Penciclovir
featured

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 318461

CAS#: 39809-25-1 (free base)

Description: Penciclovir, also known as BRL-39123, is a guanosine analogue antiviral drug used for the treatment of various herpesvirus infections. It is a nucleoside analogue which exhibits low toxicity and good selectivity. Because penciclovir is absorbed poorly when given orally it is used more as a topical treatment, and is the active ingredient in the cold sore medications Denavir, Vectavir and Fenivir.

Chemical Structure

img
Penciclovir
CAS# 39809-25-1 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 318461
Name: Penciclovir
CAS#: 39809-25-1 (free base)
Chemical Formula: C10H15N5O3
Exact Mass: 253.12
Molecular Weight: 253.262
Elemental Analysis: C, 47.42; H, 5.97; N, 27.65; O, 18.95

Price and Availability

Size Price Availability Quantity
100mg USD 450
200mg USD 650
500mg USD 850
1g USD 1150
2g USD 1650
Bulk inquiry

Related CAS #: 97845-62-0 (Na)   39809-25-1 (free base)  

Synonym: BRL-39123; BRL 39123; BRL39123; VSA 671; VSA671; VSA-671; Penciclovir; Denavir, Vectavir and Fenivir.

IUPAC/Chemical Name: 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-3H-purin-6-one

InChi Key: JNTOCHDNEULJHD-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: C1=NC2=C(N1CCC(CO)CO)NC(=NC2=O)N

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Instruction:
View handling instruction
Biological target: Penciclovir (VSA 671) is a potent and selective anti-herpesvirus agent with EC50 values of 0.5, 0.8 µg/ml for HSV-1 (HFEM), HSV-2 (MS), respectively.
In vitro activity: The metabolism and mode of action of penciclovir [9-(4-hydroxy-3-hydroxymethylbut-1-yl)guanine; BRL 39123] were studied and compared with those of acyclovir. (S)-Penciclovir-triphosphate inhibited HSV-1 and HSV-2 DNA polymerase competitively with dGTP, the Ki values being 8.5 and 5.8 microM, respectively, whereas for acyclovir-triphosphate, the Ki value was 0.07 microM for the two enzymes. Both compounds had relatively low levels of activity against the cellular DNA polymerase alpha, with Ki values of 175 and 3.8 microM, respectively. Reference: Antimicrob Agents Chemother. 1992 Dec;36(12):2747-57. https://pubmed.ncbi.nlm.nih.gov/1336346/
In vivo activity: PCV was compared with the phosphonyl derivative, HPMPA in mice infected with EHV-1. Both drugs were shown to be effective in vivo, limiting wild-type virus replication in respiratory tissues, and reducing viraemia. The treated mice also showed less clinical signs and reduced histopathology compared with placebo-treated controls. Reference: Antiviral Res. 1992 May;18(1):77-89. https://pubmed.ncbi.nlm.nih.gov/1329646/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 19.8 78.09
Water 1.5 5.92

Preparing Stock Solutions

The following data is based on the product molecular weight 253.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Hussein IT, Menashy RV, Field HJ. Penciclovir is a potent inhibitor of feline herpesvirus-1 with susceptibility determined at the level of virus-encoded thymidine kinase. Antiviral Res. 2008 Jun;78(3):268-74. doi: 10.1016/j.antiviral.2007.10.015. Epub 2008 Feb 12. PMID: 18325606. 3. Earnshaw DL, Bacon TH, Darlison SJ, Edmonds K, Perkins RM, Vere Hodge RA. Mode of antiviral action of penciclovir in MRC-5 cells infected with herpes simplex virus type 1 (HSV-1), HSV-2, and varicella-zoster virus. Antimicrob Agents Chemother. 1992 Dec;36(12):2747-57. doi: 10.1128/AAC.36.12.2747. PMID: 1336346; PMCID: PMC245539. 4. de la Fuente R, Awan AR, Field HJ. The acyclic nucleoside analogue penciclovir is a potent inhibitor of equine herpesvirus type 1 (EHV-1) in tissue culture and in a murine model. Antiviral Res. 1992 May;18(1):77-89. doi: 10.1016/0166-3542(92)90007-r. PMID: 1329646.
In vitro protocol: 1. Hussein IT, Menashy RV, Field HJ. Penciclovir is a potent inhibitor of feline herpesvirus-1 with susceptibility determined at the level of virus-encoded thymidine kinase. Antiviral Res. 2008 Jun;78(3):268-74. doi: 10.1016/j.antiviral.2007.10.015. Epub 2008 Feb 12. PMID: 18325606. 2. Earnshaw DL, Bacon TH, Darlison SJ, Edmonds K, Perkins RM, Vere Hodge RA. Mode of antiviral action of penciclovir in MRC-5 cells infected with herpes simplex virus type 1 (HSV-1), HSV-2, and varicella-zoster virus. Antimicrob Agents Chemother. 1992 Dec;36(12):2747-57. doi: 10.1128/AAC.36.12.2747. PMID: 1336346; PMCID: PMC245539.
In vivo protocol: 1. de la Fuente R, Awan AR, Field HJ. The acyclic nucleoside analogue penciclovir is a potent inhibitor of equine herpesvirus type 1 (EHV-1) in tissue culture and in a murine model. Antiviral Res. 1992 May;18(1):77-89. doi: 10.1016/0166-3542(92)90007-r. PMID: 1329646.

Molarity Calculator

Calculate the mass, volume, or concentration required for a solution.
=
x
x
g/mol

*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

Reconstitution Calculator

The reconstitution calculator allows you to quickly calculate the volume of a reagent to reconstitute your vial. Simply enter the mass of reagent and the target concentration and the calculator will determine the rest.

=
÷

Dilution Calculator

Calculate the dilution required to prepare a stock solution.
x
=
x

1: An J, Li G, An T, Nie X. Indirect photochemical transformations of acyclovir
and penciclovir in aquatic environments increase ecological risk. Environ Toxicol
Chem. 2016 Mar;35(3):584-92. doi: 10.1002/etc.3238. Epub 2016 Feb 9. PubMed PMID:
26356329.


2: Schenkel F, Csajka C, Baglivo E, Kondo-Oestreicher M, Dayer P, Gex-Fabry M,
Daali Y. Intraocular penetration of penciclovir after oral administration of
famciclovir: a population pharmacokinetic model. J Antimicrob Chemother. 2013
Jul;68(7):1635-41. doi: 10.1093/jac/dkt064. Epub 2013 Mar 28. PubMed PMID:
23539240.


3: Semenkow SL, Johnson NM, Maggs DJ, Margulies BJ. Controlled release delivery
of penciclovir via a silicone (MED-4750) polymer: kinetics of drug delivery and
efficacy in preventing primary feline herpesvirus infection in culture. Virol J.
2014 Feb 22;11:34. doi: 10.1186/1743-422X-11-34. PubMed PMID: 24558980; PubMed
Central PMCID: PMC3939932.


4: Thomasy SM, Covert JC, Stanley SD, Maggs DJ. Pharmacokinetics of famciclovir
and penciclovir in tears following oral administration of famciclovir to cats: a
pilot study. Vet Ophthalmol. 2012 Sep;15(5):299-306. doi:
10.1111/j.1463-5224.2011.00984.x. Epub 2012 Feb 16. PubMed PMID: 22339892.


5: Thomasy SM, Whittem T, Bales JL, Ferrone M, Stanley SD, Maggs DJ.
Pharmacokinetics of penciclovir in healthy cats following oral administration of
famciclovir or intravenous infusion of penciclovir. Am J Vet Res. 2012
Jul;73(7):1092-9. doi: 10.2460/ajvr.73.7.1092. PubMed PMID: 22738064.


6: Brock AP, Isaza R, Hunter RP, Richman LK, Montali RJ, Schmitt DL, Koch DE,
Lindsay WA. Estimates of the pharmacokinetics of famciclovir and its active
metabolite penciclovir in young Asian elephants (Elephas maximus). Am J Vet Res.
2012 Dec;73(12):1996-2000. doi: 10.2460/ajvr.73.12.1996. PubMed PMID: 23176429;
PubMed Central PMCID: PMC3886626.


7: Groth AD, Contreras MT, Kado-Fong HK, Nguyen KQ, Thomasy SM, Maggs DJ. In
vitro cytotoxicity and antiviral efficacy against feline herpesvirus type 1 of
famciclovir and its metabolites. Vet Ophthalmol. 2014 Jul;17(4):268-74. doi:
10.1111/vop.12094. Epub 2013 Sep 23. PubMed PMID: 24112415.


8: Kanneti R, Bhavesh D, Paramar D, Shivaprakash R, Bhatt PA. Determination of
penciclovir in human plasma by liquid chromatography-electrospray ionization
tandem mass spectrometry: application to a clinical pharmacokinetic study. Biomed
Chromatogr. 2011 Apr;25(4):458-65. doi: 10.1002/bmc.1468. PubMed PMID: 21374647.


9: Prasse C, Wagner M, Schulz R, Ternes TA. Biotransformation of the antiviral
drugs acyclovir and penciclovir in activated sludge treatment. Environ Sci
Technol. 2011 Apr 1;45(7):2761-9. doi: 10.1021/es103732y. Epub 2011 Mar 9. PubMed
PMID: 21388176.


10: Yu A, Guo C, Zhou Y, Cao F, Zhu W, Sun M, Zhai G. Skin irritation and the
inhibition effect on HSV-1 in vivo of penciclovir-loaded microemulsion. Int
Immunopharmacol. 2010 Oct;10(10):1305-9. doi: 10.1016/j.intimp.2010.07.015. Epub
2010 Aug 18. PubMed PMID: 20727429.


11: Tsujimura K, Yamada M, Nagata S, Yamanaka T, Nemoto M, Kondo T, Kurosawa M,
Matsumura T. Pharmacokinetics of penciclovir after oral administration of its
prodrug famciclovir to horses. J Vet Med Sci. 2010 Mar;72(3):357-61. Epub 2009
Dec 4. PubMed PMID: 19959884.


12: Zhu W, Guo C, Yu A, Gao Y, Cao F, Zhai G. Microemulsion-based hydrogel
formulation of penciclovir for topical delivery. Int J Pharm. 2009 Aug
13;378(1-2):152-8. doi: 10.1016/j.ijpharm.2009.05.019. Epub 2009 May 20. PubMed
PMID: 19463929.


13: Lv Q, Yu A, Xi Y, Li H, Song Z, Cui J, Cao F, Zhai G. Development and
evaluation of penciclovir-loaded solid lipid nanoparticles for topical delivery.
Int J Pharm. 2009 May 8;372(1-2):191-8. doi: 10.1016/j.ijpharm.2009.01.014. Epub
2009 Jan 22. PubMed PMID: 19429280.


14: Chen XS, Han GZ, Guo ZP, Lu NZ, Chen J, Wang JB; Penciclovir Multicenter
Genital Herpes Clinical Study Group. A comparison of topical application of
penciclovir 1% cream with acyclovir 3% cream for treatment of genital herpes: a
randomized, double-blind, multicentre trial. Int J STD AIDS. 2000
Sep;11(9):568-73. PubMed PMID: 10997497.


15: Lin L, Chen XS, Cui PG, Wang JB, Guo ZP, Lu NZ, Bi ZG, Jia H, Yang XY;
Topical Penciclovir Clinical Study Group. Topical application of penciclovir
cream for the treatment of herpes simplex facialis/labialis: a randomized,
double-blind, multicentre, aciclovir-controlled trial. J Dermatolog Treat. 2002
Jun;13(2):67-72. PubMed PMID: 12060504.


16: Raborn GW, Martel AY, Lassonde M, Lewis MA, Boon R, Spruance SL; Worldwide
Topical Penciclovir Collaborative Study Group. Effective treatment of herpes
simplex labialis with penciclovir cream: combined results of two trials. J Am
Dent Assoc. 2002 Mar;133(3):303-9. PubMed PMID: 11934185.


17: Thomasy SM, Maggs DJ, Moulin NK, Stanley SD. Pharmacokinetics and safety of
penciclovir following oral administration of famciclovir to cats. Am J Vet Res.
2007 Nov;68(11):1252-8. PubMed PMID: 17975982.


18: Sarisky RT, Bacon TH, Boon RJ, Duffy KE, Esser KM, Leary J, Locke LA, Nguyen
TT, Quail MR, Saltzman R. Profiling penciclovir susceptibility and prevalence of
resistance of herpes simplex virus isolates across eleven clinical trials. Arch
Virol. 2003 Sep;148(9):1757-69. PubMed PMID: 14505088.


19: Smith RL, Morroni J, Wilcox CL. Lack of effect of treatment with penciclovir
or acyclovir on the establishment of latent HSV-1 in primary sensory neurons in
culture. Antiviral Res. 2001 Oct;52(1):19-24. PubMed PMID: 11530184.


20: Spruance SL, Rea TL, Thoming C, Tucker R, Saltzman R, Boon R. Penciclovir
cream for the treatment of herpes simplex labialis. A randomized, multicenter,
double-blind, placebo-controlled trial. Topical Penciclovir Collaborative Study
Group. JAMA. 1997 May 7;277(17):1374-9. PubMed PMID: 9134943.