Description: Penciclovir sodium (BRL39123) is a guanosine analog used as an antiviral drug for the treatment of various herpesvirus infections. It has activity against HSV types 1 and 2 with IC50 of 0.04-1.8 μg/mL and 0.06-4.4 μg/mL, respectively. As a nucleoside analogue, Penciclovir exhibits low toxicity and good selectivity. Penciclovir is absorbed poorly when given orally, thus it is used as a topical treatment, and is the active ingredient in the cold sore medications such as Denavir, Vectavir and Fenivir.
Physicochemical Properties
| Molecular Formula | C10H14N5O3-.NA+ |
| Molecular Weight | 275.23966 |
| Exact Mass | 275.099 |
| CAS # | 97845-62-0 |
| Related CAS # | Penciclovir;39809-25-1 |
| PubChem CID | 135524782 |
| Appearance | Typically exists as solid at room temperature |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 5 |
| Heavy Atom Count | 19 |
| Complexity | 354 |
| Defined Atom Stereocenter Count | 0 |
| SMILES | C1=NC2=C(N1CCC(CO)C[O-])N=C(NC2=O)N.[Na+] |
| InChi Key | BRPTUOYNOCSFRJ-UHFFFAOYSA-N |
| InChi Code | InChI=1S/C10H14N5O3.Na/c11-10-13-8-7(9(18)14-10)12-5-15(8)2-1-6(3-16)4-17;/h5-6,16H,1-4H2,(H3,11,13,14,18);/q-1;+1 |
| Chemical Name | sodium;4-(2-amino-6-oxo-1H-purin-9-yl)-2-(hydroxymethyl)butan-1-olate |
| HS Tariff Code | 2934.99.9001 |
| Storage |
Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition | Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs) |
Biological Activity
| ln Vitro | Penciclovir sodium (0-100 µg/ml) exhibits anti-herpesvirus action, with EC50s for HSV-1 (HFEM), HSV-2 (MS), VZV (Ellen), CMV (AD-169), BHV-1 (Oxford 1964), BHV-2 (New York 1), EHV-1 (Quai Hals), FHV-1 (B927), and SVV, respectively, 0.5, 0.8, 2.4, 52, 100, 1.2, 1.6, 0.9, >100 µg/ml[1]. To uninfected human cells, penciclovir sodium (0–100 µg/ml) exhibits no toxicity[1]. |
| ln Vivo | Penciclovir sodium (100 mg/kg; subcutaneous injection; once daily for 5 days) reduces death in mice [2]. |
| Cell Assay |
Cell Cytotoxicity Assay[1] Cell Types: MRC-5,WISH, Flow 4000, Flow 12000, RPMI 2650, WI-38, WI-38 VA13, Hs68, HEp-2, RD, SCC-13, Primary cells Tested Concentrations: 0-100 µg/ml Incubation Duration: Experimental Results: demonstrated no-toxic with IC50s of >100, >100, 100, >100, 60, >100, >100, >100, >100, >100, >100, >100 for MRC-5,WISH, Flow 4000, Flow 12000, RPMI 2650, WI-38, WI-38 VA13, Hs68, HEp-2, RD, SCC-13, Primary cells, respectively. |
| Animal Protocol |
Animal/Disease Models: Threeweeks old female balb/c (Bagg ALBino) mouse [2] Doses: 100 mg/kg Route of Administration: Sc; one time/day for 5 days Experimental Results: Virus titers in respiratory organs of w/t and PR3 infected mice reduce. |
| References |
[1]. Penciclovir: a review of its spectrum of activity, selectivity, and cross-resistance pattern. Antiviral Chemistry and Chemotherapy, 1993, (1): 3-11. [2]. 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. |
| Additional Infomation | Penciclovir Sodium is the sodium salt form of penciclovir, a synthetic acyclic guanine derivative with antiviral activity, mainly used to treat infections from herpes simplex virus (HSV) types 1 and 2. In HSV infected cells, penciclovir is phosphorylated by viral thymidine kinase and subsequently converted by cellular kinases into the active metabolite, penciclovir triphosphate, which competitively inhibits viral HSV polymerase by blocking deoxyguanosine triphosphate substrate binding. As a result, herpes viral DNA synthesis and replication are selectively inhibited. |
Solubility Data
| Solubility (In Vitro) | May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples |
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.6332 mL | 18.1660 mL | 36.3319 mL | |
| 5 mM | 0.7266 mL | 3.6332 mL | 7.2664 mL | |
| 10 mM | 0.3633 mL | 1.8166 mL | 3.6332 mL |