Drug Information

General Information
Drug ID
DR00301
Drug Name
Doxorubicin
Synonyms
14-Hydroxydaunomycin; 14-Hydroxydaunorubicine; ADM; ADR; Adiblastine (hydrochloride salt); Adr iablatina (hydrochloride salt); Adriablastin; Adriablastine (hydrochloride salt); Adriablatina (hydrochloride salt); Adriacin (hydrochloride salt); Adriamycin; Adriamycin PFS; Adriamycin PFS (TN); Adriamycin PFS (hydrochloride salt); Adriamycin RDF; Adriamycin RDF (TN); Adriamycin RDF (hydrochloride salt); Adriamycin semiquinone; Adriblas tina; Adriblastin; Adriblastina; Adriblastina (TN); Adriblastina (hydrochloride salt); Adriblatina (hydrochloride salt); Aerosolized Doxorubicin; Caelyx (TN); Conjugate of doxorubicin with humanized monoclonal antibody LL1 against CD74; Conjugate of doxorubicin with monoclonal antibody P4/D10 against GP120; DM2; DOX-SL; Doxil; Doxorubicin (USAN/INN); Doxorubicin Hydrochloride; Doxorubicin [USAN:INN:BAN]; Doxorubicin citrate; Doxorubicin hydrochloride (hydrochloride salt); Doxorubicin-P4/D10; Doxorubicin-P4/D10 conjugate; Doxorubicin-hLL1; Doxorubicin-hLL1 conjugate; Doxorubicina; Doxorubicina [INN-Spanish]; Doxorubicine; Doxorubicine [INN-French]; Doxorubicinum; Doxorubicinum [INN-Latin]; FI 106; Farmablastina (hydrochloride salt); Hydroxydaunomycin hydrochlor ide (hydrochloride salt); Hydroxydaunomycin hydrochloride (hydrochloride salt); Hydroxydaunorubicin hydrochloride (hydrochloride salt); JT9100000; Myocet; Myocet (TN); NDC 38242-874; RDF Rubex; Resmycin; Rubex; Rubex (TN); Rubex (hydrochloride salt); TLC D-99; ThermoDox
Drug Type
Small molecular drug
Indication Leukemia [ICD11:2A60-2B33] Approved [1]
Hodgkin lymphoma [ICD11:2B30] 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-TZSSRYMLSA-N
CAS Number
CAS 23214-92-8
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
31703
PubChem SID
11466466 ,11467586 ,11486131 ,11533222 ,11538021 ,14910387 ,14910388 ,17397983 ,24769891 ,26704333 ,26709766 ,34673809 ,46507641 ,47440542 ,47515588 ,47589229 ,47736754 ,47811027 ,47811028 ,48035406 ,4809 ,48185239 ,48414671 ,48415928 ,49698493 ,49846798 ,49855190 ,50063935 ,53787595 ,53837797 ,56310844 ,56311108 ,56311939 ,56312034 ,56312063 ,56312270 ,56312524 ,56312768 ,56313130 ,56313308 ,56313325 ,56313365 ,56313675 ,56313990 ,56314080 ,56314176 ,596007 ,7887074 ,7979129 ,8172352
ChEBI ID
ChEBI:28748
TTD Drug ID
D07VLY
DT(s) Transporting This Drug ABCB5 Transporter Info ATP-binding cassette sub-family B member 5 Substrate [2]
ABCB8 Transporter Info ATP-binding cassette sub-family B member 8 Substrate [3]
ABCG1 Transporter Info ATP-binding cassette sub-family G member 1 Substrate [4]
BCRP Transporter Info Breast cancer resistance protein Substrate [5]
FLIPT2 Transporter Info Fly-like putative transporter 2 Substrate [6]
MCT1 Transporter Info Monocarboxylate transporter 1 Substrate [7]
MRP1 Transporter Info Multidrug resistance-associated protein 1 Substrate [8]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [9]
P-GP Transporter Info P-glycoprotein 1 Substrate [10]
P-GP Transporter Info P-glycoprotein 1 Substrate [11]
Drug-Transporter Activity Data
Drug-Transporter Activity Data BCRP Transporter Info Km =5 microM Spodoptera frugiperda (Sf9) cells-BCRP [12]
P-GP Transporter Info Km =3 microM KB-V1 cells-overexpress MDR1 [13]
References
1 Doxorubicin was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 ABCB5-mediated doxorubicin transport and chemoresistance in human malignant melanoma. Cancer Res. 2005 May 15;65(10):4320-33.
3 ABCB8 mediates doxorubicin resistance in melanoma cells by protecting the mitochondrial genome. Mol Cancer Res. 2009 Jan;7(1):79-87.
4 ABCG1 and Pgp identify drug resistant, self-renewing osteosarcoma cells. Cancer Lett. 2019 Jul 1;453:142-157.
5 Doxorubicin transport by RALBP1 and ABCG2 in lung and breast cancer. Int J Oncol. 2007 Mar;30(3):717-25.
6 Influence of pharmacogenetics on response and toxicity in breast cancer patients treated with doxorubicin and cyclophosphamide. Br J Cancer. 2010 Mar 16;102(6):1003-9.
7 Circadian rhythms in gene expression: Relationship to physiology, disease, drug disposition and drug action. Adv Drug Deliv Rev. 2010 Jul 31;62(9-10):904-17.
8 The role of bioreductive activation of doxorubicin in cytotoxic activity against leukaemia HL60-sensitive cell line and its multidrug-resistant sublines. Br J Cancer. 2005 Jul 11;93(1):89-97.
9 Involvement of the drug transporters p glycoprotein and multidrug resistance-associated protein Mrp2 in telithromycin transport. Antimicrob Agents Chemother. 2006 Jan;50(1):80-7.
10 MDR1 (ABCB1) G1199A (Ser400Asn) polymorphism alters transepithelial permeability and sensitivity to anticancer agents. Cancer Chemother Pharmacol. 2009 Jun;64(1):183-8.
11 Fingerprint-based in silico models for the prediction of P-glycoprotein substrates and inhibitors. Bioorg Med Chem. 2012 Sep 15;20(18):5388-95.
12 Functional characterization of the human multidrug transporter, ABCG2, expressed in insect cells. Biochem Biophys Res Commun. 2001 Jul 6;285(1):111-7.
13 Partial purification and reconstitution of the human multidrug-resistance pump: characterization of the drug-stimulatable ATP hydrolysis. Proc Natl Acad Sci U S A. 1992 Sep 15;89(18):8472-6.

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