124832-27-5 Usage
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.
Chemical Properties
White Crystalline Powder
Originator
Glaxo Wellcome (United Kingdom)
Uses
Different sources of media describe the Uses of 124832-27-5 differently. You can refer to the following data:
1. Acyclovir (A192400) impurity. The L-Valine ester prodrug of Acyclovir.
2. Valaciclovir hydrochloride is an antiviral drug used in the management of herpes simplex, herpes zoster, and herpes B.
General Description
Valacyclovir (Valtrex) is the hydrochloride salt of the Lvalylester of acyclovir. The compound is a water-solublecrystalline solid, and it is a prodrug intended to increase thebioavailability of acyclovir by increasing lipophilicity.Valacyclovir is hydrolyzed rapidly and almost completely toacyclovir following oral administration.Valacyclovir has been approved for the treatment of herpeszoster (shingles) in immunocompromised patients. Theside effect profile observed in valacyclovir is comparablewith bioequivalent doses of acyclovir.
Pharmacokinetics
The binding of valacyclovir to human plasma proteins ranges between 13.5 to 17.9%. The plasma elimination half-life of acyclovir is 2.5 to 3.3 hours. The bioavailability of valacyclovir hydrochloride is 54%, compared to approximately 20% for oral acyclovir, and it is as effective as acyclovir in decreasing the duration of pain associated with posttherapeutic neuralgia and episodes of genital lesion healing.
Side effects
The adverse effects are similar to acyclovir, which include nausea, headache, vomiting, constipation, and anorexia.
Check Digit Verification of cas no
The CAS Registry Mumber 124832-27-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,4,8,3 and 2 respectively; the second part has 2 digits, 2 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 124832-27:
(8*1)+(7*2)+(6*4)+(5*8)+(4*3)+(3*2)+(2*2)+(1*7)=115
115 % 10 = 5
So 124832-27-5 is a valid CAS Registry Number.
InChI:InChI=1/C13H20N6O4/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20)/t8-/m0/s1
124832-27-5Relevant articles and documents
Preparation method of valaciclovir hydrochloride
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Paragraph 0027-0029; 0032; 0033, (2019/05/08)
The invention relates to a preparation method of valaciclovir hydrochloride. The preparation method comprises following steps: (1) CBZ-L-valine-acyclovir synthesis: adding N,N-dimethyl formamide, N-carbobenzyloxy-L-valine, 4-dimethylamino pyridine, and ac
PROCESS FOR THE PREPARATION OF VALACYCLOVIR HYDROCHLORIDE
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Paragraph 0043, (2014/10/16)
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.
An efficient and large scale process for synthesis of valacyclovir
Prasada Raju,Vedantham, Ravindra,Khunt, Mayur D.,Mathad, Vijayavitthal T.,Dubey, Pramod K.,Chakravarthy, Akula Kalyan
experimental part, p. 4092 - 4098 (2010/11/05)
A facile, commercially viable and large scale process is developed for an antiviral drug substance, valacyclovir hydrochloride. Several process related critical factors including organic and heavy metal impurities are efficiently addressed in this process.
