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

• ChemBase ID: 459
• Molecular Formular: C13H20N6O4
• Molecular Mass: 324.3357
• Monoisotopic Mass: 324.15460315
• SMILES: O(C(=O)[C@@H](N)C(C)C)CCOCn1c2[nH]c(nc(=O)c2nc1)N
• Canonical SMILES: CC([C@@H](C(=O)OCCOCn1cnc2c1[nH]c(N)nc2=O)N)C
• InChI: InChI=1S/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
• InChIKey: HDOVUKNUBWVHOX-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
• IUPAC Traditional name: valaciclovir
• Brand Name: Valtrex; Zelitrex
• Synonyms: Valaciclovir Hcl; Valaciclovir Hydrochloride; Valacyclover Hydrochloric; Valacyclover Hydrochloride; Valacyclovir Hydrochloride; Valacyclovir; valaciclovir; Valaciclovir

Database IDs

• CAS Number: 124832-27-5
• PubChem SID: 46508197; 160963922
• PubChem CID: 60773

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.103873
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -1.9993745
• LogD (pH = 7.4): -0.486973
• Log P: -0.45152116
• Molar Refractivity: 80.6341 cm^3
• Polarizability: 31.018381 Å^3
• Polar Surface Area: 146.85 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.84
• LOG S: -1.96
• Solubility (Water): 3.55e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): -0.3

DETAILS

DrugBank - DB00577

• Drug Groups: approved; investigational
• Description: Valaciclovir (INN) or valacyclovir (USAN) is an antiviral drug used in the management of herpes simplex and herpes zoster (shingles). It is a prodrug, being converted in vivo to aciclovir. It is marketed by GlaxoSmithKline under the trade name Valtrex or Zelitrex. [Wikipedia]
• Indication: For the treatment or suppression of cold sores (herpes labialis), herpes zoster (shingles), genital herpes in immunocompetent individuals, and recurrent genital herpes in HIV-infected individuals.
• Pharmacology: Valaciclovir (INN) or Valacyclovir (USAN) is a prodrug and synthetic purine nucleoside analogue with inhibitory activity against herpes simplex virus types 1 (HSV-1), 2 (HSV-2), varicella-zoster virus (VZV), Epstein-Barr virus (EBV), and cytomegalovirus (CMV). Valaciclovir is almost completely converted to acyclovir and L-valine. The inhibitory activity of valaciclovir is highly selective due to its affinity for the enzyme thymidine kinase (TK) encoded by HSV and VZV. This viral enzyme converts acyclovir into acyclovir monophosphate, which is then converted into acyclovir diphosphate and triphosphate by cellular enzymes. Acyclovir is selectively converted to the active triphosphate form by cells infected with herpes viruses.
• Toxicity: Adverse effects of overexposure might include headache and nausea.
• Affected Organisms: Human Herpes Virus
• Biotransformation: Valaciclovir is rapidly and almost entirely (~99%) converted to the active compound, acyclovir, and L-valine by first-pass intestinal and hepatic metabolism by enzymatic hydrolysis. Neither valaciclovir nor acyclovir is metabolized by cytochrome P450 enzymes.
• Absorption: After oral administration, valaciclovir hydrochloride is rapidly absorbed from the gastrointestinal tract. The absolute bioavailability of acyclovir after administration of valaciclovir is 54.5% ± 9.1%.
• Half Life: 2.5-3.3 hours
• Protein Binding: 13-18%
• Elimination: Acyclovir accounted for 89% of the radioactivity excreted in the urine.
• Clearance: * Renal cl=255 +/- ?86 mL/min [healthy]; * apparent cl=86.3 +/- 21.3 mL/min/1.73?m2 [dialysis patients]; * apparent cl=679.16 +/- 162.76 mL/min/1.73?m2 [healthy]
• References: O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. Pubmed