Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H13N3O5 |
Molecular Weight | 243.2166 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O
InChI
InChIKey=UHDGCWIWMRVCDJ-CCXZUQQUSA-N
InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6-,7+,8-/m1/s1
Molecular Formula | C9H13N3O5 |
Molecular Weight | 243.2166 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/021041s023lbl.pdfCurator's Comment: Description was created using several sources including:
http://www.ebi.ac.uk/chebi/searchId.do?chebiId=28680
http://www.tandfonline.com/doi/abs/10.1517/17425247.2010.527330
Sources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/021041s023lbl.pdf
Curator's Comment: Description was created using several sources including:
http://www.ebi.ac.uk/chebi/searchId.do?chebiId=28680
http://www.tandfonline.com/doi/abs/10.1517/17425247.2010.527330
Cytarabine is a pyrimidine nucleoside analog. Cytarabine or cytosine arabinoside (Cytosar-U or Depocyt) is a chemotherapy agent used mainly in the treatment of cancers of white blood cells such as acute myeloid leukemia (AML) and non-Hodgkin lymphoma. It also has antiviral and immunosuppressant properties. Cytarabine is an antimetabolite antineoplastic agent that inhibits the synthesis of DNA. It is a cell cycle phase-specific, affecting cells only during the S phase of cell division. Intracellularly, cytarabine is converted into cytarabine-5-triphosphate (ara-CTP), which is the active metabolite. The mechanism of action is not completely understood, but it appears that ara-CTP acts primarily through inhibition of DNA polymerase. Incorporation into DNA and RNA may also contribute to cytarabine cytotoxicity. Cytarabine is cytotoxic to a wide variety of proliferating mammalian cells in culture.The drug has a short plasma half-life, low stability and limited bioavailability. Overdosing of patients with continuous infusions may lead to side effects. Thus, various prodrug strategies and delivery systems have been explored extensively to enhance the half-life, stability and delivery of cytarabine. Alternative, delivery systems of cytarabine have emerged for the treatment of different cancers. The liposomal-cytarabine formulation has been approved for the treatment of lymphomatous meningitis.
CNS Activity
Originator
Sources: https://en.wikipedia.org/wiki/Cytarabine
Curator's Comment: Cytarabine was first synthesized in 1959 by Richard Walwick, Walden Roberts, and Charles Dekker at the University of California, Berkeley. It was approved by the United States Food and Drug Administration in June 1969, and was initially marketed in the U.S. by Upjohn under the trade name Cytosar-U and is at present manufactured by Pfizer, Sicor Pharmaceuticals and Teva. CYTOSAR (cytarabine injection) was developed in September 1994 Dana-Farber Cancer Institute and is manufactured by Pfizer and Perrigo. DEPOCYT - (cytarabine injection, lipid complex) manufactured by Manufactured by: Pacira Pharmaceuticals Inc., distributed by Sigma-Tau Pharmaceutical, Inc. is an intrathecal cancer chemotherapeutic agent approved by FDA is used for the treatment of lymphomatous meningitis.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL5367 Sources: http://www.drugbank.ca/drugs/DB00987 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
|||
Sources: www.accessdata.fda.gov/drugsatfda_docs/label/2011/021041s023lbl.pdf |
Primary | CYTARABINE Approved UseCytarabine in combination with other approved anticancer drugs is indicated for remission induction in acute non-lymphocytic leukemia of adults and children. It has also been found useful in the treatment of acute lymphocytic leukemia and the blast phase of chronic myelocytic leukemia. Intrathecal administration of cytarabine injection (preservative-free only) is indicated for the prophylaxis and treatment of meningeal leukemia. Launch Date1969 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
62.2 μg/mL |
100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: DAUNORUBICIN |
CYTARABINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1900 μg × h/mL |
100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: DAUNORUBICIN |
CYTARABINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40.4 h |
100 mg/m² 1 times / day multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: DAUNORUBICIN |
CYTARABINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
80 h |
50 mg single, intrathecal dose: 50 mg route of administration: Intrathecal experiment type: SINGLE co-administered: |
CYTARABINE cerebrospinal fluid | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
4.5 g/m2 2 times / day multiple, intravenous Highest studied dose Dose: 4.5 g/m2, 2 times / day Route: intravenous Route: multiple Dose: 4.5 g/m2, 2 times / day Sources: |
unhealthy, 16-76 |
Disc. AE: Cerebellar disorder NOS, Diarrhea... AEs leading to discontinuation/dose reduction: Cerebellar disorder NOS (grade 4, 66.7%) Sources: Diarrhea (grade 3, 66.7%) |
4.5 g/m2 2 times / day multiple, intravenous Highest studied dose Dose: 4.5 g/m2, 2 times / day Route: intravenous Route: multiple Dose: 4.5 g/m2, 2 times / day Sources: |
unhealthy, 16-76 |
Disc. AE: Cerebellar disorder NOS, Cerebellar disorder NOS... AEs leading to discontinuation/dose reduction: Cerebellar disorder NOS (grade 4, 33.3%) Sources: Cerebellar disorder NOS (grade 5, 16.7%) |
3 g/m2 2 times / day multiple, intravenous MTD Dose: 3 g/m2, 2 times / day Route: intravenous Route: multiple Dose: 3 g/m2, 2 times / day Sources: |
unhealthy, 16-76 |
|
100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Disc. AE: Bone marrow depression, Leukopenia... AEs leading to discontinuation/dose reduction: Bone marrow depression Sources: Leukopenia Thrombocytopenia Anemia Nausea Vomiting Diarrhea Abdominal pain Oral ulceration Hepatic dysfunction NOS |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Diarrhea | grade 3, 66.7% Disc. AE |
4.5 g/m2 2 times / day multiple, intravenous Highest studied dose Dose: 4.5 g/m2, 2 times / day Route: intravenous Route: multiple Dose: 4.5 g/m2, 2 times / day Sources: |
unhealthy, 16-76 |
Cerebellar disorder NOS | grade 4, 66.7% Disc. AE |
4.5 g/m2 2 times / day multiple, intravenous Highest studied dose Dose: 4.5 g/m2, 2 times / day Route: intravenous Route: multiple Dose: 4.5 g/m2, 2 times / day Sources: |
unhealthy, 16-76 |
Cerebellar disorder NOS | grade 4, 33.3% Disc. AE |
4.5 g/m2 2 times / day multiple, intravenous Highest studied dose Dose: 4.5 g/m2, 2 times / day Route: intravenous Route: multiple Dose: 4.5 g/m2, 2 times / day Sources: |
unhealthy, 16-76 |
Cerebellar disorder NOS | grade 5, 16.7% Disc. AE |
4.5 g/m2 2 times / day multiple, intravenous Highest studied dose Dose: 4.5 g/m2, 2 times / day Route: intravenous Route: multiple Dose: 4.5 g/m2, 2 times / day Sources: |
unhealthy, 16-76 |
Abdominal pain | Disc. AE | 100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Anemia | Disc. AE | 100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Bone marrow depression | Disc. AE | 100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Diarrhea | Disc. AE | 100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Hepatic dysfunction NOS | Disc. AE | 100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Leukopenia | Disc. AE | 100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Nausea | Disc. AE | 100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Oral ulceration | Disc. AE | 100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Thrombocytopenia | Disc. AE | 100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Vomiting | Disc. AE | 100 mg/m2 1 times / day multiple, intravenous Recommended Dose: 100 mg/m2, 1 times / day Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/ Page: 4.0 |
yes [IC50 6.6 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15204103/ Page: 4.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Ocular toxicology. | 1994 Dec |
|
Differential p53 phosphorylation and activation of apoptosis-promoting genes Bax and Fas/APO-1 by irradiation and ara-C treatment. | 1998 Jul |
|
Protection by short-chain fatty acids against 1-beta-D-arabinofuranosylcytosine-induced intestinal lesions in germfree mice. | 1999 Apr |
|
Pseudotumor cerebri secondary to intermediate-dose cytarabine HCl. | 1999 May |
|
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 |
|
Visual loss following high-dose cytosine arabinoside (ARA-C). | 2000 Mar |
|
Misdiagnosis of broad-complex tachycardia. | 2000 Nov-Dec |
|
Cerebellar toxicity of cytosine arabinoside: clinical and neuropsychological signs. | 2000 Oct 24 |
|
Treatment for primary CNS lymphoma: the next step. | 2000 Sep |
|
Cell cycle-related changes in regulatory volume decrease and volume-sensitive chloride conductance in mouse fibroblasts. | 2001 Apr |
|
The neuron-glia signal beta-neuregulin promotes Schwann cell motility via the MAPK pathway. | 2001 Apr 1 |
|
Value of high-dose cytarabine during interval therapy of a Berlin-Frankfurt-Munster-based protocol in increased-risk children with acute lymphoblastic leukemia and lymphoblastic lymphoma: results of the European Organization for Research and Treatment of Cancer 58881 randomized phase III trial. | 2001 Apr 1 |
|
The combination of chemotherapy and systemic immunotherapy with soluble B7-immunoglobulin G leads to cure of murine leukemia and lymphoma and demonstration of tumor-specific memory responses. | 2001 Apr 15 |
|
Involvement of oxygen radicals in cytarabine-induced apoptosis in human polymorphonuclear cells. | 2001 Apr 15 |
|
Parotid mucoepidermoid carcinoma following chemotherapy for childhood acute lymphoblastic leukemia. | 2001 Apr-May |
|
Prognostic value of day 14 blast percentage and the absolute blast index in bone marrow of children with acute lymphoblastic leukemia. | 2001 Apr-May |
|
Temporary response of localized intracranial mast cell sarcoma to combination chemotherapy. | 2001 Feb |
|
Primary central nervous system lymphoma in childhood presenting as progressive panhypopituitarism. | 2001 Feb |
|
Bilateral breast relapse in acute myelogenous leukemia. | 2001 Feb |
|
Dose-intensive epirubicin-based chemotherapy is superior to an intensive intravenous cyclophosphamide, methotrexate, and fluorouracil regimen in metastatic breast cancer: a randomized multinational study. | 2001 Feb 15 |
|
Survival in patients with intermediate or high grade non-Hodgkin's lymphoma: meta-analysis of randomized studies comparing third generation regimens with CHOP. | 2001 Feb 2 |
|
Characterization of DNA fragmentation events caused by genotoxic and non-genotoxic agents. | 2001 Feb 20 |
|
Allogeneic bone marrow transplantation in children failing prior autologous bone marrow transplantation. | 2001 Jan |
|
The biology and treatment of chronic myelogenous leukemia. | 2001 Jan |
|
Aseptic meningitis in a child after systemic treatment with high dose cytarabine. | 2001 Jan |
|
Chemotherapy and marrow transplantation for congenital leukaemia. | 2001 Jan |
|
Induction of differentiation of acute promyelocytic leukemia cells by a cytidine deaminase-resistant analogue of 1-beta-D-arabinofuranosylcytosine, 1-(2-deoxy-2-methylene-beta-D-erythro-pentofuranosyl)cytidine. | 2001 Jan 1 |
|
Primary central nervous system lymphoma 1991-1997: outcome and late adverse effects after combined modality treatment. | 2001 Jan 1 |
|
Reduced cellular transport and activation of fluoropyrimidine nucleosides and resistance in human lymphocytic cell lines selected for arabinosylcytosine resistance. | 2001 Jan 1 |
|
Targeting and anti-tumor efficacy of liposomal 5'-O-dipalmitoylphosphatidyl 2'-C-cyano-2'-deoxy-1-beta-D-arabino-pentofuranosylcytosine in mice lung bearing B16BL6 melanoma. | 2001 Jan 10 |
|
Upregulation of preprodynorphin and preproenkephalin mRNA expression by selective activation of group I metabotropic glutamate receptors in characterized primary cultures of rat striatal neurons. | 2001 Jan 31 |
|
The CAG regimen (low-dose cytarabine, aclarubicin hydrochloride and granulocyte colony-stimulating factor) for the treatment of elderly acute myelomonocytic leukaemia: a case study. | 2001 Jan-Feb |
|
Therapy of acute myeloid leukemia. | 2001 Jan-Feb |
|
Outcome of relapsed or refractory childhood B-cell acute lymphoblastic leukaemia and B-cell non-Hodgkin's lymphoma treated with the UKCCSG 9003/9002 protocols. | 2001 Mar |
|
Neutrophilic eccrine hidradenitis in two neutropaenic patients. | 2001 Mar |
|
[All-trans retinoic acid combined with low-dose cytosine arabinoside treatment for acute myelogenous leukemia with trilineage myelodysplasia--a case report]. | 2001 Mar |
|
Cytogenetic subgroups in acute myeloid leukemia differ in proliferative activity and response to GM-CSF. | 2001 Mar |
|
Idarubicin improves blast cell clearance during induction therapy in children with AML: results of study AML-BFM 93. AML-BFM Study Group. | 2001 Mar |
|
Synergistic activity of the new ABL-specific tyrosine kinase inhibitor STI571 and chemotherapeutic drugs on BCR-ABL-positive chronic myelogenous leukemia cells. | 2001 Mar |
|
Combination chemotherapy utilizing continuous infusion of intermediate-dose cytarabine for refractory or recurrent acute myeloid leukemia. | 2001 Mar |
Sample Use Guides
Induction therapy: DepoCyt (cytarabine liposome injection), 50 mg, administered intrathecally (intraventricular or lumbar puncture) every 14 days for 2 doses (weeks 1 and 3).
Consolidation therapy: DepoCyt, 50 mg, administered intrathecally (intraventricular or lumbar puncture) every 14 days for 3 doses (weeks 5, 7 and 9) followed by 1 additional dose at week 13.
Maintenance: DepoCyt, 50 mg, administered intrathecally (intraventricular or lumbar puncture) every 28 days for 4 doses (weeks 17, 21, 25 and 29).
Route of Administration:
Intratracheal
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/24527217
Curator's Comment: The effect of Ara-C (0.1 μM) treatment on HUVEC proliferation alone or in drug combinations compared to drug-free control cultures. Results are expressed as mean percentage ± SEM from three independent experiments (six replicates per condition) relative to corresponding untreated control cultures.
Human umbilical vein endothelial cells (HUVECs) and human osteosarcoma cell line (Cal72) were incubated with various concentrations of Cytarabine (Ara-C) (0.01–20 μM) for 3 days
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Apr 02 08:11:33 GMT 2025
by
admin
on
Wed Apr 02 08:11:33 GMT 2025
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Record UNII |
04079A1RDZ
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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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WHO-ATC |
L01XY01
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FDA ORPHAN DRUG |
234806
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NDF-RT |
N0000175595
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NDF-RT |
N0000000233
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EMA ASSESSMENT REPORTS |
DEPOCYT (AUTHORIZED: MENINGEAL NEOPLASMS)
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FDA ORPHAN DRUG |
265808
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NCI_THESAURUS |
C1557
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WHO-ESSENTIAL MEDICINES LIST |
8.2
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FDA ORPHAN DRUG |
73393
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LIVERTOX |
NBK548291
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WHO-ATC |
L01BC01
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EU-Orphan Drug |
EU/3/11/942
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WHO-VATC |
QL01BC01
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968804
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ALTERNATIVE | |||
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205-705-9
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PRIMARY | |||
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DTXSID3022877
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DB00987
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SUB06880MIG
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C408
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3041
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04079A1RDZ
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m4051
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6253
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CYTARABINE
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CHEMBL803
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1162002
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04079A1RDZ
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147-94-4
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D003561
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28680
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100000089874
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1709
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3049
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287459
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CHROMATOGRAPHIC PURITY (HPLC/UV)
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
IMPURITY -> PARENT |
|
||
|
IMPURITY -> PARENT |
|
Related Record | Type | Details | ||
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ACTIVE MOIETY |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Volume of Distribution | PHARMACOKINETIC |
|
|
|||
Biological Half-life | PHARMACOKINETIC |
|
|
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