Ganciclovir sodium

Names

[ Name ]:
Ganciclovir sodium

[Synonym ]:
Sodium 2-amino-9-{[(1,3-dihydroxy-2-propanyl)oxy]methyl}-6-oxo-6,9-dihydropurin-1-ide
Ganciclovir Sodium Salt
sodium 2-amino-9-{[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl}-9h-purin-6-olate
Cymevene
Ganciclovir monosodium salt
1,3-propanediol, 2-[(2-amino-6-hydroxy-9H-purin-9-yl)methoxy]-, monosodium salt
2-amino-9-{[2-hydroxy-1-(hydroxyméthyl)éthoxy]méthyl}-9H-purin-6-olate de sodium
6H-Purin-6-one, 2-amino-1,9-dihydro-9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-, sodium salt (1:1)
Ganciclovir sodium
Unii-02L083W284

Biological Activity

[Description]:

Ganciclovir (BW 759) sodium, a nucleoside analogue and an orally active antiviral agent, shows activity against CMV. Ganciclovir sodium also has activity in vitro against members of the herpes group and some other DNA viruses. Ganciclovir sodium inhibits the in vitro replication of human herpes viruses (HSV 1 and 2, CMV) and adenovirus serotypes 1, 2, 4, 6, 8, 10, 19, 22 and 28. Ganciclovir sodium has an IC50 of 5.2 μM for feline herpesvirus type-1 (FHV-1)[1][2][3].

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HSV

Research Areas >> Infection

Signaling Pathways >> Cell Cycle/DNA Damage >> Nucleoside Antimetabolite/Analog

Signaling Pathways >> Anti-infection >> CMV

[Target]

CMV

HSV-1

HSV-2

FHV-1:5.2 μM (IC50)

[In Vitro]

Ganciclovir sodium 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[4].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 sodium is metabolized to the triphosphate form by primarily three cellular enzymes: a deoxyguanosine kinase induced by CMV-infected cells; guanylate kinase; and phosphoglycerate kinase[5].

[In Vivo]

Ganciclovir sodium (1-80 mg/kg; i.h.; daily for 5 days) delays MCMV-induced wasting syndrome and mortality[6]. Animal Model: Severe combined immunodeficiency (SCID) mice (MCMV infection)[6] Dosage: 1-80 mg/kg Administration: I.h.; daily for 5 days Result: Dose dependently delayed MCMV-induced wasting syndrome and mortality.

[References]

[1]. Faulds D, et al. Ganciclovir. A review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy in cytomegalovirus infections. Drugs. 1990;39(4):597-638.

[2]. 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.

[3]. Boujemla I, et al. Pharmacokinetics and tissue diffusion of ganciclovir in mice and rats. Antiviral Res. 2016;132:111-115.

[4]. Fletcher CV, et al. Evaluation of ganciclovir for cytomegalovirus disease. DICP. 1989 Jan;23(1):5-12.

[5]. Matthews T, et al. Antiviral activity and mechanism of action of ganciclovir. Rev Infect Dis. 1988 Jul-Aug;10 Suppl 3:S490-4.

[6]. Duan J, Paris W, Kibler P, Bousquet C, Liuzzi M, Cordingley MG. Dose and duration-dependence of ganciclovir treatment against murine cytomegalovirus infection in severe combined immunodeficient mice. Antiviral Res. 1998;39(3):189-197.

Chemical & Physical Properties

[ Density]:
1.81g/cm3

[ Boiling Point ]:
675ºC at 760mmHg

[ Melting Point ]:
250ºC (decomposition)

[ Molecular Formula ]:
C₉H₁₂N₅NaO₄

[ Molecular Weight ]:
277.212

[ Flash Point ]:
362ºC

[ Exact Mass ]:
277.078705

[ PSA ]:
142.37000

[ Storage condition ]:
-20℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: UP0791632

CHEMICAL NAME :: 6H-Purin-6-one, 1,9-dihydro-2-amino-9-((2-hydroxy-1-(hydroxymethyl)et hoxy)methyl)-, monosodium salt

CAS REGISTRY NUMBER :: 107910-75-8

LAST UPDATED :: 199712

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C9-H12-N5-O4.Na

MOLECULAR WEIGHT :: 277.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TEST SYSTEM :: Rodent - mouse

DOSE/DURATION :: 1744 umol/kg/24H (Intermittent)

REFERENCE :: MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 369,65,1996

Safety Information

[ HS Code ]:
2933990090

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%