DOXORUBICIN

First approved in 1974

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H29NO11
Molecular Weight	543.5203
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]1([H])[C@]([H])([C@]([H])(C[C@@]([H])(O1)O[C@@]2([H])C[C@@](Cc3c2c(c4c(C(=O)c5cccc(c5C4=O)OC)c3O)O)(C(=O)CO)O)N)O

InChI

InChIKey=AOJJSUZBOXZQNB-TZSSRYMLSA-N

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

HIDE SMILES / InChI

Molecular Formula	C27H29NO11
Molecular Weight	543.5203
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.drugbank.ca/drugs/DB00997
Curator's Comment:: Description was created based on several sources, including https://www.drugs.com/dosage/doxorubicin.html

Doxorubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Doxorubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Doxorubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. Doxorubicin is used to produce regression in disseminated neoplastic conditions like acute lymphoblastic leukemia, acute myeloblastic leukemia, Wilms’ tumor, neuroblastoma, soft tissue and bone sarcomas, breast carcinoma, ovarian carcinoma, transitional cell bladder carcinoma, thyroid carcinoma, gastric carcinoma, Hodgkin’s disease, malignant lymphoma and bronchogenic carcinoma in which the small cell histologic type is the most responsive compared to other cell types. Doxorubicin is also indicated for use as a component of adjuvant therapy in women with evidence of axillary lymph node involvement following resection of primary breast cancer.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
DNA topoisomerase II alpha 34 Target ID: CHEMBL1806 Sources: http://www.drugbank.ca/drugs/DB00997	Inhibitor 7687
DNA topoisomerase II 60 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17194596	Inhibitor 7687	2.67 µM [IC50]
A673 5 Target ID: CHEMBL614517 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27688190	Inhibitor 7687	200.0 nM [IC50]
HepG2 13 Target ID: CHEMBL395 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27669220	Inhibitor 7687	24.68 µM [IC50]
Human ovarian cancer cell line 5 Target ID: CHEMBL613895 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26694484	Inhibitor 7687	0.074 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Ovarian cancer 144 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050718s045lbl.pdf	Primary	Approved 7968	DOXIL Approved Use Indicated for: Ovarian cancer After failure of platinum-based chemotherapy. AIDS-related Kaposi’s Sarcoma After failure of prior systemic chemotherapy or intolerance to such therapy. Multiple Myeloma Launch Date 8.1647999E11
AIDS-related Kaposi’s sarcoma 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050718s045lbl.pdf	Primary	Approved 7968	DOXIL Approved Use Indicated for: Ovarian cancer After failure of platinum-based chemotherapy. AIDS-related Kaposi’s Sarcoma After failure of prior systemic chemotherapy or intolerance to such therapy. Multiple Myeloma Launch Date 8.1647999E11
Multiple myeloma 144 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050718s045lbl.pdf	Primary	Approved 7968	DOXIL Approved Use Indicated for: Ovarian cancer After failure of platinum-based chemotherapy. AIDS-related Kaposi’s Sarcoma After failure of prior systemic chemotherapy or intolerance to such therapy. Multiple Myeloma Launch Date 8.1647999E11

C_max

Value	Dose	Co-administered	Analyte	Population
2 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26115930	60 mg/m² 1 times / day steady-state, intravenous dose: 60 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered:		DOXORUBICIN plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
7.4 μM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26115930	60 mg/m² 1 times / day steady-state, intravenous dose: 60 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered:		DOXORUBICIN plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
34.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26115930	60 mg/m² 1 times / day steady-state, intravenous dose: 60 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered:		DOXORUBICIN plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
25% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050467s073lbl.pdf			DOXORUBICIN plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
150 mg/m2 1 times / day multiple, intravenous Overdose Dose: 150 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 150 mg/m2, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy, 17 years n = 1 Health Status: unhealthy Age Group: 17 years Sex: F Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	Other AEs: Mucositis, Chills... Other AEs: Mucositis (severe, 1 patient) Chills (1 patient) Pyrexia (1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
300 mg/m2 single, intravenous Overdose Dose: 300 mg/m2 Route: intravenous Route: single Dose: 300 mg/m2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: acute lymphoblastic leukemia Age Group: 58 years Sex: M Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	Other AEs: Sinus tachycardia, Neutropenia... Other AEs: Sinus tachycardia (1 patient) Neutropenia (grade 4, 1 patient) Thrombocytopenia (1 patient) Mucositis (severe, 1 patient) Sepsis (severe, 1 patient) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
60 mg/m2 1 times / 3 weeks multiple, intravenous Recommended Dose: 60 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	Disc. AE: Tissue injury... Other AEs: Acute myeloid leukaemia, Myelodysplastic syndrome... AEs leading to discontinuation/dose reduction: Tissue injury (severe) Other AEs: Acute myeloid leukaemia Myelodysplastic syndrome Myelosuppression (severe) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
300 mg/m2 1 times / 3 weeks multiple, intravenous (total) Dose: 300 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 300 mg/m2, 1 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	Other AEs: Cardiomyopathy... Other AEs: Cardiomyopathy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf

AEs

AE	Significance	Dose	Population
Chills	1 patient	150 mg/m2 1 times / day multiple, intravenous Overdose Dose: 150 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 150 mg/m2, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy, 17 years n = 1 Health Status: unhealthy Age Group: 17 years Sex: F Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Pyrexia	1 patient	150 mg/m2 1 times / day multiple, intravenous Overdose Dose: 150 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 150 mg/m2, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy, 17 years n = 1 Health Status: unhealthy Age Group: 17 years Sex: F Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Mucositis	severe, 1 patient	150 mg/m2 1 times / day multiple, intravenous Overdose Dose: 150 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 150 mg/m2, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy, 17 years n = 1 Health Status: unhealthy Age Group: 17 years Sex: F Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Sinus tachycardia	1 patient	300 mg/m2 single, intravenous Overdose Dose: 300 mg/m2 Route: intravenous Route: single Dose: 300 mg/m2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: acute lymphoblastic leukemia Age Group: 58 years Sex: M Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Thrombocytopenia	1 patient	300 mg/m2 single, intravenous Overdose Dose: 300 mg/m2 Route: intravenous Route: single Dose: 300 mg/m2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: acute lymphoblastic leukemia Age Group: 58 years Sex: M Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Neutropenia	grade 4, 1 patient	300 mg/m2 single, intravenous Overdose Dose: 300 mg/m2 Route: intravenous Route: single Dose: 300 mg/m2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: acute lymphoblastic leukemia Age Group: 58 years Sex: M Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Mucositis	severe, 1 patient	300 mg/m2 single, intravenous Overdose Dose: 300 mg/m2 Route: intravenous Route: single Dose: 300 mg/m2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: acute lymphoblastic leukemia Age Group: 58 years Sex: M Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Sepsis	severe, 1 patient	300 mg/m2 single, intravenous Overdose Dose: 300 mg/m2 Route: intravenous Route: single Dose: 300 mg/m2 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: acute lymphoblastic leukemia Age Group: 58 years Sex: M Population Size: 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Acute myeloid leukaemia		60 mg/m2 1 times / 3 weeks multiple, intravenous Recommended Dose: 60 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Myelodysplastic syndrome		60 mg/m2 1 times / 3 weeks multiple, intravenous Recommended Dose: 60 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Myelosuppression	severe	60 mg/m2 1 times / 3 weeks multiple, intravenous Recommended Dose: 60 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Tissue injury	severe Disc. AE	60 mg/m2 1 times / 3 weeks multiple, intravenous Recommended Dose: 60 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf
Cardiomyopathy		300 mg/m2 1 times / 3 weeks multiple, intravenous (total) Dose: 300 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 300 mg/m2, 1 times / 3 weeks Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2020/050467s078,050629s030lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 1222 AKR1C3 9 NDUFS2 5 NDUFS3 5 NDUFS7 5 NQO1 5 XDH 5 MRP1 75 MRP2 172 BCRP 461 SLC22A16 5 MRP5 36 OATP1A2 55 OATP1B1 353 OATP1B3 303	CYP1A1 98 CYP1A2 618 CYP1B1 50 CYP2B2 12 CYP2E1 116 CYP2J3 5 CYP2C11 11 CYP2B1 23 CYP2C23 7

Drug as perpetrator

Target	Modality	Activity
CYP2B1 38	inducer 1333 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	no
CYP2C23 7	inducer 1333 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	no
CYP2C11 12	inducer 1333 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	weak
CYP1A1 188	inducer 1333 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP1A2 1406	inducer 1333 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP1B1 64	inducer 1333 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP2B2 13	inducer 1333 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP2E1 841	inducer 1333 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP2J3 5	inducer 1333 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes

Drug as victim

Target	Modality	Activity	Metabolite
SLC22A16 5	substrate 2751 Sources: https://www.sciencedirect.com/science/article/pii/S0006291X05011873 Page: -	yes [Km 5.2 uM]
AKR1C3 9	substrate 2751 Sources: https://www.pharmgkb.org/literature/8369411 Page: -	yes
BCRP 461	substrate 2751 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
MRP1 75	substrate 2751 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
MRP2 172	substrate 2751 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
MRP5 36	substrate 2751 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes	GS-DOX 5
NDUFS2 5	substrate 2751 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
NDUFS3 5	substrate 2751 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
NDUFS7 5	substrate 2751 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
NQO1 5	substrate 2751 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
OATP1A2 55	substrate 2751 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes
OATP1B1 353	substrate 2751 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes
OATP1B3 303	substrate 2751 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes
P-gp 1222	substrate 2751 Sources: https://link.springer.com/article/10.1007/s12272-011-0411-x Page: -	yes
XDH 5	substrate 2751 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:28748	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28748
MolPort	MolPort-006-124-025	https://www.molport.com/shop/molecule-link/MolPort-006-124-025
ZINC	ZINC000003918087	http://zinc15.docking.org/substances/ZINC000003918087
eMolecules	36788175	https://www.emolecules.com/cgi-bin/more?vid=36788175

PubMed

Title	Date	PubMed
Experimental animal models of adriamycin cardiotoxicity.	1979 May	110445
[Changes in left ventricular function during chemotherapy with doxorubicin].	1999 Jul	11045157
Nonmetastatic osteosarcoma of the extremity: results of a neoadjuvant chemotherapy protocol (IOR/OS-3) with high-dose methotrexate, intraarterial or intravenous cisplatin, doxorubicin, and salvage chemotherapy based on histologic tumor response.	1999 Nov-Dec	10774566
Comparison of the protective effects of amifostine and dexrazoxane against the toxicity of doxorubicin in spontaneously hypertensive rats.	2000	10755322
Decreased cortisol secretion by adrenal glands perfused with the P-glycoprotein inhibitor valspodar and mitotane or doxorubicin.	2000 Apr	10898547
Adriamycin-induced heart failure: mechanism and modulation.	2000 Apr	10888230
Doxorubicin-induced late cardiotoxicity: delayed impairment of Ca2+-handling mechanisms in the sarcoplasmic reticulum in the rat.	2000 Apr	10772060
Glomerular basement membrane anionic sites in adriamycin nephropathy: effect of saline loading and nitric oxide modulation.	2000 Apr	10754413
Anthracyclines trigger apoptosis of both G0-G1 and cycling peripheral blood lymphocytes and induce massive deletion of mature T and B cells.	2000 Apr 1	10766178
Pegylated liposomal doxorubicin (doxil): reduced clinical cardiotoxicity in patients reaching or exceeding cumulative doses of 500 mg/m2.	2000 Aug	11038041
The influence of coordinate overexpression of glutathione phase II detoxification gene products on drug resistance.	2000 Aug	10900222
Fas-mediated apoptosis in adriamycin-induced cardiomyopathy in rats: In vivo study.	2000 Aug 1	10920071
Deregulated manganese superoxide dismutase expression and resistance to oxidative injury in p53-deficient cells.	2000 Aug 15	10969820
Cytokine gene expression in Adriamycin nephropathy: effects of antioxidant nuclear factor kappaB inhibitors in established disease.	2000 Dec	11124598
Progressive cardiac dysfunction in adriamycin-induced cardiomyopathy rats.	2000 Dec	11113713
High incidence of adriamycin cardiotoxicity in children even at low cumulative doses: role of radionuclide cardiac angiography.	2000 Dec	11101737
Proteasome-mediated degradation of the coactivator p300 impairs cardiac transcription.	2000 Dec	11073966
Doxorubicin and paclitaxel in advanced breast carcinoma: importance of prior adjuvant anthracycline therapy.	2000 Dec 1	11147586
Adjuvant doxorubicin and cyclophosphamide versus cyclophosphamide, methotrexate, and 5-fluorouracil chemotherapy in premenopausal women with axillary lymph node positive breast carcinoma.	2000 Dec 15	11135211
Curcumin prevents adriamycin nephrotoxicity in rats.	2000 Jan	10694226
Liposomal doxorubicin (Caelyx) in advanced pretreated soft tissue sarcomas: a phase II study of the Italian Sarcoma Group (ISG).	2000 Jan-Feb	10769710
Manic episode in an ifosfamide-treated patient.	2000 Jan-Feb	10766557
Influence of Adriamycin and paraquat on antioxidant enzyme expression in primary rat hepatocytes.	2000 Jul	10959798
Oxidative stress interferes with cancer chemotherapy: inhibition of lymphoma cell apoptosis and phagocytosis.	2000 Jul 1	10891466
Beta-blockade in adriamycin-induced cardiomyopathy.	2000 Jun	10908085
Evaluation of cardiac adrenergic neuronal damage in rats with doxorubicin-induced cardiomyopathy using iodine-131 MIBG autoradiography and PGP 9.5 immunohistochemistry.	2000 Jun	10901455
The influence of thymoquinone on doxorubicin-induced hyperlipidemic nephropathy in rats.	2000 Mar 7	10755708
Cardiac sequelae of doxorubicin and paclitaxel as induction chemotherapy prior to high-dose chemotherapy and peripheral blood progenitor cell transplantation in women with high-risk primary or metastatic breast cancer.	2000 May	10828864
Lovastatin potentiates antitumor activity and attenuates cardiotoxicity of doxorubicin in three tumor models in mice.	2000 May	10815931
Expression of agrin, dystroglycan, and utrophin in normal renal tissue and in experimental glomerulopathies.	2000 May	10793086
Caffeine-potentiated radiochemotherapy and function-saving surgery for high-grade soft tissue sarcoma.	2000 May-Jun	10928167
Phase II study of pegylated liposomal doxorubicin: inactive in recurrent small-cell lung cancer. A Hellenic Cooperative Oncology Group Study.	2000 Nov	11142478
Detection of doxorubicin cardiotoxicity by using iodine-123 BMIPP early dynamic SPECT: quantitative evaluation of early abnormality of fatty acid metabolism with the Rutland method.	2000 Nov-Dec	11144469
Progressive adriamycin nephropathy in mice: sequence of histologic and immunohistochemical events.	2000 Oct	11012915
Bilateral blindness and lumbosacral myelopathy associated with high-dose carmustine and cisplatin therapy.	2000 Sep	11020424
Phase 2 trial of liposomal doxorubicin (40 mg/m(2)) in platinum/paclitaxel-refractory ovarian and fallopian tube cancers and primary carcinoma of the peritoneum.	2000 Sep	10985896
Prevention of doxorubicin (adriamycin)-induced cardiomyopathy by simultaneous administration of angiotensin-converting enzyme inhibitor assessed by acoustic densitometry.	2000 Sep	10975594
Human carbonyl reductase overexpression in the heart advances the development of doxorubicin-induced cardiotoxicity in transgenic mice.	2000 Sep 15	11016643
ACE inhibition preserves heparan sulfate proteoglycans in the glomerular basement membrane of rats with established adriamycin nephropathy.	2001	11053977
Mobilization of hematopoietic progenitor cells with a combination of docetaxel, adriamycin, 5-fluorouracil and filgrastim in breast cancer patients.	2001 Jan	11146579
Low-grade ovarian cancer in an adolescent patient.	2001 Jan	11136580
Targeted systemic chemotherapy using magnetic liposomes with incorporated adriamycin for osteosarcoma in hamsters.	2001 Jan	11115548
Reversal of LRP-associated drug resistance in colon carcinoma SW-620 cells.	2001 Jan 1	11149411
Long-term cardiac sequelae in operable breast cancer patients given adjuvant chemotherapy with or without doxorubicin and breast irradiation.	2001 Jan 1	11134193
Characterization of adriamycin-induced G2 arrest and its abrogation by caffeine in FL-amnion cells with or without p53.	2001 Jan 1	11120603
Nuclear factor kappaB-dependent mechanisms coordinate the synergistic effect of PMA and cytokines on the induction of superoxide dismutase 2.	2001 Jan 1	11115408
Serum pancreastatin levels predict response to hepatic artery chemoembolization and somatostatin analogue therapy in metastatic neuroendocrine tumors.	2001 Jan 12	11111016
Repression of cyclin B1 expression after treatment with adriamycin, but not cisplatin in human lung cancer A549 cells.	2001 Jan 26	11162602
Mycosis fungoides and pregnancy.	2001 Jan-Feb	11115598
Human mismatch repair and G*T mismatch binding by hMutSalpha in vitro is inhibited by adriamycin, actinomycin D, and nogalamycin.	2001 Mar 30	11134041

Patents

Sample Use Guides

In Vivo Use Guide

When used in combination with other chemotherapy drugs, the most commonly used dosage of doxorubicin is 40 to 60 mg/m2 IV every 21 to 28 days. Alternatively, 60 to 75 mg/m2 IV once every 21 days.

Route of Administration: Intravenous

In Vitro Use Guide

Alkalinization of extracellular pH by urease (2 U/ml) and urea (> or = 2 mM) was found to enhance the antitumor efficacy of doxorubicin (50 uM)

Substance Class	Chemical Created by `admin` on `Fri Jun 25 22:01:58 UTC 2021` Edited by `admin` on `Fri Jun 25 22:01:58 UTC 2021`
Record UNII	80168379AG
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DOXORUBICIN

Official Name

English

DOXORUBICIN [HSDB]

Common Name

English

DOXORUBICIN [VANDF]

Common Name

English

ADRIABLASTIN

Common Name

English

DOXORUBICIN [MART.]

Common Name

English

DOXORUBICIN [MI]

Common Name

English

NSC-123127

Code

English

5,12-NAPHTHACENEDIONE, 10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (8S-CIS)-

Common Name

English

EPIRUBICIN HYDROCHLORIDE IMPURITY C [EP]

Common Name

English

DOXORUBICIN [WHO-DD]

Common Name

English

EPIRUBICIN IMPURITY C

Common Name

English

EPIRUBICIN HYDROCHLORIDE IMPURITY, DOXORUBICIN- [USP]

Common Name

English

VALRUBICIN IMPURITY, DOXORUBICIN [USP]

Common Name

English

EPIRUBICIN HYDROCHLORIDE SPECIFIED IMPURITY C [EP]

Common Name

English

NSC-759155

Code

English

DOXORUBICIN [INN]

Common Name

English

ADRIBLASTINA

Brand Name

English

(8S,10S)-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-8-GLYCOLOYL-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-5,12-NAPHTHACENEDIONE

Common Name

English

DOXORUBICIN [USAN]

Common Name

English

HYDROXYDAUNORUBICIN

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000007530