Ganciclovir

Modify Date: 2024-01-02 14:11:27

Ganciclovir Structure
Ganciclovir structure
 Common Name Ganciclovir
CAS Number 82410-32-0 Molecular Weight 255.231
Density 1.8±0.1 g/cm3 Boiling Point 657.0±65.0 °C at 760 mmHg
Molecular Formula C9H13N5O4 Melting Point 250°C
MSDS Chinese USA Flash Point 351.1±34.3 °C
Symbol GHS08
GHS08		 Signal Word Danger

 Use of Ganciclovir


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).

 Names

Name ganciclovir
Synonym More Synonyms

 Ganciclovir 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
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.

 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

 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
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

 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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 Synonyms

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
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