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G2536

Sigma-Aldrich

Ganciclovir

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

Sinonimo/i:

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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CHF 658.00

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CHF 658.00

About This Item

Formula empirica (notazione di Hill):
C9H13N5O4
Numero CAS:
Peso molecolare:
255.23
Numero MDL:
Codice UNSPSC:
12352200
ID PubChem:
NACRES:
NA.77

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Nome del prodotto

Ganciclovir, ≥99% (HPLC), powder

Livello qualitativo

Saggio

≥99% (HPLC)

Stato

powder

Colore

white

Solubilità

0.1 M HCl: 10 mg/mL

ε (coefficiente d’estinzione)

12.0 at 256 nm at 1 mM

Spettro attività antibiotica

viruses

Modalità d’azione

DNA synthesis | interferes

Ideatore

Roche

Temperatura di conservazione

2-8°C

Stringa SMILE

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)
IRSCQMHQWWYFCW-UHFFFAOYSA-N

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Descrizione generale

Chemical structure: nucleoside

Applicazioni

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

Azioni biochim/fisiol

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.[1] The cell cycle is irreversibly arrested at the G2-M checkpoint.[2] Gap junction involvement in the ganciclovir bystander effect has been studied.[3] Ganciclovir has been used to study loss of telomeres[4] and to evaluate sensitivity of viruses to antiviral treatments.[5]

Caratteristiche e vantaggi

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 sulla preparazione

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.

Pittogrammi

Health hazard

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Muta. 1B - Repr. 2

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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


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Sigma-Aldrich

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Sigma-Aldrich

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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
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
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
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

Articoli

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.

Discover Bioactive Small Molecules for ADME/Tox

Questions

1–3 of 3 Questions  
  1. Can Ganciclovir G2536 be dissolved in DMSO for in vitro testing?

    1 answer
    1. Yes, Ganciclovir G2536 can be dissolved in DMSO for in vitro application. Additionally, Ganciclovir is available in SML2346 as a ready-made DMSO solution, which is directly applicable for in vitro application.

      Helpful?

  2. can ganciclovir be dissolved in PBS or saline? can ganciclovir be neutralized by 0.1M NaOH after dissolving in 0.1M HCl

    1 answer
    1. Product G2536, Ganciclovir is tested for solubility in 0.1M HCl at 10 mg/mL. The compound is also soluble in DMSO at 5 mg/mL. While pH adjustment for neutralization has not been tested, this is a typical practice in pharmaceutical-grade solutions for injection. It is anticipated that no issues would arise regarding stability or precipitation.

      See below for a link to a typical product insert, page 14 under Description:
      https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/209347lbl.pdf

      Helpful?

  3. Can ganciclovir be resuspended in solutions other than HCl? If so, what is the solubility and storage condition? Thank you.

    1 answer
    1. References state that this chemical 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.

      Helpful?

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