2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6,9-dihydro-3H-purin-6-one

• ChemBase ID: 184
• Molecular Formular: C10H15N5O3
• Molecular Mass: 253.2578
• Monoisotopic Mass: 253.11748937
• SMILES: OCC(CCn1c2[nH]c(nc(=O)c2nc1)N)CO
• Canonical SMILES: OCC(CCn1cnc2c1[nH]c(N)nc2=O)CO
• InChI: InChI=1S/C10H15N5O3/c11-10-13-8-7(9(18)14-10)12-5-15(8)2-1-6(3-16)4-17/h5-6,16-17H,1-4H2,(H3,11,13,14,18)
• InChIKey: JNTOCHDNEULJHD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6,9-dihydro-3H-purin-6-one
• IUPAC Traditional name: denavir; penciclovir
• Brand Name: Denavir
• Synonyms: PE2; Penciclovirum [INN-Latin]; Penciclovir

Database IDs

• CAS Number: 39809-25-1
• PubChem SID: 46506498; 160963647
• PubChem CID: 4725

CALCULATED PROPERTIES

JChem

• Acid pKa: 8.010395
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.5503044
• LogD (pH = 7.4): -1.6381645
• Log P: -1.5479089
• Molar Refractivity: 64.5919 cm^3
• Polarizability: 23.673088 Å^3
• Polar Surface Area: 125.76 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.86
• LOG S: -1.53
• Solubility (Water): 7.45e+00 g/l

PROPERTIES

Physical Property

• Solubility: 1.7mg/ml
• Hydrophobicity(logP): -1.1

Pharmacology Properties

• Target: Others

Product Information

• Salt Data: Free Base

DETAILS

DrugBank - DB00299

• Drug Groups: approved
• Description: Penciclovir is a guanine analogue antiviral drug used for the treatment of various herpesvirus infections. It is a nucleoside analogue which exhibits low toxicity and good selectivity. [Wikipedia]
• Indication: Used to treat recurrent cold sores on the lips and face from various herpesvirus invections.
• Pharmacology: Penciclovir is the active metabolite of the oral product famciclovir. The more favorable results observed with topical penciclovir versus topical acyclovir for the treatment of herpes labialis may be due to the longer intracellular half-life of penciclovir in HSV-infected cells. The activated drug inhibits the viral DNA polymerase. This impairs the ability of the virus to replicate within the cell.
• Toxicity: Symptoms of overdose include headache, abdominal pain, increased serum lipase, nausea, dyspepsia, dizziness, and hyperbilirubinemia.
• Affected Organisms: Herpes simplex virus
• Biotransformation: Hepatic
• Absorption: Measurable penciclovir concentrations were not detected in plasma or urine of healthy male volunteers (n= 12) following single or repeat application of the 1% cream at a dose of 180 mg penciclovir daily.
• Half Life: 2 hours
• Protein Binding: Less than 20%.
• External Links: Wikipedia; RxList; Drugs.com