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Merck
CN

G2536

Ganciclovir

≥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:
Molecular Weight:
255.23
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77
MDL number:
Assay:
≥99% (HPLC)
Form:
powder
Quality level:
Technical Service
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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.

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.
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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pictograms

Health hazard

signalword

Danger

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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Articles

DNA损伤和修复机制对于维持DNA完整性至关重要。细胞DNA的损伤与突变、癌症发展等有关。

DNA damage and repair mechanism is vital for maintaining DNA integrity. Damage to cellular DNA is involved in mutagenesis, the development of cancer among others.

Bioactive small molecules for immune system signaling target identification/validation and antibiotics, antivirals, and antifungals offered.

View All Articles

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
J K McGavin et al.
Drugs, 61(8), 1153-1183 (2001-07-24)
Ganciclovir is a nucleoside guanosine analogue which incorporates ganciclovir triphosphate (the active moiety) into DNA during elongation, thereby inhibiting viral replication. Comparative studies of pre-emptive and prophylactic ganciclovir therapies in bone marrow transplant (BMT) recipients have shown similar rates of
Takashi E Komatsu et al.
Antiviral research, 101, 12-25 (2013-11-05)
Human cytomegalovirus (HCMV) is a pathogen that can be life-threatening in immunocompromised individuals. Valganciclovir and its parent drug ganciclovir are currently the principle drugs used for the treatment or prevention of HCMV disease. The development of HCMV resistance to ganciclovir/valganciclovir



Global Trade Item Number

SKUGTIN
G2536-100MG04061833629017