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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)

Quality Level

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)

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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
A Jeney et al.
European journal of cancer & clinical oncology, 22(5), 557-562 (1986-05-01)
The aim of this study was to explain why 5-ethyldeoxyuridine (EUdR) showed cytotoxic activity against Ehrlich ascites tumour (EAT) cells in vitro but not in vivo. In vitro studies showed that EUdR was phosphorylated to nucleotides which inhibit thymidylate synthetase
A M Cheraghali et al.
The Journal of pharmacy and pharmacology, 47(7), 595-600 (1995-07-01)
The accumulation of 5-ethyl-2'-deoxyuridine (EDU), (--)-trans-(5S,6S)-5-bromo-5-ethyl-6-methoxy-5,6- dihydro-2'-deoxyuridine [(5S,6S)-BMEDU], (+)-trans-(5R,6R) -5-bromo-ethyl-6-methoxy-5,6-dihydro- 2'-deoxyuridine [(5R,6R)-BMEDU], (+)-trans-(5R,6R)-5-bromo- 5-ethyl-6-ethoxy-5,6-dihydro-2'-deoxy- uridine (BEEDU), (+)-trans-(5R,6R)-5-bromo-5-ethyl-6-ethoxy -5,6-dihydro-5'-O-valeryl-2'deoxyuridine (VBEEDU) [formula: see text] and (+)-trans-(5R,6R)-5-bromo-5-ethyl-6-ethoxy-5, 6-dihydro-3'-5'-di-O-valeryl-2'-deoxyuridine [formula: see text] (DVBEEDU) in lung and other tissues was investigated in male Balb-C mice
A Megyeri et al.
Acta physiologica Hungarica, 84(3), 309-310 (1996-01-01)
It is supposed that the toxic effect of 5-fluorouracil (5FU) on tumour cells may be increased by pretreatment with ethyldeoxyuridine (EDU). We studied the effect of this combination on neutrophil count in mice. Our present studies demonstrated that the neutropenia
R Kaul et al.
Arzneimittel-Forschung, 39(3), 366-368 (1989-03-01)
The penetration of 5-ethyl-2'-deoxyuridine (edoxudine, Aedurid) from gel base with and without the addition of urea and other adjuvant has been studied in an in vitro model using guinea pig skin. The formulation of 3% edoxudine gel with 5% urea

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