Ganciclovir

Names

[ Name ]:
Ganciclovir

[Synonym ]:
6H-Purin-6-one, 2-amino-1,9-dihydro-9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-
Vitrasert
Gancyclovir
HHEMG
T56 BN DN FN HNJ D1OY1Q1Q GZ IQ
MFCD00870588
Ganciclovir
Cymevene
bwb759u
2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-3,9-dihydro-6H-purin-6-one
2'-ndg
6H-Purin-6-one, 2-amino-1,9-dihydro-9-((2-hydroxy-1-(hydroxymethyl)ethoxy)methyl)-
DHPG
biolf62
T56 BN DN FVM INJ B1OY1Q1Q HZ
cymevan
Cytovene
1,3-Propanediol, 2-[(2,3-dihydro-6-hydroxy-2-imino-9H-purin-9-yl)methoxy]-
2-Amino-9-{[(1,3-dihydroxy-2-propanyl)oxy]methyl}-1,9-dihydro-6H-purin-6-one
BW B759U
bw-759u
GVC
2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-1,9-dihydro-6H-purin-6-one
2-Amino-1,9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one
2-[(6-Hydroxy-2-imino-2,3-dihydro-9H-purin-9-yl)methoxy]-1,3-propanediol
bw-759

Biological Activity

[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).

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HSV

Research Areas >> Infection

[Target]

IC50: 5.2 μM (FHV-1)[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].

[Animal admin]

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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.8±0.1 g/cm3

[ Boiling Point ]:
657.0±65.0 °C at 760 mmHg

[ Melting Point ]:
250°C

[ Molecular Formula ]:
C₉H₁₃N₅O₄

[ Molecular Weight ]:
255.231

[ Flash Point ]:
351.1±34.3 °C

[ Exact Mass ]:
255.096756

[ PSA ]:
139.28000

[ LogP ]:
-3.62

[ Vapour Pressure ]:
0.0±2.1 mmHg at 25°C

[ Index of Refraction ]:
1.761

[ Storage condition ]:
2-8°C

[ Water Solubility ]:
0.1 M HCl: 10 mg/mL

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: MF8407000

CHEMICAL NAME :: Guanine, 9-((2-hydroxy-1-(hydroxymethyl)ethoxy)methyl)-

CAS REGISTRY NUMBER :: 82410-32-0

LAST UPDATED :: 199109

DATA ITEMS CITED :: 6

MOLECULAR FORMULA :: C9-H13-N5-O4

MOLECULAR WEIGHT :: 255.27

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 900 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >1 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >150 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :: Sister chromatid exchange

TEST SYSTEM :: Human Lymphocyte

DOSE/DURATION :: 10 mg/L

REFERENCE :: LIFSAK Life Sciences. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1-8, 1962-69; V.14- 1974- Volume(issue)/page/year: 38,281,1986

Safety Information

[ Symbol ]:

GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H360

[ Precautionary Statements ]:
P201-P280-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T:Toxic

[ Risk Phrases ]:
R46;R60;R61

[ Safety Phrases ]:
S53-S36/37/39-S45

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
MF8407000

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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%

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