Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C27H29NO10 |
Molecular Weight | 527.5199 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=C2C(=O)C3=C(O)C4=C(C[C@](O)(C[C@@H]4O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)C(C)=O)C(O)=C3C(=O)C2=CC=C1
InChI
InChIKey=STQGQHZAVUOBTE-VGBVRHCVSA-N
InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1
Molecular Formula | C27H29NO10 |
Molecular Weight | 527.5199 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.drugs.com/dosage/daunorubicin.htmlCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22260166 | https://www.ncbi.nlm.nih.gov/pubmed/7932544 | https://www.ncbi.nlm.nih.gov/pubmed/13146115 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050467s070lbl.pdf
Sources: https://www.drugs.com/dosage/daunorubicin.html
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/22260166 | https://www.ncbi.nlm.nih.gov/pubmed/7932544 | https://www.ncbi.nlm.nih.gov/pubmed/13146115 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/050467s070lbl.pdf
Daunorubicin, also known as daunomycin, is a chemotherapy medication used to treat cancer. Specifically, it is used for acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), chronic myelogenous leukemia (CML), and Kaposi's sarcoma. Similar to doxorubicin, daunorubicin interacts with DNA by intercalation and inhibition of macromolecular biosynthesis. This inhibits the progression of the enzyme topoisomerase II, which relaxes supercoils in DNA for transcription. Daunorubicin stabilizes the topoisomerase II complex after it has broken the DNA chain for replication, preventing the DNA double helix from being resealed and thereby stopping the process of replication. On binding to DNA, daunomycin intercalates, with its daunosamine residue directed toward the minor groove. It has the highest preference for two adjacent G/C base pairs flanked on the 5' side by an A/T base pair. Daunorubicin should only be administered in a rapid intravenous infusion. It should not be administered intramuscularly or subcutaneously, since it may cause extensive tissue necrosis. It should also never be administered intrathecally (into the spinal canal), as this will cause extensive damage to the nervous system and may lead to death.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1806 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22260166 |
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Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7932544 |
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Target ID: CHEMBL3004 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9647783 |
70.0 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | CERUBIDINE Approved UseDaunorubicin hydrochloride injection in combination with other approved anticancer drugs is indicated for remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults. Launch Date1979 |
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Primary | CERUBIDINE Approved UseDaunorubicin hydrochloride injection in combination with other approved anticancer drugs is indicated for remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults. Launch Date1979 |
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Primary | CERUBIDINE Approved UseDaunorubicin hydrochloride injection in combination with other approved anticancer drugs is indicated for remission induction in acute nonlymphocytic leukemia (myelogenous, monocytic, erythroid) of adults and for remission induction in acute lymphocytic leukemia of children and adults. Launch Date1979 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
26 μg/mL |
44 mg/m² 1 times / 2 days multiple, intravenous dose: 44 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: Cytarabine |
DAUNORUBICIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
637 μg × h/mL |
44 mg/m² 1 times / 2 days multiple, intravenous dose: 44 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: Cytarabine |
DAUNORUBICIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
31.5 h |
44 mg/m² 1 times / 2 days multiple, intravenous dose: 44 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: Cytarabine |
DAUNORUBICIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3% |
DAUNORUBICIN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
190 mg/m2 1 times / 3 weeks multiple, intravenous Highest studied dose Dose: 190 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 190 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 10 |
DLT: Neutropenia, Leucopenia... Dose limiting toxicities: Neutropenia (grade 4, 100%) Sources: Leucopenia (grade 4, 100%) Thrombocytopenia (grade 4, 16.7%) Anemia (grade 4, 16.7%) |
155 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 155 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 155 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 10 |
DLT: Neutropenia, Leucopenia... Disc. AE: Cardiac failure... Dose limiting toxicities: Neutropenia (grade 4, 100%) AEs leading toLeucopenia (grade 4, 50%) discontinuation/dose reduction: Cardiac failure (grade 5, 16.7%) Sources: |
50 mg/m2 1 times / 4 weeks multiple, intravenous Recommended Dose: 50 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / 4 weeks Sources: |
unhealthy, 27-87 Health Status: unhealthy Age Group: 27-87 Sex: M+F Sources: |
Disc. AE: Skin toxicity... AEs leading to discontinuation/dose reduction: Skin toxicity (4.2%) Sources: |
20 mg/m2 1 times / 2 weeks multiple, intravenous Recommended Dose: 20 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 20 mg/m2, 1 times / 2 weeks Sources: |
unhealthy, 38.7 Health Status: unhealthy Age Group: 38.7 Sex: M+F Sources: |
Disc. AE: Skin eruption... AEs leading to discontinuation/dose reduction: Skin eruption (0.9%) Sources: |
80 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 80 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 80 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 60 |
|
100 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 60 |
DLT: Acute diverticular perforation... Dose limiting toxicities: Acute diverticular perforation Sources: |
100 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 63 |
Disc. AE: Ejection fraction decreased, Prolonged neutropenia... Other AEs: Granulocytopenia, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Ejection fraction decreased (5.3%) Other AEs:Prolonged neutropenia (2.6%) Granulocytopenia (grade 4, 21%) Sources: Thrombocytopenia (grade 4, 8%) Febrile neutropenia (grade 4, 11%) |
50 mg/m2 1 times / 4 weeks multiple, intravenous Recommended Dose: 50 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / 4 weeks Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Infusion related reaction, Myelosuppression... AEs leading to discontinuation/dose reduction: Infusion related reaction (acute) Sources: Myelosuppression (severe) Cardiotoxicity Congestive heart failure Hepatic impairment Reaction anaphylactic anaphylactoid (grade 3-5) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Leucopenia | grade 4, 100% DLT |
190 mg/m2 1 times / 3 weeks multiple, intravenous Highest studied dose Dose: 190 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 190 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 10 |
Neutropenia | grade 4, 100% DLT |
190 mg/m2 1 times / 3 weeks multiple, intravenous Highest studied dose Dose: 190 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 190 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 10 |
Anemia | grade 4, 16.7% DLT |
190 mg/m2 1 times / 3 weeks multiple, intravenous Highest studied dose Dose: 190 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 190 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 10 |
Thrombocytopenia | grade 4, 16.7% DLT |
190 mg/m2 1 times / 3 weeks multiple, intravenous Highest studied dose Dose: 190 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 190 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 10 |
Neutropenia | grade 4, 100% DLT |
155 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 155 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 155 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 10 |
Leucopenia | grade 4, 50% DLT |
155 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 155 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 155 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 10 |
Cardiac failure | grade 5, 16.7% Disc. AE |
155 mg/m2 1 times / 3 weeks multiple, intravenous MTD Dose: 155 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 155 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 10 |
Skin toxicity | 4.2% Disc. AE |
50 mg/m2 1 times / 4 weeks multiple, intravenous Recommended Dose: 50 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / 4 weeks Sources: |
unhealthy, 27-87 Health Status: unhealthy Age Group: 27-87 Sex: M+F Sources: |
Skin eruption | 0.9% Disc. AE |
20 mg/m2 1 times / 2 weeks multiple, intravenous Recommended Dose: 20 mg/m2, 1 times / 2 weeks Route: intravenous Route: multiple Dose: 20 mg/m2, 1 times / 2 weeks Sources: |
unhealthy, 38.7 Health Status: unhealthy Age Group: 38.7 Sex: M+F Sources: |
Acute diverticular perforation | DLT, Disc. AE | 100 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 60 |
Prolonged neutropenia | 2.6% Disc. AE |
100 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 63 |
Ejection fraction decreased | 5.3% Disc. AE |
100 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 63 |
Febrile neutropenia | grade 4, 11% | 100 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 63 |
Granulocytopenia | grade 4, 21% | 100 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 63 |
Thrombocytopenia | grade 4, 8% | 100 mg/m2 1 times / 3 weeks multiple, intravenous Studied dose Dose: 100 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 63 |
Cardiotoxicity | Disc. AE | 50 mg/m2 1 times / 4 weeks multiple, intravenous Recommended Dose: 50 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / 4 weeks Sources: |
unhealthy Health Status: unhealthy Sources: |
Congestive heart failure | Disc. AE | 50 mg/m2 1 times / 4 weeks multiple, intravenous Recommended Dose: 50 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / 4 weeks Sources: |
unhealthy Health Status: unhealthy Sources: |
Hepatic impairment | Disc. AE | 50 mg/m2 1 times / 4 weeks multiple, intravenous Recommended Dose: 50 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / 4 weeks Sources: |
unhealthy Health Status: unhealthy Sources: |
Infusion related reaction | acute Disc. AE |
50 mg/m2 1 times / 4 weeks multiple, intravenous Recommended Dose: 50 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / 4 weeks Sources: |
unhealthy Health Status: unhealthy Sources: |
Reaction anaphylactic anaphylactoid | grade 3-5 Disc. AE |
50 mg/m2 1 times / 4 weeks multiple, intravenous Recommended Dose: 50 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / 4 weeks Sources: |
unhealthy Health Status: unhealthy Sources: |
Myelosuppression | severe Disc. AE |
50 mg/m2 1 times / 4 weeks multiple, intravenous Recommended Dose: 50 mg/m2, 1 times / 4 weeks Route: intravenous Route: multiple Dose: 50 mg/m2, 1 times / 4 weeks Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 203 uM] | ||||
yes [Ki 49.4 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/12859862/ |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
PubMed
Title | Date | PubMed |
---|---|---|
[Effects of all-trans retinoic acid, arsenic trioxide and daunorubicin on tissue factor expression in NB4 cells]. | 1999 Sep |
|
TEL/AML1 gene fusion is related to in vitro drug sensitivity for L-asparaginase in childhood acute lymphoblastic leukemia. | 2000 Aug 1 |
|
Focal degradation of cytoplasmic organelles in cardiomyocytes during regenerative and plastic myocardial insufficiency. | 2000 Dec |
|
High-dose cytosine arabinoside and daunorubicin induction therapy for adult patients with de novo non M3 acute myelogenous leukemia: impact of cytogenetics on achieving a complete remission. | 2000 Jul |
|
Low-dose daunorubicin in induction treatment of childhood acute lymphoblastic leukemia: no long-term cardiac damage in a randomized study of the Dutch Childhood Leukemia Study Group. | 2000 Jul |
|
Comparison of anthracycline-induced death of human leukemia cells: programmed cell death versus necrosis. | 2002 Dec |
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Role of exogenous melatonin in reducing the cardiotoxic effect of daunorubicin and doxorubicin in the rat. | 2002 Feb |
|
Safety and early efficacy assessment of liposomal daunorubicin (DaunoXome) in adults with refractory or relapsed acute myeloblastic leukaemia: a phase I-II study. | 2002 Feb |
|
Phase IV study of liposomal daunorubicin (DaunoXome) in AIDS-related Kaposi sarcoma. | 2002 Feb |
|
A novel, extraneuronal role for cyclin-dependent protein kinase 5 (CDK5): modulation of cAMP-induced apoptosis in rat leukemia cells. | 2002 Jun 7 |
|
Liposomal encapsulation diminishes daunorubicin-induced generation of reactive oxygen species, depletion of ATP and necrotic cell death in human leukaemic cells. | 2002 May |
|
Resistance of bcr-abl-positive acute lymphoblastic leukemia to daunorubicin is not mediated by mdr1 gene expression. | 2002 Nov |
|
Vincristine neurotoxicity in the presence of hereditary neuropathy. | 2003 Jan |
|
Human intestinal absorption of imidacloprid with Caco-2 cells as enterocyte model. | 2004 Jan 1 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/dosage/daunorubicin.html
Usual Adult Dose for Acute Nonlymphocytic Leukemia: Under 60 years of age: 45 mg/m2 IV over 2 to 5 minutes once a day on days 1, 2, and 3 for the first course and on days 1 and 2 for subsequent courses) with cytosine arabinoside (ara-C) intravenously once a day (usually for 7 days for the first course and 5 days for subsequent courses) as remission induction therapy.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28381182
In order to determine the viability of HL-60, K562, THP-1, and HEK293T cells, they were trypsinized, counted, and seeded into 96-well plates and were treated with serial dilutions (0.0001, 0.001, 0.01, 0.1, 1 mkM) of DNR (Daunorubicin). Cell viability was determined 48 h after DNR treatment using the luminescent cell viability assay (Promega) through luminescence testing by BMG NOVOstar machine.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:22:58 GMT 2025
by
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on
Mon Mar 31 18:22:58 GMT 2025
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Record UNII |
ZS7284E0ZP
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175414
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NCI_THESAURUS |
C1594
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FDA ORPHAN DRUG |
265808
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WHO-ATC |
L01DB02
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NDF-RT |
N0000007530
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WHO-ESSENTIAL MEDICINES LIST |
8.2
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WHO-ATC |
L01XY01
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NDF-RT |
N0000000176
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NDF-RT |
N0000007530
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LIVERTOX |
NBK548259
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NDF-RT |
N0000007530
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EU-Orphan Drug |
EU/3/11/942
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WHO-VATC |
QL01DB02
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2257
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SUB06917MIG
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DAUNORUBICIN
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CHEMBL178
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DB00694
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30323
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DTXSID7022883
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C62091
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D003630
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m4104
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ZS7284E0ZP
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100000086006
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20830-81-3
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41977
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3109
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786
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244-069-7
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64677
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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