Penciclovir

Penciclovir
Clinical data
Pronunciation	/ˌpɛnˈsaɪkloʊˌvɪər/
Trade names	Denavir
AHFS/Drugs.com	Monograph
MedlinePlus	a697027
Pregnancy; category	AU: B1; ;
Routes of; administration	Topical
ATC code	D06BB06 (WHO) J05AB13 (WHO);
Legal status
Legal status	AU: S2 (Pharmacy medicine); US: ℞-only;
Pharmacokinetic data
Bioavailability	1.5% (oral), negligible (topical)
Protein binding	<20%
Metabolism	Viral thymidine kinase
Elimination half-life	2.2–2.3 hours
Excretion	Renal
Identifiers
	IUPAC name 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-1H-purin-6(9H)-one;
CAS Number	39809-25-1 ;
PubChem CID	135398748;
DrugBank	DB00299 ;
ChemSpider	4563 ;
UNII	359HUE8FJC;
KEGG	D05407 ;
ChEBI	CHEBI:7956 ;
ChEMBL	ChEMBL1540 ;
CompTox Dashboard (EPA)	DTXSID9046491 ;
ECHA InfoCard	100.189.687
Chemical and physical data
Formula	C10H15N5O3
Molar mass	253.262 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	275 to 277 °C (527 to 531 °F)
	SMILES O=C2/N=C(\Nc1n(cnc12)CCC(CO)CO)N;
	InChI 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) ; Key:JNTOCHDNEULJHD-UHFFFAOYSA-N ;
	(verify)

Penciclovir 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 (by mouth) it is more often used as a topical treatment. It is the active ingredient in the cold sore medications Denavir (NDC 0135-0315-52), Vectavir and Fenivir. Famciclovir is a prodrug of penciclovir with improved oral bioavailability.

Penciclovir was approved for medical use in 1996.^[2]

^ "Penciclovir". Merriam-Webster.com Dictionary. Retrieved 2016-01-22.
^ Long SS, Pickering LK, Prober CG (2012). Principles and Practice of Pediatric Infectious Disease. Elsevier Health Sciences. p. 1502. ISBN 978-1437727029.

[1] "Penciclovir". Merriam-Webster.com Dictionary. Retrieved 2016-01-22.

[2] Long SS, Pickering LK, Prober CG (2012). Principles and Practice of Pediatric Infectious Disease. Elsevier Health Sciences. p. 1502. ISBN 978-1437727029.

[1]

[2]

Clinical data

Pronunciation	/ˌpɛnˈsaɪkloʊˌvɪər/^[1]
Trade names	Denavir
AHFS/Drugs.com	Monograph
MedlinePlus	a697027
Pregnancy category	AU: B1
Routes of administration	Topical
ATC code	D06BB06 (WHO) J05AB13 (WHO)
Legal status
Legal status	AU: S2 (Pharmacy medicine) US: ℞-only
Pharmacokinetic data
Bioavailability	1.5% (oral), negligible (topical)
Protein binding	<20%
Metabolism	Viral thymidine kinase
Elimination half-life	2.2–2.3 hours
Excretion	Renal
Identifiers
IUPAC name 2-amino-9-[4-hydroxy-3-(hydroxymethyl)butyl]-1H-purin-6(9H)-one
CAS Number	39809-25-1^Y
PubChem CID	135398748
DrugBank	DB00299^Y
ChemSpider	4563^Y
UNII	359HUE8FJC
KEGG	D05407^Y
ChEBI	CHEBI:7956^Y
ChEMBL	ChEMBL1540^Y
CompTox Dashboard (EPA)	DTXSID9046491
ECHA InfoCard	100.189.687
Chemical and physical data
Formula	C₁₀H₁₅N₅O₃
Molar mass	253.262 g·mol⁻¹
3D model (JSmol)	Interactive image
Melting point	275 to 277 °C (527 to 531 °F)
SMILES O=C2/N=C(\Nc1n(cnc12)CCC(CO)CO)N
InChI 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)^Y Key:JNTOCHDNEULJHD-UHFFFAOYSA-N^Y
(verify)