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General Description:

Edoxudine, identified by CAS number 15176-29-1, is a notable compound with significant therapeutic applications. Edoxudine is a deoxythymidine analog with activity against herpes simplex virus. It is a potent and selective inhibitor of herpes simplex virus type 1 and 2. The obtained product is an antiviral ointment. The activity of edoxudine against herpes simplex virus was first recognized in 1967. It was later recognized to be effective in vivo in a preclinical model of keratitis caused by herpes virus. It was developed by McNeil Pharmaceutical and approved by Health Canada on December 31, 1992. This medication was later discontinued from the market in 1998.

Indications:

This drug is primarily indicated for: Edoxudine was used in Europe, in the form of a topical antiviral, for the treatment of human herpes keratitis. Human herpes keratitis is an inflammation of the cornea in the eye caused by herpes simplex virus infection. This infection is a cause of significant morbidity whose incidence is significantly increased in the presence of recurrent infection and it can even produce corneal blindness. Edoxudine 3% cream was also indicated for the treatment of dermal herpes simplex virus. This virus can produce an infection ubiquitously and it is highly contagious. There are two types of herpes virus, type 1 that is mainly transmitted by oral-to-oral contact and type 2 that is sexually transmitted. Its use in specific medical scenarios underscores its importance in the therapeutic landscape.

Metabolism:

Edoxudine undergoes metabolic processing primarily in: In preclinical trials it has been reported that edoxudine presents a biotransformation marked by a cleavage of the glycoside bond. The degradation of edoxudine, after oral administration, seems to be processed by the activity of phosphorylases presented in the gastrointestinal tract and by pre-systemic metabolism. This metabolic pathway ensures efficient processing of the drug, helping to minimize potential toxicity and side effects.

Absorption:

The absorption characteristics of Edoxudine are crucial for its therapeutic efficacy: Edoxudine cream is able to penetrate the skin in a very rapid manner. This easy penetration allows edoxudine to have a greater activity when compared with other topical antivirals that have better antiviral activity in vitro. In preclinical trials in mice, after intravenous administration of edoxudine, the mean residence time was 25 min. Edoxudine presented a bioavailability of 49% with a Cmax and tmax of 2.4 mcg/g and 31.1 min respectively. The AUC in plasma of edoxudine is significantly higher when administered orally when compared with intravenous administration. The drug's ability to rapidly penetrate into cells ensures quick onset of action.

Half-life:

The half-life of Edoxudine is an important consideration for its dosing schedule: In preclinical trials on mice, after intravenous administration, edoxudine presented a very short distribution half-life of 1.4 min. In the same trials, the elimination half-life was reported to be of 24.1 min. This determines the duration of action and helps in formulating effective dosing regimens.

Protein Binding:

Edoxudine exhibits a strong affinity for binding with plasma proteins: The plasma protein binding of edoxudine is very low and it is reported to be of about 7%. It is mainly found in a bound state to albumin. This property plays a key role in the drug's pharmacokinetics and distribution within the body.

Volume of Distribution:

Edoxudine is distributed throughout the body with a volume of distribution of: This pharmacokinetic property is not available. This metric indicates how extensively the drug permeates into body tissues.

Clearance:

The clearance rate of Edoxudine is a critical factor in determining its safe and effective dosage: The plasma clearance of edoxudine is reported to be 85 ml/min. It reflects the efficiency with which the drug is removed from the systemic circulation.

Pharmacodynamics:

Edoxudine exerts its therapeutic effects through: In reports, it has been indicated that at antivirally active doses, edoxudine is phosphorylated to a much greater extent by hepatitis-infected cells when compared to mock-infected cells. Once phosphorylated, edoxudine is more highly incorporated into viral DNA than cellular DNA. The level of incorporation into viral DNA highly seems to be correlated with the concentration of edoxudine. The suppression of viral DNA synthesis caused a shutoff of viral replication and the viral titration is significantly reduced.The effect of edoxudine is also proven to reduce significantly the lesion area produced by the viral activity to an even 44% reduction. The drug's ability to modulate various physiological processes underscores its efficacy in treating specific conditions.

Mechanism of Action:

Edoxudine functions by: Edoxudine is a potent inhibitor of the replication of herpes simplex virus type 1 and 2. For the activation of this drug, the action of viral thymidine kinase is required to phosphorylate this molecule in order to form the 5'-monophosphate derivative. Then, it is needed to be further phosphorylated by cellular enzymes until the formation of the 5'-triphosphate derivative which is a competitive inhibitor of the viral-coded DNA polymerase. The advantage of edoxudine is that it is highly selective, this characteristic can be seen by its preferential phosphorylation in herpes-infected cells and its preferential incorporation into viral DNA. This mechanism highlights the drug's role in inhibiting or promoting specific biological pathways, contributing to its therapeutic effects.

Toxicity:

Classification:

Edoxudine belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. These are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2, classified under the direct parent group Pyrimidine 2'-deoxyribonucleosides. This compound is a part of the Organic compounds, falling under the Nucleosides, nucleotides, and analogues superclass, and categorized within the Pyrimidine nucleosides class, specifically within the Pyrimidine 2'-deoxyribonucleosides subclass.

Categories:

Edoxudine is categorized under the following therapeutic classes: Anti-Infective Agents, Antiviral Agents, Deoxyribonucleosides, Dermatologicals, Nucleic Acids, Nucleotides, and Nucleosides, Nucleosides, Pyrimidine Nucleosides, Pyrimidines. These classifications highlight the drug's diverse therapeutic applications and its importance in treating various conditions.

Experimental Properties:

Further physical and chemical characteristics of Edoxudine include:

• Water Solubility: >38.4 mcg/ml
• Melting Point: 153 ºC
• logP: -1.09
• pKa: 9.98