Valacyclovir hydrochloride

White Crystalline PowderValacyclovir 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 metabol

Valacyclovir hydrochloride is an organic molecular entity.|Valacyclovir Hydrochloride is the hydrochloride salt of valacyclovir. Valacyclovir is an acyclovir prodrug that, after metabolization, inhibits viral DNA replication. It is used in the management of herpes simplex and varicella zoster infections, as well as prophylactically for human cytomegalovirus infections.|A prodrug of acyclovir that is used in the treatment of HERPES ZOSTER and HERPES SIMPLEX VIRUS INFECTION of the skin and mucous membranes, including GENITAL HERPES.

To a 1L capacity hydrogenator charged a compound of formula II (50g), concentrated hydrochloric acid (9.6ml), 5percent palladium on carbon (5g) and water (350ml) and hydrogenate the reaction mass under hydrogen pressure of 3 kg/cm 2 to 8 kg/cm 2 at a temperature of 25-30°C for 6 to 12 hours. The reaction mass was filtered under vacuum and washed with water. The filtrate was then distilled off under vacuum. The reaction mass was then cooled and isopropyl alcohol was added to the reaction mass. The reaction mass was further cooled to a temperature of 5-10°C and maintained for 1 hour. The product valacyclovir hydrochloride obtained was filtered and washed with isopropyl alcohol.Yield 92percent and purity 99.8percentANALYTICAL METHOD FOR ANALYSISHPLC column : USP LI, 4.6 x 150 mm, 3.5 ???(Zorbax SB-C18, Part No. 863953-914)Detector : UV 250nmMobile phase A : In a 1000ml volumetric flask add 2.8ml of triethylamine, 800ml of purified water and adjust the pH to 5.00 + 0.05 with glacial acetic acid. Complete the volume with purified water.Mobile Phase B AcetonitrileInjection volume 50??, Column temperature 30°CFlow rate l.OmL/minutesGradientTo a 1L capacity hydrogenator charged a compound of formula II (50 g), concentrated hydrochloric acid (9.6 ml), 5percent palladium on carbon (5 g) and water (350 ml) and hydrogenate the reaction mass under hydrogen pressure of 3 kg/cmPreparation of Solution-A Boc-L-Valacyclovir crude (50 g) was charged into mixture of methylene chloride (375 ml) and methanol (125 ml) at 25-30°C and stirred the reaction mass at 25- 30°C to get the clear solution-A. Preparation of Solution-B Cone. Hydrochloric acid (56 ml) was added to DM water (224 ml) over a period of 15-20 min at 20-25°C. Thereafter methanol (56 ml) was added slowly to the obtained solution at 20-25°C. Above separately prepared solution-A (Flow rate-8 ml/min) and solution-B (Flow rate-5.5 ml/min) were fed to the continuous flow micro reactor at 80°C. The elute reaction mass from micro reactor was continuously collected at 0-5°C. As the feed solutions A & B are consumed micro reactor is flush with methylene chloride (50 ml: 50 ml) each feed. Immediately after the collection of reaction mass, aqueous layer and lower organic layers were separated. The pH of the aqueous layer containing product was adjusted to about 2.5 to 2.8 with triethyl amine (~ 46.28 g) at 0-5 °C). Ethanol (300 ml) at 0-5°C was added slowly to the solution. The obtained reaction mass was distilled under reduced pressure (400-40 mm Hg) to get white. The obtained solid mass was cooled at 25-30°C and ethanol (300 ml) was added and continued stirring the above slurry mass at 25-30°C for 60-80 min. The solid was filtered and washed with chill ethanol (100 ml. 0-5°C). The obtained solid is dried in vacuum dryer at 40-45°C till moisture content is 5-8percent. Yield: 31 g Purity: 99percent (by HPLC)

Valaciclovir hydrochloride is an antiviral drug used in the management of herpes simplex, herpes zoster, and herpes B.

Molecular Weight:360.80
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:8
Exact Mass:360.1312809
Monoisotopic Mass:360.1312809
Topological Polar Surface Area:147
Heavy Atom Count:24
Complexity:483
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes