GCV

Ganciclovir
Cat. No.
BT1760
Source
Synonyms
Appearance
Sterile Filtered White lyophilized (freeze-dried) powder.
Purity
Greater than 99.0%.
Usage
Prospec's products are furnished for LABORATORY RESEARCH USE ONLY. The product may not be used as drugs, agricultural or pesticidal products, food additives or household chemicals.
Shipped with Ice Packs
In Stock

Description

Ganciclovir is a white to off-white crystalline powder with a molecular formula of C9H13N5O4 and a molecular weight of 255.23.

Product Specs

Introduction
Ganciclovir (GCV) is a pro-drug nucleoside analog that requires phosphorylation for activation. It is a valuable tool in cancer research, particularly in gene therapy studies. GCV is structurally similar to 2'-deoxy-guanosine and functions by being phosphorylated into a deoxyguanosine triphosphate (dGTP) analog. This analog competitively inhibits the incorporation of dGTP by viral DNA polymerase, effectively halting viral DNA elongation. When a viral suicide gene encoding thymidine kinase is expressed, it converts the non-toxic pro-drug GCV into its active phosphorylated form. This active form is then integrated into the DNA of replicating eukaryotic cells, leading to the death of the dividing malignant cell. This process results in irreversible cell cycle arrest at the G2-M checkpoint. The role of gap junctions in the bystander effect of ganciclovir has been a subject of investigation. Furthermore, GCV has been employed to study telomere loss and assess viral sensitivity to antiviral therapies. In molecular biology, GCV is utilized to select against random recombination events, particularly when homologous recombination of a specific gene is desired.
Description
Ganciclovir is a white to off-white crystalline powder. Its molecular formula is C9H13N5O4, and its molecular weight is 255.23.
Physical Appearance
White lyophilized (freeze-dried) powder that has been sterilized by filtration.
Solubility
To reconstitute the lyophilized Ganciclovir, it is recommended to dissolve it in sterile 18 megaohm-cm H2O at a concentration of at least 100 micrograms per milliliter. This solution can then be further diluted in other aqueous solutions as needed.
Stability
While lyophilized Ganciclovir remains stable at room temperature for up to 3 weeks, it is recommended to store it at 4 degrees Celsius for optimal long-term stability.
Purity
Greater than 99.0% pure.

Product Science Overview

Introduction

Ganciclovir is an antiviral medication primarily used to treat cytomegalovirus (CMV) infections. It is particularly effective in immunocompromised individuals, such as those with AIDS or those who have undergone organ transplants . Ganciclovir is marketed under various brand names, including Cytovene, Cymevene, and Vitrasert .

History and Development

Ganciclovir was patented in 1980 and approved for medical use in 1988 . It was developed as a potent inhibitor of herpesvirus DNA replication, making it a valuable tool in the treatment of CMV infections . The drug’s development was driven by the need for effective antiviral therapies for immunocompromised patients who are particularly vulnerable to CMV infections.

Chemical Structure and Properties

Ganciclovir is a synthetic analog of 2’-deoxy-guanosine, a component of DNA. Its chemical formula is C9H13N5O4, and it has a molar mass of 255.234 g/mol . The drug is metabolized to its active triphosphate form by cellular enzymes, which then inhibits viral DNA polymerase more effectively than cellular polymerase .

Mechanism of Action

Ganciclovir’s antiviral activity is highly selective. It requires conversion to its active form by a virus-encoded enzyme, thymidine kinase (TK), which is present in CMV-infected cells . Once activated, ganciclovir triphosphate inhibits viral DNA polymerase, preventing the replication of viral DNA and thereby controlling the infection .

Preparation Methods

Ganciclovir is available in various forms, including intravenous (IV) infusion, oral capsules, and intravitreal implants . The IV form is typically used for severe infections and is prepared by reconstituting a dry powder equivalent to 500 mg of ganciclovir in a sterile environment . The reconstituted solution is then administered via a volumetric pump over one hour to minimize venous irritation .

Clinical Uses

Ganciclovir is indicated for the treatment of:

  • CMV retinitis in severely immunocompromised individuals
  • CMV pneumonitis in bone marrow transplant recipients
  • Prevention of CMV disease in bone marrow and solid organ transplant recipients
  • Acute CMV colitis in HIV/AIDS patients

It has also been used with some success in treating Human herpesvirus 6 infections and herpes simplex virus epithelial keratitis .

Adverse Effects

Ganciclovir is associated with a range of serious hematological adverse effects, including granulocytopenia, neutropenia, anemia, and thrombocytopenia . Other common side effects include fever, nausea, vomiting, diarrhea, abdominal pain, and increased liver enzymes . Due to its potential carcinogenic, teratogenic, and mutagenic effects, ganciclovir is handled as a cytotoxic drug in clinical settings .

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