124832-27-5 Usage
Description
Valacyclovir hydrochloride is an orally active L-valyl ester prodrug of the potent antiviral agent acyclovir. It is a water-soluble crystalline solid that increases the bioavailability of acyclovir by enhancing its lipophilicity. As a prodrug, valacyclovir is rapidly absorbed after oral administration and extensively converted to acyclovir via first-pass metabolism, achieving plasma levels comparable to those seen with intravenous administration of acyclovir.
Uses
Used in Antiviral Treatment:
Valacyclovir hydrochloride is used as an antiviral drug for the management of herpes simplex, herpes zoster, and herpes B infections. It is employed as a prodrug to improve the pharmacokinetic profile of acyclovir, allowing for rapid absorption and conversion to the active compound acyclovir in virus-infected cells.
Used in Herpes Simplex Virus Infections:
Valacyclovir hydrochloride is used as a treatment for herpes simplex virus (HSV) infections of the skin and mucous membranes, including initial and recurrent genital herpes. It is used for its improved pharmacokinetic profile compared to acyclovir, providing effective management of these infections.
Used in Herpes Zoster (Shingles) Treatment:
Valacyclovir hydrochloride is used as a treatment for herpes zoster (shingles) in immunocompromised patients. It has been approved for this use due to its effectiveness in managing the condition and its comparable side effect profile with bioequivalent doses of acyclovir.
Used in Cytomegalovirus Infection Suppression:
Valacyclovir hydrochloride is reportedly in clinical trials for the suppression of cytomegalovirus infection and disease in renal transplant patients, demonstrating its potential use in managing viral infections in immunocompromised populations.
Originator
Glaxo Wellcome (United Kingdom)
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.