Ganciclovir

Antiviral drug for CMV infections CAS# 82410-32-0

Ganciclovir

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Chemical structure

Ganciclovir

3D structure

Chemical Properties of Ganciclovir

Cas No. 82410-32-0 SDF Download SDF
PubChem ID 3454 Appearance Powder
Formula C9H13N5O4 M.Wt 255.23
Type of Compound N/A Storage Desiccate at -20°C
Synonyms BW 759; 2'-Nor-2'-deoxyguanosine
Solubility DMSO : 60 mg/mL (235.08 mM; Need ultrasonic)
H2O : 3.67 mg/mL (14.38 mM; Need ultrasonic)
Chemical Name 2-amino-9-(1,3-dihydroxypropan-2-yloxymethyl)-3H-purin-6-one
SMILES C1=NC2=C(N1COC(CO)CO)NC(=NC2=O)N
Standard InChIKey IRSCQMHQWWYFCW-UHFFFAOYSA-N
Standard InChI 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)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Ganciclovir

DescriptionGanciclovir is a potent inhibitor of viruses of the herpes family, including cytomegalovirus (CMV), with an IC50 of 5.2 μM for feline herpesvirus type-1 (FHV-1).In Vitro:Ganciclovir is an acyclic deoxyguanosine analog structurally similar to acyclovir but with superior activity against CMV. The median ganciclovir concentration required to inhibit viral replication by 50 percent is 2.15 mumol versus 72 mumol for acyclovir[2].The primary mechanism of ganciclovir action against CMV is inhibition of the replication of viral DNA by ganciclovir-5'-triphosphate (ganciclovir-TP). This inhibition includes a selective and potent inhibition of the viral DNA polymerase.Ganciclovir is metabolized to the triphosphate form by primarily three cellular enzymes: a deoxyguanosine kinase induced by CMV-infected cells; guanylate kinase; and phosphoglycerate kinase[3].In Vivo:In adult rats, the intracochlear diffusion of ganciclovir is shown to achieve the same concentration as in blood. In gestating mice, transplacental diffusion is observed, with a fetal-to-maternal blood ratio of 0.5. In newborn mice, the plasma concentration profile of ganciclovir shows a peak at 2 h followed by a gradual decrease. In adult mice, the concentration peaked at 1 h, but becomes undetectable by 2 h after injection. Counts of white blood cells, red blood cells and platelets decreases significantly in ganciclovir-treated newborn mice[4].

References:
[1]. Maggs DJ, et al. In vitro efficacy of ganciclovir, cidofovir, penciclovir, foscarnet, idoxuridine, and acyclovir against feline herpesvirus type-1. Am J Vet Res. 2004 Apr;65(4):399-403. [2]. Fletcher CV, et al. Evaluation of ganciclovir for cytomegalovirus disease. DICP. 1989 Jan;23(1):5-12. [3]. Matthews T, et al. Antiviral activity and mechanism of action of ganciclovir. Rev Infect Dis. 1988 Jul-Aug;10 Suppl 3:S490-4. [4]. BoujemLa I, et al. Pharmacokinetics and tissue diffusion of ganciclovir in mice and rats. Antiviral Res. 2016 Aug;132:111-5.

Protocol

Animal Administration [4]
Rats: Two albino rats non-immunized for MCMV are used in the study. After being weighed, two adult rats undergo peritoneal injections. The first rat receives 50 mg/kg of ganciclovir twice a day (i.e. 100 mg/kg/day), for a total of 3 days or 6 injections. The second rat is used as a negative control and received intraperitoneal injections of glucose solution. After the 6th injection, the two rats are sacrified; blood and perilymphatic fluids are collected for analysis[4]. Mice: Non-inbred Oncins France 1 (OF1) mice are used in the study. Ganciclovir is diluted in 5% glucose serum to a concentration of 5 mg/mL and administered intraperitoneally in newborn mice at a dose of 50 mg/kg twice a day. Five injections are administered in total[4].

References:
[1]. Maggs DJ, et al. In vitro efficacy of ganciclovir, cidofovir, penciclovir, foscarnet, idoxuridine, and acyclovir against feline herpesvirus type-1. Am J Vet Res. 2004 Apr;65(4):399-403. [2]. Fletcher CV, et al. Evaluation of ganciclovir for cytomegalovirus disease. DICP. 1989 Jan;23(1):5-12. [3]. Matthews T, et al. Antiviral activity and mechanism of action of ganciclovir. Rev Infect Dis. 1988 Jul-Aug;10 Suppl 3:S490-4. [4]. BoujemLa I, et al. Pharmacokinetics and tissue diffusion of ganciclovir in mice and rats. Antiviral Res. 2016 Aug;132:111-5.

Ganciclovir Dilution Calculator

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Ganciclovir Molarity Calculator

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Preparing Stock Solutions of Ganciclovir

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.918 mL 19.5902 mL 39.1803 mL 78.3607 mL 97.9509 mL
5 mM 0.7836 mL 3.918 mL 7.8361 mL 15.6721 mL 19.5902 mL
10 mM 0.3918 mL 1.959 mL 3.918 mL 7.8361 mL 9.7951 mL
50 mM 0.0784 mL 0.3918 mL 0.7836 mL 1.5672 mL 1.959 mL
100 mM 0.0392 mL 0.1959 mL 0.3918 mL 0.7836 mL 0.9795 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Ganciclovir

Ganciclovir (DHPG) is a potent antiviral drug used to treatment of cytomegalovirus (CMV) infections [1].

Ganciclovir (DHPG) is a nucleoside analogue and has shown the activity against viral thymidine kinase (tk) in the Herpesviridae family, including human cytomegalovirus and herpes simplex virus types I and II as well as Epstein-Barr virus. In addition, Ganciclovir has been reported to inhibit the proliferation of uninfected cells, most significantly of bone marrow cells, because of the function of inhibiting viral replication. Apart from these, Ganciclovir has been revealed to reduce the activation of microglial in wild-type C57BL/6 mice and inhibit proliferation of microglial in wild-type FvB mice [1].

References:
[1] Ding Z1, Mathur V, Ho PP, James ML, Lucin KM, Hoehne A, Alabsi H, Gambhir SS, Steinman L, Luo J, Wyss-Coray T. Antiviral drug ganciclovir is a potent inhibitor of microglial proliferation and neuroinflammation. J Exp Med. 2014 Feb 10; 211(2):189-98.

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References on Ganciclovir

Combined environmental risk assessment for the antiviral pharmaceuticals ganciclovir and valganciclovir in Europe.[Pubmed:28198039]

Environ Toxicol Chem. 2017 Aug;36(8):2205-2216.

Potential environmental risks of the old antiviral pharmaceuticals Ganciclovir (GCV) and valGanciclovir (VGCV) were reassessed based on new environmental fate and chronic ecotoxicity tests and on actual use data for Europe. ValGanciclovir is hydrolyzed to GCV by intestinal and hepatic esterases, and hence the new environmental tests only refer to GCV. A sorption study showed that GCV will not sorb significantly, excluding the soil as a relevant environmental compartment. Despite earlier data suggesting nondegradability, a new water/sediment fate test showed GCV to be primarily and ultimately degraded and to be nonpersistent. The chronic ecotoxicity tests with algae and daphnids resulted in no inhibition at the highest tested concentrations, whereas a fish partial life cycle test, selected in view of mammalian mutagenicity and reprotoxicity data, showed effects on growth of the young fish, but not on gametogenesis, fertilization, embryogenesis, or teratogenicity. Predicted environmental concentrations were derived based on actual per capita use data for European countries for 2004 to 2014, and the highest was selected for the risk assessment. A comparison of predicted environmental concentrations with predicted no-effect concentrations shows no significant risk for wastewater treatment, surface waters, groundwater, or sediment. In addition, potential risks to (semi)aquatic top predators or to human consumers of water and fish are exceedingly low. Environ Toxicol Chem 2017;36:2205-2216. (c) 2017 The Author. Environmental Toxicology and Chemistry Published by Wiley Periodicals, Inc. on behalf of SETAC.

[Intravitreal ganciclovir as an additional therapy option in acute retinal necrosis].[Pubmed:28105484]

Ophthalmologe. 2017 Sep;114(9):838-842.

Acute retinal necrosis (ARN) is a rare viral inflammatory disease, characterized by uveitis, retinal vasculitis, and necrosis in the late stages. Therapeutic management is based on the clinical findings. The positive outcome in our patient (VA 0.6) indicates that, beside the management of retinal detachment and lens opacification, additional intravitreal injections of 2 mg Ganciclovir may achieve better results than systemic/topical antiviral application alone.

Risk Factors and Outcomes of Ganciclovir-Resistant Cytomegalovirus Infection in Solid Organ Transplant Recipients.[Pubmed:28369203]

Clin Infect Dis. 2017 Jul 1;65(1):57-63.

Background: Ganciclovir-resistant (ganR) cytomegalovirus (CMV) is an emerging and important problem in solid organ transplant (SOT) recipients. Only through direct comparison of ganR- and Ganciclovir-sensitive (ganS) CMV infection can risk factors and outcomes attributable specifically to Ganciclovir resistance appropriately be determined. Methods: We performed a retrospective, case-control (1:3) study of SOT recipients with genotypically confirmed ganR-CMV (n = 37) and ganS-CMV infection (n = 109), matched by donor/recipient CMV serostatus, year and organ transplanted, and clinical manifestation. We used chi2 (categorical) and Mann-Whitney (continuous) tests to determine predisposing factors and morbidity attributable to resistance, and Kaplan-Meier plots to analyze survival differences. Results: The rate of ganR-CMV was 1% (37/3467) overall and 4.1% (32/777) among CMV donor-positive, recipient-negative patients, and was stable over the study period. GanR-CMV was associated with increased prior exposure to Ganciclovir (median, 153 vs 91 days, P < .001). Eighteen percent (3/17) of lung transplant recipients with ganR-CMV had received <6 weeks of prior Ganciclovir (current guideline-recommended resistance testing threshold), and all non-lung recipients had received >/=90 days (median, 160 [range, 90-284 days]) prior to diagnosis of ganR-CMV. GanR-CMV was associated with higher mortality (11% vs 1%, P = .004), fewer days alive and nonhospitalized (73 vs 81, P = .039), and decreased renal function (42% vs 19%, P = .008) by 3 months after diagnosis. Conclusions: GanR-CMV is associated with longer prior antiviral duration and higher attributable morbidity and mortality than ganS-CMV. Upcoming revised CMV guidelines should incorporate organ transplant-specific thresholds of prior drug exposure to guide rational ganR-CMV testing in SOT recipients. Improved strategies for prevention and treatment of ganR-CMV are warranted.

Description

Ganciclovir is a potent herpes simplex virus (HSV)inhibitor, including cytomegalovirus (CMV), with an IC50 of 5.2 μM for feline herpesvirus type-1 (FHV-1).

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