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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:
39809-25-1
Molecular Weight:
253.26
MDL number:
MFCD15142866
UNSPSC Code:
51102829
PubChem Substance ID:
329819986
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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Qingzhi Lv et al.
International journal of pharmaceutics, 372(1-2), 191-198 (2009-05-12)
The objective of this investigation was to develop solid lipid nanoparticles (SLNs) of penciclovir and evaluate the potential of SLNs as the carrier of penciclovir for topical delivery. Penciclovir-loaded SLNs were prepared by a double (W/O/W) emulsion technique. The SLNs
Teresa H Bacon et al.
Clinical microbiology reviews, 16(1), 114-128 (2003-01-15)
Acyclovir, penciclovir, and their prodrugs have been widely used during the past two decades for the treatment of herpesvirus infections. In spite of the distribution of over 2.3 x 10(6) kg of these nucleoside analogues, the prevalence of acyclovir resistance
D L Earnshaw et al.
Antimicrobial agents and chemotherapy, 36(12), 2747-2757 (1992-12-01)
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. In uninfected MRC-5 cells, low concentrations of the triphosphates of penciclovir and acyclovir were occasionally just detectable, the limit of detection
Weiwei Zhu et al.
International journal of pharmaceutics, 378(1-2), 152-158 (2009-05-26)
The purpose of this study was to investigate microemulsion-based hydrogel (MBH) as a topical delivery system for penciclovir. Topical delivery of penciclovir in the forms of microemulsion, MBH and the commercial cream was evaluated in vitro and in vivo. The
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
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