78097-04-8

Basic information

• Product Name: 1-(2-Hydroxyethoxymethyl)uracil
• Synonyms: 1-(2-Hydroxyethoxymethyl)uracil;Acyclouridine;1-(2-hydroxyethoxymethyl)pyrimidine-2,4-dione
• CAS NO: 78097-04-8
• Molecular Formula: C₇H₁₀N₂O₄
• Molecular Weight: 186.1653
• Mol File: 78097-04-8.mol
• Article Data: 11

Chemical Properties

• Appearance: /
• Density: 1.351g/cm³
• Refractive Index: 1.528
• CAS DataBase Reference: 1-(2-Hydroxyethoxymethyl)uracil(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-Hydroxyethoxymethyl)uracil(78097-04-8)
• EPA Substance Registry System: 1-(2-Hydroxyethoxymethyl)uracil(78097-04-8)

Safety Data

• Hazardous Substances Data: 78097-04-8(Hazardous Substances Data)

Usage

Description

1-(2-Hydroxyethoxymethyl)uracil, commonly known as idoxuridine, is a nucleoside analog and antiviral medication derived from the chemical compound uracil. It possesses antiviral properties and is used to treat specific viral infections, particularly those caused by the herpes simplex virus. Idoxuridine functions by inhibiting the replication of viral DNA, thus preventing the spread and growth of the virus.

Uses

Used in Ophthalmology:
1-(2-Hydroxyethoxymethyl)uracil is used as a topical treatment for herpes simplex keratitis, a viral infection of the eye. It is administered in the form of eye drops or ointment to directly target the infection and alleviate symptoms. The application of idoxuridine helps to reduce the severity and duration of the infection, providing relief to the patient.
However, it is important to note that idoxuridine can cause side effects such as irritation and a burning sensation in the eyes. Therefore, its use should be under the supervision of a healthcare professional to ensure safe and effective treatment.

InChI:InChI=1/C7H10N2O4/c10-3-4-13-5-9-2-1-6(11)8-7(9)12/h1-2,10H,3-5H2,(H,8,11,12)

Upstream product

• 646-06-0 1,3-DIOXOLANE 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 
• 40510-88-1 1-acetoxy-2-chloromethoxyethane 
• 66-22-8 4-Hydroxy-1H-pyrimidin-2-one 
• 66-22-8 uracil 
• 78096-99-8 Benzoic acid 2-(4-ethoxy-2-oxo-2H-pyrimidin-1-ylmethoxy)-ethyl ester 
• 58305-05-8 (2-benzoyloxyethyl)oxymethyl chloride 
• 85446-60-2 1-(2-benzyloxyethoxymethyl)-uracil 
• 78097-03-7 1-<<2-(benzoyloxy)ethoxy>methyl>uracil 
• 80504-44-5 1,2-dihydro-4-methoxy-2-oxo-1-(2'-benzoyloxyethoxymethyl)pyrimidine 
• 81777-41-5 1-<(2-acetoxyethoxy)methyl>uracil 

Downstream Products

• 123027-47-4 1-<<2-(tert-butyldimethylsiloxy)ethoxy>methyl>-6-(phenylthio)uracil 
• 123027-52-1 1-<(2-hydroxyethoxy)methyl>-6-(phenylthio)uracil 
• 136632-02-5 1-<(2-hydroxyethoxy)methyl>-6-(phenylselenenyl)uracil 
• 136631-96-4 1-<<2-<(tert-butyldimethylsilyl)oxy>ethoxy>methyl>-6-(phenylselenenyl)uracil 
• 80504-52-5 2-((2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methoxy)ethyl 4-methylbenzenesulfonate 
• 80504-58-1 1-(2'-azidoethoxymethyl)uracil 
• 78692-74-7 1-<(2-hydroxyethoxy)methyl>-5-iodouracil 
• 78097-11-7 1-<(2-hydroxyethoxy)methyl>-5-bromouracil 
• 153081-01-7 1-<(2-hydroxyethoxy)methyl>-5-(phenylselenyl)uracil 

Relevant articles and documents

Design, modeling & synthesis of 1,2,3-triazole-linked nucleoside-amino acid conjugates as potential antibacterial agents

Copper-catalyzed azide-alkyne cycloadditions (CuAAC or click chemistry) are convenient methods to easily couple various pharmacophores or bioactive molecules. A new series of 1,2,3- Triazole-linked nucleoside-amino acid conjugates have been designed and synthesized in 57-76% yields using CuAAC. The azido group was introduced on the 50-position of uridine or the acyclic analogue using the tosyl-azide exchange method and alkylated serine or proparylglycine was the alkyne. Modeling studies of the conjugates in the active site of LpxC indicate they have promise as antibacterial agents.

Acyclic nucleoside analogues as inhibitors of Plasmodium falciparum dUTPase

We report the discovery of novel uracil-based acyclic compounds as inhibitors of deoxyuridine 5′-triphosphate nucleotidohydrolase (dUTPase), an enzyme involved in nucleotide metabolism that has been identified as a promising target for the development of

Potentiation of the antitumor effect of 5-fluoro-2'-deoxyuridine esters in combination with acyclothymidine esters on L1210 in mice via oral administration

Fifteen pyrimidine-related compounds were evaluated for their ability to inhibit enzymatic degradation of 5-fluoro-2'-deoxyuridine (FUdR). Acyclothymidine [5-methyl-1-(2'-hydroxyethoxymethyl)uracil] showed the highest inhibitory effect on the phosphorolytic degradation of FUdR in various tissue homogenates derived from mouse, rat, and beagle organs. Both the drug (FUdR) and the inhibitor (acyclothymidine) were esterified with appropriate aliphatic acids in order to synchronize their behavior after simultaneous oral administration. The antitumor activity of orally administered FUdR esters was potentiated by the simultaneous oral administration of the acyclothymidine esters, but not by acyclothymidine.