Valaciclovir

Base Information

• Chemical Name: Valaciclovir
• CAS No.: 124832-26-4
• Molecular Formula: C13H21ClN6O4
• Molecular Weight: 324.34
• Hs Code.: 3002909099
• Mol file: 124832-26-4.mol

Synonyms:256U87;L-VACV;L-Valine ester with 9-[(2-hydroxyethoxy)methyl]guanine;ValACV;Valcivir;L-Valine,2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester;

Chemical Property of Valaciclovir

Chemical Property:

• Appearance/Colour: white to off-white crystalline powder
• Boiling Point: 588.4 °C at 760 mmHg
• PKA: 9.34±0.20(Predicted)
• Flash Point: 309.7 °C
• PSA: 151.14000
• Density: 1.55 g/cm³
• LogP: 0.48390
• Solubility.: Soluble in DMSO

Purity/Quality:

99% ^*data from raw suppliers

Valaciclovirhydrochloride 98%purewithdatedHPLCUVchromatogram ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Description: Valaciclovir (also known as BW256U87 or valaciclovir, and marketed under the trade name of Valtrexs by GlaxoSmithKline) is the hydrochloride salt of the L-valyl ester of aciclovir that was developed originally by Wellcome Research Laboratories. This aciclovir prodrug is rapidly and virtually completely converted to aciclovir following oral administration. As oral administration of valaciclovir results in aciclovir plasma levels nearly equivalent to those achieved by intravenous administration, its efficacy is superior to that of oral aciclovir for the treatment of zoster and equivalent to oral aciclovir in the treatment of first and recurrent episodes of genital herpes.
• Uses: The L-Valine ester prodrug of Acyclovir. Valacyclovir (Valtrex) is the 1-valine ester (prodrug) of acyclovir that exhibits no activity until hydrolyzed in the intestinal wall or liver to acyclovir and its active metabolite. Its modified structure allows increased intestinal absorption and concomitant higher plasma levels of acyclovir. It demonstrates activity against HSV types 1 and 2, varicella-zoster virus, and cytomegalovirus. It exerts its effects by interfering with DNA synthesis through phosphorylation by viral thymidine kinase and subsequent inhibition of viral DNA polymerase, thereby inhibiting viral replication. Valtrex is indicated for the treatment of acute herpes zoster and recurrent genital herpes in immunocompetent adults. The most common side effects are headache, nausea, and vomiting.
• Indications: Valacyclovir (Valtrex) is the 1-valine ester (prodrug) of acyclovir that exhibits no activity until hydrolyzed in the intestinal wall or liver to acyclovir and its active metabolite. Its modified structure allows increased intestinal absorption and concomitant higher plasma levels of acyclovir. It demonstrates activity against HSV types 1 and 2, varicella-zoster virus, and cytomegalovirus. It exerts its effects by interfering with DNA synthesis through phosphorylation by viral thymidine kinase and subsequent inhibition of viral DNA polymerase, thereby inhibiting viral replication. Valtrex is indicated for the treatment of acute herpes zoster and recurrent genital herpes in immunocompetent adults. The most common side effects are headache, nausea, and vomiting.Valacyclovir is the only antiviral agent approved for herpes labialis, for a 3-day course in the episodic treatment of recurrent genital herpes (2). Valacyclovir is indicated for recurrent genital herpes and is administered at 500 mg twice daily for 3 days at the onset of prodromal symptoms or at the first sign of infection.
• Therapeutic Function: Antiviral
• Clinical Use: Antiviral: Herpes zoster and simplex Prevention of cytomegalovirus (CMV) disease after renal transplantation
• Drug interactions: Potentially hazardous interactions with other drugs Ciclosporin: may alter ciclosporin levels; possibly increased risk of nephrotoxicity. Mycophenolate: higher concentrations of both aciclovir and mycophenolic acid on concomitant administration. Tacrolimus: possibly increased risk of nephrotoxicity

Technology Process of Valaciclovir

There total 10 articles about Valaciclovir 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:

2-[(2-amino-1,6-dihydro-6-oxo-9H-purine-9-yl)methoxy]ethyl N-[(benzyloxy)carbonyl]-L-valinate (124832-31-1) → Valacyclovir (124832-26-4)

Guidance literature:

palladium; In N-methyl-acetamide; water;

Reference yield:

Boc-L-valacyclovir (502421-44-5) → Valacyclovir (124832-26-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h; Cooling with ice;

DOI:10.1016/j.ejpb.2015.12.002

Reference yield:

valacyclovir (142963-59-5) → Valacyclovir (124832-26-4) + D-Valacyclovir

Guidance literature:

With 3,3’-diphenyl-1,1’-binaphthyl)-20-crown-6-based CSP II with residual silanol protecting n-octyl groups; In water; acetonitrile; at 20 ℃; Solvent; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/chir.22424

upstream raw materials:

2-[(2-amino-1,6-dihydro-6-oxo-9H-purine-9-yl)methoxy]ethyl N-[(benzyloxy)carbonyl]-L-valinate

N-Boc-(S/R)-valine

D,L-valine

valacyclovir

Downstream raw materials:

N-formyl-valacyclovir

C₂₀H₂₃Cl₂N₇O₅

C₂₀H₂₄FN₇O₅

C₂₀H₂₄BrN₇O₅

Refernces

• 1、 Ahn, Seong Ae,Hyun, Myung Ho. "Liquid chromatographic resolution of amino acid esters of acyclovir including racemic valacyclovir on crown ether-based chiral stationary phases". . p. 268 - 273. Retrieved 2015/03/18.
• 2、 -. "Crystalline forms of valacyclovir hydrochloride". . . Retrieved 2008/06/13.