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39809-25-1 molecular structure
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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 and InChIs

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

Cite this record

CBID:184 http://www.chembase.cn/molecule-184.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
39809-25-1
PubChem SID
160963647
46506498
PubChem CID
4725

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Selleck Chemicals
S4184 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 8.010395  H Acceptors
H Donor LogD (pH = 5.5) -1.5503044 
LogD (pH = 7.4) -1.6381645  Log P -1.5479089 
Molar Refractivity 64.5919 cm3 Polarizability 23.673088 Å3
Polar Surface Area 125.76 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.86  LOG S -1.53 
Solubility (Water) 7.45e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1.7mg/ml expand Show data source
Hydrophobicity(logP)
-1.1 expand Show data source
Target
Others expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00299 external link
Item Information
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

REFERENCES

REFERENCES

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PATENTS

PATENTS

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