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V900339

Sigma-Aldrich

Cytosine β-D-arabinofuranoside

Vetec™, reagent grade, 90%

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Synonym(s):
(β-D-Arabinofuranosyl)cytosine, Ara-C, Arabinocytidine, Arabinosylcytosine, Cytarabine, Cytosine arabinoside
Empirical Formula (Hill Notation):
C9H13N3O5
CAS Number:
147-94-4
Molecular Weight:
243.22
Beilstein:
89175
EC Number:
205-705-9
MDL number:
MFCD00066487
PubChem Substance ID:
329829757

grade

reagent grade

product line

Vetec™

Assay

90%

storage temp.

2-8°C

SMILES string

NC1=NC(=O)N(C=C1)[C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O

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

InChI key

UHDGCWIWMRVCDJ-CCXZUQQUSA-N

Gene Information

human ... POLA1(5422) , POLA2(23649) , POLD1(5424) , POLD2(5425) , POLD3(10714) , POLD4(57804) , POLE(5426) , POLE2(5427) , POLE3(54107) , PRIM1(5557) , PRIM2(5558)

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Biochem/physiol Actions

Ara-C incorporates into DNA and inhibits DNA replication by forming cleavage complexes with topoisomerase I resulting in DNA fragmentation; does not inhibit RNA synthesis. Anti-leukemia agent.

Legal Information

Vetec is a trademark of Merck KGaA, Darmstadt, Germany

Pictograms

Exclamation markHealth hazard
GHS07,GHS08

Signal Word

Warning

Hazard Statements

H317 - H361fd

Hazard Classifications

Repr. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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Bob Löwenberg
Blood, 121(1), 26-28 (2013-01-05)
High-dose cytarabine applied during remission induction or as consolidation after attainment of a complete remission has become an established element in the treatment of adults with acute myeloid leukemia. Recent evidence has challenged the need for these exceptionally high-dose levels
Jorge E Romaguera et al.
British journal of haematology, 150(2), 200-208 (2010-06-10)
Mantle cell lymphoma (MCL) has a poor overall survival after treatment with conventional chemotherapy. Intense chemoimmunotherapy without consolidation stem cell transplantation is a potential therapeutic option. We report on a prospective Phase II study with rituximab in combination with fractionated
M Low et al.
Internal medicine journal, 43(3), 294-297 (2012-07-05)
Although induction chemotherapy comprising high-dose cytarabine (HiDAC) in combination with idarubicin and etoposide or 'ICE' for adult acute myeloid leukaemia (AML) produces a complete remission rate of nearly 80%, gastrointestinal toxicity is significant. Omission of etoposide may produce similar clinical
Bhupender S Chhikara et al.
Expert opinion on drug delivery, 7(12), 1399-1414 (2010-10-23)
Cytarabine is a polar nucleoside drug used for the treatment of myeloid leukemia and non-Hodgkin's lymphoma. 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
Julie M Vose et al.
Journal of clinical oncology : official journal of the American Society of Clinical Oncology, 31(13), 1662-1668 (2013-03-13)
This clinical trial evaluated standard-dose radioimmunotherapy with a chemotherapy-based transplantation regimen followed by autologous hematopoietic cell transplantation versus rituximab with the same regimen in patients with relapsed diffuse large B-cell lymphoma (DLBCL). Patients with chemotherapy-sensitive persistent or relapsed DLBCL were
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