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

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 7709
DNA topoisomerase II 61 Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17194596	Inhibitor 7709	2.67 µM [IC50]
A673 5 Target ID: CHEMBL614517 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27688190	Inhibitor 7709	200.0 nM [IC50]
HepG2 13 Target ID: CHEMBL395 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27669220	Inhibitor 7709	24.68 µM [IC50]
Human ovarian cancer cell line 5 Target ID: CHEMBL613895 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26694484	Inhibitor 7709	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 8003	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 8003	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 145 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2013/050718s045lbl.pdf	Primary	Approved 8003	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 1399 AKR1C3 9 NDUFS2 5 NDUFS3 5 NDUFS7 5 NQO1 5 XDH 5 MRP1 93 MRP2 179 BCRP 506 SLC22A16 5 MRP5 36 OATP1A2 57 OATP1B1 369 OATP1B3 319	CYP1A1 106 CYP1A2 642 CYP1B1 55 CYP2B2 12 CYP2E1 117 CYP2J3 5 CYP2C11 11 CYP2B1 23 CYP2C23 7

Drug as perpetrator

Target	Modality	Activity
CYP2B1 38	inducer 1443 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	no
CYP2C23 7	inducer 1443 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	no
CYP2C11 12	inducer 1443 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	weak
CYP1A1 199	inducer 1443 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP1A2 1532	inducer 1443 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP1B1 71	inducer 1443 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP2B2 13	inducer 1443 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP2E1 866	inducer 1443 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes
CYP2J3 5	inducer 1443 Sources: https://www.sciencedirect.com/science/article/pii/S1537189108000864 Page: -	yes

Drug as victim

Target	Modality	Activity	Metabolite
SLC22A16 5	substrate 3107 Sources: https://www.sciencedirect.com/science/article/pii/S0006291X05011873 Page: -	yes [Km 5.2 uM]
AKR1C3 9	substrate 3107 Sources: https://www.pharmgkb.org/literature/8369411 Page: -	yes
BCRP 506	substrate 3107 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
MRP1 93	substrate 3107 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
MRP2 179	substrate 3107 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
MRP5 36	substrate 3107 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes	GS-DOX 5
NDUFS2 5	substrate 3107 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
NDUFS3 5	substrate 3107 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
NDUFS7 5	substrate 3107 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
NQO1 5	substrate 3107 Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: -	yes
OATP1A2 57	substrate 3107 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes
OATP1B1 369	substrate 3107 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes
OATP1B3 319	substrate 3107 Sources: https://www.sciencedirect.com/science/article/pii/S0378427401003915 Page: -	yes
P-gp 1399	substrate 3107 Sources: https://link.springer.com/article/10.1007/s12272-011-0411-x Page: -	yes
XDH 5	substrate 3107 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
Protective effects of carvedilol against doxorubicin-induced cardiomyopathy in rats.	1999	10503942
Topical DMSO treatment for pegylated liposomal doxorubicin-induced palmar-plantar erythrodysesthesia.	1999	10447577
Potential inhibitors of HIV integrase.	1999 Apr-May	10432664
Sodium bicarbonate treatment reduces renal injury, renal production of transforming growth factor-beta, and urinary transforming growth factor-beta excretion in rats with doxorubicin-induced nephropathy.	1999 Aug	10430982
Doxorubicin induces slow ceramide accumulation and late apoptosis in cultured adult rat ventricular myocytes.	1999 Aug 1	10536670
Doxorubicin-induced cardiomyopathy.	1999 Feb 25	10049088
Doxorubicin-induced cardiomyopathy.	1999 Feb 25	10049085
[Changes in left ventricular function during chemotherapy with doxorubicin].	1999 Jul	11045157
Toxic epidermal necrolysis and graft vs. host disease: a clinical spectrum but a diagnostic dilemma.	1999 Jul	10457124
Effect of allopurinol in the course of adriamycin induced nephropathy.	1999 Mar	10088175
Role of thromboxane in the altered vascular reactivity of pregnant rats with adriamycin nephropathy.	1999 May	10344349
Low-dose vincristine-associated bilateral vocal cord paralysis.	1999 Oct	10578547
Renal protective effects of blocking the intrarenal renin-angiotensin system.	1999 Sep	10515446
Preclinical evaluation of the cardiac toxicity of HMR-1826, a novel prodrug of doxorubicin.	1999 Sep	10487608
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
Doxorubicin and paclitaxel in advanced breast carcinoma: importance of prior adjuvant anthracycline therapy.	2000 Dec 1	11147586
Curcumin prevents adriamycin nephrotoxicity in rats.	2000 Jan	10694226
Mechanism of doxorubicin-induced inhibition of sarcoplasmic reticulum Ca(2+)-ATPase gene transcription.	2000 Jan 7-21	10625299
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
Doxorubicin-induced cardiomyopathy.	2000 Jul	10910374
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
Deficiency of the stress kinase p38alpha results in embryonic lethality: characterization of the kinase dependence of stress responses of enzyme-deficient embryonic stem cells.	2000 Mar 6	10704466
Lovastatin potentiates antitumor activity and attenuates cardiotoxicity of doxorubicin in three tumor models in mice.	2000 May	10815931
Renal antioxidant enzymes and fibrosis-related markers in the rat adriamycin model.	2000 Oct	11014987
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
Human carbonyl reductase overexpression in the heart advances the development of doxorubicin-induced cardiotoxicity in transgenic mice.	2000 Sep 15	11016643
Mobilization of hematopoietic progenitor cells with a combination of docetaxel, adriamycin, 5-fluorouracil and filgrastim in breast cancer patients.	2001 Jan	11146579
Reversal of LRP-associated drug resistance in colon carcinoma SW-620 cells.	2001 Jan 1	11149411
Characterization of adriamycin-induced G2 arrest and its abrogation by caffeine in FL-amnion cells with or without p53.	2001 Jan 1	11120603

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)

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