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Key Documents

P0035

Sigma-Aldrich

Penciclovir

Synonym(s):

2-Amino-1,9-dihydro-9-[4-hydroxy-3-(hydroxymethyl)butyl]-6H-purin-6-one, BRL-39123

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About This Item

Empirical Formula (Hill Notation):
C10H15N5O3
CAS Number:
Molecular Weight:
253.26
MDL number:
UNSPSC Code:
51102829
PubChem Substance ID:
NACRES:
NA.76

form

powder

solubility

0.02 M potassium phosphate: soluble 2 mg/mL

antibiotic activity spectrum

viruses

Mode of action

DNA synthesis | interferes
enzyme | inhibits

SMILES string

NC1=NC(=O)c2ncn(CCC(CO)CO)c2N1

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)

InChI key

JNTOCHDNEULJHD-UHFFFAOYSA-N

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Application

Penciclovir is a selective antiherpesvirus agent, particularly against herpes simplex virus types 1 and 2 (HSV-1 and HSV-2) and varicella-zoster virus (VZV).

Biochem/physiol Actions

Penciclovir is converted to its active form, penciclovir triphosphate, by cellular kinases. It inhibits viral DNA polymerase by competing with deoxyguanosine triphosphate. It inhibits DNA synthesis of virus-infected cells. Penciclovir has in vitro activity against herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). It does not inhibit DNA synthesis in non-infected cells. Mode of resistance is via qualitative changes in viral thymidine kinase or DNA polymerase.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

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Eva Marie Quijano Cardé et al.
Frontiers in veterinary science, 7, 587952-587952 (2020-11-17)
Cyprinid Herpesvirus 3 (CyHV-3), more commonly known as Koi Herpesvirus (KHV), is a re-emergent virus causing acute systemic infection with high mortality rates in koi fish (Cyprinus carpio). Survivors from outbreaks can become latent carriers, with viral reactivation under stressful
Raymund R Razonable
Mayo Clinic proceedings, 86(10), 1009-1026 (2011-10-04)
Most viral diseases, with the exception of those caused by human immunodeficiency virus, are self-limited illnesses that do not require specific antiviral therapy. The currently available antiviral drugs target 3 main groups of viruses: herpes, hepatitis, and influenza viruses. With
Carsten Prasse et al.
Environmental science & technology, 45(7), 2761-2769 (2011-03-11)
The biotransformation of the two antiviral drugs, acyclovir (ACV) and penciclovir (PCV), was investigated in contact with activated sludge. Biodegradation kinetics were determined, and transformation products (TPs) were identified using Hybrid Linear Ion Trap- FT Mass Spectrometry (LTQ Orbitrap Velos)
A Fontanellas et al.
Gene therapy, 16(1), 136-141 (2008-08-01)
Non-invasive in vivo imaging of transgene expression is currently providing very important means to optimize gene therapy regimes. Results in non-human primates are considered the most predictive models for the outcome in patients. In this study, we have documented that
M-H Schmid-Wendtner et al.
Skin pharmacology and physiology, 17(5), 214-218 (2004-09-29)
Human herpesviruses can be found worldwide and cause many viral infections in immunocompetent as well as in immunocompromised patients. Herpes simplex virus (HSV) diseases can be the cause of life-threatening disease, especially in neonates. After initial infection, HSV persists latently

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