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C1768

Cytarabine

Name: Cytarabine
Brand: SIGMA

≥90% (HPLC), crystalline, DNA replication inhibitor

Synonym(s):

(β-D-Arabinofuranosyl)cytosine, Ara-C, Arabinocytidine, Arabinosylcytosine, Cytarabine, Cytosine arabinoside

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₃N₃O₅

CAS Number:

147-94-4

Molecular Weight:

243.22

NACRES:

NA.77

PubChem Substance ID:

24892435

UNSPSC Code:

12352200

EC Number:

205-705-9

MDL number:

MFCD00066487

Beilstein/REAXYS Number:

89175

Assay:

≥90% (HPLC)

Form:

crystalline

Quality level:

200

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Properties

Product Name

Cytosine β-D-arabinofuranoside, crystalline, ≥90% (HPLC)

Quality Level

200

assay

≥90% (HPLC)

form

crystalline

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), POLB(5423), POLD1(5424), POLD2(5425), POLD3(10714), POLD4(57804), POLE(5426), POLE2(5427), POLE3(54107), PRIM1(5557), PRIM2(5558)
mouse ... Cda(72269)

Description

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.

Features and Benefits

This compound is a featured product for Apoptosis research. Click here to discover more featured Apoptosis products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

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ppe

Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges

pictograms

GHS08

signalword

Danger

hcodes

H340,H361fd

pcodes

P201 - P202 - P280 - P308 + P313 - P405 - P501

Hazard Classifications

Muta. 1B - Repr. 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

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Articles

DNA损伤和修复

DNA损伤和修复机制对于维持DNA完整性至关重要。细胞DNA的损伤与突变、癌症发展等有关。

DNA Damage and Repair

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Discover Bioactive Small Molecules for Cell Cycle

Cell cycle phases (G1, S, G2, M) regulate cell growth, DNA replication, and division in proliferating cells.

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Structure-activity relationship and molecular mechanisms of ethyl 2-amino-6-(3,5-dimethoxyphenyl)-4-(2-ethoxy-2-oxoethyl)-4H-chromene-3-carboxylate (CXL017) and its analogues.

Sonia G Das et al.

Journal of medicinal chemistry, 54(16), 5937-5948 (2011-07-26)

Multidrug resistance (MDR) in cancer is a phenomenon in which administration of a single chemotherapeutic agent causes cross-resistance of cancer cells to a variety of therapies even with different mechanisms of action. Development of MDR against standard therapies is a

Antitumor studies. Part 1: design, synthesis, antitumor activity, and AutoDock study of 2-deoxo-2-phenyl-5-deazaflavins and 2-deoxo-2-phenylflavin-5-oxides as a new class of antitumor agents.

Hamed I Ali et al.

Bioorganic & medicinal chemistry, 15(1), 242-256 (2006-10-20)

Novel 2-deoxo-2-phenyl-5-deazaflavins and 2-deoxo-2-phenylflavin-5-oxides were prepared as a new class of antitumor agents and showed significant antitumor activities against NCI-H 460, HCT 116, A 431, CCRF-HSB-2, andKB cell lines. In vivo investigation, 2-deoxo-10-methyl-2-phenyl-5-deazaflavin exhibited the effective antitumor activity against A

High-dose cytarabine (24 g/m2) in combination with idarubicin (HiDAC-3) results in high first-cycle response with limited gastrointestinal toxicity in adult acute myeloid leukaemia.

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

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Global Trade Item Number

SKU	GTIN
C1768-500MG	04061833468029
C1768-100MG	04061833468005
C1768-1G	04061833468012
C1768-5G	04061833023846