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

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H29NO11.ClH
Molecular Weight 579.98
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOXORUBICIN HYDROCHLORIDE

SMILES

Cl.[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=MWWSFMDVAYGXBV-RUELKSSGSA-N
InChI=1S/C27H29NO11.ClH/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;1H/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

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

8.1647999E11
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

8.1647999E11
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
Experimental animal models of adriamycin cardiotoxicity.
1979 May
Use of dexrazoxane as a cardioprotectant in patients receiving doxorubicin or epirubicin chemotherapy for the treatment of cancer. The Provincial Systemic Treatment Disease Site Group.
1999 Apr
Altered expression of the MYCN oncogene modulates MRP gene expression and response to cytotoxic drugs in neuroblastoma cells.
1999 Apr 29
Dose of doxorubicin determines severity of renal damage and responsiveness to ACE-inhibition in experimental nephrosis.
1999 Apr-Jun
Anticancer drug sensitivity and expression of multidrug resistance markers in early passage human sarcomas.
1999 Aug
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
Doxorubicin induces slow ceramide accumulation and late apoptosis in cultured adult rat ventricular myocytes.
1999 Aug 1
Increase in doxorubicin cytotoxicity by carvedilol inhibition of P-glycoprotein activity.
1999 Dec 1
Doxorubicin cardiotoxicity: growing importance.
1999 Jul
Abdominal-wall myositis secondary to intra-arterial chemotherapy for femoral osteosarcoma.
1999 Jul
Dose-finding study of docetaxel and doxorubicin in first-line treatment of patients with metastatic breast cancer.
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
Exposure to hydrocarbons and renal disease: an experimental animal model.
1999 May-Jul
Primary desmoplastic small cell tumor of soft tissues and bone of the hand.
1999 Nov
Low-dose vincristine-associated bilateral vocal cord paralysis.
1999 Oct
Adriamycin-induced heart failure: mechanism and modulation.
2000 Apr
Pegylated liposomal doxorubicin (doxil): reduced clinical cardiotoxicity in patients reaching or exceeding cumulative doses of 500 mg/m2.
2000 Aug
The protective effect of glutathione administration on adriamycin-induced acute cardiac toxicity in rats.
2000 Aug
Fas-mediated apoptosis in adriamycin-induced cardiomyopathy in rats: In vivo study.
2000 Aug 1
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
Progressive cardiac dysfunction in adriamycin-induced cardiomyopathy rats.
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
Doxorubicin and paclitaxel in advanced breast carcinoma: importance of prior adjuvant anthracycline therapy.
2000 Dec 1
Adjuvant doxorubicin and cyclophosphamide versus cyclophosphamide, methotrexate, and 5-fluorouracil chemotherapy in premenopausal women with axillary lymph node positive breast carcinoma.
2000 Dec 15
Neural crest-derived defects in experimental esophageal atresia.
2000 Feb
Differential sensitivities of MRP1-overexpressing lung tumor cells to cytotoxic metals.
2000 Jan 3
Liposomal doxorubicin (Caelyx) in advanced pretreated soft tissue sarcomas: a phase II study of the Italian Sarcoma Group (ISG).
2000 Jan-Feb
Manic episode in an ifosfamide-treated patient.
2000 Jan-Feb
Cardiac peroxynitrite formation and left ventricular dysfunction following doxorubicin treatment in mice.
2000 Jul
Effects of probucol on changes of antioxidant enzymes in adriamycin-induced cardiomyopathy in rats.
2000 Jun
Beta-blockade in adriamycin-induced cardiomyopathy.
2000 Jun
Evaluation of cardiac adrenergic neuronal damage in rats with doxorubicin-induced cardiomyopathy using iodine-131 MIBG autoradiography and PGP 9.5 immunohistochemistry.
2000 Jun
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
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
Phase II study of pegylated liposomal doxorubicin: inactive in recurrent small-cell lung cancer. A Hellenic Cooperative Oncology Group Study.
2000 Nov
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
Bilateral blindness and lumbosacral myelopathy associated with high-dose carmustine and cisplatin therapy.
2000 Sep
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
Prevention of doxorubicin (adriamycin)-induced cardiomyopathy by simultaneous administration of angiotensin-converting enzyme inhibitor assessed by acoustic densitometry.
2000 Sep
Human carbonyl reductase overexpression in the heart advances the development of doxorubicin-induced cardiotoxicity in transgenic mice.
2000 Sep 15
Low-grade ovarian cancer in an adolescent patient.
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
Serum pancreastatin levels predict response to hepatic artery chemoembolization and somatostatin analogue therapy in metastatic neuroendocrine tumors.
2001 Jan 12
Repression of cyclin B1 expression after treatment with adriamycin, but not cisplatin in human lung cancer A549 cells.
2001 Jan 26
Human mismatch repair and G*T mismatch binding by hMutSalpha in vitro is inhibited by adriamycin, actinomycin D, and nogalamycin.
2001 Mar 30
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 Wed Jul 05 22:50:37 UTC 2023
Edited
by admin
on Wed Jul 05 22:50:37 UTC 2023
Record UNII
82F2G7BL4E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOXORUBICIN HYDROCHLORIDE
EMA EPAR   EP   MART.   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
Common Name English
IMX-110 COMPONENT DOXORUBICIN HYDROCHLORIDE
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 HYDROCHLORIDE
Common Name English
ADRIAMYCIN, HYDROCHLORIDE
Common Name English
DOXORUBICIN HYDROCHLORIDE [ORANGE BOOK]
Common Name English
DOXORUBICIN HYDROCHLORIDE [USP-RS]
Common Name English
Doxorubicin hydrochloride [WHO-DD]
Common Name English
DOXORUBICIN HYDROCHLORIDE [EMA EPAR]
Common Name English
CAELYX
Brand Name English
DOXORUBICIN HYDROCHLORIDE LIPOSOME [VANDF]
Common Name English
DOXORUBICINI HYDROCHLORIDUM [WHO-IP LATIN]
Common Name English
DOXORUBICIN HYDROCHLORIDE [MART.]
Common Name English
DOXIL
Brand Name English
DOXORUBICIN HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
DOXORUBICIN HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
HYDROXYDAUNOMYCIN HYDROCHLORIDE
Common Name English
DOXORUBICIN HCL
Common Name English
DOXORUBICIN HYDROCHLORIDE [VANDF]
Common Name English
DOXORUBICIN HYDROCHLORIDE [WHO-IP]
Common Name English
ADRIAMYCIN
Brand Name English
DOXORUBICIN HYDROCHLORIDE LIPOSOME
VANDF  
Common Name English
ADRIABLASTINA CS
Common Name English
ADRIAMYCIN [IARC]
Common Name English
RUBEX
Brand Name 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-(HYDROXYLACETYL)-1-METHOXY-, HYDROCHLORIDE (8S-CIS)-
Common Name English
Liposomal doxorubicin hydrochloride [WHO-DD]
Common Name English
DOXORUBICIN LIPOSOMAL COMPLEX OF THE HYDROCHLORIDE [MI]
Common Name English
DOXORUBICIN HYDROCHLORIDE [JAN]
Common Name English
Classification Tree Code System Code
EU-Orphan Drug EU/3/10/833
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
NCI_THESAURUS C67502
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
EMA ASSESSMENT REPORTS CAELYX (AUTHORIZED: MULTIPLE MYELOMA)
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
EMA ASSESSMENT REPORTS CAELYX (AUTHORIZED: OVARIAN NEOPLASMS)
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
EMA ASSESSMENT REPORTS MYOCET (AUTHORIZED: BREAST NEOLPLASMA)
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
FDA ORPHAN DRUG 229006
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
FDA ORPHAN DRUG 191704
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
FDA ORPHAN DRUG 210705
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
FDA ORPHAN DRUG 628318
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
FDA ORPHAN DRUG 311910
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
Code System Code Type Description
ECHA (EC/EINECS)
246-818-3
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
FDA UNII
82F2G7BL4E
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
CHEBI
28748
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
MERCK INDEX
M4757
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY Merck Index
RXCUI
142433
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DOXORUBICIN HYDROCHLORIDE
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY Description: A red-orange, crystalline powder. Solubility: Soluble in water and methanol R; practically insoluble in ether R. Category: Cytotoxic drug. Storage: Doxorubicin hydrochloride should be kept in a tightly closed container. Additional information: Doxorubicin hydrochloride is hygroscopic; it is poisonous: CAUTION: Doxorubicin hydrochloride must behandled with care, avoiding contact with the skin and inhalation of airborne particles. Definition. Doxorubicin hydrochloride contains not less than 97.0% and not more than 102.0% of C27H29NO11,HCl, calculatedwith reference to the anhydrous substance.
EVMPD
SUB06391MIG
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
RS_ITEM_NUM
1225703
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
DAILYMED
82F2G7BL4E
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
CAS
25316-40-9
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
PUBCHEM
443939
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
ChEMBL
CHEMBL53463
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
NCI_THESAURUS
C1326
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
RXCUI
466523
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
ALTERNATIVE
EVMPD
SUB01827MIG
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
EVMPD
SUB126795
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
ALTERNATIVE
DRUG BANK
DBSALT000060
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
EPA CompTox
DTXSID3030636
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
SMS_ID
100000089971
Created by admin on Wed Jul 05 22:50:37 UTC 2023 , Edited by admin on Wed Jul 05 22:50:37 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
IMPURITY -> PARENT
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY