2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)(3,3,4,4-2H4)butyl acetate

• ChemBase ID: 168861
• Molecular Formular: C14H19N5O4
• Molecular Mass: 321.33176
• Monoisotopic Mass: 321.14370411
• SMILES: n1c(nc2c(c1)ncn2CCC(COC(=O)C)COC(=O)C)N
• Canonical SMILES: CC(=O)OCC(CCn1cnc2c1nc(N)nc2)COC(=O)C
• InChI: InChI=1S/C14H19N5O4/c1-9(20)22-6-11(7-23-10(2)21)3-4-19-8-17-12-5-16-14(15)18-13(12)19/h5,8,11H,3-4,6-7H2,1-2H3,(H2,15,16,18)
• InChIKey: GGXKWVWZWMLJEH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)(3,3,4,4-^2H₄)butyl acetate
• IUPAC Traditional name: 2-[(acetyloxy)methyl]-4-(2-aminopurin-9-yl)(3,3,4,4-^2H₄)butyl acetate
• Synonyms: 2-[2-(2-Amino-9H-purin-9-yl)ethyl]-1,3-propanediol Diacetate Ester-d4; 9-[4-Acetoxy-3-(acetoxymethyl)but-1-yl]-2-aminopurine-d4; 9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-aminopurine-d4; BRL 42810-d4; FCV-d4; Famcivir-d4; Famcyclovir-d4; Famtrex-d4; Famvir-d4; Famciclovir-d4

Database IDs

• CAS Number: 1020719-42-9
• PubChem SID: 162262993
• PubChem CID: 45039244

CALCULATED PROPERTIES

• Acid pKa: 16.700941
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -0.6100203
• LogD (pH = 7.4): -0.4855497
• Log P: -0.48368603
• Molar Refractivity: 81.5353 cm^3
• Polarizability: 31.537825 Å^3
• Polar Surface Area: 122.22 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Hot Water; Methanol
• Apperance: Off-White Solid
• Melting Point: 102-104°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F101127

A deuterated prodrug of Penciclovir (P221500), which is used as an antiviral.

REFERENCES

• Hodge, V.R.A., et al.: Antimicrob. Ag. Chemother., 33, 1765 (1989)