Ganciclovir
- CAS No.
- 82410-32-0
- Chemical Name:
- Ganciclovir
- Synonyms
- Vitrasert;GANCYCLOVIR;Cytovene;Denosine;Ganciclovir CRS;2-AMINO-1,9-[[2-HYDROXY-1-(HYDROXYMETHYL)ETHOXY]METHYL]6H-PURIN-6-ONE(GANCICLOVIR);GVC;HHEMG;bw-759;2'-ndg
- CBNumber:
- CB6203364
- Molecular Formula:
- C9H13N5O4
- Molecular Weight:
- 255.23
- MOL File:
- 82410-32-0.mol
- MSDS File:
- SDS
- Modify Date:
- 2025/2/24 16:12:34
| Melting point | 250°C |
|---|---|
| Boiling point | 398.46°C (rough estimate) |
| Density | 1.3559 (rough estimate) |
| refractive index | 1.7610 (estimate) |
| Flash point | 9℃ |
| storage temp. | 2-8°C |
| solubility | 0.1 M HCl: 10 mg/mL |
| form | powder |
| pka | 9.33±0.20(Predicted) |
| color | white |
| Water Solubility | 3.6g/L(25 ºC) |
| ε(extinction coefficient) | 12.0 at 256nm at 1mM |
| Merck | 14,4363 |
| InChI | 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) |
| InChIKey | IRSCQMHQWWYFCW-UHFFFAOYSA-N |
| SMILES | N1C2=C(N=C(N)NC2=O)N(COC(CO)CO)C=1 |
| CAS DataBase Reference | 82410-32-0(CAS DataBase Reference) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS08 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Danger | |||||||||
| Hazard statements | H340-H361fd | |||||||||
| Precautionary statements | P201-P308+P313 | |||||||||
| Hazard Codes | T | |||||||||
| Risk Statements | 46-60-61 | |||||||||
| Safety Statements | 53-36/37/39-45 | |||||||||
| RIDADR | UN1230 - class 3 - PG 2 - Methanol, solution | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | MF8407000 | |||||||||
| HS Code | 29335990 | |||||||||
| Hazardous Substances Data | 82410-32-0(Hazardous Substances Data) | |||||||||
| Toxicity | LD50 i.p. in mice: 1-2 g/kg (Martin) | |||||||||
| NFPA 704 |
|
Ganciclovir price More Price(5)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | PHR1593 | Ganciclovir Pharmaceutical Secondary Standard; Certified Reference Material | 82410-32-0 | 1G | ₹15966.88 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | G2536 | Ganciclovir ≥99% (HPLC), powder | 82410-32-0 | 100MG | ₹45887.18 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | 345700 | Ganciclovir - CAS 82410-32-0 - Calbiochem A nucleoside analog structurally related to Acyclovir. | 82410-32-0 | 50MG | ₹25950 | 2022-06-14 | Buy |
| TCI Chemicals (India) | G0315 | Ganciclovir | 82410-32-0 | 5G | ₹12500 | 2022-05-26 | Buy |
| TCI Chemicals (India) | G0315 | Ganciclovir | 82410-32-0 | 25G | ₹14700 | 2022-05-26 | Buy |
Ganciclovir Chemical Properties,Uses,Production
Description
Ganciclovir is a parenterally-active antiviral agent indicated for sight- or life-threatening cytomegalovirus (CMV) infections in immunocompromised patients. Its suppressive effects on bone marrow and renal tubular secretion/absorption are reported to present potential limitations on adjunct therapies involving zidovudine, vincristine, adriamycin and amphotericin B. Recently, the emergence of CMV strains resistant to ganciclovir therapy has been reported.
Chemical Properties
White Powder
Uses
Ganciclovir is a nucleoside analog structurally related to Acyclovir (A192400). Ganciclovir is an antiviral.
Indications
Ganciclovir (Cytovene) is an acyclic analogue of 2 deoxyguanosine with inhibitory activity toward all herpesviruses, especially CMV.
Definition
ChEBI: An oxopurine that is guanine substituted by a [(1,3-dihydroxypropan-2-yl)oxy]methyl group at position 9. Ganciclovir is an antiviral drug used to treat or prevent AIDS-related cytomegalovirus infections.
Acquired resistance
Prolonged, repeated courses lead to the selection of resistant strains, occurring in 8% of patients receiving the drug for >3 months. Studies of laboratory-derived resistant strains indicate that drug resistance can result from alterations in the phosphonotransferase encoded by the gene region UL 27, the viral DNA polymerase (gene region UL 54), or both.
General Description
Ganciclovir, 9-[(1,3-dihydroxy-2-propoxy) methyl]guanine)or DHPG (Cytovene), is an analog of acyclovir, with an additional hydroxymethyl group on the acyclic side chain.
After administration, similar to acyclovir, ganciclovir isphosphorylated inside the cell by a virally encoded proteinkinase to the monophosphate.Host cell enzymes catalyzethe formation of the triphosphate, which reaches more than10-fold higher concentrations in infected cells than in uninfectedcells.
The clinical usefulness of ganciclovir is limited by thetoxicity of the drug. Ganciclovir causes myelosuppression,producing neutropenia, thrombocytopenia, and anemia.These effects are probably associated with inhibition of hostcell DNA polymerase.Potential central nervous systemside effects include headaches, behavioral changes, and convulsions.Ganciclovir is mutagenic, carcinogenic, and teratogenicin animals.
Pharmaceutical Applications
A synthetic 2′-deoxyguanosine nucleoside analog, supplied as the l-valine ester, valganciclovir, for oral administration and as the sodium salt for parenteral use. A slow-release ocular implant device is also available.
Mechanism of action
Ganciclovir sodium is an acyclic deoxyguanosine analogue of acyclovir. Ganciclovir inhibits DNA polymerase. Its active form is ganciclovir triphosphate, which is an inhibitor of viral rather than of cellular DNA polymerase. The phosphorylation of ganciclovir does not require a virus-specific thymidine kinase for its activity against CMV. The mechanism of action is similar to that of acyclovir; however, ganciclovir is more toxic than acyclovir to human cells.
Pharmacology
Activation of ganciclovir first requires conversion to ganciclovir monophosphate by viral enzymes: protein kinase pUL97 in CMV or thymidine kinase in HSV. Host cell enzymes then perform two additional phosphorylations. The resultant ganciclovir triphosphate competes with dGTP for access to viral DNA polymerase. Its incorporation into the growing DNA strand causes chain termination in a manner similar to that of acyclovir. Ganciclovir triphosphate is up to 100-fold more concentrated in CMV-infected cells than in normal cells and is preferentially incorporated into DNA by viral polymerase. However, mammalian bone marrow cells are sensitive to growth inhibition by ganciclovir.
Clinical Use
Intravenous ganciclovir is indicated for the treatment of CMV retinitis in immunocompromised individuals, including those with AIDS, and for the prevention of CMV infection in organ transplant recipients.Oral ganciclovir is less effective than the intravenous preparation but carries a lower risk of adverse effects. It is Intravenous ganciclovir is indicated for the treatment of CMV retinitis in immunocompromised individuals, including those with AIDS, and for the prevention of CMV infection in organ transplant recipients.Oral ganciclovir is less effective than the intravenous preparation but carries a lower risk of adverse effects. It is
Side effects
Myelosuppression is the most common serious adverse effect of ganciclovir treatment; therefore, patients’ blood counts should be closely monitored. Neutropenia and anemia have been reported in 25 to 30% of patients, and thrombocytopenia has been seen in 5 to 10%. Elevated serum creatinine may occur following ganciclovir treatment, and dosage adjustment is required for patients with renal impairment. In animal studies, ganciclovir causes decreased sperm production, teratogenesis, and tumor formation.
Purification Methods
Recrystallise gangcyclovir from MeOH. Alternatively dissolve 90g of it in 700mL of 2O, filter and cool (ca 94% recovery). UV: max in MeOH 254nm ( 12,880), 270sh nm ( 9,040); its solubility in 2O at 25o is 4.3mg/mL at pH 7.0. ANTIVIRAL. [Ogilvie et al. Can J Chem 60 3005 1982, Ashton et al. Biochem Biophys Res Commun 108 1716 1982, Martin et al. J Med Chem 26 759 1983.]
Precautions
Ganciclovir interacts with a number of medications,some of which are used to treat HIV or transplant patients.Ganciclovir may cause severe neutropenia whenused in combination with zidovudine. Ganciclovir increasesserum levels of didanosine, whereas probeneciddecreases ganciclovir elimination. Nephrotoxicity mayresult if other nephrotoxic agents (e.g., amphotericin B,cyclosporine, NSAIDs) are administered in conjunctionwith ganciclovir.
Ganciclovir Preparation Products And Raw materials
Raw materials
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chevron_rightPreparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| SUJALAM CHEMICALS | +91-9422560788 +91-9422560788 | Maharashtra, India | 42 | 58 | Inquiry |
| Hetero Drugs Limited | +91-4023704923 +91-4023704923 | Telangana, India | 296 | 58 | Inquiry |
| Besil Chem LLP | +91-7760252666 +91-9880731835 | Bangalore, India | 163 | 58 | Inquiry |
| Ralington Pharma | +91-7948911722 +91-9687771722 | Gujarat, India | 1350 | 58 | Inquiry |
| Vishrudh laboratories pvt ltd | +91-9666132889 +91-8097369002 | Telangana, India | 117 | 58 | Inquiry |
| Bakul Pharma Private Limited | +91-2261697900 +91-2261697900 | Maharashtra, India | 66 | 58 | Inquiry |
| Aspen Biopharma Labs Pvt Ltd | +91-9248058660 +91-9248058662 | Telangana, India | 234 | 58 | Inquiry |
| Molsyns Research | +91-9586858886 +91-9586858886 | Gujarat, India | 418 | 58 | Inquiry |
| SETV ASRV LLP | +91-9731133411 +91-9731133411 | Telangana, India | 437 | 58 | Inquiry |
| AUROBINDO PHARMA LTD | +91 (40) 6672 1200 | New Delhi, India | 209 | 58 | Inquiry |
| Supplier | Advantage |
|---|---|
| SUJALAM CHEMICALS | 58 |
| Hetero Drugs Limited | 58 |
| Besil Chem LLP | 58 |
| Ralington Pharma | 58 |
| Vishrudh laboratories pvt ltd | 58 |
| Bakul Pharma Private Limited | 58 |
| Aspen Biopharma Labs Pvt Ltd | 58 |
| Molsyns Research | 58 |
| SETV ASRV LLP | 58 |
| AUROBINDO PHARMA LTD | 58 |
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