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

CNS Active
3828
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
158
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 2.67 µM [IC50]
Binding Agent
1059
Inhibitor
8228
Inhibitor
8228
 2.67 µM [IC50]
A673
8
Target ID: CHEMBL614517
Inhibitor
8228
 200.0 nM [IC50]
Inhibitor
8228
 24.68 µM [IC50]
Inhibitor
8228
 0.074 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
663
Unknown

Approved Use

Unknown
Primary
Phase II
1144
Unknown

Approved Use

Unknown
Primary
Phase II
1144
Unknown

Approved Use

Unknown
Primary
Phase II
1144
Unknown

Approved Use

Unknown
Primary
Phase II
1144
Unknown

Approved Use

Unknown
Primary
Approved
8360
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
Approved
8360
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
Approved
8360
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
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
1527

AKR1C3
13

NDUFS2
8

NDUFS3
8

NDUFS7
8

NQO1
8

XDH
8

MRP1
106

MRP2
201

BCRP
555

SLC22A16
8

MRP5
40

OATP1A2
61

OATP1B1
403

OATP1B3
347
CYP1A1
109

CYP1A2
689

CYP1B1
52

CYP2B2
15

CYP2E1
126

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
1673
 yes
CYP1B1
68
 yes
CYP2B2
16
 yes
CYP2E1
964
 yes
CYP2J3
8
 yes
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
SLC22A16
8
 yes [Km 5.2 uM]
AKR1C3
13
 yes
BCRP
555
 yes
MRP1
106
 yes
MRP2
201
 yes
MRP5
40
 yes
GS-DOX
8
NDUFS2
8
 yes
NDUFS3
8
 yes
NDUFS7
8
 yes
NQO1
8
 yes
OATP1A2
61
 yes
OATP1B1
403
 yes
OATP1B3
347
 yes
P-gp
1527
 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
[Changes in left ventricular function during chemotherapy with doxorubicin].
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
Comparison of the protective effects of amifostine and dexrazoxane against the toxicity of doxorubicin in spontaneously hypertensive rats.
2000
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
Glomerular basement membrane anionic sites in adriamycin nephropathy: effect of saline loading and nitric oxide modulation.
2000 Apr
Anthracyclines trigger apoptosis of both G0-G1 and cycling peripheral blood lymphocytes and induce massive deletion of mature T and B cells.
2000 Apr 1
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
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
Curcumin prevents adriamycin nephrotoxicity in rats.
2000 Jan
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
Influence of Adriamycin and paraquat on antioxidant enzyme expression in primary rat hepatocytes.
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
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
The influence of thymoquinone on doxorubicin-induced hyperlipidemic nephropathy in rats.
2000 Mar 7
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
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
ACE inhibition preserves heparan sulfate proteoglycans in the glomerular basement membrane of rats with established adriamycin nephropathy.
2001
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
Long-term cardiac sequelae in operable breast cancer patients given adjuvant chemotherapy with or without doxorubicin and breast irradiation.
2001 Jan 1
Characterization of adriamycin-induced G2 arrest and its abrogation by caffeine in FL-amnion cells with or without p53.
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
Mycosis fungoides and pregnancy.
2001 Jan-Feb
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

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8
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17
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17
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12
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8
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8
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14
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397
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11
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14
JP2003511357A
8
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8
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81
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12
JP2004534728A
78
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8
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48
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17
JP2007508039A
113
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11
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442
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14
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10
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11
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15
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32
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19
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8
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10
JP4744782B2
8
JP4758474B2
86
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13
JP4813746B2
12
JP4818917B2
31
JPH01301627A
20
JPH02167294A
8
JPH03251761A
8
JPH0363226A
8
JPH0368595A
8
JPH06107546A
8
JPH06256376A
8
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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 Thu Jul 06 00:42:00 UTC 2023
Edited
by admin
on Thu Jul 06 00:42:00 UTC 2023
Record UNII
80168379AG
Record Status Validated (UNII)
Record Version
  • Download
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 Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
FDA ORPHAN DRUG 199904
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
FDA ORPHAN DRUG 276009
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
FDA ORPHAN DRUG 553116
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
FDA ORPHAN DRUG 820821
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
NDF-RT N0000007530
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 8.2
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
FDA ORPHAN DRUG 248107
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
FDA ORPHAN DRUG 469215
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
FDA ORPHAN DRUG 844921
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
FDA ORPHAN DRUG 808521
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
WHO-VATC QL01DB01
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
NDF-RT N0000000176
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
NDF-RT N0000007530
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
FDA ORPHAN DRUG 139800
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
FDA ORPHAN DRUG 286109
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
NCI_THESAURUS C67502
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
NDF-RT N0000175414
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
FDA ORPHAN DRUG 117398
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
LIVERTOX NBK548622
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
EU-Orphan Drug EU/3/15/1513
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
WHO-ATC L01DB01
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
Code System Code Type Description
EPA CompTox
DTXSID8021480
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
RXCUI
3639
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY RxNorm
ChEMBL
CHEMBL53463
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
EVMPD
SUB35582
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
IUPHAR
7069
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
DRUG CENTRAL
960
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
LACTMED
Doxorubicin
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
CAS
23214-92-8
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
ECHA (EC/EINECS)
245-495-6
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
NSC
123127
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
MESH
D004317
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
DAILYMED
80168379AG
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
NSC
759155
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
FDA UNII
80168379AG
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
DRUG BANK
DB00997
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
SMS_ID
100000085265
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
CHEBI
28748
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
INN
3005
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
WIKIPEDIA
DOXORUBICIN
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
NCI_THESAURUS
C456
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
CHEBI
64816
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
MERCK INDEX
M4757
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY Merck Index
EVMPD
SUB06391MIG
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
PUBCHEM
31703
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
HSDB
3070
Created by admin on Thu Jul 06 00:42:00 UTC 2023 , Edited by admin on Thu Jul 06 00:42:00 UTC 2023
PRIMARY
Related Record Type Details
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
DNA TOPOISOMERASE 2-ALPHA
TARGET -> INHIBITOR
BINDING
MULTIDRUG RESISTANCE PROTEIN 1
TRANSPORTER -> SUBSTRATE
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
MRP-1
TRANSPORTER -> SUBSTRATE
Structure of DOXORUBICIN HYDROCHLORIDE
SALT/SOLVATE -> PARENT
ATP-BINDING CASSETTE SUB-FAMILY B MEMBER 5
TRANSPORTER -> SUBSTRATE
Responsible for the resistance to doxorubicin of a subset of malignant melanomas.
Related Record Type Details
Structure of DOXORUBICINONE
METABOLITE -> PARENT
MAJOR
Structure of ALDOXORUBICIN
PRODRUG -> METABOLITE ACTIVE
Reacts with the Cys-34 of albumin gets transported to tumor microenvironment and released in acidic environment.
Structure of DOXORUBICINOL
METABOLITE -> PARENT
Structure of 7-DEOXYDOXORUBICINONE
METABOLITE -> PARENT
Related Record Type Details
Structure of VALRUBICIN
PARENT -> IMPURITY
Structure of DAUNORUBICIN HYDROCHLORIDE
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of EPIRUBICIN HYDROCHLORIDE
PARENT -> IMPURITY
Related Record Type Details
Structure of DOXORUBICIN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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