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Ganciclovir(CAS No. 82410-32-0)

Ganciclovir C9H13N5O4 (cas 82410-32-0) Molecular Structure

82410-32-0 Structure

Identification and Related Records

【CAS Registry number】
【Molecular Formula】
C9H13N5O4 (Products with the same molecular formula)
【Molecular Weight】
【Canonical SMILES】
【MOL File】

Chemical and Physical Properties

white powder
1.81 g/cm3
【Melting Point】
【Boiling Point】
675 oC at 760 mmHg
【Flash Point】
675 oC at 760 mmHg
0.1 M HCl: 10 mg/mL
0.1 M HCl: 10 mg/mL
Exposure to temperatures exceeding 40 C should be avoided. When stored as directed, the sterile powder has an expiration date of 3 years following the date of manufacture.
【Storage temp】
【Spectral properties】
Maximum absorption (methanol): 254 nm (E= 12,880)
【Computed Properties】
Molecular Weight:255.23062 [g/mol]
Molecular Formula:C9H13N5O4
H-Bond Donor:4
H-Bond Acceptor:4
Rotatable Bond Count:5
Tautomer Count:9
Exact Mass:255.096754
MonoIsotopic Mass:255.096754
Topological Polar Surface Area:135
Heavy Atom Count:18
Formal Charge:0
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:4
Feature 3D Donor Count:5
Feature 3D Cation Count:1
Feature 3D Ring Count:2
Effective Rotor Count:5
Conformer Sampling RMSD:0.6
CID Conformer Count:51

Safety and Handling

【Hazard Codes】
【Risk Statements】
【Safety Statements 】

Common adverse drug reactions >=1% of patients) include: neutropenia, granulocytopenia, thrombocytopenia, fever, nausea, vomiting, dyspepsia, diarrhoea, abdominal pain, flatulence, anorexia, raised liver enzymes, headache, confusion, hallucination, anaemia, pain and phlebitis at injection site (due to high pH), sweating, rash.
Hazard Codes:?ToxicT
Risk Statements: 46-60-61?
R46:May cause heritable genetic damage.?
R60:May impair fertility.?
R61:May cause harm to the unborn child.
Safety Statements: 53-36/37/39-45?
S53:Avoid exposure - obtain special instructions before use.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
WGK Germany: 3
RTECS of Ganciclovir (CAS NO.82410-32-0): MF8407000

Vials, containing granciclovir sodium equivalent to 500 mg ganciclovir.
Parenteral: Sterile, for iv infusion, 500 mg (of ganciclovir), Cytovene, Syntex. /Ganciclovir sodium/
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl ganciclovir sodium, approved on the basis of safety and effectiveness by FDA under sections 505 and 507 of the Federal Food, Drug, and Cosmetic Act. /Ganciclovir sodium/

?Ganciclovir (CAS NO.82410-32-0), its Synonyms are 2'-NDG ; 2'-Nor-2'-deoxyguanosine ; 2-Amino-1,9-((2-hydroxy-1-(hydroxymethyl)ethoxy)methyl)-6-H-purin-6-one ; 6H-Purin-6-one, 2-amino-1,9-dihydro-9-((2-hydroxy-1-(hydroxymethyl)ethoxy)methyl)- ; 9-((1,3-Dihydroxy-2-propoxy)methyl)guanine ; 9-((2-Hydroxy-1-(hydroxymethyl)ethoxy)methyl)guanine ; Guanine, 9-((2-hydroxy-1-(hydroxymethyl)ethoxy)methyl)- ; Hydroxyacyclovir . It is white powder.

Use and Manufacturing


An antiviral

Biomedical Effects and Toxicity

【Pharmacological Action】
- Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly.
【Therapeutic Uses】
Antimetabolites; Antiviral Agents
Medication: Indicated for the treatment of cytomegalovirus retinitis in immunocompromised individuals, including patients with AIDS
Ganciclovir is used for the treatment of cytomegalovirus retinitis in immunocompromised patients. While ganciclovir has been considered the drug of choice for the treatment of this condition and may remain so in many patients, recent evidence suggests that foscarnet may be associated with improved survival for initial treatment of cytomegalovirus retinitis in patients with underlying acquired immunodeficiency syndrome (AIDS) and relatively normal renal function; ... . Ganciclovir also has been used for the treatment of other cytomegalovirus infections (eg, GI infections, pneumonitis) in immunocompromised patients, but experience with the drug in these extraocular infections is less extensive, and safety and efficacy remain to be established. Despite this lack of experience inextraocular infections, ganciclovir has been considered the drug of choice for cytomegalovirus infections when antiviral therapy is warranted. While the safety and efficacy of ganciclovir compared with foscarnet for the treatment of cytomegalovirus infections other than retinitis remain to be established, some clinicians state that pending further accumulation of data, ganciclovir may offer some advantages over foscarnet secondary to patient tolerance and patient acceptability, and the choice of antiviral agent for cytomegalovirus infections should be individualized.
【Biomedical Effects and Toxicity】
Ganciclovir is absorbed poorly from the GI tract. Following oral administration of an aqueous solution of ganciclovir sodium, 7% or less of a 10 to 20 mg/kg dose appears to be absorbed, based on urinary recovery, and relative oral bioavailability appears to decrease with increasing dose and multiple administration. Plasma ganciclovir concentrations required for therapeutic antiviral activity currently are not known. Although peak plasma ganciclovir concentrations achieved after oral administration of 20 mg/kg every 6 hr have exceeded the in vitro ID50 (concentration of the drug required to produce 50% inhibition of viral plaque formation) of many strains of cytomegalovirus, the ID50 for many other susceptible strains of the virus exceed peak plasma concentrations achievable with this oral dosage; therefore, iv administration of the drug currently is preferred. In a study in several adults with acquired immunodeficiency syndrome and cytomegalovirus retinitis receiving an oral ganciclovir dosage of 20 mg/kg every 6 hr, peak plasma concentrations of the drug were achieved within 1 hr and averaged about 0.76 ug/ml at steady state; steady state trough plasma concentrations prior to a dose averaged about 0.27 g/ml. /Ganciclovir sodium/
In a limited number of immunocompromised patients with cytomegalovirus infections and normal renal function who received a ganciclovir dosage of 5 mg/kg every 12 hr by iv infusion over 1 hr, peak plasma concentrations of the drug obtained at the end of the infusion and averaged 9.5-11.6 ug/ml (range: 3.1-24.1 ug/ml) and trough plasma concentrations obtained just prior to a dose averaged 1.6 ug/ml (range: 0.11-3.5 ug/ml). Somewhat lower peak and trough concentrations (averaging 6.6-8.3 and 0.56-1 ug/ml, respectively) were achieved after the first dose. Peak and trough plasma concentrations of the drug following iv infusion over 1 hr of 2.5 mg/kg every 8 hr averaged 4.09-5.36 (range: 1.66-7.78 ug/ml) and 0.33-1.07 ug/ml (range: 0.2-1.66 ug/ml), respectively, in immunocompromised patients with cytomegalovirus infections and normal renal function. In a limited number of such patients receiving 5 mg/kg every 8 hr by iv infusion over 1 hr, peak and trough plasma concentrations averaged 6.53-11.41 and 1.13-2.23 ug/ml, respectively. Accumulation of the drug does not appear to occur in patients with normal renal function receiving iv dosages of 3-15 mg/kg daily in divided doses. /Ganciclovir sodium/
Limited data suggest that minimal systemic absorption of ganciclovir occurs following intravitreal injection of the drug, although adequate intravitreal ganciclovir concentrations appear to be achievable with such administration. In a patient with cytomegalovirus retinitis receiving five 200 ug intravitreal doses over 15 days, systemic plasma ganciclovir concentrations achieved during therapy were less than 0.1 ug/ml. A vitreous humor concentration of 1.17 ug/ml and an aqueous humor concentration of 0.66 ug/ml were achieved 51.4 hr after the initial dose in this patient, and a vitreous humor concentration of 0.1 ug/ml was achieved 97.3 hr after the fourth dose. Data from rabbits also indicate that antiviral intravitreal concentrations of the drug are achievable with small intravitreal but not subconjunctival doses of ganciclovir. Following intravitreal injection of a single 400 ug dose in rabbits, vitreous humor ganciclovir concentrations averaged 543, 423, 57.7, 16, 2.02, and 1.2 ug/ml 2, 5, 12, 24, 48, and 60 hr after injection. Following subconjunctival injection of a single 1.25-mg dose in rabbits, ganciclovir concentrations 1, 2, 3, and 8 hr after injection averaged 0.09, 0.31, 0.16, and 0.02 ug/ml, respectively, in vitreous humor and 2.18, 3.27, 2.22, and 0.07 ug/ml, respectively, in aqueous humor. /Ganciclovir sodium/
Distribution of ganciclovir into human body tissues and fluids has not been fully elucidated. Autopsy findings in several patients receiving the drug iv suggest that ganciclovir concentrates in the kidney, with substantially lower concentrations occurring in lung, liver, brain, and testes. While efficacy of the drug in cytomegalovirus pneumonitis has been substantially less than in many other infections (eg, retinitis) with the virus to date, lung ganciclovir concentrations that exceed the ID50 for cytomegalovirus appear to be achievable with usual iv dosages. Concentrations attained in lung and liver were 99 and 92%, respectively, of those attained concurrently in heart blood in several adults receiving the drug iv. Following iv administration in mice, ganciclovir was distributed widely, achieving highest concentrations in the kidney and lowest concentrations in the brain. Substantial distribution of ganciclovir into lung, liver, heart, spleen, stomach, intestines, muscle, and testes also occurred, exceeding concurrent blood concentrations in these tissues; concentrations achieved in brain, eyes, and fat were lower than concurrent blood concentrations. Accumulation of the drug did not appear to occur, although measurable concentrations persisted for at least 30 hr in stomach, liver, and intestines in these animals. In addition, there was no evidence of testicular ganciclovir accumulation in several humans receiving 15 mg/kg iv daily for 8-13 days.
Ganciclovir is 1-2% bound to plasma proteins. The volume of distribution of the drug at steady state (Vss) averaged 32.8-44.5 l/1.73 sq m (range: 17-59.1 l/1.73 sq m) in patients with normal renal function receiving ganciclovir iv. The mean volume of distribution of ganciclovir in the central compartment averaged 15.26 l/1.73 sq m (range: 11-22.5 l/1.73 sq m) in patients with normal renal function receiving the drug iv. The volume of ganciclovir distribution appears to be reduced in patients with renal impairment.
Data on intraocular concentrations of ganciclovir are limited, but it appears that the drug has good ocular distribution following iv administration. In one adult patient, subretinal ganciclovir concentrations were 0.87 and 2 times concurrent plasma concentrations 5.5 and 8 hr after iv administration, respectively. In another adult patient, the aqueous and vitreous humor ganciclovir concentrations were 0.4 and 0.6 times those of simultaneous plasma concentrations 2.5 hr after iv infusion of the drug; 21 hr after iv infusion, plasma concentrations were undetectable, while the Vitreous humor concentration was still 0.2 ug/ml. In an adult with cytomegalovirus retinitis, the apparent volume of distribution of ganciclovir in vitreous humor was 11.7 ml following intravitreal injection, suggesting that the drug may distribute into the retina.
Ganciclovir crosses the blood-brain barrier. In several adult patients, the concentration of ganciclovir in CSF following iv administration averaged 41% (range: 24-70%) of the corresponding plasma concentration of the drug. Autopsy findings revealed similar evidence of CNS distribution of the drug in several other patients, with brain tissue concentrations of ganciclovir averaging 38% of corresponding blood concentrations.
It is not known whether ganciclovir is distributed into milk in humans, but the drug appears to distribute into milk in animals. The drug also apparently crosses the placenta in animals.
The elimination half-life of ganciclovir from the vitreous humor after intravitreal injection was estimated to be 13.3 hr in a patient with cytomegalovirus retinitis. In this patient, intravitreal ganciclovir concentrations were estimated to exceed the ID50 (0.66 ug/ml) of the virus for about 62 hr after a single 200 ug intravitreal dose. In rabbits, the elimination half-life from vitreous humor after intravitreal injection of a single 400 ug dose was 8.6 hr, and intravitreal ganciclovir concentrations exceeded the ID50 (range: 0.24-1.5 g/ml) of many strains of cytomegalovirus for at least 60 hr.
/Ganciclovir/ appears to undergo little, if any, extrarenal elimination, with approximately 90-99% of an iv dose reportedly being excreted unchanged in urine. Renal excretion of ganciclovir appears to occur principally via glomerular filtration, although limited renal tubular secretion also may occur.
Total body clearance of ganciclovir from plasma reportedly averages 170- 203 ml/min per 1.73 sq m in adults with normal renal function. Total body clearance of the drug is decreased in adults with renal impairment and appears to correlate positively with creatinine clearance. In a limited number of patients, total body clearance from plasma averaged 128, 57, or 30 ml/minute per 1.73 sq m in adults with creatinine clearances of 50-79, 25-49, or less than 25 ml/min per 1.73 sq m, respectively.
Ganciclovir is removed by hemodialysis. The amount of ganciclovir removed during hemodialysis depends on several factors (eg, type of coil used, dialysis flow rate); however, in several patients, a 4 hr period of hemodialysis removed into the dialysate approximately 40-50% of a dose.

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