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Key Documents

E9386

Sigma-Aldrich

5-Ethyl-2′-deoxyuridine

Synonym(s):

EUdR, Edoxudine

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About This Item

Empirical Formula (Hill Notation):
C11H16N2O5
CAS Number:
Molecular Weight:
256.26
EC Number:
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

Assay

≥95% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless to yellow

storage temp.

−20°C

SMILES string

CCC1=CN(C2CC(O)C(CO)O2)C(=O)NC1=O

InChI

1S/C11H16N2O5/c1-2-6-4-13(11(17)12-10(6)16)9-3-7(15)8(5-14)18-9/h4,7-9,14-15H,2-3,5H2,1H3,(H,12,16,17)

InChI key

XACKNLSZYYIACO-UHFFFAOYSA-N

Biochem/physiol Actions

5-Ethyl-2′-deoxyuridine (EUdR) is used as a 5-fluorouracil (FU) modulator. EtdUrd may be used to enhance the therapeutic index of 5-FU by reducing the catabolism, prolonging the plasma and intratumoral concentrations of 5-FU, and offering protection to normal organs by increasing the endogenous uridine levels.
5-Ethyl-2′-deoxyuridine is an analog of pyrimidine, uridine. It is an effective antiviral agent and inhibits cell division in leukemic tumor cells. 5-Ethyl-2′-deoxyuridine interacts with 2′-deoxycytidine phosphate (dCTP) biosynthesis pathway to elicit antiproliferative effects.

Linkage

Homolog of thymidine

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Csilla Katona et al.
Magyar onkologia, 48(3), 243-251 (2004-11-03)
Pharmacologic modulation of 5-fluorouracil (5-FU) metabolism provides a possibility for the enhancement of its clinical efficacy. The purpose of the present work was to study the effect of 5-ethyl-2'-deoxyuridine (EUdR), a potent 5-FU modulator, on different molecular mechanisms, influenced by
A M Cheraghali et al.
Antiviral research, 25(3-4), 259-267 (1994-12-01)
Pharmacokinetic parameters for 5-ethyl-2'-deoxyuridine (EDU) were determined following intravenous (iv) and oral (po) dosing in male Balb-C mice and iv dosing in male Sprague-Dawley rats. The concentrations of EDU in blood after 100 mg/kg iv bolus injections into mice and
P S Imperia et al.
Antiviral research, 9(4), 263-272 (1988-07-01)
Using an in vitro system we measured the corneal epithelial cytotoxicity and the antiviral activity of the antiviral agents idoxuridine (IDU), trifluridine (TFT), ethyldeoxyuridine (EDU), and (E)-5-(2-Bromovinyl)-2'-deoxyuridine (BVDU). Confluent rabbit corneal epithelial cell cultures were established, and the antiviral agents
E De Clercq et al.
The Journal of biological chemistry, 262(31), 14905-14911 (1987-11-05)
5-Ethyl-2'-deoxyuridine (EDU) is a potent and selective inhibitor of the replication of herpes simplex virus type 1 (HSV-1) and 2 (HSV-2), which is currently being pursued for the topical treatment of HSV-1 and HSV-2 infections in humans. Using [4-14C]EDU as
A M Cheraghali et al.
Drug design and discovery, 12(1), 53-61 (1994-07-01)
The radiochemical syntheses of the [4-14C]-(-)-trans-(5S,6S)-5-bromo-5- ethyl-6-methoxy-5,6-dihydro-2'-deoxyuridine [2,(5S,6S)-BMEDU] and (+)-trans-(5R,6R)-5-bromo-5-ethyl-6- methoxy-5,6-dihydro-2'-deoxyuridine [3,(5R,6R)-BMEDU] are reported. These BMEDU diastereomers were synthesized in 21 and 25% radiochemical yield, respectively, by direct addition of methyl hypobromite to the 5,6-olefinic bond of [4-14C]-5-ethyl-2'-deoxyuridine (EDU). The

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