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G2536

Sigma-Aldrich

Ganciclovir

≥99% (HPLC), powder

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
Empirical Formula (Hill Notation):
C9H13N5O4
CAS Number:
Molecular Weight:
255.23
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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

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This Item
3457001288306Y0001129
Ganciclovir ≥99% (HPLC), powder

Sigma-Aldrich

G2536

Ganciclovir

Ganciclovir A nucleoside analog structurally related to Acyclovir.

Sigma-Aldrich

345700

Ganciclovir

Ganciclovir United States Pharmacopeia (USP) Reference Standard

USP

1288306

Ganciclovir

Ganciclovir European Pharmacopoeia (EP) Reference Standard

Y0001129

Ganciclovir

form

powder

form

solid

form

-

form

-

color

white

color

white

color

-

color

-

solubility

0.1 M HCl: 10 mg/mL

solubility

water: 2 mg/mL, DMSO: 5 mg/mL

solubility

-

solubility

-

originator

Roche

originator

-

originator

-

originator

-

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

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.

Pictograms

Health hazard

Signal Word

Danger

Hazard Statements

Hazard Classifications

Muta. 1B - Repr. 2

Storage Class Code

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

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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T1503
Product Number
-
25G
Pack Size/Quantity

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705578-5MG-PW

PL860-CGA/SHF-1EA

MMYOMAG-74K-13

1000309185

enter as 1.000309185)

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Acycloguanosine ≥99% (HPLC), powder

Sigma-Aldrich

A4669

Acycloguanosine

Sigma-Aldrich

Sigma-Aldrich

C2235

CB 1954

Acyclovir Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1254

Acyclovir

Aciclovir European Pharmacopoeia (EP) Reference Standard

A0220000

Aciclovir

Penciclovir

Sigma-Aldrich

P0035

Penciclovir

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
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
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
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
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

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