2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]-3-hydroxypropyl (2S)-2-amino-3-methylbutanoate

• ChemBase ID: 1387
• Molecular Formular: C14H22N6O5
• Molecular Mass: 354.36168
• Monoisotopic Mass: 354.16516783
• SMILES: O(C(COC(=O)[C@@H](N)C(C)C)CO)Cn1c2[nH]c(nc(=O)c2nc1)N
• Canonical SMILES: OCC(OCn1cnc2c1[nH]c(N)nc2=O)COC(=O)[C@H](C(C)C)N
• InChI: InChI=1S/C14H22N6O5/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)/t8?,9-/m0/s1
• InChIKey: WPVFJKSGQUFQAP-GKAPJAKFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]-3-hydroxypropyl (2S)-2-amino-3-methylbutanoate
• IUPAC Traditional name: @valganciclovir
• Brand Name: Cymeval; Valcyt; Valcyte
• Synonyms: Cymeval; L-valine, ester with ganciclovir; valganciclovir; Valganciclovir

Database IDs

• CAS Number: 175865-60-8
• PubChem SID: 46505524; 160964847
• PubChem CID: 64147

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.103863
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -2.6297038
• LogD (pH = 7.4): -1.1173067
• Log P: -1.08186
• Molar Refractivity: 86.5966 cm^3
• Polarizability: 33.522167 Å^3
• Polar Surface Area: 167.08 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.81
• LOG S: -1.87
• Solubility (Water): 4.79e+00 g/l

DETAILS

DrugBank - DB01610

• Drug Groups: approved; investigational
• Description: Valganciclovir hydrochloride (Valcyte, manufactured by Roche) is an antiviral medication used to treat cytomegalovirus infections. As the L-valyl ester of ganciclovir, it is actually a prodrug for ganciclovir. After oral administration, it is rapidly converted to ganciclovir by intestinal and hepatic esterases.
• Indication: Valganciclovir is an antiviral medication used for the treatment of cytomegalovirus infections.
• Pharmacology: Valganciclovir is an antiviral medication used to treat cytomegalovirus infections. As the L-valyl ester of ganciclovir, it is actually a prodrug for ganciclovir. After oral administration, it is rapidly converted to ganciclovir by intestinal and hepatic esterases. After this, it (being an analogue of guanosine) gets incorporated into DNA and thus cannot be properly read by DNA polymerase. This results in the termination of the elongation of viral DNA.
• Toxicity: It is expected that an overdose of valganciclovir could also possibly result in increased renal toxicity.
• Affected Organisms: Human Herpes Virus
• Biotransformation: Rapidly hydrolyzed in the intestinal wall and liver to ganciclovir. No other metabolites have been detected.
• Absorption: Valganciclovir is well absorbed from the gastrointestinal tract and the absolute bioavailability from valganciclovir tablets (following administration with food) is approximately 60%.
• Half Life: Approximately 4.08 hours. Increased in patients with renal function impairment.
• Protein Binding: Plasma protein binding of ganciclovir is 1% to 2% over concentrations of 0.5 and 51 mg/mL.
• Elimination: The major route of elimination of valganciclovir is by renal excretion as ganciclovir through glomerular filtration and active tubular secretion.
• Distribution: * 0.703 ± 0.134 L/kg
• Clearance: * 3.07+/- 0.64 mL/min/kg [IV administration]; * 5.3 L/hr [Patient with creatinine clearance of 70.4 mL/min]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com