Valacyclovir hydrochloride

Base Information

• Chemical Name: Valacyclovir hydrochloride
• CAS No.: 124832-27-5
• Molecular Formula: C13H21ClN6O4
• Molecular Weight: 360.801
• Hs Code.: 29335990
• Mol file: 124832-27-5.mol

Synonyms:L-Valine,2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester,monohydrochloride (9CI);L-Valine, ester with 9-((2-hydroxyethoxy)methyl)guanine,;Valacyclovir HCL;

Chemical Property of Valacyclovir hydrochloride

Chemical Property:

• Appearance/Colour: White to off-white crystalline power
• Vapor Pressure: 7.95E-14mmHg at 25°C
• Melting Point: 170-172 °C
• Refractive Index: 1.673
• Boiling Point: 588.4 °C at 760 mmHg
• Flash Point: 309.7 °C
• PSA: 151.14000
• Density: 1.55g/cm3
• LogP: 1.28590
• Storage Temp.: Refrigerator
• Solubility.: H2O: >20mg/mL

Purity/Quality:

99% ^*data from raw suppliers

Valacyclovir Hydrochloride Hydrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Valacyclovir hydrochloride, an orally active L-valyl ester of the potent antiviral agent aciclovir, was launched in 1995 in the United Kingdom for the treatment of herpes simplex virus (HSV) infections of the skin and mucous membranes, including initial and recurrent genital herpes. As a prodrug, valaciclovir has an improved pharmacokinetic profile to aciclovir. It is rapidly absorbed after oral administration and extensively converted to aciclovir via first-pass metabolism to achieve plasma levels of aciclovir comparable to those seen with aciclovir via i.v. route. Valacyclovir is then activated selectively in virus-infected cells by viral thymidine kinase to form aciclovir triphosphate in a stepwise fashion. This active species inhibits viral DNA polymerase via irreversible binding to the active site of the enzyme. Once aciclovir is incorporated into the elongating viral DNA, it terminates replication of the viral DNA strand, an antiviral mechanism unique to aciclovir. Valacyclovir is reportedly in clinical trials for the suppression of cytomegalovirus infection and disease in renal transplant patients.
• Uses: Acyclovir (A192400) impurity. The L-Valine ester prodrug of Acyclovir. Valaciclovir hydrochloride is an antiviral drug used in the management of herpes simplex, herpes zoster, and herpes B.

Technology Process of Valacyclovir hydrochloride

There total 9 articles about Valacyclovir hydrochloride 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: 98.5%

2-[(2-amino-1,6-dihydro-6-oxo-9H-purine-9-yl)methoxy]ethyl N-[(benzyloxy)carbonyl]-L-valinate (124832-31-1) → valacyclovir Hydrochloride (124832-27-5)

Guidance literature:

2-[(2-amino-1,6-dihydro-6-oxo-9H-purine-9-yl)methoxy]ethyl N-[(benzyloxy)carbonyl]-L-valinate; With 5 % alumina-supported palladium; hydrogen; In N,N-dimethyl-formamide; at 30 ℃; under 2942.29 Torr;

With hydrogenchloride; In water; at 10 ℃; pH=3 - 4;

Reference yield: 86.0%

CBZ-L-valineacyclovir (124832-32-2) → valacyclovir hydrochloride (124832-27-5,136489-37-7)

Guidance literature:

CBZ-L-valineacyclovir; With formic acid; palladium on activated charcoal; In methanol; water; at 20 - 40 ℃; for 2h; Inert atmosphere;

With hydrogenchloride; In methanol; water; at 20 - 40 ℃; for 10h;

Reference yield:

2-[(2-amino-1,6-dihydro-6-oxo-9H-purine-9-yl)methoxy]ethyl N-[(benzyloxy)carbonyl]-L-valinate (124832-31-1) → 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl) methoxy]ethyl-L-valinate hydrochloride + valacyclovir Hydrochloride (124832-27-5)

Guidance literature:

With hydrogenchloride; formic acid; palladium; In water; acetone;

upstream raw materials:

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

acycloguanosine

9-[(acetoxyethoxy)methyl]guanine

Valacyclovir

Downstream raw materials:

acycloguanosine

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF VALACYCLOVIR". Page/Page column 13-15. . Retrieved 2017/09/15.
• 2、 -. "A PROCESS FOR THE PREPARATION OF VALACYCLOVIR HYDROCHLORIDE". Page/Page column 10-11. . Retrieved 2013/06/06.