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Merck
CN

F3503

5-Fluoro-2′-deoxyuridine 5′-monophosphate sodium salt

~85%, solid

Synonym(s):

FdUMP

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About This Item

Empirical Formula (Hill Notation):
C9H12FN2O8P
CAS Number:
103226-10-4
Molecular Weight:
326.17
UNSPSC Code:
41106305
PubChem Substance ID:
24894845
NACRES:
NA.51
MDL number:
MFCD00057409

Key Documents

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Product Name

5-Fluoro-2′-deoxyuridine 5′-monophosphate sodium salt, ~85%

SMILES string

[Na].OC1CC(OC1COP(O)(O)=O)N2C=C(F)C(=O)NC2=O

InChI

1S/C9H12FN2O8P.Na.H/c10-4-2-12(9(15)11-8(4)14)7-1-5(13)6(20-7)3-19-21(16,17)18;;/h2,5-7,13H,1,3H2,(H,11,14,15)(H2,16,17,18);;

InChI key

DGEOOGBABXVZPJ-UHFFFAOYSA-N

assay

~85%

form

solid

solubility

water: 50 mg/mL, clear, colorless to faint yellow or tan

storage temp.

−20°C

Quality Level

200

Related Categories

Application

It has been used:

  • as an anti-mitotic agent for culturing mouse primary cortical neurons.
  • as a component of feeding media in the culturing of mouse primary cortical neurons.
  • in studies on the activity and function of thymidylate synthase (TS).

Biochem/physiol Actions

5-Fluoro-2′-deoxyuridine 5′-monophosphate sodium salt (FdUMP) is an DNA synthesis inhibitor. FdUMP along with RNA synthesis inhibitor 3′-C-ethinylcytidine induces cell death in cervical cancer cells at nanomolar concentrations.

General description

5- 5-fluoro-2′-deoxyuridylate (FdUMP) is an intracellularly generated metabolite of 5-Fluorouracil (5-FU), a widely used reagent in molecular biology to study DNA synthesis and metabolism.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Carc. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000480359
0000480359
0000415658
0000415658
0000276418

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W H Gmeiner
Current medicinal chemistry, 12(2), 191-202 (2005-01-11)
Thymidylate synthase (TS) is a well-validated target for cancer chemotherapy. TS was established as the principal target of the widely used anticancer drug 5-fluorouracil (5FU). The 5FU metabolite FdUMP forms a covalent complex with TS that is stabilized by 5-formyl
Induction of apoptosis in cervical cancer cells by the duplex drug 5-FdU--ECyd, coupling 2?-deoxy-5-fluorouridine and 3?-C-ethinylcytidine
Schott S and Bruning A
Gynecologic Oncology, 135(2), 342-348 (2014)
Yoshihiro Nabeya et al.
Cancer science, 102(8), 1509-1515 (2011-05-13)
Thymidylate synthase (TS) plays a major role in the response to 5-fluorouracil (5-FU) by binding directly to the 5-FU metabolite, 5-fluoro-dUMP (FdUMP). The change in the TS expression levels after 5-FU administration was examined in parallel to 5-FU responsiveness in
G-rich motifs within phosphorothioate-based antisense oligonucleotides (ASOs) drive activation of FXN expression through indirect effects
Wang F, et al.
Nucleic Acids Research, 50(22), 12657-12673 (2022)
Adam Jarmuła et al.
Bioorganic & medicinal chemistry letters, 18(8), 2701-2708 (2008-03-26)
Molecular dynamics simulations and free energy calculations are presented, exploring previously described experimentally studied interactions of a series of 2'-fluoro-substituted dUMP/FdUMP analogues with thymidylate synthase (TS). The results show the inhibitory behaviors of 2'-F-ara-UMP, 2',2''-diF-dUMP and 2',5-diF-ara-UMP to be dependent
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