G2536

Ganciclovir

≥99% (HPLC), powder

• Synonym(s): 2-Amino-1,9-dihydro-9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one, 9-(1,3-Dihydroxy-2-propoxymethyl)guanine, DHPG
• Empirical Formula (Hill Notation): C₉H₁₃N₅O₄
• CAS Number: 82410-32-0
• Molecular Weight: 255.23
• MDL number: MFCD00870588
• UNSPSC Code: 12352200
• PubChem Substance ID: 24278453
• NACRES: NA.77

Properties

• Quality Level: 300
• assay: ≥99% (HPLC)
• form: powder
• color: white
• solubility: 0.1 M HCl: 10 mg/mL
• ε (extinction coefficient): 12.0 at 256 nm at 1 mM
• antibiotic activity spectrum: viruses
• mode of action: DNA synthesis | interferes
• originator: Roche
• storage temp.: 2-8°C
• SMILES string: NC1=Nc2c(ncn2COC(CO)CO)C(=O)N1
• InChI: 1S/C9H13N5O4/c10-9-12-7-6(8(17)13-9)11-3-14(7)4-18-5(1-15)2-16/h3,5,15-16H,1-2,4H2,(H3,10,12,13,17)
• InChI key: IRSCQMHQWWYFCW-UHFFFAOYSA-N

Description

General description

Chemical structure: nucleoside

Application

Ganciclovir is used in molecular biology for selection against random recombination events when homologous recombination of a gene of interest is required.

Biochem/physiol Actions

Ganciclovir is a pro-drug nucleoside analog that is activated by phosphorylation. It is useful in the study of gene therapy in cancer research.
Upon expression of a viral suicide gene encoding thymidine kinase, the non-toxic pro-drug is converted to a phosphorylated active analog and is incorporated into the DNA of replicating eukaryotic cells, causing death of the malignant dividing cell. The cell cycle is irreversibly arrested at the G2-M checkpoint. Gap junction involvement in the ganciclovir bystander effect has been studied. Ganciclovir has been used to study loss of telomeres and to evaluate sensitivity of viruses to antiviral treatments.

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound was developed by Roche. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Preparation Note

Ganciclovir is soluble in 0.1 M HCl (10 mg/ml), DMSO (5 mg/ml), water (2 mg/ml), hot methanol, and ethanol (<1 mg/ml).
This product should be stored desiccated at 2-8 °C. Under these conditions the product is stable for 3 years.

Safety Information

• pictograms: GHS08
• signalword: Danger
• hcodes: H340 - H361fd
• pcodes: P201 - P202 - P280 - P308 + P313 - P405 - P501
• Hazard Classifications: Muta. 1B - Repr. 2
• Storage Class: 6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type P3 (EN 143) respirator cartridges