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Merck

G2536

Ganciclovir

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

Synonyme(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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A propos de cet article

Formule empirique (notation de Hill) :
C9H13N5O4
Numéro CAS:
82410-32-0
Poids moléculaire :
255.23
UNSPSC Code:
12352200
PubChem Substance ID:
24278453
NACRES:
NA.77
MDL number:
MFCD00870588
Assay:
≥99% (HPLC)
Form:
powder
Quality level:
300

Principaux documents

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Nom du produit

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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Catégories apparentées

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

Health hazard
GHS08

signalword

Danger

Hazard Classifications

Muta. 1B - Repr. 2

Classe de stockage

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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Certificats d'analyse (COA)

Lot/Batch Number
0000365343
0000327960
0000327960
0000365343
0000287003

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Consulter la Bibliothèque de documents

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
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
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
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