2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 73249
• Molecular Formular: C9H13N5O4
• Molecular Mass: 255.23062
• Monoisotopic Mass: 255.09675392
• SMILES: [nH]1c(nc2c(c1=O)ncn2COC(CO)CO)N
• Canonical SMILES: OCC(OCn1cnc2c1nc(N)[nH]c2=O)CO
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: @ganciclovir; gancyclovir; 2-amino-9-{[(1,3-dihydroxypropan-2-yl)oxy]methyl}-6,9-dihydro-1H-purin-6-one
• Synonyms: 2-Amino-1,9-dihydro-9-[[2-hydroxy-1-(hydroxymethyl)ethoxy]methyl]-6H-purin-6-one; 2'-NDG; 2'-Nor-2'-deoxyguanosine; 9-(1,3-Dihydroxy-2-propoxymethyl)guanine; BW 759; BW 759U; BW-B 759U; Biolf 62; DHPG; Denosine; Gancyclovir; Ganguard; Ganquard; HHEMG; Hydroxyacyclovir; Natclovir; RS 21592; Vitrasert; Ganciclovir; Cytovene; Ganciclovir; 2-amino-9-(((1,3-dihydroxypropan-2-yl)oxy)methyl)-1H-purin-6(9H)-one

Database IDs

• CAS Number: 82410-32-0
• MDL Number: MFCD00870588
• PubChem SID: 24278453; 162038169
• PubChem CID: 3454

CALCULATED PROPERTIES

• Acid pKa: 10.159807
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.1799848
• LogD (pH = 7.4): -2.1805685
• Log P: -2.1799026
• Molar Refractivity: 61.0293 cm^3
• Polarizability: 22.50675 Å^3
• Polar Surface Area: 134.99 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble10 mg/mL; DMSO; Hot Methanol; Hot Water
• Apperance: white powder; White Solid
• Melting Point: 251-252°C
• Absorption Wavelength: ε1mM/256 nm 12.0

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: MF8407000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 46-60-61
• Safety Statements: 53-36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-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
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Inhibitor of viral-DNA-synthesis

Product Information

• Purity: ≥99% (HPLC); 97%
• Salt Data: Free Base
• Application(s): Active against herpes simplex virus types 1 and 2; Administered (ivn) in treatment of cytomegalovirus; Antiviral agent
• Quality Level: PREMIUM

DETAILS

Selleck Chemicals - S1878

Research Area: Infection
Biological Activity:

Sigma Aldrich - G2536

Application
Ganciclovir is used in molecular biology for selection against random recombination events when homologous recombination of a gene of interest is required.
Biochem/physiol Actions
Ganciclovir is a pro-drug nucleoside analog that is activated by phosphorylation. It is useful in the study of gene therapy in cancer research.Upon expression of a viral suicide gene encoding thymidine kinase, the non-toxic pro-drug is converted to a phosphorylated active analog and is incorporated into the DNA of replicating eukaryotic cells, causing death of the malignant dividing cell.1 The cell cycle is irreversibly arrested at the G2-M checkpoint.2 Gap junction involvement in the ganciclovir bystander effect has been studied.3 Ganciclovir has been used to study loss of telomeres4 and to evaluate sensitivity of viruses to antiviral treatments.5

Toronto Research Chemicals - G235000

Ganciclovir is a nucleoside analog structurally related to Acyclovir (A192400). Ganciclovir is an antiviral.

REFERENCES

• Halloran, P.J. and Fenton, R.G.: Cancer Res., 58, 3855 (1998)
• Rubsam, L.Z., et al.: Cancer Res., 59, 669 (1998)
• Yamasaki, H., et al.: C.R. Acad. Sci. III, 322, 151 (1999)
• Ashton, W.T. et al., Biochem. Biophys. Res. Commun., 1982, 108, 1716, (synth, uv, pmr, props)
• Martin, J.C. et al., J. Med. Chem., 1983, 26, 759, (synth, uv, pmr, cmr, props)
• Matthews, T. et al., Rev. Infect. Dis., S490, 1988, 10, (rev)
• Faulds, D. et al., Drugs, 1990, 39, 597, (rev, pharmacol)
• Capparell, E. et al., Ganciclovir Ther. Cytomegalovirus Infect. 1991, (ed. S.A. Spector) Dekker, 1991, 71, (rev)
• Alhede, B. et al., J.O.C., 1991, 56, 2139-2143, (synth, cmr)
• Freie, H.M.P., Med. Klin. (Munich), (Suppl. 1), 1992, 87, 20, (rev)
• Verheyden, J.P.H., Chron. Drug Discovery, 1993, 3, 299, (ganciclovir, rev)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 546
• Noble, S. et al., Drugs, 1998, 56, 115-146, (rev)
• Boryski, J. et al., Synthesis, 1999, 625-628, (synth, uv)
• Gao, H. et al., Synthesis, 2000, 329-351, (rev)
• McGavin, J.K. et al., Drugs, 2001, 61, 1153-1183, (rev)