E9386
5-Ethyl-2′-deoxyuridine
Synonym(s):
EUdR, Edoxudine
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All Photos(3)
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
Recommended Products
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)
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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.
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
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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