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

CNS Active
3913
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

Originator

Approval Year

1974
168
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 2.67 µM [IC50]
Binding Agent
1064
Inhibitor
8297
Inhibitor
8297
 2.67 µM [IC50]
A673
8
Target ID: CHEMBL614517
Inhibitor
8297
 200.0 nM [IC50]
Inhibitor
8297
 24.68 µM [IC50]
Inhibitor
8297
 0.074 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Approved
8429
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
Approved
8429
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
Approved
8429
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
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

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:
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
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
Page: p.574
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
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
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
Page: p.574
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
Page: p.574
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
Page: p.574
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
Page: p.574
unhealthy, ADULT
n = 2
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Population Size: 2
Sources:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
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:
https://pubmed.ncbi.nlm.nih.gov/25312684
Page: p.574
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
P-gp
1537

AKR1C3
13

NDUFS2
8

NDUFS3
8

NDUFS7
8

NQO1
8

XDH
8

MRP1
107

MRP2
205

BCRP
561

SLC22A16
8

MRP5
40

OATP1A2
62

OATP1B1
406

OATP1B3
350
CYP1A1
108

CYP1A2
701

CYP1B1
51

CYP2B2
15

CYP2E1
128

CYP2J3
8

CYP2C11
14

CYP2B1
26

CYP2C23
10
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2B1
41
 no
CYP2C23
10
 no
CYP2C11
15
 weak
CYP1A1
218
 yes
CYP1A2
1692
 yes
CYP1B1
67
 yes
CYP2B2
16
 yes
CYP2E1
970
 yes
CYP2J3
8
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
SLC22A16
8
 yes [Km 5.2 uM]
AKR1C3
13
 yes
BCRP
561
 yes
MRP1
107
 yes
MRP2
205
 yes
MRP5
40
 yes
GS-DOX
8
NDUFS2
8
 yes
NDUFS3
8
 yes
NDUFS7
8
 yes
NQO1
8
 yes
OATP1A2
62
 yes
OATP1B1
406
 yes
OATP1B3
350
 yes
P-gp
1537
 yes
XDH
8
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
ChEBI
CHEBI:28748
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28748
Chem Scene
CS-0077171
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0077171
MedChem Express
HY-16261B
https://www.medchemexpress.com/search.html?q=HY-16261B&ft=&fa=&fp=
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
50284280
https://orderbb.emolecules.com/search/#?query=50284280
eMolecules
36788175
https://www.emolecules.com/cgi-bin/more?vid=36788175
mcule
MCULE-8506890923
https://mcule.com/MCULE-8506890923/
PubMed

PubMed

TitleDatePubMed
Experimental animal models of adriamycin cardiotoxicity.
1979 May
Protective effects of carvedilol against doxorubicin-induced cardiomyopathy in rats.
1999
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
[Changes in left ventricular function during chemotherapy with doxorubicin].
1999 Jul
Doxorubicin cardiotoxicity: growing importance.
1999 Jul
Nonmetastatic osteosarcoma of the extremity: results of a neoadjuvant chemotherapy protocol (IOR/OS-3) with high-dose methotrexate, intraarterial or intravenous cisplatin, doxorubicin, and salvage chemotherapy based on histologic tumor response.
1999 Nov-Dec
Low-dose vincristine-associated bilateral vocal cord paralysis.
1999 Oct
Renal protective effects of blocking the intrarenal renin-angiotensin system.
1999 Sep
A canine model of heart failure by intracoronary adriamycin injection: hemodynamic and energetic results.
1999 Sep
Decreased cortisol secretion by adrenal glands perfused with the P-glycoprotein inhibitor valspodar and mitotane or doxorubicin.
2000 Apr
Adriamycin-induced heart failure: mechanism and modulation.
2000 Apr
Doxorubicin-induced late cardiotoxicity: delayed impairment of Ca2+-handling mechanisms in the sarcoplasmic reticulum in the rat.
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
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
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
Signal transducer and activator of transcription 3 in the heart transduces not only a hypertrophic signal but a protective signal against doxorubicin-induced cardiomyopathy.
2000 Jan 4
Influence of Adriamycin and paraquat on antioxidant enzyme expression in primary rat hepatocytes.
2000 Jul
Doxorubicin-induced cardiomyopathy.
2000 Jul
Cardiac peroxynitrite formation and left ventricular dysfunction following doxorubicin treatment in mice.
2000 Jul
Oxidative stress interferes with cancer chemotherapy: inhibition of lymphoma cell apoptosis and phagocytosis.
2000 Jul 1
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
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
Caffeine-potentiated radiochemotherapy and function-saving surgery for high-grade soft tissue sarcoma.
2000 May-Jun
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
Renal antioxidant enzymes and fibrosis-related markers in the rat adriamycin model.
2000 Oct
Progressive adriamycin nephropathy in mice: sequence of histologic and immunohistochemical events.
2000 Oct
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
Mobilization of hematopoietic progenitor cells with a combination of docetaxel, adriamycin, 5-fluorouracil and filgrastim in breast cancer patients.
2001 Jan
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
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

Patents

JP1038021A
8
JP2001511768A
17
JP2001512418A
17
JP2001527049A
12
JP2002504526A
8
JP2002514656A
8
JP2002540172A
8
JP2002541200A
14
JP2002541233A
400
JP2002542270A
11
JP2003503313A
14
JP2003511357A
8
JP2003525696A
8
JP2004523497A
81
JP2004532301A
12
JP2004534728A
78
JP2005528891A
8
JP2006514009A
48
JP2006516548A
17
JP2007508039A
114
JP2007528354A
11
JP2009526755A
447
JP2010515545A
14
JP2010519305A
10
JP2011063524A
8
JP2011178784A
8
JP2011510954A
143
JP2011525180A
180
JP2011528040A
12
JP3300342B2
8
JP4041066B2
11
JP4301440B2
15
JP4527401B2
32
JP4601549B2
19
JP4662473B2
8
JP4672257B2
10
JP4744782B2
8
JP4758474B2
87
JP4790413B2
13
JP4813746B2
12
JP4818917B2
31
JPH01301627A
20
JPH02167294A
8
JPH03251761A
8
JPH0363226A
8
JPH0368595A
8
JPH06107546A
8
JPH06256376A
8
JPH08322582A
8
JPH0834746A
8
JPH11269065A
9
WO2012167255
8

Sample Use Guides

In Vivo Use Guide
When used in combination with other chemotherapy drugs, the most commonly used dosage of doxorubicin is 40 to 60 mg/m2 IV every 21 to 28 days. Alternatively, 60 to 75 mg/m2 IV once every 21 days.
Route of Administration: Intravenous
In Vitro Use Guide
Alkalinization of extracellular pH by urease (2 U/ml) and urea (> or = 2 mM) was found to enhance the antitumor efficacy of doxorubicin (50 uM)
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:19:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:19:48 GMT 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 Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
NCI_THESAURUS C67502
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
EMA ASSESSMENT REPORTS CAELYX (AUTHORIZED: MULTIPLE MYELOMA)
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
EMA ASSESSMENT REPORTS CAELYX (AUTHORIZED: OVARIAN NEOPLASMS)
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
EMA ASSESSMENT REPORTS MYOCET (AUTHORIZED: BREAST NEOLPLASMA)
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
FDA ORPHAN DRUG 229006
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
FDA ORPHAN DRUG 191704
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
FDA ORPHAN DRUG 210705
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
FDA ORPHAN DRUG 628318
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
FDA ORPHAN DRUG 311910
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
Code System Code Type Description
ECHA (EC/EINECS)
246-818-3
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
FDA UNII
82F2G7BL4E
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
CHEBI
28748
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
MERCK INDEX
m4757
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY Merck Index
RXCUI
142433
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
DOXORUBICIN HYDROCHLORIDE
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 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 Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
RS_ITEM_NUM
1225703
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
DAILYMED
82F2G7BL4E
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
CAS
25316-40-9
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
PUBCHEM
443939
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL53463
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
NCI_THESAURUS
C1326
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
RXCUI
466523
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
ALTERNATIVE
EVMPD
SUB01827MIG
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
EVMPD
SUB126795
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
ALTERNATIVE
DRUG BANK
DBSALT000060
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID3030636
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
SMS_ID
100000089971
Created by admin on Fri Dec 15 15:19:48 GMT 2023 , Edited by admin on Fri Dec 15 15:19:48 GMT 2023
PRIMARY
Related Record Type Details
Structure of DOXORUBICIN
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of Acetone
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (GC)
USP
Structure of DOXORUBICINONE
IMPURITY -> PARENT
Structure of DAUNOMYCINONE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of DAUNORUBICIN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of DOXORUBICIN
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966