Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C9H13N3O5.ClH |
Molecular Weight | 279.678 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O
InChI
InChIKey=KCURWTAZOZXKSJ-JBMRGDGGSA-N
InChI=1S/C9H13N3O5.ClH/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);1H/t4-,6-,7+,8-;/m1./s1
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 Date-1.71072E10 |
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 |
---|---|---|
[Topotecan: a new field of use]. | 1999 Nov-Dec |
|
Pseudotumor cerebri induced by all-trans-retinoic acid in a child treated for acute promyelocytic leukemia. | 2000 Apr |
|
Differential transport of cytosine-containing nucleosides by recombinant human concentrative nucleoside transporter protein hCNT1. | 2000 Jan-Feb |
|
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 |
|
Oxidative stress interferes with cancer chemotherapy: inhibition of lymphoma cell apoptosis and phagocytosis. | 2000 Jul 1 |
|
Visual loss following high-dose cytosine arabinoside (ARA-C). | 2000 Mar |
|
A phase-II trial of all trans retinoic acid and low-dose cytosine arabinoside for the treatment of high-risk myelodysplastic syndromes. | 2000 Mar |
|
Expression and prognostic significance of IAP-family genes in human cancers and myeloid leukemias. | 2000 May |
|
Treatment of patients with recurrent and primary refractory acute myelogenous leukemia using mitoxantrone and intermediate-dose cytarabine: a pharmacologically based regimen. | 2000 May 1 |
|
Cytosine arabinoside induced acute interstitial nephritis in a patient treated for refractory anemia with excess of blasts in transformation. | 2000 Nov |
|
Misdiagnosis of broad-complex tachycardia. | 2000 Nov-Dec |
|
Heterotopia in microcephaly induced by cytosine arabinoside: hippocampus in the neocortex. | 2000 Oct |
|
Cerebellar toxicity of cytosine arabinoside: clinical and neuropsychological signs. | 2000 Oct 24 |
|
Treatment for primary CNS lymphoma: the next step. | 2000 Sep |
|
Primary high-grade mucosa-associated lymphoid tissue-type lymphoma of the cervix presenting as a common endocervical polyp. | 2001 Apr |
|
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 |
|
The neuron-glia signal beta-neuregulin promotes Schwann cell motility via the MAPK pathway. | 2001 Apr 1 |
|
In vitro cytotoxic effects of a tyrosine kinase inhibitor STI571 in combination with commonly used antileukemic agents. | 2001 Apr 1 |
|
Involvement of oxygen radicals in cytarabine-induced apoptosis in human polymorphonuclear cells. | 2001 Apr 15 |
|
Induction therapy of adult acute lymphocytic leukemia without the use of vincristine or prednisone. | 2001 Feb |
|
Chemotherapy for acute myelogenous leukemia in the elderly with cytarabine, mitoxantrone, and granulocyte-macrophage colony-stimulating factor. | 2001 Feb |
|
Primary central nervous system lymphoma in childhood presenting as progressive panhypopituitarism. | 2001 Feb |
|
Bilateral breast relapse in acute myelogenous leukemia. | 2001 Feb |
|
[Is it useful to perform a (67)gallium scintigraphy in the follow-up of patients with gastric lymphoma?]. | 2001 Feb |
|
Mutations in ras proto-oncogenes are associated with lower mdr1 gene expression in adult acute myeloid leukaemia. | 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 |
|
Topoisomerase II inhibitor induced leukemia in a patient with AIDS. | 2001 Feb 16 |
|
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 |
|
Aseptic meningitis in a child after systemic treatment with high dose cytarabine. | 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 |
|
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 |
|
Simultaneous treatment with 1-beta-D-arabinofuranosylcytosine and daunorubicin induces cross-resistance to both drugs due to a combination-specific mechanism in HL60 cells. | 2001 Jan 1 |
|
Bcl-X(L)-caspase-9 interactions in the developing nervous system: evidence for multiple death pathways. | 2001 Jan 1 |
|
Primary central nervous system lymphoma 1991-1997: outcome and late adverse effects after combined modality treatment. | 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 |
|
JP-8 jet fuel-induced DNA damage in H4IIE rat hepatoma cells. | 2001 Jan 25 |
|
Standard chemotherapy with or without high-dose chemotherapy for aggressive non-Hodgkin's lymphoma: randomized phase III EORTC study. | 2001 Jan 3 |
|
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 |
|
Serum LDH, a prognostic factor in elderly patients with acute myelogenous leukaemia. | 2001 Jan 5 |
|
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 |
|
[All-trans retinoic acid combined with low-dose cytosine arabinoside treatment for acute myelogenous leukemia with trilineage myelodysplasia--a case report]. | 2001 Mar |
|
Motor nervous pathway function is impaired after treatment of childhood acute lymphoblastic leukemia: a study with motor evoked potentials. | 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 |
|
Combination chemotherapy utilizing continuous infusion of intermediate-dose cytarabine for refractory or recurrent acute myeloid leukemia. | 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
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:44:16 UTC 2023
by
admin
on
Wed Jul 05 22:44:16 UTC 2023
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Record UNII |
33K3DB6591
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C1557
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CHEMBL803
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