Synonym
2'-Nor-2'-deoxyguanosine, BW 759, Ganciclovir
IUPAC/Chemical Name
2-amino-1,9-dihydro-9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one
InChi Key
IRSCQMHQWWYFCW-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=C(N=C(N)N1)C2=C1N(C=N2)COC(CO)CO
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Ganciclovir (RS-21592, BW-759, 2'-Nor-2'-deoxyguanosine) is an antiviral drug for feline herpesvirus type-1 with IC50 of 5.2 μM in
a cell-free assay.
In vitro activity:
A correlation was found between the dose of ganciclovir exposure and a decrease in total cell number when duration exceeded 2 days
(r(2)=0.92 and 0.93 after 7 and 14 days, respectively). High levels (20 mg/l) of ganciclovir were not more toxic than lowest levels (1
mg/l) for the shortest durations of ganciclovir exposure (1 and 2 days). Moreover, 50% cytotoxic concentrations markedly decreased
with the duration of ganciclovir exposure (374-3 mg/l from 1 to 14 days respectively) after 14 days of culture.
Reference: Antivir Chem Chemother. 2009;19(6):257-62. https://pubmed.ncbi.nlm.nih.gov/19641234/
In vivo activity:
Ganciclovir (GCV)-treated CMV-infected mice had lower ABR (P < 0.0001, Kruskal-Wallis test) and DPOAE (P < 0.0001)
thresholds compared to CMV-infected untreated mice, indicating that GCV protected mice from CMV-induced hearing loss. Viral
load in infected populations undergoing GCV treatment was significantly decreased (P = 0.03) relative to untreated mice. GCV
treatment alone had no effect on ABR and DPOAE compared to untreated, uninfected controls (P = 0.1, P = 0.24, respectively). GCVtreated mice received increased protection from OHC loss when compared to untreated groups, with total OHC losses of
approximately 7% and 14%, respectively (P < 0.05). Neutropenia was absent after 7 days of GCV treatment.
Reference: Laryngoscope. 2020 Apr;130(4):1064-1069. https://pubmed.ncbi.nlm.nih.gov/31184781/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
36.8 |
144.09 |
|
| Water |
1.7 |
6.54 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
255.23
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Janoly-Dumenil A, Rouvet I, Bleyzac N, Bertrand Y, Aulagner G, Zabot MT. Effect of duration and intensity of ganciclovir
exposure on lymphoblastoid cell toxicity. Antivir Chem Chemother. 2009;19(6):257-62. doi: 10.1177/095632020901900605. PMID:
19641234.
2. Ding Z, 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. doi:
10.1084/jem.20120696. Epub 2014 Feb 3. PMID: 24493798; PMCID: PMC3920559.
3. Haller TJ, Price MS, Lindsay SR, Hillas E, Seipp M, Firpo MA, Park AH. Effects of ganciclovir treatment in a murine model of
cytomegalovirus-induced hearing loss. Laryngoscope. 2020 Apr;130(4):1064-1069. doi: 10.1002/lary.28134. Epub 2019 Jun 11.
PMID: 31184781.
4. Ding Z, 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. doi:
10.1084/jem.20120696. Epub 2014 Feb 3. PMID: 24493798; PMCID: PMC3920559.
In vitro protocol:
1. Janoly-Dumenil A, Rouvet I, Bleyzac N, Bertrand Y, Aulagner G, Zabot MT. Effect of duration and intensity of ganciclovir
exposure on lymphoblastoid cell toxicity. Antivir Chem Chemother. 2009;19(6):257-62. doi: 10.1177/095632020901900605. PMID:
19641234.
2. Ding Z, 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. doi:
10.1084/jem.20120696. Epub 2014 Feb 3. PMID: 24493798; PMCID: PMC3920559.
In vivo protocol:
1. Haller TJ, Price MS, Lindsay SR, Hillas E, Seipp M, Firpo MA, Park AH. Effects of ganciclovir treatment in a murine model of
cytomegalovirus-induced hearing loss. Laryngoscope. 2020 Apr;130(4):1064-1069. doi: 10.1002/lary.28134. Epub 2019 Jun 11.
PMID: 31184781.
2. Ding Z, 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. doi:
10.1084/jem.20120696. Epub 2014 Feb 3. PMID: 24493798; PMCID: PMC3920559.
1. Balfour, H.H., Jr. Management of cytomegalovirus disease with antiviral drugs. Rev.Infect.Dis. 12(Suppl. 7), S849-S860 (1990).
2. Bean, B. Antiviral therapy: Current concepts and practices. Clin.Microbiol.Rev. 5(2), 146-182 (1992).
3. Rasmussen, L., Chen, P.T., Mullenax, J.G., et al. Inhibition of human cytomegalovirus replication by 9-(1,3-dihydroxy-2-propoxymethyl)guanine alone and in combination with human interferons. Antimicrob. Agents Chemother. 26(4), 441-445 (1984).
4. Freitas, V.R., Smee, D.F., Chernow, M., et al. Activity of 9-(1,3-dihydroxy-2-propoxymethyl)guanine compared with that of acyclovir against human, monkey, and rodent cytomegaloviruses. Antimicrob. Agents Chemother. 28(2), 240-245 (1985).
