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Merck

SML2346

Ganciclovir

≥99% (HPLC), DMSO solution, viral DNA elongation inhibitor

Synonym(s):

Ganciclovir ready made solution, 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:
82410-32-0
Molecular Weight:
255.23
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD12197280

Key Documents

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Product Name

Ganciclovir ready made solution, ≥99% (HPLC), 10 mM in DMSO

SMILES string

[n]1(c2[nH]c(n[c](c2nc1)=O)N)COC(CO)CO

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

DMSO solution

concentration

10 mM in DMSO

storage temp.

2-8°C

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Application

Ganciclovir ready-made solution has been used in combination with resveratrol to study its effect on melanoma cells. It has also been used as a synthetic substrate for viral thymidine kinase to study its effects on human-inducible pluripotent stem cells.

Biochem/physiol Actions

Ganciclovir is a nucleoside guanosine analog that contains an active moiety, ganciclovir triphosphate. This active moiety can inhibit viral replication by interrupting the viral DNA during elongation. Ganciclovir is a potent agent in preventing cytomegalovirus (CMV) retinitis disease in human immunodeficiency virus (HIV) patients. It exhibits therapeutic effects against CMV disease involving the lungs, liver, and gastrointestinal tract. Ganciclovir can be enzymatically phosphorylated to an active triphosphate analog by herpes simplex virus thymidine kinase (HSV-TK) or host-encoded deoxyguanosine kinase. It has the potential to treat allogeneic bone marrow, kidney, heart, liver, and lung transplantations.

Other Notes

Ganciclovir ready made solution in DMSO is provided at 10mM concentration (2.55mg/mL). It is suggested to dilute the provided ready made solution to a working concentration of 2-100μM for cell culture applications.

pictograms

Health hazard
GHS08

signalword

Danger

hcodes

H340

Hazard Classifications

Muta. 1B

Storage Class

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

wgk

WGK 2

flash_point_f

188.6 °F - closed cup

flash_point_c

87 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
0000432865
0000432865
0000389715
0000389715
0000360327

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A Tseng et al.
The Canadian journal of infectious diseases = Journal canadien des maladies infectieuses, 7(3), 183-194 (1996-05-01)
To review the pharmacology and pharmacokinetics of intravenous, oral and intraocular ganciclovir, and to discuss the role of these various formulations in the management of cytomegalovirus (CMV) retinitis in AIDS patients. A MEDLINE search (1987 through November 1995) of English-language
Targeting of herpes simplex virus 1 thymidine kinase gene sequences into the OCT4 locus of human induced pluripotent stem cells.
Ou, et al.
PLoS ONE, 8, e81131-e81131 (2015)
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
J S Cannon et al.
Journal of virology, 73(6), 4786-4793 (1999-05-11)
Human herpesvirus 8 (HHV-8) sensitivity to the nucleoside analog ganciclovir (GCV) suggests the presence of a virally encoded kinase that catalyzes the initial phosphorylation of GCV. Analysis of the HHV-8 genome identified two candidate kinases: proteins encoded by open reading
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
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