penciclovir Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antivirals bicyclic heterocycle compounds 2079 39809-25-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • penciclovir
  • denavir
  • penciclovir sodium
The antiviral compound penciclovir has inhibitory activity against herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). In cells infected with HSV-1 or HSV-2, the viral thymidine kinase phosphorylates penciclovir to a monophosphate form that, in turn, is converted by cellular kinases to the active form penciclovir triphosphate. Biochemical studies demonstrate that penciclovir triphosphate inhibits HSV polymerase competitively with deoxyguanosine triphosphate. Consequently, herpes viral DNA synthesis and, therefore, replication are selectively inhibited.
  • Molecular weight: 253.26
  • Formula: C10H15N5O3
  • CLOGP: -2.90
  • LIPINSKI: 0
  • HAC: 8
  • HDO: 4
  • TPSA: 125.76
  • ALOGS: -1.53
  • ROTB: 5

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 170 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 75 % Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability) 77 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 1.10 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 8.40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.84 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.10 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 24, 1996 FDA DENCO ASSET

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC D06BB06 DERMATOLOGICALS
ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
CHEMOTHERAPEUTICS FOR TOPICAL USE
Antivirals
ATC J05AB13 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Nucleosides and nucleotides excl. reverse transcriptase inhibitors
FDA MoA N0000020060 DNA Polymerase Inhibitors
FDA EPC N0000175468 Herpesvirus Nucleoside Analog DNA Polymerase Inhibitor
FDA EXT N0000175459 Nucleoside Analog
CHEBI has role CHEBI:36044 antiviral drug
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000998 Antiviral Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Herpes labialis indication 1475003

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.73 acidic
pKa2 12.97 acidic
pKa3 13.57 acidic
pKa4 4.72 Basic
pKa5 2.6 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
1% DENAVIR MYLAN N020629 Sept. 24, 1996 RX CREAM TOPICAL 6579981 June 17, 2020 TREATMENT OF RECURRENT HERPES LABIALIS (COLD SORES) IN ADULTS

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA polymerase catalytic subunit Enzyme INHIBITOR DRUGBANK CHEMBL
Thymidine kinase Kinase IC50 4.07 CHEMBL
Thymidine kinase Kinase IC50 4.96 CHEMBL

External reference:

IDSource
4020992 VUID
N0000148462 NUI
C0164815 UMLSCUI
D02124 KEGG_DRUG
359HUE8FJC UNII
6437 INN_ID
108918003 SNOMEDCT_US
4020992 VANDF
006111 NDDF
5242 MMSL
59839 RXNORM
386939003 SNOMEDCT_US
CHEBI:7956 CHEBI
CHEMBL1540 ChEMBL_ID
DB00299 DRUGBANK_ID
97845-62-0 SECONDARY_CAS_RN
135398748 PUBCHEM_CID
CHEMBL2079793 ChEMBL_ID
C053539 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Denavir HUMAN PRESCRIPTION DRUG LABEL 1 0378-9720 CREAM 10 mg TOPICAL NDA 16 sections
Denavir HUMAN PRESCRIPTION DRUG LABEL 1 54868-4956 CREAM 10 mg TOPICAL NDA 12 sections