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About This Item
Empirical Formula (Hill Notation):
C9H13N5O4
CAS Number:
Molecular Weight:
255.23
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Product Name
Ganciclovir, ≥99% (HPLC), powder
Quality Level
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
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.
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.
This product should be stored desiccated at 2-8 °C. Under these conditions the product is stable for 3 years.
Ganciclovir is tested for solubility in 0.1M HCl at 10 mg/mL. The compound is also soluble in DMSO at 5 mg/mL.
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signalword
Danger
hcodes
Hazard Classifications
Muta. 1B - Repr. 2
Storage Class
6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
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