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 |
|||
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 |
|||
Primary | Unknown Approved UseUnknown |
|||
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 Date8.1647999E11 |
|||
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 Date8.1647999E11 |
|||
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 Date8.1647999E11 |
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 |
---|---|---|
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
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
Thu Jul 06 00:42:00 UTC 2023
by
admin
on
Thu Jul 06 00:42:00 UTC 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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-
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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Code System | Code | Type | Description | ||
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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
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PRIMARY | |||
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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
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PRIMARY | RxNorm | ||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY | Merck Index | ||
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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
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PRIMARY | |||
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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
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PRIMARY | |||
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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
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PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
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BINDER->LIGAND |
BINDING
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TARGET -> INHIBITOR |
BINDING
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TRANSPORTER -> SUBSTRATE | |||
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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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