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
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
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 |
DescriptionCurator'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
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7124341https://clinicaltrials.gov/ct2/show/NCT02014844
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
Sources: https://books.google.ru/books?id=_J2ti4EkYpkC&pg=PA1397&lpg=PA1397&dq=DOXORUBICIN retrieved from Pharmaceutical Manufacturing Encyclopedia William Andrew Publishing, p.1397https://encrypted.google.com/patents/WO2012167255A1
Curator's Comment: Introduced as Adriblastina by Farmitalia, Italy, in 1971
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28846045 |
2.67 µM [IC50] | ||
Target ID: CHEMBL3253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28846045 |
|||
Target ID: CHEMBL1806 Sources: http://www.drugbank.ca/drugs/DB00997 |
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Target ID: CHEMBL2094255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17194596 |
2.67 µM [IC50] | ||
Target ID: CHEMBL614517 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27688190 |
200.0 nM [IC50] | ||
Target ID: CHEMBL395 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27669220 |
24.68 µM [IC50] | ||
Target ID: CHEMBL613895 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26694484 |
0.074 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | DOXIL Approved UseIndicated 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 Date1995 |
|||
Primary | DOXIL Approved UseIndicated 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 Date1995 |
|||
Primary | DOXIL Approved UseIndicated 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 Date1995 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26115930 |
60 mg/m² 1 times / day steady-state, intravenous dose: 60 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
DOXORUBICIN plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.4 μM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26115930 |
60 mg/m² 1 times / day steady-state, intravenous dose: 60 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
DOXORUBICIN plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
34.8 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/26115930 |
60 mg/m² 1 times / day steady-state, intravenous dose: 60 mg/m² route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
DOXORUBICIN plasma | Homo sapiens population: UNHEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25% |
DOXORUBICIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
150 mg/m2 1 times / day multiple, intravenous Overdose Dose: 150 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 150 mg/m2, 1 times / day Sources: |
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) Sources: Chills (1 patient) Pyrexia (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: |
Other AEs: Sinus tachycardia, Neutropenia... Other AEs: Sinus tachycardia (1 patient) Sources: Neutropenia (grade 4, 1 patient) Thrombocytopenia (1 patient) Mucositis (severe, 1 patient) Sepsis (severe, 1 patient) |
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 Health Status: unhealthy Sources: |
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 Sources: Myelodysplastic syndrome Myelosuppression (severe) |
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 Health Status: unhealthy Sources: |
Other AEs: Cardiomyopathy... Other AEs: Cardiomyopathy Sources: |
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%) AEs leading toFebrile neutropenia (grade 3, 50%) discontinuation/dose reduction: Anemia (grade 3, 50%) Sources: Page: p.574Neutropenia (grade 3, 50%) |
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%) AEs leading toNeutropenia (5.6%) Sepsis (5.6%) discontinuation/dose reduction: Septic shock (grade 5, 5.6%) Sources: Page: p.574Anemia (grade 3, 5.6%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Chills | 1 patient | 150 mg/m2 1 times / day multiple, intravenous Overdose Dose: 150 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 150 mg/m2, 1 times / day Sources: |
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 Health Status: unhealthy Sources: |
|
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 Health Status: unhealthy Sources: |
|
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
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 Health Status: unhealthy Sources: |
|
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
no | |||
Page: - |
no | |||
Page: - |
weak | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
yes [Km 5.2 uM] | |||
Sources: https://www.pharmgkb.org/literature/8369411 Page: - |
yes | |||
Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: - |
yes | |||
Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: - |
yes | |||
Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: - |
yes | |||
Page: - |
yes | |||
Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: - |
yes | |||
Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: - |
yes | |||
Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: - |
yes | |||
Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Page: - |
yes | |||
Sources: https://www.pharmgkb.org/pathway/PA165292177 Page: - |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Myocardial injury induced by a single dose of adriamycin: an electron microscopic study. | 1976 Sep-Oct |
|
Doxorubicin-induced congestive heart failure in elderly patients with metastatic breast cancer, with long-term follow-up: the M.D. Anderson experience. | 1999 |
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Reversal of doxorubicin-induced cardiac metabolic damage by L-carnitine. | 1999 Apr |
|
Inhibitory effects of combinations of HER-2/neu antibody and chemotherapeutic agents used for treatment of human breast cancers. | 1999 Apr 1 |
|
Altered expression of the MYCN oncogene modulates MRP gene expression and response to cytotoxic drugs in neuroblastoma cells. | 1999 Apr 29 |
|
Anticancer drug sensitivity and expression of multidrug resistance markers in early passage human sarcomas. | 1999 Aug |
|
Doxorubicin induces slow ceramide accumulation and late apoptosis in cultured adult rat ventricular myocytes. | 1999 Aug 1 |
|
Phase II trial of doxorubicin and paclitaxel plus granulocyte colony-stimulating factor in metastatic breast cancer: an Eastern Cooperative Oncology Group Study. | 1999 Dec |
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Increase in doxorubicin cytotoxicity by carvedilol inhibition of P-glycoprotein activity. | 1999 Dec 1 |
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Doxorubicin-induced cardiomyopathy. | 1999 Feb 25 |
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Doxorubicin cardiotoxicity: growing importance. | 1999 Jul |
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Correlation between serum levels of cardiac troponin-T and the severity of the chronic cardiomyopathy induced by doxorubicin. | 1999 Jul |
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Effect of proteinuria reduction on prevention of focal glomerulosclerosis by angiotensin-converting enzyme inhibition is modifiable. | 1999 Jul |
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Abdominal-wall myositis secondary to intra-arterial chemotherapy for femoral osteosarcoma. | 1999 Jul |
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Coordinate alterations in the expression of BRCA1, BRCA2, p300, and Rad51 in response to genotoxic and other stresses in human prostate cancer cells. | 1999 Jun 15 |
|
Effect of captopril on doxorubicin-induced nephrotoxicity in normal rats. | 1999 Mar |
|
Effect of allopurinol in the course of adriamycin induced nephropathy. | 1999 Mar |
|
Delayed methotrexate clearance in a patient with sickle cell anemia and osteosarcoma. | 1999 Mar-Apr |
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Role of thromboxane in the altered vascular reactivity of pregnant rats with adriamycin nephropathy. | 1999 May |
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Zinc accumulation in adriamycin-induced cardiomyopathy in rats: effects of melatonin, a cardioprotective antioxidant. | 1999 May |
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Phase II trial of high-dose liposome-encapsulated doxorubicin with granulocyte colony-stimulating factor in metastatic breast cancer. TLC D-99 Study Group. | 1999 May |
|
Reduction of the cardiotoxicity of doxorubicin in rabbits and dogs by encapsulation in long-circulating, pegylated liposomes. | 1999 May |
|
Primary desmoplastic small cell tumor of soft tissues and bone of the hand. | 1999 Nov |
|
Decreased cortisol secretion by adrenal glands perfused with the P-glycoprotein inhibitor valspodar and mitotane or doxorubicin. | 2000 Apr |
|
Pegylated liposomal doxorubicin (doxil): reduced clinical cardiotoxicity in patients reaching or exceeding cumulative doses of 500 mg/m2. | 2000 Aug |
|
The influence of coordinate overexpression of glutathione phase II detoxification gene products on drug resistance. | 2000 Aug |
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The protective effect of glutathione administration on adriamycin-induced acute cardiac toxicity in rats. | 2000 Aug |
|
Deregulated manganese superoxide dismutase expression and resistance to oxidative injury in p53-deficient cells. | 2000 Aug 15 |
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Cytokine gene expression in Adriamycin nephropathy: effects of antioxidant nuclear factor kappaB inhibitors in established disease. | 2000 Dec |
|
High incidence of adriamycin cardiotoxicity in children even at low cumulative doses: role of radionuclide cardiac angiography. | 2000 Dec |
|
Proteasome-mediated degradation of the coactivator p300 impairs cardiac transcription. | 2000 Dec |
|
Adjuvant doxorubicin and cyclophosphamide versus cyclophosphamide, methotrexate, and 5-fluorouracil chemotherapy in premenopausal women with axillary lymph node positive breast carcinoma. | 2000 Dec 15 |
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Comparison of doxorubicin- and MEN 10755-induced long-term progressive cardiotoxicity in the rat. | 2000 Jan |
|
Mechanism of doxorubicin-induced inhibition of sarcoplasmic reticulum Ca(2+)-ATPase gene transcription. | 2000 Jan 7-21 |
|
Evaluation of cardiac adrenergic neuronal damage in rats with doxorubicin-induced cardiomyopathy using iodine-131 MIBG autoradiography and PGP 9.5 immunohistochemistry. | 2000 Jun |
|
Cardiac sequelae of doxorubicin and paclitaxel as induction chemotherapy prior to high-dose chemotherapy and peripheral blood progenitor cell transplantation in women with high-risk primary or metastatic breast cancer. | 2000 May |
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Lovastatin potentiates antitumor activity and attenuates cardiotoxicity of doxorubicin in three tumor models in mice. | 2000 May |
|
Expression of agrin, dystroglycan, and utrophin in normal renal tissue and in experimental glomerulopathies. | 2000 May |
|
Renal antioxidant enzymes and fibrosis-related markers in the rat adriamycin model. | 2000 Oct |
|
Bilateral blindness and lumbosacral myelopathy associated with high-dose carmustine and cisplatin therapy. | 2000 Sep |
|
Human carbonyl reductase overexpression in the heart advances the development of doxorubicin-induced cardiotoxicity in transgenic mice. | 2000 Sep 15 |
|
ACE inhibition preserves heparan sulfate proteoglycans in the glomerular basement membrane of rats with established adriamycin nephropathy. | 2001 |
|
Low-grade ovarian cancer in an adolescent patient. | 2001 Jan |
|
Targeted systemic chemotherapy using magnetic liposomes with incorporated adriamycin for osteosarcoma in hamsters. | 2001 Jan |
|
Reversal of LRP-associated drug resistance in colon carcinoma SW-620 cells. | 2001 Jan 1 |
|
Long-term cardiac sequelae in operable breast cancer patients given adjuvant chemotherapy with or without doxorubicin and breast irradiation. | 2001 Jan 1 |
|
Nuclear factor kappaB-dependent mechanisms coordinate the synergistic effect of PMA and cytokines on the induction of superoxide dismutase 2. | 2001 Jan 1 |
|
Repression of cyclin B1 expression after treatment with adriamycin, but not cisplatin in human lung cancer A549 cells. | 2001 Jan 26 |
|
Mycosis fungoides and pregnancy. | 2001 Jan-Feb |
|
Aldoxorubicin for the treatment of soft tissue sarcoma. | 2017 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/doxorubicin.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16475272
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
Edited
Fri Dec 15 17:21:26 GMT 2023
by
admin
on
Fri Dec 15 17:21:26 GMT 2023
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Record UNII |
80168379AG
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Record Status |
Validated (UNII)
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Record Version |
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N0000007530
Created by
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FDA ORPHAN DRUG |
199904
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admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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FDA ORPHAN DRUG |
276009
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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FDA ORPHAN DRUG |
553116
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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FDA ORPHAN DRUG |
820821
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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NDF-RT |
N0000007530
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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WHO-ESSENTIAL MEDICINES LIST |
8.2
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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FDA ORPHAN DRUG |
248107
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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FDA ORPHAN DRUG |
469215
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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FDA ORPHAN DRUG |
844921
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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FDA ORPHAN DRUG |
808521
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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WHO-VATC |
QL01DB01
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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NDF-RT |
N0000000176
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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NDF-RT |
N0000007530
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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FDA ORPHAN DRUG |
139800
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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FDA ORPHAN DRUG |
286109
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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NCI_THESAURUS |
C67502
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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NDF-RT |
N0000175414
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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FDA ORPHAN DRUG |
117398
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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LIVERTOX |
NBK548622
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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EU-Orphan Drug |
EU/3/15/1513
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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WHO-ATC |
L01DB01
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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Code System | Code | Type | Description | ||
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DTXSID8021480
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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3639
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | RxNorm | ||
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CHEMBL53463
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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SUB35582
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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7069
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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960
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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Doxorubicin
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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23214-92-8
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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245-495-6
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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123127
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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D004317
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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80168379AG
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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759155
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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80168379AG
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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DB00997
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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100000085265
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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28748
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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3005
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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DOXORUBICIN
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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C456
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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64816
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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m4757
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | Merck Index | ||
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SUB06391MIG
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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31703
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY | |||
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3070
Created by
admin on Fri Dec 15 17:21:26 GMT 2023 , Edited by admin on Fri Dec 15 17:21:26 GMT 2023
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PRIMARY |
Related Record | Type | Details | ||
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE |
Dogs homozygous or heterozygous for the ABCB1-1Δ mutation are significantly more likely than normal dogs to develop haematological and gastrointestinal toxicity.
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TARGET -> INHIBITOR |
BINDING
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TRANSPORTER -> SUBSTRATE | |||
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TRANSPORTER -> SUBSTRATE |
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SALT/SOLVATE -> PARENT |
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TRANSPORTER -> SUBSTRATE |
Responsible for the resistance to doxorubicin of a subset of malignant melanomas.
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Related Record | Type | Details | ||
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METABOLITE -> PARENT |
MAJOR
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PRODRUG -> METABOLITE ACTIVE |
Reacts with the Cys-34 of albumin gets transported to tumor microenvironment and released in acidic environment.
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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PARENT -> IMPURITY |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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PARENT -> IMPURITY |
Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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