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

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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

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Alberto Diez-Torrubia et al.

Journal of medicinal chemistry, 53(2), 559-572 (2009-12-17)

Here we explore the applicability of the dipeptidyl peptidase IV (DPPIV/CD26) based prodrug approach to a variety of amine-containing drugs. Efficient procedures have been developed for the synthesis of dipeptide and tetrapeptide amide prodrugs including N-acylation protocols of the exocyclic

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Global Trade Item Number

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