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E9386

Sigma-Aldrich

5-Ethyl-2′-deoxyuridine

Synonym(e):

EUdR, Edoxudine

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About This Item

Empirische Formel (Hill-System):
C11H16N2O5
CAS-Nummer:
15176-29-1
Molekulargewicht:
256.26
EG-Nummer:
239-226-1
MDL-Nummer:
MFCD00079191
UNSPSC-Code:
41106305
PubChem Substanz-ID:
24894696
NACRES:
NA.51

Biologische Quelle

synthetic (organic)

Assay

≥95% (HPLC)

Form

powder

Löslichkeit

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

Lagertemp.

−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)

InChIKey

XACKNLSZYYIACO-UHFFFAOYSA-N

Biochem./physiol. Wirkung

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.

Verlinkung

Homolog of thymidine

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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5-Jod-2′-desoxyuridin ≥99% (HPLC)

Sigma-Aldrich

I7125

5-Jod-2′-desoxyuridin

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
J R Nikoleit et al.
Annals of ophthalmology, 20(10), 385-387 (1988-10-01)
We investigated the toxicity of intravitreal zinc sulfate, zinc gluconate, and ethyldeoxyuridine (EDU) in albino rabbits. Various concentrations of EDU were added to the infusion solution during pars plana vitrectomy. Retinal changes were observed by light microscopy after intravitreal injections
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
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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