145986-11-4

Basic information

• Product Name: Oxathiolan 5fu-.B.
• Synonyms: 2,4(1H,3H)-Pyrimidinedione, 5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-, (2R-cis)-;Aids004772;Aids-004772;Oxathiolan 5fu-.B.;cis 5-Fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)- pyrimidinedione;(2R-cis)-5-Fluoro-1-[2-(hydroxyMethyl)-1,3-oxathiolan-5-yl]-2,4(1H,3H)-pyriMidinedione;EMtricitabine iMpurity (2,3'-dideoxy-5-fluoro-3-thiouridine);Emtricitabine Impurity IV 5-fluoro-1-[(2R,5S)-2-(hydroxymethyl)-1,3-oxathiolan-5-yl]uracil
• CAS NO: 145986-11-4
• Molecular Formula: C8H9FN2O4S
• Molecular Weight: 248.2314632
• Product Categories: Bases & Related Reagents;Drug Analogues;Heterocycles;Nucleotides;Sulfur & Selenium Compounds;Drug Analogues, Heterocycles, Nucleotides, Bases & Related Reagents, Sulfur & Selenium Compounds
• Mol File: 145986-11-4.mol
• Article Data: 1

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.65g/cm³
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Ethanol (Slightly, Heated), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: Oxathiolan 5fu-.B.(CAS DataBase Reference)
• NIST Chemistry Reference: Oxathiolan 5fu-.B.(145986-11-4)
• EPA Substance Registry System: Oxathiolan 5fu-.B.(145986-11-4)

Safety Data

• Hazardous Substances Data: 145986-11-4(Hazardous Substances Data)

Usage

Description

Oxathiolan 5fu-.B. is an antiviral nucleoside analog that is also recognized as an impurity found in emtricitabine (E525000). It is a white solid with significant potential in the pharmaceutical industry due to its antiviral properties.

Uses

Used in Pharmaceutical Industry:
Oxathiolan 5fu-.B. is used as an antiviral agent for its ability to inhibit viral replication and reduce the severity of viral infections. Its role as an impurity in emtricitabine highlights its potential in the development of antiviral medications and therapies.
Used in Research and Development:
In the field of research and development, Oxathiolan 5fu-.B. serves as a valuable compound for studying the mechanisms of viral replication and the development of antiviral drugs. Its presence in emtricitabine provides insights into the interactions between different compounds and their effects on viral activity.
Used in Quality Control and Impurity Profiling:
Oxathiolan 5fu-.B. is used in the quality control processes of pharmaceutical manufacturing, specifically in the assessment and management of impurities in emtricitabine. This helps ensure the safety, efficacy, and overall quality of the final drug product.
Used in Drug Synthesis:
As an antiviral nucleoside analog, Oxathiolan 5fu-.B. may also be utilized in the synthesis of new antiviral drugs, potentially leading to the development of more effective treatments for various viral infections.

Relevant articles and documents

Asymmetric Synthesis and Biological Evaluation of β-L-(2R,5S)- and α-L-(2R,5R)-1,3-Oxathiolane-Pyrimidine and -Purine Nucleosides as Potential Anti-HIV Agents

In order to study the structure-acivity relationships of L-oxathiolanyl nucleosides as potential anti-HIV agents, a series of enantiomerically pure L-oxathiolanyl pyrimidine and purine nucleosides were synthesized and evaluated for anti-HIV-1 activity in human peripheral blood mononuclear (PBM) cells.The key intermediate 8 was synthesized starting from L-gulose via 1,6-thiaanhydro-L-gulopyranose.The acetate 8 was condensed with thymine, 5-substituted uracils and cytosines, 6-chloropurine, and 6-chloro-2-fluoropurine to give pyrimidine and purine nucleosides.Upon evaluation of these final nucleosides, the 5-fluorocytosine derivative 51 was found to be the most potent compound among those tested.In the case of 5-substituted cytosine analogues, the antiviral potency was found to be in the following decreasing order: cytosine (β-isomer) > 5-iodocytosine (β-isomer) > 5-fluorocytosine (α-isomer) > 5-methylcytosine (α-isomer) > 5-methylcytosine (β-isomer) > 5-bromocytosine (β-isomer) > 5-chlorocytosine (β-isomer).Among the thymine, uracil, and 5-substituted uracil derivatives, thymine (α-isomer) and uracil (β-isomer) derivatives exhibited moderate anti-HIV activity.In the purine series, the antiviral potency is found to be in the following decreasing order: adenine (β-isomer) > 6-chloropurine (β-isomer) > 6-chloropurine (α-isomer) > 2-NH2-6-Cl-purine (β-isomer) > guanine (β-isomer) > N6-methyladenine (α-isomer) > N6-methyladenine (β-isomer).The cytotoxicity was also determined in human PBM cells as well as Vero cells.None of the synthesized nucleosides was toxic up to 100 μ in PBM cells.