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

• ChemBase ID: 309
• Molecular Formular: C14H19N5O4
• Molecular Mass: 321.33176
• Monoisotopic Mass: 321.14370411
• SMILES: O(CC(CCn1c2nc(ncc2nc1)N)COC(=O)C)C(=O)C
• 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)butyl acetate
• IUPAC Traditional name: famciclovir; 2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate
• Brand Name: Famvir
• Synonyms: Famciclovirum [INN-Latin]; FCV; Famciclovir; Famvir; 2-(2-(2-Amino-9H-purin-9-yl)ethyl)-1,3-propanediol diacetate ester; BRL 42810; Famciclovir; 2-[2-(2-Amino-9H-purin-9-yl)ethyl]-1,3-propanediol Diacetate Ester; 9-[4-Acetoxy-3-(acetoxymethyl)but-1-yl]-2-aminopurine; 9-[4-Acetoxy-3-(acetoxymethyl)butyl]-2-aminopurine; Famcivir; Famcyclovir; Famtrex; 2-[(acetyloxy)methyl]-4-(2-amino-9H-purin-9-yl)butyl acetate

Database IDs

• CAS Number: 104227-87-4
• MDL Number: MFCD00866964
• PubChem SID: 46507561; 160963772
• PubChem CID: 3324

CALCULATED PROPERTIES

JChem

• 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: 31.461538 Å^3
• Polar Surface Area: 122.22 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.13
• LOG S: -2.39
• Solubility (Water): 1.32e+00 g/l

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: ≥10 mg/mL; Methanol; Water
• Apperance: solid; White to Off-White Solid
• Melting Point: 102-104°C
• Hydrophobicity(logP): 0.085; 0.6

Safety Information

• Storage Condition: -20°C; -20°C Freezer; desiccated
• RTECS: TY3164000
• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Consequently, herpes viral DNA synthesis and replication are selectively inhibited.; Guanine analogue; In cells infected with HSV-1, HSV-2 or VZV, viral thymidine kinase phosphorylates penciclovir to a monophosphate form; Penciclovir triphosphate selectively inhibits viral DNA polymerase by competing with deoxyguanosine triphosphate; Prodrug of penciclovir with improved oral bioavailability; that, in turn, is converted to penciclovir triphosphate by cellular (human) kinases; Undergoes rapid biotransformation to penciclovir

Product Information

• Purity: ≥98% (HPLC); 95%
• Salt Data: Free Base
• Application(s): Antiviral drug; Used for the treatment of various herpes virus infections, most commonly for herpes zoster (shingles).
• Empirical Formula (Hill Notation): C14H19N5O4

DETAILS

DrugBank - DB00426

• Drug Groups: approved
• Description: Famciclovir is a guanine analogue antiviral drug used for the treatment of various herpes virus infections, most commonly for herpes zoster (shingles). It is a prodrug form of penciclovir with improved oral bioavailability. Famciclovir is marketed under the trade name Famvir (Novartis).
• Indication: For the treatment of acute herpes zoster (shingles). Also for the treatment or suppression of recurrent genital herpes in immunocompetent patients and treatment of recurrent mucocutaneous herpes simplex infections in HIV infected patients.
• Pharmacology: Famciclovir is a prodrug that undergoes rapid biotransformation to the active antiviral compound penciclovir. Penciclovir is an anti-viral drug which has inhibitory activity against herpes simplex virus types 1 (HSV-1) and 2 (HSV-2) and varicella zoster virus (VZV). Therefore, herpes viral DNA synthesis and replication are selectively inhibited.
• Toxicity: Symptoms of overdose include constipation, diarrhea, dizziness, fatigue, fever, headache, nausea, and vomiting.
• Affected Organisms: Human Herpes Virus
• Biotransformation: Hepatic
• Absorption: 77 %
• Half Life: 10 hours
• Protein Binding: 20-25%
• Elimination: Active tubular secretion contributes to the renal elimination of penciclovir.
• Distribution: * 1.08±0.17 L/kg [healthy male subjects following a single intravenous dose of penciclovir at 400 mg administered as a 1-hour intravenous infusion]
• Clearance: * 36.6 +/- 6.3 L/hr [healthy male]; * 0.48 +/- 0.09 L/hr/kg [healthy male]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S2467

Research Area: Infection
Biological Activity:
Famciclovir(Famvir) is a guanine analogue antiviral drug used for the treatment of various herpesvirus infections, most commonly for herpes zoster (shingles). It is a prodrug form of penciclovir with improved oral bioavailability. Use of Famciclovir in this manner, known as post-exposure prophylaxis, has been shown to reduce the amount of latent virus in the neural ganglia. [1][2]

Sigma Aldrich - F7932

Biochem/physiol Actions
Famciclovir is an antiretroviral guanosine analog used to treat herpesvirus infections and hepatitis B. Famciclovir is rapidly converted to penciclovir. Viral thymidine kinase phosphorylates penciclovir to a monophosphate form that celular kinases convert in turn to penciclovir triphosphate. Penciclovir triphosphate competitively inhibits viral DNA polymerase and thus viral replication. Prolonged administration can lead to resistance; it is often manifested as selection of pre-existing resistant strains with mutations in the reverse transcriptase domain of the DNA polymerase gene.1
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. F7932.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Toronto Research Chemicals - F101125

Used as an antiviral. Prodrug of Penciclovir (P221500).

REFERENCES

• Thackray AM et al. J Infect Dis. 1996 Feb;173(2)
• Hodge, V.R.A., et al.: Antimicrob. Ag. Chemother., 33, 1765 (1989)
• Eur. Pat., 1986, Beecham, 182 024; CA, 105, 133669, (synth, pmr, pharmacol)
• Vere Hodge, R.A. et al., Antimicrob. Agents Chemother., 1989, 33, 1765, (synth, pharmacokinet)
• Genn, G.R. et al., J. Med. Chem., 1989, 32, 1738, (synth)
• Winton, C.F. et al., Anal. Proc. (London), 1990, 27, 181, (hplc)
• Harnden, M.R. et al., Nucleosides Nucleotides, 1990, 9, 499, (cryst struct)
• Vere Hodge, R.A., Antiviral Chem. Chemother., 1993, 4, 67, (rev)
• Sutton, D. et al., Antiviral Res., 1993, 4, 37, (rev)
• Vere Hodge, R.A. et al., Chirality, 1993, 5, 577, (metab)
• Filer, C.W. et al., Xenobiotica, 1994, 24, 357, (metab, pharmacokinet, human)
• Cirelli, R. et al., Antiviral Res., 1996, 29, 141, (rev, pharmacol)
• Brand, B. et al., Tetrahedron, 1999, 55, 5239-5252, (synth, pmr, cmr)
• Freer, R. et al., Tetrahedron, 2000, 56, 4589-4595, (synth, pmr, cmr)