G2536

Ganciclovir

Name: Ganciclovir
Brand: SIGMA

≥99% (HPLC), powder, viral DNA elongation inhibitor

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

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₃N₅O₄

CAS Number:

82410-32-0

Molecular Weight:

255.23

UNSPSC Code:

12352200

PubChem Substance ID:

24278453

NACRES:

NA.77

MDL number:

MFCD00870588

Product Name

Ganciclovir, ≥99% (HPLC), powder

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

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

Quality Level

300

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Preparation Note

Ganciclovir is tested for solubility in 0.1M HCl at 10 mg/mL. The compound is also soluble in DMSO at 5 mg/mL.

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.

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.

General description

Chemical structure: nucleoside

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

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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Partial Ablation of Non-Myogenic Progenitor Cells as a Therapeutic Approach to Duchenne Muscular Dystrophy.

Zhanguo Gao et al.

Biomolecules, 11(10) (2021-10-24)

Duchenne muscular dystrophy (DMD), caused by the loss of dystrophin, remains incurable. Reduction in muscle regeneration with DMD is associated with the accumulation of fibroadipogenic progenitors (FAPs) differentiating into myofibroblasts and leading to a buildup of the collagenous tissue aggravating

Cytomegalovirus UL97 mutations in the era of ganciclovir and maribavir.

Sunwen Chou

Reviews in medical virology, 18(4), 233-246 (2008-04-03)

Mutations in the human CMV UL97 kinase gene are a major mechanism of viral resistance to two anti-CMV drugs, ganciclovir (GCV) and maribavir (MBV). GCV, the most widely used and established therapy for CMV, is a substrate for the UL97

Ganciclovir in solid organ transplant recipients: is there a role for clinical pharmacokinetic monitoring?

Julie Cates Scott et al.

Therapeutic drug monitoring, 26(1), 68-77 (2004-01-30)

The authors use a previously published decision-making algorithm to address the role of clinical pharmacokinetic monitoring of ganciclovir, the drug of choice for prophylaxis and treatment of cytomegalovirus (CMV) in solid organ transplant recipients. Ganciclovir pharmacokinetics have been studied in

Hepatitis B virus variants with lamivudine-related mutations in the DNA polymerase and the 'a' epitope of the surface antigen are sensitive to ganciclovir.

C J Oon et al.

Antiviral research, 41(3), 113-118 (1999-05-13)

Lamivudine is a new antiviral agent effective against hepatitis B viral (HBV) infections but can result in virus-drug resistance associated with mutations in the conserved 'YM552DD' motif of the HBV DNA polymerase. Due to their overlapping coding regions in the

Chromosome healing in mouse embryonic stem cells.

C N Sprung et al.

Proceedings of the National Academy of Sciences of the United States of America, 96(12), 6781-6786 (1999-06-09)

The addition of new telomeres to the ends of broken chromosomes, termed chromosome healing, has been extensively studied in unicellular organisms; however, its role in the mammalian cell response to double-strand breaks is unknown. A system for analysis of chromosome

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