ellence (TN); Epi-DX; Epiadriamycin; Epidoxorubicin; Epirubicin (INN); Epirubicin (TN); Epirubicin [INN:BAN]; Epirubicina; Epirubicina [INN-Spanish]; Epirubicina [Spanish]; Epirubicine; Epirubicine [French]; Epirubicine [INN-French]; Epirubicinum; Epirubicinum [INN-Latin]; Epirubicinum [Latin]; Farmorubicin (TN); IMI 28; Pharmorubicin (TN); Pharmorubicin Pfs; Pidorubicin; Pidorubicina; Pidorubicina [INN-Spanish]; Pidorubicine; Pidorubicine [INN-French]; Pidorubicinum; Pidorubicinum [INN-Latin]; Ridorubicin; WP 697
Drug Type
Small molecular drug
Indication Node-positive breast cancer [ICD11:2C60-2C6Z] Approved [1]
Therapeutic Class
Anticancer Agents
Structure
3D MOL 2D MOL
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
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
CAS Number
CAS 56420-45-2
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
XLogP
1.3
PubChem CID
41867
PubChem SID
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 ,13409 ,14716206 ,14812446 ,14837077 ,24769893 ,26704252 ,26710264 ,34707467 ,46507282 ,46530809 ,48415946 ,49995002 ,50070726 ,53787927 ,56311421 ,56313206 ,56313988 ,57288587 ,57288773 ,57312617 ,77126435 ,793944 ,8177324 ,96024597
ChEBI ID
ChEBI:47898
TTD Drug ID
D0C9XJ
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [3]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [2]
P-GP Transporter Info P-glycoprotein 1 Substrate [2]
Drug-Transporter Activity Data
Drug-Transporter Activity Data MRP1 Transporter Info Km =0.097 microM Human cervical cancer cell line (Hela)-MRP1 [3]
References
1 Epirubicin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
3 Sulindac sulfide selectively increases sensitivity of ABCC1 expressing tumor cells to doxorubicin and glutathione depletion. J Biomed Res. 2016 Mar;30(2):120-133.

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