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MedKoo Cat#: 318461 | Name: Penciclovir
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Description:

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

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

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

Theoretical Analysis

MedKoo Cat#: 318461

Name: Penciclovir

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

Chemical Formula: C10H15N5O3

Exact Mass: 253.1175

Molecular Weight: 253.26

Elemental Analysis: C, 47.42; H, 5.97; N, 27.65; O, 18.95

Price and Availability

Size Price Availability Quantity
100mg USD 450.00
200mg USD 650.00
500mg USD 850.00
1g USD 1,150.00
2g USD 1,650.00
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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/
Solvent mg/mL mM
Solubility
DMSO 19.8 78.09
Water 1.5 5.92
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.
1: Andronova VL, Galegov GA, Vozdvizhenskaya OA, Levit GL, Krasnov VP, Charushin VN. Combined Effect of Basic Antiherpetic Drugs with a New Inhibitor of the Terminase Complex of Herpes Simplex Virus Type 1 in Vero Cell Cultures. Dokl Biol Sci. 2024 Aug;517(1):55-58. doi: 10.1134/S0012496624701035. Epub 2024 Jul 1. PMID: 38955885. 2: Arman M, Alam S, Maruf RA, Shams Z, Islam MN. Molecular modeling of some commercially available antiviral drugs and their derivatives against SARS-CoV-2 infection. Narra J. 2024 Apr;4(1):e319. doi: 10.52225/narra.v4i1.319. Epub 2024 Apr 30. PMID: 38798846; PMCID: PMC11125382. 3: Griffioen JA, Fayette MA, Proudfoot JS, Howard LL, Papich MG. Penciclovir pharmacokinetics after oral and rectal administration of famciclovir in African elephants (Loxodonta africana) shows that effective concentrations can be achieved from rectal administration, despite lower absorption. Am J Vet Res. 2024 May 1;85(7):ajvr.24.02.0039. doi: 10.2460/ajvr.24.02.0039. PMID: 38684186. 4: Szotowska I, Ledwoń A. Antiviral Chemotherapy in Avian Medicine-A Review. Viruses. 2024 Apr 12;16(4):593. doi: 10.3390/v16040593. PMID: 38675934; PMCID: PMC11054683. 5: Meng J, Su Y, Zhu H, Cai T. Shape memory and self-healing in a molecular crystal with inverse temperature symmetry breaking. Chem Sci. 2024 Mar 8;15(15):5738-5745. doi: 10.1039/d3sc06800e. PMID: 38638237; PMCID: PMC11023024. 6: Nobre DAB, Moura MDG, de Arruda JAA, Felix FA, Diniz PB, Duarte ECB, Abreu LG, Gomez RS, Mesquita RA. Identification of Epstein-Barr virus after topical treatment for oral hairy leukoplakia: A preliminary study. Int J STD AIDS. 2024 Jul;35(8):627-634. doi: 10.1177/09564624241246298. Epub 2024 Apr 12. PMID: 38606785. 7: Xu R, Gao Q, Zhang Y, Lin Y, Li Y, Su L, Zhou S, Cao Y, Gao P, Li P, Luo F, Chen R, Zhang X, Nie S, Xu X; CRDS study Investigators. Associations between Different Antivirals and Hospital-Acquired Acute Kidney Injury in Adults with Herpes Zoster. Clin J Am Soc Nephrol. 2024 Jun 1;19(6):694-703. doi: 10.2215/CJN.0000000000000452. Epub 2024 Mar 26. PMID: 38527975; PMCID: PMC11168829. 8: Abd Ali AAkool W, Kashanian S, Hadidi S. Molecular interaction of antiviral drug penciclovir with DNA and HSA insights from experimental and docking studies. J Biomol Struct Dyn. 2024 Jan 23:1-11. doi: 10.1080/07391102.2024.2303382. Epub ahead of print. PMID: 38263739. 9: Merkus VI, Leupold MS, Rockel SP, Schmidt TC. Ozonation products of purine derivatives, the basic structures of antiviral micropollutants. Sci Total Environ. 2024 Feb 20;912:169073. doi: 10.1016/j.scitotenv.2023.169073. Epub 2023 Dec 2. PMID: 38049003. 10: Mathialagan S, Chung G, Pye K, Rodrigues AD, Varma MVS, Brown C. Significance of Organic Anion Transporter 2 and Organic Cation Transporter 2 in Creatinine Clearance: Mechanistic Evaluation Using Freshly Prepared Human Primary Renal Proximal Tubule Cells. J Pharmacol Exp Ther. 2024 Jan 2;388(1):201-208. doi: 10.1124/jpet.123.001890. PMID: 37977812. 11: Cheng J, Huang J, Cao W, Huang L, Mao X, Chen L, Zhou J, Wang N. Case Report: Fatal cytomegalovirus pneumonia after CAR-T cell therapy in the long- term follow-up. Front Immunol. 2023 Oct 2;14:1226148. doi: 10.3389/fimmu.2023.1226148. PMID: 37849765; PMCID: PMC10577281. 12: Xie S, Yang X, Xia H, Lai J, Liu Q, Lu Z, He D, Liu X. Clinical features of varicella-zoster virus caused neurological diseases detected by metagenomic next-generation sequencing. Open Med (Wars). 2023 Jul 10;18(1):20230744. doi: 10.1515/med-2023-0744. PMID: 37465353; PMCID: PMC10350883. 13: Uppal T, Tuffo K, Khaiboullina S, Reganti S, Pandori M, Verma SC. Screening of SARS-CoV-2 antivirals through a cell-based RNA-dependent RNA polymerase (RdRp) reporter assay. Cell Insight. 2022 Jun 29;1(4):100046. doi: 10.1016/j.cellin.2022.100046. PMID: 37192863; PMCID: PMC9239919. 14: Sun WW, Xie YB, Deng TT, Huang J, Liu JK, Wu B. Acid-Promoted Cyclization Reaction of the Guanine Base with 1,1,3,3-Tetramethoxypropane: A Method for the Preparation of M1 dG and its Derivatives. Curr Protoc. 2023 May;3(5):e741. doi: 10.1002/cpz1.741. PMID: 37140206. 15: Liu T, Shao QQ, Wang WJ, Liu TL, Jin XM, Xu LJ, Huang GY, Chen Z. The Chinese herbal prescription JieZe-1 inhibits caspase-1-dependent pyroptosis induced by herpes simplex virus-2 infection in vitro. J Integr Med. 2023 May;21(3):277-288. doi: 10.1016/j.joim.2023.03.003. Epub 2023 Mar 9. PMID: 36973158. 16: Tang AM, Xu JY, Wang R, Li YM. Treatment of a large area perioral viral herpes infection following noninvasive ventilation: A case report. World J Clin Cases. 2023 Mar 16;11(8):1857-1861. doi: 10.12998/wjcc.v11.i8.1857. PMID: 36969999; PMCID: PMC10037274. 17: Manikanttha M, Deepti K, Tej MB, Tej MB, Gopi Reddy A, Kapavarapu R, Barange DK, V Basaveswara Rao M, Pal M. Ultrasound assisted Cu-catalyzed Ullmann- Goldberg type coupling-cyclization in a single pot: Synthesis and in silico evaluation of 11H-pyrido[2,1-b]quinazolin-11-ones against SARS-CoV-2 RdRp. J Mol Struct. 2023 May 15;1280:135044. doi: 10.1016/j.molstruc.2023.135044. Epub 2023 Jan 28. PMID: 36743447; PMCID: PMC9884102. 18: Giannetti M, Mazzuca C, Ripani G, Palleschi A. Inspection on the Mechanism of SARS-CoV-2 Inhibition by Penciclovir: A Molecular Dynamic Study. Molecules. 2022 Dec 26;28(1):191. doi: 10.3390/molecules28010191. PMID: 36615385; PMCID: PMC9821970. 19: Yu Z, Zhao Y, Jin J, Zhu J, Yu L, Han G. Antiviral treatment in outpatients with herps zoster in six major areas of China, 2010-2019. Front Public Health. 2022 Jul 29;10:942377. doi: 10.3389/fpubh.2022.942377. PMID: 35968424; PMCID: PMC9372588. 20: Mo J, Lu Y, Jiang S, Yan G, Xing T, Xu D, He Y, Xie B, Lan G, Chen B, Liang J. Effects of the Probiotic, Lactobacillus delbrueckii subsp. bulgaricus, as a Substitute for Antibiotics on the Gastrointestinal Tract Microbiota and Metabolomics Profile of Female Growing-Finishing Pigs. Animals (Basel). 2022 Jul 11;12(14):1778. doi: 10.3390/ani12141778. PMID: 35883325; PMCID: PMC9311557.