124832-31-1

Basic information

• Product Name: Cbz-Valaciclovir
• Synonyms: CBZ VALACYCLOVIR;2-[(2-AMINO-6-OXO-1,6-DIHYDRO-9H-PURIN-9-YL)METHOXY]ETHYL N-(BENZYLOXYCARBONYL)-L-VALINATE;Cbz-Valaciclovir;N-[(Phenylmethoxy)carbonyl]-L-valine 2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester;Valacyclovir Related Compound E (25 mg) (2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl N-[(benzyloxy)carbonyl]-L-valinate);2-[(2-AMino-6-oxo-1,6-dihydro-9H-purin-9-yl)Methoxy]ethyl N-(benzyloxycarbonyl)-L-valinate;Valaciclovir impurity E (PhEur);Valaciclovir Related Compound E (USP)
• CAS NO: 124832-31-1
• Molecular Formula: C₂₁H₂₆N₆O₆
• Molecular Weight: 458.47
• EINECS: 1312995-182-4
• Mol File: 124832-31-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Density: 1.429 g/cm³
• Refractive Index: 1.644
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.34±0.20(Predicted)
• CAS DataBase Reference: Cbz-Valaciclovir(CAS DataBase Reference)
• NIST Chemistry Reference: Cbz-Valaciclovir(124832-31-1)
• EPA Substance Registry System: Cbz-Valaciclovir(124832-31-1)

Safety Data

• WGK Germany: 1
• Hazardous Substances Data: 124832-31-1(Hazardous Substances Data)

Usage

Uses

N-[(Phenylmethoxy)carbonyl]-L-valine 2-[(2-Amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl Ester (Valaciclovir EP Impurity E; Valaciclovir USP Related Compound E) can be used for the synthesis of L-Valacyclovir Hydrochloride (V085000), which is a drug used to treat infections caused by certain types of viruses.

InChI:InChI=1/C21H26N6O6/c1-13(2)15(24-21(30)33-10-14-6-4-3-5-7-14)19(29)32-9-8-31-12-27-11-23-16-17(27)25-20(22)26-18(16)28/h3-7,11,13,15H,8-10,12H2,1-2H3,(H,24,30)(H3,22,25,26,28)/t15-/m0/s1

Upstream product

• 59277-89-3 acycloguanosine 
• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 5683-33-0 2-(Dimethylamino)pyridine 
• 102728-64-3 9-[(acetoxyethoxy)methyl]guanine 

Downstream Products

• 124832-26-4 Valacyclovir 
• 124832-27-5 valacyclovir Hydrochloride 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF VALACYCLOVIR HYDROCHLORIDE

The present invention provides a process for the preparation of 2-[(2-amino-1,6-dihydro-6-oxo-9H-yl)]ethyl L-valine ester hydrochloride (valacyclovir hydrochloride) of formula I comprising deprotection of N-[(benzyloxy)carbonyl]-L-valine-2-[(2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy]ethyl ester, of formula II using 5% palladium on carbon as a catalyst and mineral acid in the presence of water, avoiding use of organic solvents under hydrogen pressure to yield valacyclovir hydrochloride having yield of ≧90% and purity of ≧99.5%, pharmaceutically acceptable grade. The valacyclovir hydrochloride obtained using the process of the present invention is valacyclovir hydrochloride polymorphic Form I.

VALACYCLOVIR PROCESS

A process for preparing valacyclovir or a salt thereof.

USE OF VALACICLOVIR FOR THE MANUFACTURE OF A MEDICAMENT FOR THE TREATMENT OF GENITAL HERPES BY A SINGLE DAILY APPLICATION

The invention relates to the antiviral drug valaciclovir, the valine ester of 9-[(2-hydroxyethoxy)methyl]guanine (aciclovir), which is known as an effective treatment for genital herpes in a dosage regime of 40 mg, twice to 5 times daily. More specificall