175865-59-5 Usage
Description
Valganciclovir hydrochloride, a prodrug of the antiviral ganciclovir, was launched in the
US for the oral treatment of cytemegalovirus (CMV) retinitis, a sight-threatening
complication in patients with AIDS. This L-Valyl ester prodrug can be prepared in three
steps from the nucleoside analog ganciclovir by trimethylsilyl-protection of the amino
group, coupling with N-benzyloxycarbonyl-L-valine-N-carboxyanhydride, hydrolysis with
hydrochloric acid and hydrogenolysis of the Cbz-protecting group. Valganciclovir is well
absorbed and rapidly hydrolyzed to ganciclovir by intracellular esterases in the intestinal
mucosal cells and by hepatic esterases. Unlike ganciclovir, valganciclovir was
demonstrated to be actively transported by the intestinal peptide transporter PEPT1 in
Caco-2 cells. As a consequence, its absolute bioavailability in human was 10-fold higher
compared to ganciclovir (6%). In clinical trials, it was shown that a twice-daily 900 mg dose
of valganciclovir resulted in similar systemic ganciclovir exposure to 5 mg/kg twice-daily
intravenous injection of ganciclovir. Valganciclovir concentrations could not be quantified in
most patients within three to four hours. In a randomized non-blind phase III clinical trial,
oral valganciclovir (900 mg twice daily for three weeks then 900 mg once daily for one
week) was as effective as intravenous ganciclovir (5 mg/kg twice daily for three weeks
then 5 mg/kg once daily). Oral treatment with valganciclovir avoided catheter-related
infection that sometimes occurred with intravenous ganciclovir.
Chemical Properties
White Crystalline Solid
Originator
Roche (Switzerland)
Uses
Different sources of media describe the Uses of 175865-59-5 differently. You can refer to the following data:
1. Valganciclovir hydrochloride hydrate may be used in HIV-related cell signaling studies.
2. A pro-drug of ganciclovir. Used in treatment of retro-virus
3. antibacterial, inhibits protein synthesis
4. Valganciclovir is the valyl ester prodrug of ganciclovir , an antiviral agent used for the treatment of HIV associated retinitis and for the prevention of post transplant cytomegalovirus (CMV) infections. Upon oral administration, intestinal and hepatic esterases rapidly convert valganciclovir to ganciclovir, which can inhibit viral DNA synthesis (IC50 = 0.95 μM) by targeting the CMV polymerase.
Brand name
Valcyte (Roche).
General Description
Valganciclovir Hydrochloride is the L-valyl ester of ganciclovir and an antiviral drug, widely used to treat cytomegalovirus infections.Certified pharmaceutical secondary standards for application in quality control provide pharma laboratories and manufacturers with a convenient and cost-effective alternative to pharmacopeia primary standards.
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
-
, (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
-
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.
