Valacyclovir synthesis

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  1. Valacyclovir synthesis


    International Journal of Organic Chemistry Vol.3 No.4(2013), Article ID:41376,5 pages DOI:10.4236/ijoc.2013.34036 New Method of Palladium Metal Trapping through Resins in Antiviral Drug: Valacyclovir HCl Keshava Navin Kumar [email protected] © 2013 Keshava Navin Kumar Reddy et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Received October 4, 2013; revised November 8, 2013; accepted November 23, 2013 Keywords: Valacyclovir Hydrochloride; Antiviral Drug; N-Phthalimide-L-Valine Ester; Monomethylamine; Commercially Scalable Process; Less Cycle Time ABSTRACT This process describes a novel technique for effective trapping of “Pd” metal through resins during the process development of L-valine, 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl) methoxy] ethyl ester, and mono hydrochloride known as a Valacyclovir hydrochloride (1). This technique is suitable for large-scale production of 1 and it is described here Pd metal trapping by using different resins. Introduction Valacyclovir (Valtrex) is an orally active prodrug of the antiviral drug acyclovir [1,2]. Valacyclovir is the L-Valyl ester of the antiviral drug acyclovir which is active against herpes simplex virus types 1 and 2 and varicella zoster virus [3-5]. After oral administration, the prodrug Valacyclovir is rapidly absorbed from the gastrointestinal tract and nearly completely converted to acyclovir and L-valine. Acyclovir is a specific and selective inhibitor of viral herpes replication and is neither highly lipid nor aqueous soluble, with limited and variable oral bioavailability (15% - 21%) that decreases with increasing doses. Valaciclovir, also spelled valacyclovir, is an antiviral drug used in the management of herpes simplex, herpes zoster (shingles), and herpes B. It is a prodrug, which is converted to aciclovir in a persons body. Common adverse drug reactions (≥1% of patients) associated with valaciclovir therapy are the same as for aciclovir, its active metabolite, and include: nausea, vomiting, diarrhea and headache. Infrequent adverse effects (0.1–1% of patients) include: agitation, vertigo, confusion, dizziness, edema, arthralgia, sore throat, constipation, abdominal pain, rash, weakness and/or renal impairment. Rare adverse effects ( Valaciclovir belongs to a family of molecules first described and patented by Paolo Cornaglia Ferraris in 1982 (patents EP0077460 A2, CA1258149A1, DE3273785D1, EP0077460A3, EP0077460B1, US4567182). Valaciclovir is a prodrug, an esterified version of aciclovir that has greater oral bioavailability (about 55%) than aciclovir (10–20%). It is converted by esterases to the active drug aciclovir, as well as the amino acid valine, via hepatic first-pass metabolism.

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    Mechanism of Action Valacyclovir is rapidly converted to acyclovir, which inhibits DNA synthesis. Acyclovir is a synthetic purine nucleoside analogue with. The synthesis of valacyclovir. The same approach was implemented with another protecting group on an amino acid moiety and, valacyclovir was prepared by reaction of N-Boc-L-valine with acyclovir using 1-3-dimethyl-aminopropyl-3-ethylcarbodiimide hydrochloride EDC as coupling agent and HCl in the deprotection step 160. Synthesized include those that had the guanine moiety of L-valacyclovir substituted with purine. Starting materials for synthesis, solvents for HPLC, and.

    -Valacyclovir, a prodrug of acyclovir, is a substrate for the peptide transporter (Pep T1) in the intestinal mucosa, which accounts for its higher than expected oral bioavailability. The substrate activity of -valacyclovir for Pep T1 is surprising, particularly when one considers that the molecule has the structural features of a nucleoside rather than a peptide. In an attempt to better understand the structure–transport relationships (STR) for the interactions of -valacyclovir with Pep T1, analogs of this molecule with structural changes in the guanine moiety were synthesized and their substrate activity for Pep T1 in Caco-2 cell monolayers was determined. The analogs synthesized include those that had the guanine moiety of -valacyclovir substituted with purine, benzimidazole, and 7-azaindole. A cost-effective and improved process was developed for the synthesis of the antiviral drug Valacyclovir hydrochloride 1. The process involves the Streglich condensation between 4 and 6 to obtain N-Phthalimide-L-Valine ester 5, which was deprotected by using 40% monomethylamine Overall, the chemistry has been developed and used to prepare Valacyclovir drug 1 in an overall yield of 61 %.

    Valacyclovir synthesis

    Valacyclovir -, Acyclovir - an overview ScienceDirect Topics

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  5. Review of reported synthetic approaches. The synthesis of valacyclovir 49 reported till date, mainly starts from acyclovir 45 by its condensation with.

    • Chapter-3 - Shodhganga.
    • S ynthesis of analogs of L-valacyclovir and. - Semantic Scholar.
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    The L-valyl ester of acyclovir valacyclovir is obtained in this manner Beauchamp and Kren- itsky, 1993. Valacyclovir is such a prodrug, which is derived from. Synthesis of Acyclovir Metal Complexes Spectral, Electrochemical, Thermal, and. Investigation and DNA-Binding Studies of Valacyclovir-CopperII Complex. Valacyclovir is rapidly converted to acyclovir, which inhibits DNA synthesis. Acyclovir is a synthetic purine nucleoside analogue with inhibitory activity against herpes simplex virus types 1 HSV-1, 2 HSV-2, and varicella-zoster virus VZV.

     
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