U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of DOXORUBICIN

SMILES

[H][C@@]1(C[C@H](N)[C@H](O)[C@H](C)O1)O[C@H]2C[C@@](O)(CC3=C(O)C4=C(C(=O)C5=C(OC)C=CC=C5C4=O)C(O)=C23)C(=O)CO

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
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/28846045 | https://clinicaltrials.gov/ct2/show/NCT02049905 | https://www.ncbi.nlm.nih.gov/pubmed/26378637 | https://clinicaltrials.gov/ct2/show/NCT02014844 | https://www.ncbi.nlm.nih.gov/pubmed/25312684 | https://clinicaltrials.gov/ct2/show/NCT02200757

Aldoxorubicin (INNO-206) is a tumor-targeted doxorubicin conjugate developed by CytRx for treating relapsed and refractory sarcomas, especially L-sarcomas. Aldoxorubicin is a rationally-engineered cytotoxic which delivers a well-established anti-cancer agent, doxorubicin, into the tumor. Currently, in late-stage clinical trials, Aldoxorubicin appears to overcome the key limitations of doxorubicin, including cumulative dose restrictions. Aldoxorubicin utilizes an acid-sensitive linker that selectively binds to albumin, which may allow the cytotoxic payload to preferentially accumulate in the tumor and potentially spare the surrounding healthy tissue. This mechanism leverages the tumor's low pH environment and accompanying dependency upon circulating albumin to fuel growth, to enable the delivery of multifold times the standard dosing of doxorubicin. The preferential uptake of Aldoxorubicin by tumor tissue and the acid sensitive release of doxorubicin allow for Aldoxorubicin to be a very promising anticancer agent. In phase I and II trials, Aldoxorubicin demonstrates superior efficacy over doxorubicin. Although the studies were not powered for OS, Aldoxorubicin shows improved PFS and tumor response in comparison to doxorubicin. The safety profile was also comparable to that of doxorubicin. Similarly, results from the recent phase III study showed a benefit in PFS in the leiomyosarcoma subtypes.

CNS Activity

Curator's Comment: Doxorubicin did not have access to areas of the brain within the blood-brain barrier, passed from the blood into the nervous parenchyma in those areas of the brain located outside the blood-brain barrier in mice

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
2.67 µM [IC50]
2.67 µM [IC50]
Target ID: CHEMBL614517
200.0 nM [IC50]
24.68 µM [IC50]
0.074 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
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
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2 μM
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

AUC

ValueDoseCo-administeredAnalytePopulation
7.4 μM × h
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
34.8 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
25%
DOXORUBICIN plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
Other AEs: Mucositis, Chills...
Other AEs:
Mucositis (severe, 1 patient)
Chills (1 patient)
Pyrexia (1 patient)
Sources:
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
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:
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:
unhealthy
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:
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:
unhealthy
Other AEs: Cardiomyopathy...
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: Page: p.574
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 2
Sources: Page: p.574
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: Page: p.574
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: Page: p.574
unhealthy, ADULT
n = 18
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources: Page: p.574
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: Page: p.574
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
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:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
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:
unhealthy, 17 years
n = 1
Health Status: unhealthy
Age Group: 17 years
Sex: F
Population Size: 1
Sources:
Sinus tachycardia 1 patient
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Thrombocytopenia 1 patient
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Neutropenia grade 4, 1 patient
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Mucositis severe, 1 patient
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
Sepsis severe, 1 patient
300 mg/m2 single, intravenous
Overdose
Dose: 300 mg/m2
Route: intravenous
Route: single
Dose: 300 mg/m2
Sources:
unhealthy, 58 years
n = 1
Health Status: unhealthy
Condition: acute lymphoblastic leukemia
Age Group: 58 years
Sex: M
Population Size: 1
Sources:
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
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:
unhealthy
Febrile neutropenia grade 3, 50%
DLT
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: Page: p.574
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 2
Sources: Page: p.574
Anemia grade 3, 50%
Disc. AE
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: Page: p.574
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 2
Sources: Page: p.574
Neutropenia grade 3, 50%
Disc. AE
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: Page: p.574
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 2
Sources: Page: p.574
Neutropenia grade 4, 50%
DLT
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: Page: p.574
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 2
Sources: Page: p.574
Dehydration 5.6%
DLT
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: Page: p.574
unhealthy, ADULT
n = 18
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources: Page: p.574
Neutropenia 5.6%
DLT
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: Page: p.574
unhealthy, ADULT
n = 18
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources: Page: p.574
Sepsis 5.6%
DLT
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: Page: p.574
unhealthy, ADULT
n = 18
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources: Page: p.574
Anemia grade 3, 5.6%
Disc. AE
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: Page: p.574
unhealthy, ADULT
n = 18
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources: Page: p.574
Septic shock grade 5, 5.6%
Disc. AE
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: Page: p.574
unhealthy, ADULT
n = 18
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 18
Sources: Page: p.574
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes [Km 5.2 uM]
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
Myocardial injury induced by a single dose of adriamycin: an electron microscopic study.
1976 Sep-Oct
Doxorubicin-induced congestive heart failure in elderly patients with metastatic breast cancer, with long-term follow-up: the M.D. Anderson experience.
1999
Reversal of doxorubicin-induced cardiac metabolic damage by L-carnitine.
1999 Apr
Inhibitory effects of combinations of HER-2/neu antibody and chemotherapeutic agents used for treatment of human breast cancers.
1999 Apr 1
Altered expression of the MYCN oncogene modulates MRP gene expression and response to cytotoxic drugs in neuroblastoma cells.
1999 Apr 29
Anticancer drug sensitivity and expression of multidrug resistance markers in early passage human sarcomas.
1999 Aug
Doxorubicin induces slow ceramide accumulation and late apoptosis in cultured adult rat ventricular myocytes.
1999 Aug 1
Phase II trial of doxorubicin and paclitaxel plus granulocyte colony-stimulating factor in metastatic breast cancer: an Eastern Cooperative Oncology Group Study.
1999 Dec
Increase in doxorubicin cytotoxicity by carvedilol inhibition of P-glycoprotein activity.
1999 Dec 1
Doxorubicin-induced cardiomyopathy.
1999 Feb 25
Doxorubicin cardiotoxicity: growing importance.
1999 Jul
Correlation between serum levels of cardiac troponin-T and the severity of the chronic cardiomyopathy induced by doxorubicin.
1999 Jul
Effect of proteinuria reduction on prevention of focal glomerulosclerosis by angiotensin-converting enzyme inhibition is modifiable.
1999 Jul
Abdominal-wall myositis secondary to intra-arterial chemotherapy for femoral osteosarcoma.
1999 Jul
Coordinate alterations in the expression of BRCA1, BRCA2, p300, and Rad51 in response to genotoxic and other stresses in human prostate cancer cells.
1999 Jun 15
Effect of captopril on doxorubicin-induced nephrotoxicity in normal rats.
1999 Mar
Effect of allopurinol in the course of adriamycin induced nephropathy.
1999 Mar
Delayed methotrexate clearance in a patient with sickle cell anemia and osteosarcoma.
1999 Mar-Apr
Role of thromboxane in the altered vascular reactivity of pregnant rats with adriamycin nephropathy.
1999 May
Zinc accumulation in adriamycin-induced cardiomyopathy in rats: effects of melatonin, a cardioprotective antioxidant.
1999 May
Phase II trial of high-dose liposome-encapsulated doxorubicin with granulocyte colony-stimulating factor in metastatic breast cancer. TLC D-99 Study Group.
1999 May
Reduction of the cardiotoxicity of doxorubicin in rabbits and dogs by encapsulation in long-circulating, pegylated liposomes.
1999 May
Primary desmoplastic small cell tumor of soft tissues and bone of the hand.
1999 Nov
Decreased cortisol secretion by adrenal glands perfused with the P-glycoprotein inhibitor valspodar and mitotane or doxorubicin.
2000 Apr
Pegylated liposomal doxorubicin (doxil): reduced clinical cardiotoxicity in patients reaching or exceeding cumulative doses of 500 mg/m2.
2000 Aug
The influence of coordinate overexpression of glutathione phase II detoxification gene products on drug resistance.
2000 Aug
The protective effect of glutathione administration on adriamycin-induced acute cardiac toxicity in rats.
2000 Aug
Deregulated manganese superoxide dismutase expression and resistance to oxidative injury in p53-deficient cells.
2000 Aug 15
Cytokine gene expression in Adriamycin nephropathy: effects of antioxidant nuclear factor kappaB inhibitors in established disease.
2000 Dec
High incidence of adriamycin cardiotoxicity in children even at low cumulative doses: role of radionuclide cardiac angiography.
2000 Dec
Proteasome-mediated degradation of the coactivator p300 impairs cardiac transcription.
2000 Dec
Adjuvant doxorubicin and cyclophosphamide versus cyclophosphamide, methotrexate, and 5-fluorouracil chemotherapy in premenopausal women with axillary lymph node positive breast carcinoma.
2000 Dec 15
Comparison of doxorubicin- and MEN 10755-induced long-term progressive cardiotoxicity in the rat.
2000 Jan
Mechanism of doxorubicin-induced inhibition of sarcoplasmic reticulum Ca(2+)-ATPase gene transcription.
2000 Jan 7-21
Evaluation of cardiac adrenergic neuronal damage in rats with doxorubicin-induced cardiomyopathy using iodine-131 MIBG autoradiography and PGP 9.5 immunohistochemistry.
2000 Jun
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
Lovastatin potentiates antitumor activity and attenuates cardiotoxicity of doxorubicin in three tumor models in mice.
2000 May
Expression of agrin, dystroglycan, and utrophin in normal renal tissue and in experimental glomerulopathies.
2000 May
Renal antioxidant enzymes and fibrosis-related markers in the rat adriamycin model.
2000 Oct
Bilateral blindness and lumbosacral myelopathy associated with high-dose carmustine and cisplatin therapy.
2000 Sep
Human carbonyl reductase overexpression in the heart advances the development of doxorubicin-induced cardiotoxicity in transgenic mice.
2000 Sep 15
ACE inhibition preserves heparan sulfate proteoglycans in the glomerular basement membrane of rats with established adriamycin nephropathy.
2001
Low-grade ovarian cancer in an adolescent patient.
2001 Jan
Targeted systemic chemotherapy using magnetic liposomes with incorporated adriamycin for osteosarcoma in hamsters.
2001 Jan
Reversal of LRP-associated drug resistance in colon carcinoma SW-620 cells.
2001 Jan 1
Long-term cardiac sequelae in operable breast cancer patients given adjuvant chemotherapy with or without doxorubicin and breast irradiation.
2001 Jan 1
Nuclear factor kappaB-dependent mechanisms coordinate the synergistic effect of PMA and cytokines on the induction of superoxide dismutase 2.
2001 Jan 1
Repression of cyclin B1 expression after treatment with adriamycin, but not cisplatin in human lung cancer A549 cells.
2001 Jan 26
Mycosis fungoides and pregnancy.
2001 Jan-Feb
Aldoxorubicin for the treatment of soft tissue sarcoma.
2017 Oct
Patents

Sample Use Guides

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
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 Dec 15 17:21:26 GMT 2023
Edited
by admin
on Fri Dec 15 17:21:26 GMT 2023
Record UNII
80168379AG
Record Status Validated (UNII)
Record Version
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Name Type Language
DOXORUBICIN
HSDB   INN   MART.   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official 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
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
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
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
FDA ORPHAN DRUG 199904
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
FDA ORPHAN DRUG 276009
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
FDA ORPHAN DRUG 553116
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
FDA ORPHAN DRUG 820821
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
NDF-RT N0000007530
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
FDA ORPHAN DRUG 248107
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
FDA ORPHAN DRUG 469215
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
FDA ORPHAN DRUG 844921
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
FDA ORPHAN DRUG 808521
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
WHO-VATC QL01DB01
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
NDF-RT N0000000176
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
NDF-RT N0000007530
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
FDA ORPHAN DRUG 139800
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
FDA ORPHAN DRUG 286109
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
NCI_THESAURUS C67502
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
NDF-RT N0000175414
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
FDA ORPHAN DRUG 117398
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
LIVERTOX NBK548622
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
EU-Orphan Drug EU/3/15/1513
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
WHO-ATC L01DB01
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID8021480
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
RXCUI
3639
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY RxNorm
ChEMBL
CHEMBL53463
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
EVMPD
SUB35582
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
IUPHAR
7069
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
DRUG CENTRAL
960
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
LACTMED
Doxorubicin
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
CAS
23214-92-8
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
ECHA (EC/EINECS)
245-495-6
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
NSC
123127
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
MESH
D004317
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
DAILYMED
80168379AG
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
NSC
759155
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
FDA UNII
80168379AG
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
DRUG BANK
DB00997
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
SMS_ID
100000085265
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
CHEBI
28748
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
INN
3005
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
WIKIPEDIA
DOXORUBICIN
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
NCI_THESAURUS
C456
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
CHEBI
64816
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
MERCK INDEX
m4757
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY Merck Index
EVMPD
SUB06391MIG
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
PUBCHEM
31703
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
HSDB
3070
Created by admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
PRIMARY
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BINDER->LIGAND
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