104227-88-5

Basic information

• Product Name: MONO-DESACETYL FAMCICLOVIR
• Synonyms: MONO-DESACETYL FAMCICLOVIR;Famciclovir Related Compound B (20 mg) [4-(2-Amino-9H-purin-9-yl)-2-(hydroxymethyl)butyl acetate];2-[2-(2-AMino-9H-purin-9-yl)ethyl]-1,3-propanediol 1-Acetate;BRL 43594;FaMciclovir Related CoMpound B;2-[2-(2-Amino-9H-purin-9-yl)ethyl]-1,3-propanediol monoacetate (ester);4-(2-Amino-9H-purin-9-yl)-2-(hydroxymethyl)butyl acetate;Famciclovir USP RC B
• CAS NO: 104227-88-5
• Molecular Formula: C12H17N5O3
• Molecular Weight: 279.3
• Product Categories: Bases & Related Reagents;Intermediates & Fine Chemicals;Metabolites & Impurities;Nucleotides;Pharmaceuticals
• Mol File: 104227-88-5.mol
• Article Data: 6

Chemical Properties

• Melting Point: 166-168℃
• Boiling Point: 525.0±60.0 °C(Predicted)
• Appearance: /
• Density: 1.46±0.1 g/cm3(Predicted)
• PKA: 14.62±0.10(Predicted)
• CAS DataBase Reference: MONO-DESACETYL FAMCICLOVIR(CAS DataBase Reference)
• NIST Chemistry Reference: MONO-DESACETYL FAMCICLOVIR(104227-88-5)
• EPA Substance Registry System: MONO-DESACETYL FAMCICLOVIR(104227-88-5)

Safety Data

• Hazardous Substances Data: 104227-88-5(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

A metabolite of Famciclovir (F101125).

Upstream product

• 104227-87-4 9-(4-acetoxy-3-acetoxymethylbutyl)-2-aminopurine 
• 1445-45-0 Trimethyl orthoacetate 
• 104227-86-3 6-deoxypenciclovir 
• 97845-60-8 9-<4-acetoxy-3-(acetoxymethyl)butyl>-2-amino-6-chloro-9H-purine 

Downstream Products

• 247081-81-8 2-amino-9-(3-acetoxymethyl-4-isopropoxycarbonyloxybut-1-yl)purine 

Relevant articles and documents

Production of recombinant human aldehyde oxidase in Escherichia coli and optimization of its application for the preparative synthesis of oxidized drug metabolites

Recombinant human aldehyde oxidase (AO) was expressed in Escherichia coli. Different cell disruption methods and conditions of cell culture in shake flasks and bioreactors and of biotransformation on an analytical scale were tested to optimize the synthesis of oxidized AO drug metabolites. The volumetric productivity was increased 24-fold by optimizing the cell culture conditions. The highest yield was achieved in a 25 L stirred tank bioreactor under non-oxygen-limited conditions and high lactose feed rate. Suspensions of highly concentrated and well-aerated whole cells at neutral pH and relatively low temperatures led to the best conversion. The solvent for the substrate and the buffering agent for the biotransformation had an important effect. In a biotransformation with AO, 210 mg of famciclovir was converted to diacetyl penciclovir a yield of 82 %. The optimized protocol represents a viable method for the preparative synthesis of oxidized AO metabolites of drugs. Drug metabolites: Recombinant human aldehyde oxidase is expressed in Escherichia coli. The highest volumetric productivity is achieved in a 25 L stirred tank bioreactor under non-oxygen-limited conditions and high lactose feed rate. In a biotransformation with concentrated whole cells at pH 7.4 and 30 °C, 210 mg of famciclovir is converted to diacetyl penciclovir in a yield of 82 %. The optimized protocol enables the preparative synthesis of oxidized aldehyde oxidase metabolites of drugs.

PROCESS FOR THE PREPARATION OF FAMCICLOVIR

The invention provides processes for making famciclovir with low levels of undesirable by-products. The present invention discloses a process comprises reacting a compound of formula I (acetic acid 2-acetoxymethyl-4-(5-amino-7-chloro-imidazo [4,5-b]pyridin-3-yl)-butyl ester) in the presence of a palladium on charcoal catalyst in a C1-C6 alkyl acetate and ammonium formate. The present invention further discloses a process comprises reacting a compound of formula I (acetic acid 2-- acetoxymethyl-4-(5-amino-7-chloro-imidazo[4,5-b]pyridin-3-yl)-butyl ester) in the presence of a palladium on charcoal catalyst in a mixture of a C1-C6 alkyl acetate, a C1-C4 alcohol and ammonium formate.

Purine derivatives and their pharmaceutical use

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