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  • 82410-32-0, 更昔洛韦, Ganciclovir, CAS:82410-32-0
  • 82410-32-0, 更昔洛韦, Ganciclovir, CAS:82410-32-0
82410-32-0, 更昔洛韦, Ganciclovir, CAS:82410-32-082410-32-0, 更昔洛韦, Ganciclovir, CAS:82410-32-0

82410-32-0, 更昔洛韦, Ganciclovir, CAS:82410-32-0

82410-32-0, 更昔洛韦,
Ganciclovir,
CAS:82410-32-0
C9H13N5O4 / 255.23
MFCD00870588

更昔洛韦, Ganciclovir

Anti-viral; DNA polymerase inhibitor; dGTP competitive inhibitor.

Ganciclovir is a nucleotide analogue used to treat cytomegalovirus infections. It is a guanine analogue initially synthesized in the 1980s as part of a series of novel anti-viral agents. Ganciclovir has significant biological activity, making it a valuable tool in scientific research. In this paper, we will discuss the physical and chemical properties of Ganciclovir, synthesis, and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.

Definition and Background:

Ganciclovir is a deoxyguanosine nucleoside analogue. It is structurally similar to acyclovir and penciclovir, both herpetic anti-viral agents used in the treatment of herpesvirus infections. However, Ganciclovir has a broader spectrum of activity and is used primarily to treat cytomegalovirus (CMV) retinitis and other CMV infections in immunocompromised individuals.

Synthesis and Characterization:

Ganciclovir is obtained by a five-step synthesis from guanine. The original synthesis was reported by Elion et al. in 1980. The process involves the protection of the 3'- and 5'-hydroxy groups of guanine with silyl compounds to prevent their reaction with the nucleophile (DMSO), thereby enabling selective oxidation of the 8-position of guanine. The final deprotection step yields Ganciclovir.

Analytical Methods:

Ganciclovir can be detected and quantified by high-performance liquid chromatography (HPLC), liquid chromatography-mass spectrometry (LC-MS), and capillary zone electrophoresis (CZE). HPLC has been well-established for the analysis of Ganciclovir in biological matrices. However, LC-MS and CZE offer enhanced sensitivity and selectivity, making them preferred methods for Ganciclovir analysis in challenging matrices.

Biological Properties:

Ganciclovir has significant biological activity against herpesviruses, especially CMV. It inhibits viral DNA synthesis by incorporating into the growing chain and inhibiting the activity of the viral polymerase. It is also active against other herpesviruses, including Epstein-Barr virus, herpes simplex virus, and varicella-zoster virus. Ganciclovir has poor oral bioavailability and is primarily administered intravenously or as an ophthalmic gel for CMV retinitis.

Toxicity and Safety in Scientific Experiments:

Ganciclovir has been found to be relatively safe in animal studies. However, it is known to be cytotoxic and may cause DNA damage if not properly handled. The drug has significant teratogenic potential and should not be used during pregnancy. It is also known to be mutagenic and has been reported to induce chromosomal aberrations in vitro.

Applications in Scientific Experiments:

Ganciclovir has been widely used in scientific research as a tool to study herpesviruses and their replication cycles. Its use in cell culture studies enables researchers to investigate the mechanisms of antiviral activity, drug resistance, and viral replication. Ganciclovir's ability to incorporate into viral DNA also makes it a valuable tool in studying DNA replication processes.

Current State of Research:

The current research on Ganciclovir involves exploring potential new applications, examining the mechanism of action, and improving formulations. Advanced analytical methods are being developed to enable accurate quantification of Ganciclovir in various matrices. Further advancements in targeted drug delivery and treatment regimens may also lead to improved therapeutic outcomes.

Potential Implications in Various Fields of Research and Industry:

Ganciclovir's antiviral activity has potential implications in the treatment of a wide range of viral infections beyond herpesviruses. It may also find applications as a tool in cancer gene therapy. Further, Ganciclovir's incorporation into DNA makes it a promising candidate for use in DNA-based vaccines.

Limitations and Future Directions:

Ganciclovir has limitations in its clinical use, including poor oral bioavailability and the potential for toxicity. Future research may focus on improving delivery methods to overcome these limitations. Researchers may also explore the use of Ganciclovir in gene therapy and as a tool in investigating DNA replication mechanisms.

List of Future Directions:

1. Developing novel Ganciclovir analogues with improved pharmacokinetics and therapeutic efficacy.

2. Exploring the use of Ganciclovir in cancer gene therapy.

3. Investigating the mechanism of action of Ganciclovir and developing more targeted drug delivery methods.

4. Investigating the effects of Ganciclovir on viral DNA replication and exploring its potential use in DNA-based vaccines.

5. Examining the potential of Ganciclovir to treat a wide range of viral infections beyond herpesviruses.

6. Further exploration of Ganciclovir's use in scientific research as a tool to study DNA replication processes.

7. Developing analytical tools for accurate quantification of Ganciclovir in biological matrices.

8. Investigating potential synergy between Ganciclovir and other antiviral agents.

9. Exploring Ganciclovir's potential in the treatment of antibiotic-resistant bacterial infections.

10. Investigating the mechanism of toxicity of Ganciclovir and exploring strategies to minimize toxicity.


Title: Ganciclovir

CAS Registry Number: 82410-32-0

CAS Name: 2-Amino-1,9-dihydro-9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one

Additional Names: 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine; 2¢-nor-2¢-deoxyguanosine; DHPG; 2¢NDG

Manufacturers' Codes: BIOLF-62; BW-B759U; BW-759; BW-759U; RS-21592

Molecular Formula: C9H13N5O4

Molecular Weight: 255.23

Percent Composition: C 42.35%, H 5.13%, N 27.44%, O 25.07%

Literature References: Nucleoside analog structurally related to acyclovir, q.v. Prepn: J. P. Verheyden, J. C. Martin, US 4355032 (1982 to Syntex); K. K. Ogilvie et al., Can. J. Chem. 60, 3005 (1982); W. T. Ashton et al., Biochem. Biophys. Res. Commun. 108, 1716 (1982); J. C. Martin et al., J. Med. Chem. 26, 759 (1983). Antiviral spectrum in vitro: K. O. Smith et al., Antimicrob. Agents Chemother. 22, 55 (1982). Mode of action study: Y.-C. Cheng et al., Proc. Natl. Acad. Sci. USA 80, 2767 (1983). Clinical treatment of cytomegalovirus infection in immunodeficient patients: S. H. Koretz et al., N. Engl. J. Med. 314, 801 (1986). Symposium on pharmacology and clinical efficacy vs cytomegalovirus: Rev. Infect. Dis. 10, Suppl. 3, S457-S572 (1988). Review: C. S. Crumpacker, N. Engl. J. Med. 335, 721-729 (1996).

Properties: Crystals from methanol, mp 250° (dec) (Verheyden, Martin); also reported as crystalline monohydrate from water, mp 248-249° (dec) (Ashton); crystals from water, mp >300° (Martin). uv max (methanol): 254 nm (e 12880). Soly in water (25°): 4.3 mg/ml at pH 7. LD50 i.p. in mice: 1-2 g/kg (Martin).

Melting point: mp 250° (dec) (Verheyden, Martin); mp 248-249° (dec) (Ashton); mp >300° (Martin)

Absorption maximum: uv max (methanol): 254 nm (e 12880)

Toxicity data: LD50 i.p. in mice: 1-2 g/kg (Martin)

 

Derivative Type: Sodium salt

CAS Registry Number: 107910-75-8

Trademarks: Cymevan (Syntex); Cymevene (Syntex); Cytovene (Syntex); Denosine (Syntex); Vitrasert (Chiron)

Molecular Formula: C9H12N5NaO4

Molecular Weight: 277.21

Percent Composition: C 38.99%, H 4.36%, N 25.26%, Na 8.29%, O 23.09%

 

Therap-Cat: Antiviral.

Keywords: Antiviral; Purines/Pyrimidinones.

CAS Number82410-32-0
Product NameGanciclovir
IUPAC Name2-amino-9-(1,3-dihydroxypropan-2-yloxymethyl)-1H-purin-6-one
Molecular FormulaC₉H₁₃N₅O₄
Molecular Weight255.23 g/mol
InChIInChI=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)
InChI KeyIRSCQMHQWWYFCW-UHFFFAOYSA-N
SMILESC1=NC2=C(N1COC(CO)CO)N=C(NC2=O)N
SynonymsRS-21592, BW-759
Canonical SMILESC1=NC2=C(N1COC(CO)CO)NC(=NC2=O)N
Isomeric SMILESC1=NC2=C(N1COC(CO)CO)NC(=NC2=O)N


CAS No: 82410-32-0 Synonyms: 2-Amino-1,9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]6H-purin-6-oneHydroxyacyclovirNatclovir MDL No: MFCD00870588 Chemical Formula: C9H13N5O4 Molecular Weight: 255.23
References: 1. Halloran, P.J. and Fenton, R.G., Cancer Res., 58, 3855 (1998)2. Rubsam, L.Z., et al., Cancer Res., 59, 669 (1999)3. Yamasaki, H., et al., C.R. Acad. Sci. III, 322, 151 (1999)

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