Famciclovir

Base Information

• Chemical Name: Famciclovir
• CAS No.: 104227-87-4
• Molecular Formula: C14H19N5O4
• Molecular Weight: 321.336
• Hs Code.: 29335990
• European Community (EC) Number: 630-411-6
• NSC Number: 758921
• UNII: QIC03ANI02
• DSSTox Substance ID: DTXSID0023038
• Nikkaji Number: J435.369B
• Wikipedia: Famciclovir
• Wikidata: Q420186
• NCI Thesaurus Code: C29044
• RXCUI: 68099
• Metabolomics Workbench ID: 42784
• ChEMBL ID: CHEMBL880
• Mol file: 104227-87-4.mol

Synonyms:1,3-Propanediol, 2-(2-(2-amino-9H-purin-9-yl)ethyl)-, diacetate (ester);9-(4-acetoxy-3-(acetoxymethyl)but-1-yl)-2-aminopurine;BRL 42810;BRL-42810;BRL42810;famciclovir;Famvir

Chemical Property of Famciclovir

Chemical Property:

• Appearance/Colour: off-white powder
• Vapor Pressure: 3.73E-12mmHg at 25°C
• Melting Point: 102-104 °C
• Refractive Index: 1.628
• Boiling Point: 550.2 °C at 760 mmHg
• PKA: 4.00±0.10(Predicted)
• Flash Point: 286.6 °C
• PSA: 122.22000
• Density: 1.4 g/cm³
• LogP: 1.12220
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: ≥10mg/mL
• XLogP3: 0
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 9
• Exact Mass: 321.14370410
• Heavy Atom Count: 23
• Complexity: 404

Purity/Quality:

98%, ^*data from raw suppliers

Famciclovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 20/21/22-45-61
• Safety Statements: 36/37/39-45-53-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: CC(=O)OCC(CCN1C=NC2=CN=C(N=C21)N)COC(=O)C
• Recent ClinicalTrials: Famciclovir in Multiple Sclerosis
• Recent EU Clinical Trials: Clinical trial to determine the effect of Famciclovir on Epstein-Barr virus activity as measured by EBV shedding in saliva of patients with Multiple Sclerosis.
• Recent NIPH Clinical Trials: Phase III Study of AK-120 in Patients with Recurrent Herpes Simplex
• Description: Famciclovir, an effective oral prodrug of the antiviral penciclovir, was launched in the UK and shortly after in the U.S.A. for the treatment of shingles (herpes zoster). As the diacetyl ester of the 6-deoxy- penciclovir, famciclovir has significantly improved oral absorption. It is converted to penciclovir in vivo with a bioavailability of 41 % in rats. Penciclovir is phosphorylated, and hence activated onty in herpesvirus infected cells. This stable metabolite, penciclovir-triphosphate, is a strong inhibitor of herpesvirus DNA polymerases and of viral DNA synthesis with long lasting effects. The high selectivity of famciclovir/penciclovir to herpes family of viruses and their rather low toxicity may make this agent superior to other existing drugs.
• Uses: Used as an antiviral. Prodrug of Penciclovir (P221500). sterol absorption inhibitor. Famciclovir (Famvir) a synthetic acyclic purine analog derived from guanine. It is the diacetyl ester (prodrug) of penciclovir, which exhibits no antiviral activity until hydrolyzed to penciclovir and its active metabolites. It is indicated for the management of acute herpes zoster infections. It has been shown to relieve acute symptoms as well as to shorten the duration of postherpetic neuralgia. It is also used for the treatment or suppression of recurrent episodes of genital herpes in immunocompetent patients and in the treatment of recurrent herpes simplex types 1 and 2 infections in patients with human immunodeficiency virus. These Secondary Standards are qualified as Certified Reference Materials. These are suitable for use in several analytical applications including but not limited to pharma release testing, pharma method development for qualitative and quantitative analyses, food and beverage quality control testing, and other calibration requirements.
• Indications: Famciclovir (Famvir) is the diacetyl ester prodrug of the acyclic guanosine analogue 6-deoxypenciclovir (Denavir).
• Therapeutic Function: Antiviral
• Clinical Use: Famciclovir is indicated for the treatment of acute herpes zoster (shingles); it is at least as effective in reducing pain and healing time. Famciclovir is generally as effective as acyclovir in the treatment of HSV. In immunocompetent patients, famciclovir is approved for the treatment and prophylaxis of recurrent genital herpes. For HIV-infected individuals, famciclovir is approved for the treatment of all recurrent mucocutaneous HSV infections. Famciclovir is utilized in the treatment and suppression of herpes simplex infections, as well as in the treatment of zoster (secondary, dermatomal infection with VZV). In addition to these FDA-approved indications, it has also shown very limited activity in the treatment of HBV infections, but it is not recommended for this indication.
• Drug interactions: Potentially hazardous interactions with other drugs Probenecid: decreased excretion of famciclovir. Increased famciclovir levels reported with mycophenolate mofetil.

Technology Process of Famciclovir

There total 62 articles about Famciclovir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

acetic anhydride (108-24-7) + 6-deoxypenciclovir (104227-86-3) → 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine (104227-87-4)

Guidance literature:

With pyridine; dmap; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1055/s-2004-829174

Reference yield: 92.12%

2-(2-((2-amino-6-chloro-5-nitrosopyrimidine-4-yl)amino)ethyl)propane-1,3-diol + acetic anhydride (108-24-7) + orthoformic acid triethyl ester (122-51-0) → 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine (104227-87-4)

Guidance literature:

2-(2-((2-amino-6-chloro-5-nitrosopyrimidine-4-yl)amino)ethyl)propane-1,3-diol; With 5%-palladium/activated carbon; ammonium formate; In ethyl acetate; at 65 ℃; for 22h;

orthoformic acid triethyl ester; With acetic acid; In ethyl acetate; at 30 ℃; for 20h;

acetic anhydride; With dmap; triethylamine; In ethyl acetate; at 30 ℃; for 1.5h; Reagent/catalyst; Temperature;

Reference yield: 91.0%

acetic anhydride (108-24-7) + 2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine hydrochloride → 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine (104227-87-4)

Guidance literature:

2-amino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine hydrochloride; With triethylamine; In dichloromethane; at 10 - 20 ℃;

acetic anhydride; With dmap; In dichloromethane; at 5 - 20 ℃;

upstream raw materials:

acetic anhydride

diethyl 2-(2-(2-aminopurine-9-yl)ethyl)malonate

9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine

4-acetoxy-3-(acetoxymethyl)-1-iodobutane

Downstream raw materials:

(R,S)-9-<4-acetoxy-3-(hydroxymethyl)but-1-yl>-2-aminopurine

(R,S)-9-<3-(hydroxymethyl)-4-<(monomethoxytrityl)oxy>but-1-yl>-2-<(monomethoxytrityl)amino>purine

9-<4-hydroxy-3-(hydroxymethyl)but-1-yl>-2-<(monomethoxytrityl)amino>purine

(R,S)-2-amino-9-<4-(benzyloxy)-3-(hydroxymethyl)but-1-yl>purine

Refernces

• 1、 -. "Preparation method of high-purity famciclovir". Paragraph 0014-0024. . Retrieved 2021/04/21.
• 2、 -. "SUBSTITUTED ARYLUREA COMPOUNDS FOR INDUCING APOPTOSIS AND COMPOSITION FOR ANTICANCER COMPRISING THE SAME". Paragraph 0131; 0136-0139. . Retrieved 2021/08/17.