175865-59-5 Usage
Description
Valganciclovir hydrochloride, a prodrug of the antiviral ganciclovir, is an L-valyl ester derivative used to treat cytomegalovirus (CMV) infections. It is a white crystalline solid that is well absorbed and rapidly hydrolyzed to ganciclovir by intracellular esterases in the intestinal mucosal cells and by hepatic esterases. Valganciclovir is actively transported by the intestinal peptide transporter PEPT1, resulting in a higher absolute bioavailability compared to ganciclovir. It was launched in the US for the oral treatment of cytomegalovirus (CMV) retinitis, a sight-threatening complication in patients with AIDS. The brand name for Valganciclovir hydrochloride is Valcyte (Roche).
Uses
Used in Antiviral Treatment:
Valganciclovir hydrochloride is used as an antiviral agent for the treatment of HIV associated retinitis and for the prevention of post-transplant cytomegalovirus (CMV) infections. It inhibits viral DNA synthesis by targeting the CMV polymerase.
Used in HIV-related Cell Signaling Studies:
Valganciclovir hydrochloride is used in HIV-related cell signaling studies, providing insights into the mechanisms of the virus and potential therapeutic targets.
Used in the Treatment of Retrovirus:
As a pro-drug of ganciclovir, valganciclovir hydrochloride is used in the treatment of retrovirus, particularly cytomegalovirus (CMV) infections.
Used in Antibacterial Applications:
Valganciclovir hydrochloride is used as an antibacterial agent, inhibiting protein synthesis in certain bacterial pathogens.
Used in Pharmaceutical Quality Control:
Valganciclovir hydrochloride is used as a certified pharmaceutical secondary standard for application in quality control, providing a convenient and cost-effective alternative to pharmacopeia primary standards for pharma laboratories and manufacturers.
Originator
Roche (Switzerland)
Biochem/physiol Actions
Valganciclovir hydrochloride hydrate is an antiviral used to treat cytomegalovirus infection. It is the prodrug of ganciclovir, a synthetic analog of 2′-deoxy-guanosine which is phosphorylated to a dGTP analog that competitively inhibits the incorporation of dGTP by viral DNA polymerase.
Check Digit Verification of cas no
The CAS Registry Mumber 175865-59-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,7,5,8,6 and 5 respectively; the second part has 2 digits, 5 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 175865-59:
(8*1)+(7*7)+(6*5)+(5*8)+(4*6)+(3*5)+(2*5)+(1*9)=185
185 % 10 = 5
So 175865-59-5 is a valid CAS Registry Number.
InChI:InChI=1/C14H22N6O5.ClH/c1-7(2)9(15)13(23)24-4-8(3-21)25-6-20-5-17-10-11(20)18-14(16)19-12(10)22;/h5,7-9,21H,3-4,6,15H2,1-2H3,(H3,16,18,19,22);1H/t8?,9-;/m0./s1
175865-59-5Relevant articles and documents
Synthetic method of valganciclovir hydrochloride
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, (2021/04/17)
The invention discloses a method for synthesizing valganciclovir hydrochloride, which comprises the following steps: with 1,3-dichloro-2-acetoxymethoxypropane as an initial raw material, preparing monochlorinated ganciclovir, and carrying out esterification, hydrolysis and deprotection salification to finally obtain the valganciclovir hydrochloride. The invention provides a synthesis method of siganciclovir hydrochloride, which avoids the problem of separation and conversion of N-7 and N-9 isomers in the diacetyl guanine condensation process. The method directly synthesizes monochlorinated ganciclovir without using ganciclovir, instead of the synthesis of monoacetyl ganciclovir in the prior art, so that the method avoids the problem of diester compound separation caused by ganciclovir residues, has the advantages of short process steps, simple operation, convenient purification and low cost, is beneficial to industrial production, and is suitable for synthesis of valganciclovir hydrochloride.
A method for preparing valganciclovir hydrochloride
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Paragraph 0018; 0036-0038, (2016/10/08)
The invention discloses a method for preparing valganciclovir hydrochloride I. The method comprises the following steps of: 1, dissolving phosphorus oxychloride into an inert solvent, and performing a reaction of the mixture and the alcoholic liquor to obtain phosphoryl halide II; 2, performing a reaction of ganciclovir and the phosphoryl halide II obtained in the step to obtain ganciclovir monoester III; 3, esterfying the ganciclovir monoester III in the step 2 and N-carbobenzoxy-L-valine to obtain ganciclovir diester IV; 4, acidizing the ganciclovir diester IV in the step 3 for dephosphorylation to obtain N-carbobenzoxy-L-valine ganciclovir monoester V; and 5, performing a hydrogenation reaction on the product in the step 4 to prepare the valganciclovir hydrochloride I. By the method, the ganciclovir monoester with high purity and yield can be produced, the post-processing is easy, and the post-processing difficulty is reduced.
A succinct synthesis of valganciclovir hydrochloride, a cytomegalovirus (CMV) retinitis inhibitor
Babu, K. Srihari,Srinivas,Madhavi,Babu,Reddy, G. Madhusudhan,Haldar,Rao, P. Narasimha,Krishna,Srinivas,Venkateshwarulu,Reddy, P. Pratap,Anand, R. Vijaya
, p. 199 - 208 (2011/05/11)
A concise and efficient synthesis of valganciclovir hydrochloride 1, a CMV retinitis inhibitor, without involving protection-deprotection sequences, is described. The synthetic utility of (2S)-azido-3-methylbutyric acid, which acts as a masked L-valine equivalent, is demonstrated in the synthesis of 1. ARKAT-USA, Inc.
