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Merck
CN

F5307

5−Fluoro−2′−deoxycytidine

≥98% (HPLC), powder

Synonym(s):

2′-deoxy-5-fluoro-Cytidine, FCDR, FdCyd

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About This Item

Empirical Formula (Hill Notation):
C9H12FN3O4
CAS Number:
10356-76-0
Molecular Weight:
245.21
NACRES:
NA.77
PubChem Substance ID:
329799711
UNSPSC Code:
12352200
MDL number:
MFCD00077348
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100

Key Documents

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Product Name

5−Fluoro−2′−deoxycytidine, ≥98% (HPLC), powder

InChI key

IDYKCXHJJGMAEV-RRKCRQDMSA-N

SMILES string

NC1=NC(=O)N(C=C1F)[C@H]2C[C@H](O)[C@@H](CO)O2

InChI

1S/C9H12FN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >20 mg/mL

storage temp.

room temp

Quality Level

100

Related Categories

Biochem/physiol Actions

5-Fluoro-2′-deoxycytidine is a mechanism based DNMT (DNA cytosine-5 methyltransferase) inhibitor, that forms a covalent link with the cysteine residue in the active site of DNMT.

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
059K4720V
059K47201
059K4720

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Duoli Guo et al.
AAPS PharmSciTech, 11(1), 247-252 (2010-02-13)
In vivo, the DNA methyltransferase inhibitor, 5-fluoro-2'-deoxycytidine (FdCyd, NSC-48006), is rapidly converted to its unwanted metabolites. Tetrahydrouridine (THU, NSC-112907), a cytidine deaminase inhibitor can block the first metabolic step in FdCyd catabolism. Clinical studies have shown that co-administration with THU
G Ia Sheflian et al.
Biokhimiia (Moscow, Russia), 58(11), 1806-1811 (1993-11-01)
Cleavage by restriction endonucleases MvaI kappa EcoRII of DNA duplexes, in which the internal deoxycytidine in one of the strands of the recognition site is substituted for 5-fluorodeoxycytidine, has been studied. It has been found that the modified strands of
M Iigo et al.
Cancer chemotherapy and pharmacology, 20(1), 1-4 (1987-01-01)
The plasma concentration of 5-fluorouracil (FUra) following the i.v. administration of FUra and guanosine 5'-monophosphate (GMP) or guanosine 5'-triphosphate (GTP) was markedly elevated. These values were more than 5-fold higher than those obtained with FUra alone over 60 min after
D A Boothman et al.
Cancer research, 47(9), 2344-2353 (1987-05-01)
Treatment of C57BL X DBA/2 F (hereafter called BD2F) mice bearing ascitic mammary adenocarcinoma-755 (ADC-755) with [3H]-5-fluoro-2'-deoxycytidine ([3H]FdCyd) plus tetrahydrouridine (H4Urd) resulted in antimetabolite pool sizes indicative of a tumor-selective, dual pathway metabolism of FdCyd via both cytidine deaminase and
E De Clercq et al.
Molecular pharmacology, 32(1), 286-292 (1987-08-01)
5-Fluorouracil, 5-fluorouridine (FUrd), 5-fluoro-2'-deoxyuridine (FdUrd), 5-fluorocytidine (FCyd), 5-fluoro-2'-deoxycytidine (FdCyd), 5-trifluoro-2'-deoxythymidine (F3dThd), and the 5'-monophosphates and 3',5'-cyclic monophosphates thereof were found to inhibit thymidine kinase-deficient (TK-) mutant strains of herpes simplex virus (HSV) at a much lower concentration than the wild-type
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