DOXORUBICIN

First approved in 1974

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H29NO11
Molecular Weight	543.5193
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C2C(=O)C3=C(O)C4=C(C[C@](O)(C[C@@H]4O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)C(=O)CO)C(O)=C3C(=O)C2=CC=C1

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	543.5193
Charge	0
Count

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

Description
Sources: http://www.cytrx.com/aldoxorubicinhttp://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 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28846045	Inhibitor 8504	2.67 µM [IC50]
Serum albumin 18 Target ID: CHEMBL3253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28846045	Binding Agent 1076
DNA topoisomerase II alpha 37 Target ID: CHEMBL1806 Sources: http://www.drugbank.ca/drugs/DB00997	Inhibitor 8504
DNA topoisomerase II 66 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17194596	Inhibitor 8504	2.67 µM [IC50]
A673 8 Target ID: CHEMBL614517 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27688190	Inhibitor 8504	200.0 nM [IC50]
HepG2 16 Target ID: CHEMBL395 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27669220	Inhibitor 8504	24.68 µM [IC50]
Human ovarian cancer cell line 8 Target ID: CHEMBL613895 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26694484	Inhibitor 8504	0.074 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Locally advanced or unresectable soft tissue sarcoma 8 Sources: https://clinicaltrials.gov/ct2/show/NCT02049905	Primary	Phase III 665	Unknown Approved Use Unknown
Kaposi’s sarcoma 13 Sources: https://clinicaltrials.gov/ct2/show/NCT02029430	Primary	Phase II 1147	Unknown Approved Use Unknown
Glioblastoma 66 Sources: https://clinicaltrials.gov/ct2/show/NCT02014844	Primary	Phase II 1147	Unknown Approved Use Unknown
Metastatic non-small cell lung cancer 13 Sources: https://clinicaltrials.gov/ct2/show/NCT02200757	Primary	Phase II 1147	Unknown Approved Use Unknown
Pancreatic ductal adenocarcinoma 14 Sources: https://clinicaltrials.gov/ct2/show/NCT01580397	Primary	Phase II 1147	Unknown Approved Use Unknown
Ovarian cancer 160 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050718s045lbl.pdf	Primary	Approved 8583	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 1995
AIDS-related Kaposi’s sarcoma 15 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050718s045lbl.pdf	Primary	Approved 8583	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 1995
Multiple myeloma 159 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050718s045lbl.pdf	Primary	Approved 8583	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 1995

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
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
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
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 Health Status: unhealthy Age Group: 17 years Sex: F 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 Health Status: unhealthy Age Group: 58 years Sex: M 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 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
450 mg/m2 1 times / 3 weeks multiple, intravenous Highest studied dose Dose: 450 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 450 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/25312684	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25312684	DLT: Neutropenia, Febrile neutropenia... Disc. AE: Anemia, Neutropenia... Dose limiting toxicities: Neutropenia (grade 4, 50%) Febrile neutropenia (grade 3, 50%) AEs leading to discontinuation/dose reduction: Anemia (grade 3, 50%) Neutropenia (grade 3, 50%) Sources: https://pubmed.ncbi.nlm.nih.gov/25312684
350 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 350 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 350 mg/m2, 1 times / 3 weeks Sources: https://pubmed.ncbi.nlm.nih.gov/25312684	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25312684	DLT: Dehydration, Neutropenia... Disc. AE: Septic shock, Anemia... Dose limiting toxicities: Dehydration (5.6%) Neutropenia (5.6%) Sepsis (5.6%) AEs leading to discontinuation/dose reduction: Septic shock (grade 5, 5.6%) Anemia (grade 3, 5.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/25312684

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	P-gp 2052 AKR1C3 13 NDUFS2 8 NDUFS3 8 NDUFS7 8 NQO1 8 XDH 8 MRP1 113 MRP2 252 BCRP 697 SLC22A16 8 MRP5 41 OATP1A2 67 OATP1B1 503 OATP1B3 435	CYP1A1 151 CYP1A2 832 CYP1B1 71 CYP2B2 15 CYP2E1 131 CYP2J3 8 CYP2C11 14 CYP2B1 26 CYP2C23 12

Drug as perpetrator

Target	Modality	Activity
CYP2B1 41	inducer 1966 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	no
CYP2C23 12	inducer 1966 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	no
CYP2C11 15	inducer 1966 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	weak
CYP1A1 272	inducer 1966 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP1A2 2333	inducer 1966 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP1B1 93	inducer 1966 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP2B2 16	inducer 1966 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP2E1 1146	inducer 1966 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP2J3 8	inducer 1966 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes

Drug as victim

Target	Modality	Activity	Metabolite
SLC22A16 8	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0006291X05011873 Page: -	yes [Km 5.2 uM]
AKR1C3 13	substrate 4014 Sources: https://www.pharmgkb.org/literature/8369411 Page: -	yes
BCRP 697	substrate 4014 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
MRP1 113	substrate 4014 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
MRP2 252	substrate 4014 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
MRP5 41	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes	GS-DOX 8
NDUFS2 8	substrate 4014 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
NDUFS3 8	substrate 4014 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
NDUFS7 8	substrate 4014 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
NQO1 8	substrate 4014 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
OATP1A2 67	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes
OATP1B1 503	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes
OATP1B3 435	substrate 4014 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes
P-gp 2052	substrate 4014 Sources: https://link.springer.com/article/10.1007/s12272-011-0411-x Page: -	yes
XDH 8	substrate 4014 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
AbovChem LLC	HY-16261A	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-16261A
BLD Pharm	BD630336	http://www.bldpharm.com/search/Search.html?keyword=BD630336
Chem Scene	CS-0077171	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0077171
eMolecules	50284280	https://orderbb.emolecules.com/search/#?query=50284280
mcule	MCULE-8506890923	https://mcule.com/MCULE-8506890923/
MedChem Express	HY-16261B	https://www.medchemexpress.com/search.html?q=HY-16261B&ft=&fa=&fp=
ChEBI	CHEBI:28748	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28748
eMolecules	36788175	https://www.emolecules.com/cgi-bin/more?vid=36788175
MolPort	MolPort-006-124-025	https://www.molport.com/shop/molecule-link/MolPort-006-124-025
ZINC	ZINC000003918087	http://zinc15.docking.org/substances/ZINC000003918087

PubMed

Title	Date	PubMed
Aldoxorubicin for the treatment of soft tissue sarcoma.	2017-10	28846045
Human mismatch repair and G*T mismatch binding by hMutSalpha in vitro is inhibited by adriamycin, actinomycin D, and nogalamycin.	2001-03-30	11134041
Repression of cyclin B1 expression after treatment with adriamycin, but not cisplatin in human lung cancer A549 cells.	2001-01-26	11162602
Serum pancreastatin levels predict response to hepatic artery chemoembolization and somatostatin analogue therapy in metastatic neuroendocrine tumors.	2001-01-12	11111016
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.	2001-01-06	11144469
Reversal of LRP-associated drug resistance in colon carcinoma SW-620 cells.	2001-01-01	11149411
Long-term cardiac sequelae in operable breast cancer patients given adjuvant chemotherapy with or without doxorubicin and breast irradiation.	2001-01-01	11134193
Characterization of adriamycin-induced G2 arrest and its abrogation by caffeine in FL-amnion cells with or without p53.	2001-01-01	11120603
Nuclear factor kappaB-dependent mechanisms coordinate the synergistic effect of PMA and cytokines on the induction of superoxide dismutase 2.	2001-01-01	11115408
Mobilization of hematopoietic progenitor cells with a combination of docetaxel, adriamycin, 5-fluorouracil and filgrastim in breast cancer patients.	2001-01	11146579
Low-grade ovarian cancer in an adolescent patient.	2001-01	11136580
Targeted systemic chemotherapy using magnetic liposomes with incorporated adriamycin for osteosarcoma in hamsters.	2001-01	11115548
ACE inhibition preserves heparan sulfate proteoglycans in the glomerular basement membrane of rats with established adriamycin nephropathy.	2001	11053977
Adjuvant doxorubicin and cyclophosphamide versus cyclophosphamide, methotrexate, and 5-fluorouracil chemotherapy in premenopausal women with axillary lymph node positive breast carcinoma.	2000-12-15	11135211
Mycosis fungoides and pregnancy.	2000-12-15	11115598
Doxorubicin and paclitaxel in advanced breast carcinoma: importance of prior adjuvant anthracycline therapy.	2000-12-01	11147586
Cytokine gene expression in Adriamycin nephropathy: effects of antioxidant nuclear factor kappaB inhibitors in established disease.	2000-12	11124598
Progressive cardiac dysfunction in adriamycin-induced cardiomyopathy rats.	2000-12	11113713
High incidence of adriamycin cardiotoxicity in children even at low cumulative doses: role of radionuclide cardiac angiography.	2000-12	11101737
Proteasome-mediated degradation of the coactivator p300 impairs cardiac transcription.	2000-12	11073966
Phase II study of pegylated liposomal doxorubicin: inactive in recurrent small-cell lung cancer. A Hellenic Cooperative Oncology Group Study.	2000-11	11142478
Renal antioxidant enzymes and fibrosis-related markers in the rat adriamycin model.	2000-10	11014987
Progressive adriamycin nephropathy in mice: sequence of histologic and immunohistochemical events.	2000-10	11012915
Human carbonyl reductase overexpression in the heart advances the development of doxorubicin-induced cardiotoxicity in transgenic mice.	2000-09-15	11016643
Bilateral blindness and lumbosacral myelopathy associated with high-dose carmustine and cisplatin therapy.	2000-09	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.	2000-09	10985896
Prevention of doxorubicin (adriamycin)-induced cardiomyopathy by simultaneous administration of angiotensin-converting enzyme inhibitor assessed by acoustic densitometry.	2000-09	10975594
Deregulated manganese superoxide dismutase expression and resistance to oxidative injury in p53-deficient cells.	2000-08-15	10969820
Caffeine-potentiated radiochemotherapy and function-saving surgery for high-grade soft tissue sarcoma.	2000-08-06	10928167
Fas-mediated apoptosis in adriamycin-induced cardiomyopathy in rats: In vivo study.	2000-08-01	10920071
Pegylated liposomal doxorubicin (doxil): reduced clinical cardiotoxicity in patients reaching or exceeding cumulative doses of 500 mg/m2.	2000-08	11038041
The influence of coordinate overexpression of glutathione phase II detoxification gene products on drug resistance.	2000-08	10900222
The protective effect of glutathione administration on adriamycin-induced acute cardiac toxicity in rats.	2000-08	10887039
Oxidative stress interferes with cancer chemotherapy: inhibition of lymphoma cell apoptosis and phagocytosis.	2000-07-01	10891466
Influence of Adriamycin and paraquat on antioxidant enzyme expression in primary rat hepatocytes.	2000-07	10959798
Doxorubicin-induced cardiomyopathy.	2000-07	10910374
Cardiac peroxynitrite formation and left ventricular dysfunction following doxorubicin treatment in mice.	2000-07	10871338
Effects of probucol on changes of antioxidant enzymes in adriamycin-induced cardiomyopathy in rats.	2000-06	10912462
Beta-blockade in adriamycin-induced cardiomyopathy.	2000-06	10908085
Evaluation of cardiac adrenergic neuronal damage in rats with doxorubicin-induced cardiomyopathy using iodine-131 MIBG autoradiography and PGP 9.5 immunohistochemistry.	2000-06	10901455
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.	2000-05	10828864
Lovastatin potentiates antitumor activity and attenuates cardiotoxicity of doxorubicin in three tumor models in mice.	2000-05	10815931
Expression of agrin, dystroglycan, and utrophin in normal renal tissue and in experimental glomerulopathies.	2000-05	10793086
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.	2000-04-25	10774566
Liposomal doxorubicin (Caelyx) in advanced pretreated soft tissue sarcomas: a phase II study of the Italian Sarcoma Group (ISG).	2000-04-19	10769710
Decreased cortisol secretion by adrenal glands perfused with the P-glycoprotein inhibitor valspodar and mitotane or doxorubicin.	2000-04	10898547
Adriamycin-induced heart failure: mechanism and modulation.	2000-04	10888230
Doxorubicin-induced late cardiotoxicity: delayed impairment of Ca2+-handling mechanisms in the sarcoplasmic reticulum in the rat.	2000-04	10772060
[Changes in left ventricular function during chemotherapy with doxorubicin].	1999-07	11045157
Experimental animal models of adriamycin cardiotoxicity.	1979-05	110445

Patents

Sample Use Guides

In Vivo Use Guide

Aldoxorubicin is administered at 350 mg/m2 (260 mg/m2 doxorubicin equivalent) intravenously on Day 1 every 21-day cycles until tumor progression or unacceptable toxicity occurs.

Route of Administration: Intravenous

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:45:21 GMT 2025` Edited by `admin` on `Mon Mar 31 18:45:21 GMT 2025`
Record UNII	80168379AG
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DOXORUBICIN

Official Name

English

ADRIBLASTINA

Preferred Name

English

DOXORUBICIN [HSDB]

Common Name

English

DOXORUBICIN [VANDF]

Common Name

English

ADRIABLASTIN

Common Name

English

DAUNORUBICIN HYDROCHLORIDE IMPURITY D [EP IMPURITY]

Common Name

English

DOXORUBICIN [MART.]

Common Name

English

DOXORUBICIN [MI]

Common Name

English

Doxorubicin [WHO-DD]

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, DOXORUBICIN- [USP IMPURITY]

Common Name

English

NSC-759155

Code

English

doxorubicin [INN]

Common 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

VALRUBICIN IMPURITY, DOXORUBICIN [USP IMPURITY]

Common Name

English

EPIRUBICIN HYDROCHLORIDE IMPURITY C [EP IMPURITY]

Common Name

English

DOXORUBICIN [USAN]

Common Name

English

HYDROXYDAUNORUBICIN

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000007530