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
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 |
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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 unknown | 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: Page: p.363, 366 |
unhealthy, 16-76 n = 6 Health Status: unhealthy Condition: Acute leukemia Age Group: 16-76 Sex: M+F Population Size: 6 Sources: Page: p.363, 366 |
Disc. AE: Cerebellar disorder NOS, Diarrhea... AEs leading to discontinuation/dose reduction: Cerebellar disorder NOS (grade 4, 66.7%) Sources: Page: p.363, 366Diarrhea (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: Page: p.2578 |
unhealthy, 16-76 n = 6 Health Status: unhealthy Condition: Acute leukemia Age Group: 16-76 Sex: M+F Population Size: 6 Sources: Page: p.2578 |
Disc. AE: Cerebellar disorder NOS, Cerebellar disorder NOS... AEs leading to discontinuation/dose reduction: Cerebellar disorder NOS (grade 4, 33.3%) Sources: Page: p.2578Cerebellar 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: Page: p.366 |
unhealthy, 16-76 n = 27 Health Status: unhealthy Condition: Acute leukemia Age Group: 16-76 Sex: M+F Population Size: 27 Sources: Page: p.366 |
|
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acute non-lymphocytic leukemia Sources: Page: p.1 |
Disc. AE: Bone marrow depression, Leukopenia... AEs leading to discontinuation/dose reduction: Bone marrow depression Sources: Page: p.1Leukopenia 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: Page: p.363, 366 |
unhealthy, 16-76 n = 6 Health Status: unhealthy Condition: Acute leukemia Age Group: 16-76 Sex: M+F Population Size: 6 Sources: Page: p.363, 366 |
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: Page: p.363, 366 |
unhealthy, 16-76 n = 6 Health Status: unhealthy Condition: Acute leukemia Age Group: 16-76 Sex: M+F Population Size: 6 Sources: Page: p.363, 366 |
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: Page: p.2578 |
unhealthy, 16-76 n = 6 Health Status: unhealthy Condition: Acute leukemia Age Group: 16-76 Sex: M+F Population Size: 6 Sources: Page: p.2578 |
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: Page: p.2578 |
unhealthy, 16-76 n = 6 Health Status: unhealthy Condition: Acute leukemia Age Group: 16-76 Sex: M+F Population Size: 6 Sources: Page: p.2578 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acute non-lymphocytic leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acute non-lymphocytic leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acute non-lymphocytic leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acute non-lymphocytic leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acute non-lymphocytic leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acute non-lymphocytic leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acute non-lymphocytic leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acute non-lymphocytic leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acute non-lymphocytic leukemia Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acute non-lymphocytic leukemia Sources: Page: p.1 |
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 |
---|---|---|
Veno-occlusive disease of the liver after chemotherapy of acute leukemia. Report of two cases. | 1976 Nov |
|
Differential p53 phosphorylation and activation of apoptosis-promoting genes Bax and Fas/APO-1 by irradiation and ara-C treatment. | 1998 Jul |
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Protection by short-chain fatty acids against 1-beta-D-arabinofuranosylcytosine-induced intestinal lesions in germfree mice. | 1999 Apr |
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Low-dose cytarabine-induced hepatic and renal dysfunction in a patient with myelodysplastic syndrome. | 1999 Mar |
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Pseudotumor cerebri secondary to intermediate-dose cytarabine HCl. | 1999 May |
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Skin toxicity after administration of low-dose cytarabine. | 1999 Oct |
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Efficacy and toxicity of IFN-alpha2b combined with cytarabine in chronic myelogenous leukaemia. | 1999 Sep |
|
Pseudotumor cerebri induced by all-trans-retinoic acid in a child treated for acute promyelocytic leukemia. | 2000 Apr |
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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 |
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Visual loss following high-dose cytosine arabinoside (ARA-C). | 2000 Mar |
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Risk factors for severe neuropsychiatric toxicity in patients receiving interferon alfa-2b and low-dose cytarabine for chronic myelogenous leukemia: analysis of Cancer and Leukemia Group B 9013. | 2000 Mar |
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Treatment for primary CNS lymphoma: the next step. | 2000 Sep |
|
Combination chemotherapy of intermediate-dose cytarabine, idarubicin, plus etoposide and subsequent mobilized donor leukocyte infusion for relapsed acute leukemia after allogeneic bone marrow transplantation. | 2001 Apr |
|
[Philadelphia chromosome-positive acute lymphoblastic leukemia with monosomy 7 successfully treated with intermediate- and high-dose ara-C]. | 2001 Feb |
|
Chemotherapy for acute myelogenous leukemia in the elderly with cytarabine, mitoxantrone, and granulocyte-macrophage colony-stimulating factor. | 2001 Feb |
|
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 |
|
Bone marrow involvement by nasal NK cell lymphoma at diagnosis is uncommon. | 2001 Feb |
|
[Is it useful to perform a (67)gallium scintigraphy in the follow-up of patients with gastric lymphoma?]. | 2001 Feb |
|
Transfusion of peripheral blood stem cells from donor homozygous for a shared HLA-haplotype: avoiding fatal transfusion-associated graft-versus-host disease while preserving anti-leukemic effect. | 2001 Feb 15 |
|
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 |
|
[Palpable mantel cell lymphoma in the breast]. | 2001 Feb 3 |
|
[Outcome of acute myelogenous leukemia in 41 patients treated with idarubicin: the prognosis of t(8;21) cases]. | 2001 Jan |
|
A multicentre, open, non-comparative phase II study of a combination of fludarabine phosphate, cytarabine and granulocyte colony-stimulating factor in relapsed and refractory acute myeloid leukaemia and de novo refractory anaemia with excess of blasts in transformation. | 2001 Jan |
|
Patients with de novo acute myeloid leukaemia and complex karyotype aberrations show a poor prognosis despite intensive treatment: a study of 90 patients. | 2001 Jan |
|
Intrathecal treatment of neoplastic meningitis due to breast cancer with a slow-release formulation of cytarabine. | 2001 Jan |
|
PBPC mobilization with chemotherapy and G-CSF in patients with chronic myeloid leukemia: quantification of bcr/abl-positive cells by interphase fluorescence in situ hybridization and competitive PCR. | 2001 Jan |
|
Fludarabine, cytarabine and topotecan (FLAT) as induction therapy for acute myeloid leukemia in the elderly: a preliminary report. | 2001 Jan |
|
De novo acute myeloid leukemia in the elderly; a consistent fraction of long-term survivors by standard-dose chemotherapy. | 2001 Jan |
|
Reduced cellular transport and activation of fluoropyrimidine nucleosides and resistance in human lymphocytic cell lines selected for arabinosylcytosine resistance. | 2001 Jan 1 |
|
Evidence against apoptosis as a major mechanism for reproductive cell death following treatment of cell lines with anti-cancer drugs. | 2001 Jan 5 |
|
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 |
|
[All-trans retinoic acid combined with low-dose cytosine arabinoside treatment for acute myelogenous leukemia with trilineage myelodysplasia--a case report]. | 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 |
|
Isodicentric 7p, idic(7)(q11.2), in acute myeloid leukemia associated with older age and favorable response to induction chemotherapy: a new clinical entity? | 2001 Mar |
|
Severe hepatic injury associated with lipid formulations of amphotericin B. | 2001 Mar 1 |
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
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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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205-705-9
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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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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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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE ACTIVE (PARENT)
METABOLITE ACTIVE (PARENT)
METABOLITE ACTIVE (PARENT)
METABOLITE INACTIVE (PARENT)
PRODRUG (METABOLITE ACTIVE)
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)