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G2536

Sigma-Aldrich

Ganciclovir

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

Sinónimos:

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

Fórmula empírica (notación de Hill):
C9H13N5O4
Número de CAS:
82410-32-0
Peso molecular:
255.23
Número MDL:
MFCD00870588
Código UNSPSC:
12352200
ID de la sustancia en PubChem:
24278453
NACRES:
NA.77

Nombre del producto

Ganciclovir, ≥99% (HPLC), powder

Nivel de calidad

300

Ensayo

≥99% (HPLC)

Formulario

powder

color

white

solubilidad

0.1 M HCl: 10 mg/mL

ε (coeficiente de extinción)

12.0 at 256 nm at 1 mM

espectro de actividad antibiótica

viruses

Modo de acción

DNA synthesis | interferes

emisor

Roche

temp. de almacenamiento

2-8°C

cadena SMILES

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)

Clave InChI

IRSCQMHQWWYFCW-UHFFFAOYSA-N

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Descripción general

Chemical structure: nucleoside

Aplicación

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

Acciones bioquímicas o fisiológicas

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.

Características y beneficios

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.

Nota de preparación

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.

Pictogramas

Health hazard
GHS08

Palabra de señalización

Danger

Frases de peligro

H340,H361fd

Clasificaciones de peligro

Muta. 1B - Repr. 2

Código de clase de almacenamiento

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificados de análisis (COA)

Lot/Batch Number
0000365343
0000327960
0000365343
0000287003
0000227538

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Visite la Librería de documentos

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
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
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
L Z Rubsam et al.
Cancer research, 59(3), 669-675 (1999-02-11)
The ability of herpes simplex virus type 1 thymidine kinase (HSV-TK)-expressing cells incubated with ganciclovir (GCV) to induce cytotoxicity in neighboring HSV-TK-negative (bystander) cells has been well documented. Although it has been suggested that this bystander cell killing occurs through
Koenraad Smets et al.
European journal of pediatrics, 165(12), 885-890 (2006-06-21)
The objective of this study is to look for evidence based or scientific guidelines for selection of newborns with congenital cytomegalovirus (CMV) infection that might benefit from treatment with ganciclovir. A literature search was conducted involving the MEDLINE database and
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