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Merck

F2773

2-Fluoroadenine-9-β-D-arabinofuranoside

DNA synthesis inhibitor

Synonym(s):

9-β-D-Arabinofuranosyl-2-fluoroadenine, F-ara-A, Fludarabine des-phosphate

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About This Item

Empirical Formula (Hill Notation):
C10H12FN5O4
CAS Number:
21679-14-1
Molecular Weight:
285.23
NACRES:
NA.77
PubChem Substance ID:
24894830
UNSPSC Code:
12352202
EC Number:
244-525-5
MDL number:
MFCD00132942
Beilstein/REAXYS Number:
1225932

Key Documents

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Product Name

2-Fluoroadenine-9-β-D-arabinofuranoside, DNA synthesis and methylation inhibitor

InChI key

HBUBKKRHXORPQB-FJFJXFQQSA-N

InChI

1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/m1/s1

SMILES string

Nc1nc(F)nc2n(cnc12)[C@@H]3O[C@H](CO)[C@@H](O)[C@@H]3O

storage temp.

2-8°C

Quality Level

200

Gene Information

human ... ADORA3(140)
rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

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Application

2-Fluoroadenine-9-β-D-arabinofuranoside (F-ara-A) has been used:
  • to assess its interaction with kinase inhibitor UCN-01 in human leukemia cells (U937 and HL-60) and primary patient samples
  • to assess its influence on endothelial cells by apoptosis assay and human microvascular endothelial cells (HMECs) by cytotoxicity assay
  • in comparative cytotoxicity studies with Alemtuzumab CDC in 17p13- chronic lymphocytic leukemia (CLL) patients

Biochem/physiol Actions

Fludarabine (the 5′-phosphate) is a prodrug that is converted to F-ara-A, which enters cells and accumulates primarily as the 5′-triphosphate. F-ara-A interferes with DNA synthesis and repair and induces apoptosis of cancer cells.
Fludarabine (the 5′-phosphate) is a prodrug that is converted to F-ara-A, which enters cells and accumulates primarily as the 5′-triphosphate. F-ara-A interferes with DNA synthesis and repair and induces apoptosis of cancer cells. F-ara-A also strongly inhibits DNA methylation, particularly methylation of cytosine in CpG dinucleotide sequences.

Disclaimer

The name fludarabine refers to 9-β-D-arabinofuranosyl-2-fluoroadenine 5′-phosphate, but is sometimes erroneously used for this compound, which lacks the phosphate.

pictograms

Health hazard
GHS08

signalword

Warning

Hazard Classifications

Muta. 2 - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000427376
0000427376
0000348121
0000348121
0000213728

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Fludarabine induces apoptosis, activation, and allogenicity in human endothelial and epithelial cells: protective effect of defibrotide
Eissner G, et al.
Blood, 100(1), 334-340 (2002)
Valentina Griggio et al.
Haematologica, 105(4), 1042-1054 (2019-07-11)
In chronic lymphocytic leukemia (CLL), the hypoxia-inducible factor 1 (HIF-1) regulates the response of tumor cells to hypoxia and their protective interactions with the leukemic microenvironment. In this study, we demonstrate that CLL cells from TP53-disrupted (TP53dis) patients have constitutively
Direct and complement dependent cytotoxicity in CLL cells from patients with high-risk early-intermediate stage chronic lymphocytic leukemia (CLL) treated with alemtuzumab and rituximab
Zent CS, et al.
Leukemia Research, 32(12), 1849-1856 (2008)
Qin Yang et al.
FEBS open bio, 11(3), 880-889 (2021-01-16)
Periodontitis is an autoimmune disease of periodontal tissues initiated by plaque. It is known that there is a close connection between periodontitis and CKD with hypertension, but the underlying mechanisms are unknown. STAT1 has been reported to play a regulatory
Budiman Kharma et al.
International journal of cancer, 133(9), 2234-2244 (2013-04-19)
Endometrial cancer, one of the most common gynecologic malignancies, is increasing in Japan, nearly doubling over the last decade. High-grade disease patients are often resistant to conventional chemotherapy with platinum agents; therefore, discovery of efficacious new drugs in this setting
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