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Compound Detail

CHEMBL1540

PENCICLOVIR
💊 Approved Drug
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💊 Approved Drug
Nc1nc(O)c2ncn(CCC(CO)CO)c2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1540
Name PENCICLOVIR
Phase Approved
Structure Type MOL
InChI Key JNTOCHDNEULJHD-UHFFFAOYSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL4594375

Known Names

BRL-39123 Denavir Fenistil NSC-759624 Penciclovir Vectavir
14
Targets
42
Activities
2
Assay Types
30
PK Parameters
20
Publications
6
Known Names
2
Indications
1
Mechanisms

Molecular Properties

253.3
MW (Da)
-0.90
ALogP
8
HBA
4
HBD
130.3
PSA (Ų)
0.54
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Prescription
Chirality Achiral

Routes of Administration

Topical

Flags

Natural Product Prodrug
USAN Stem -vir
USAN Year 1992

Extended Properties

Molecular Formula C10H15N5O3
MW 253.26
Aromatic Rings 2
Heavy Atoms 18
NP-Likeness -0.33

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Human herpesvirus 1 DNA polymerase inhibitor INHIBITOR DNA polymerase catalytic subunit ✓ ✓

Indications

Herpes Labialis Virus Diseases

ATC Classification

D06BB06
penciclovir
Level 1: DERMATOLOGICALS
Level 2: ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
J05AB13
penciclovir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Activity Summary

EC50 27 meas. best 6.85
IC50 15 meas. best 5.41

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human alphaherpesvirus 3
CHEMBL613132
 EC50 6.85 5.598 140.0 5
HepG2
CHEMBL395
 EC50 6.72 6.72 190.0 1
Human alphaherpesvirus 2
CHEMBL370
 EC50 6.7 6.3333 200.0 3
Human alphaherpesvirus 1
CHEMBL377
 EC50 6.7 5.8871 200.0 7
Hepatitis B virus
CHEMBL613497
 EC50 6.16 5.815 700.0 2
Human alphaherpesvirus 1
CHEMBL377
 IC50 5.41 5.41 3900.0 1
Vero
CHEMBL391
 IC50 5.19 5.19 6400.0 2
Vero
CHEMBL391
 EC50 5.09 5.09 8100.0 1
Thymidine kinase
CHEMBL1795127
 IC50 4.96 4.96 11000.0 1
Human immunodeficiency virus 1
CHEMBL378
 EC50 4.96 4.96 11000.0 1
ADMET
CHEMBL612558
 IC50 4.89 4.89 12800.0 1
Human alphaherpesvirus 3
CHEMBL613132
 IC50 4.8 4.45 16000.0 2
Macacine alphaherpesvirus 1
CHEMBL3301403
 EC50 4.77 4.71 17000.0 3
ADMET
CHEMBL612558
 EC50 4.75 4.75 18000.0 1
Thymidine kinase
CHEMBL1075062
 IC50 4.07 4.07 84400.0 1
CAPAN-1
CHEMBL614536
 IC50 4.03 4.03 93000.0 1
SARS-CoV-2
CHEMBL4303835
 EC50 4.02 4.02 95960.0 2
SARS-CoV-2
CHEMBL4303835
 IC50 4.02 4.02 95900.0 1
SARS-CoV
CHEMBL4303836
 EC50 4.02 4.02 95960.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 9330.0 ng.hr.mL-1 Homo sapiens
AUC 7230.0 ng.hr.mL-1 Homo sapiens
AUC 7160.0 ng.hr.mL-1 Homo sapiens
AUC 7980.0 ng.hr.mL-1 Homo sapiens
AUC 6310.0 ng.hr.mL-1 Homo sapiens
AUC 6520.0 ng.hr.mL-1 Homo sapiens
AUC 8950.0 ng.hr.mL-1 Homo sapiens
AUC 9300.0 ng.hr.mL-1 Homo sapiens
AUC 11100.0 ng.hr.mL-1 Homo sapiens
AUC 4480.0 ng.hr.mL-1 Homo sapiens
AUC 2240.0 ng.hr.mL-1 Homo sapiens
AUC 17900.0 ng.hr.mL-1 Homo sapiens
CL 8.4 mL.min-1.kg-1 Homo sapiens
CL 1.7 mL.min-1.kg-1 Homo sapiens
CL 8.4 mL.min-1.kg-1 Homo sapiens
CL 8.4 mL.min-1.kg-1 Homo sapiens
CL 36.6 L/hr Homo sapiens
CL/F 66.9 L/hr Homo sapiens
CL/F 5.8 L/hr Homo sapiens
CL/F 12.8 L/hr Homo sapiens
CL/F 27.3 L/hr Homo sapiens
CL_renal 30.1 L/hr Homo sapiens
CL_renal 1.6 L/hr Homo sapiens
CL_renal 4.2 L/hr Homo sapiens
CL_renal 13.0 L/hr Homo sapiens
CL_renal 28.5 L/hr Homo sapiens
CL_renal 21.8 L/hr Homo sapiens
CL_renal 27.7 L/hr Homo sapiens
Cmax 13464.42 nM Homo sapiens
Cmax 10976.86 nM Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Human alphaherpesvirus 3 EC50 = 140.0 nM 6.85 The effective concentration to show 50% of activity was measured on varicella zo... 10891113
HepG2 EC50 = 190.0 nM 6.72 Effective concentration necessary to decrease extracellular Hepatitis B virus DN... -
Human alphaherpesvirus 2 EC50 = 200.0 nM 6.7 Antiviral activity against herpes simplex virus 2 G infected in HEL cells assess... 30738653
Human alphaherpesvirus 1 EC50 = 200.0 nM 6.7 Antiviral activity against thymidine kinase deficient and aciclovir resistant he... 30738653
Human alphaherpesvirus 1 EC50 = 480.0 nM 6.32 Antiviral activity against Herpes simplex virus 1 KOS infected in HEL cells asse... 29670705
Human alphaherpesvirus 1 EC50 = 500.0 nM 6.3 Antiviral activity against Herpes simplex virus 1 KOS infected in human HEL cell... 28829913
Human alphaherpesvirus 2 EC50 = 600.0 nM 6.22 Antiviral activity against Herpes simplex virus 2 G infected in human HEL cells ... 28829913
Human alphaherpesvirus 3 EC50 = 620.0 nM 6.21 Antiviral activity against Varicella-Zoster virus OKA infected in human HEL cell... 28829913
Hepatitis B virus EC50 = 700.0 nM 6.16 In vitro antiviral activity against duck hepatitis B virus (DHBV) 11708924
Human alphaherpesvirus 1 EC50 = 800.0 nM 6.1 Antiviral activity against herpes simplex virus 1 KOS infected in HEL cells asse... 30738653
Human alphaherpesvirus 2 EC50 = 840.0 nM 6.08 Antiviral activity against Herpes simplex virus 2 G infected in HEL cells assess... 29670705
Hepatitis B virus EC50 = 3400.0 nM 5.47 Antiviral activity against Hepatitis B virus infected in human HepG2(2.2.15) cel... 21333535
Human alphaherpesvirus 3 EC50 = 3500.0 nM 5.46 Antiviral activity against Varicella-zoster virus Oka harboring thymidine kinase... 30738653
Human alphaherpesvirus 1 IC50 = 3900.0 nM 5.41 Inhibitory activity against herpes simplex virus type 1 (HSV-1) strain SC16 in V... 8576922
Human alphaherpesvirus 1 EC50 = 4000.0 nM 5.4 Antiviral activity against ACV-resistant thymidine kinase deficient Herpes simpl... 28829913
Human alphaherpesvirus 1 EC50 = 4700.0 nM 5.33 Antiviral activity against Herpes simplex virus 1 F infected in african green mo... 17438061
Vero IC50 = 6400.0 nM 5.19 Compound was tested for antiviral activity against Herpes Simplex virus Type-2(M... 3040998
Vero IC50 = 6400.0 nM 5.19 Compound was tested for antiviral activity against Herpes Simplex virus Type-1(H... 3040998
Vero EC50 = 8100.0 nM 5.09 Compound was tested for its antiviral activity against HSV-1(KOS strain) in vero... -
Human alphaherpesvirus 1 EC50 = 8650.0 nM 5.06 Compound was tested for in vitro antiviral activity against herpes viruses of ty... 9719596

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 312
19273678 10.1128/aac.01054-08 Homo sapiens 86
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20070106 10.1021/jm901371v Homo sapiens 8
3040998 10.1021/jm00392a020 MRC5 8
2848125 10.1021/jm00120a010 DNA polymerase catalytic subunit 5
18426954 10.1124/dmd.108.020479 ADMET 4
22190696 10.1124/dmd.111.042036 POU domain, class 2, transcription factor 2 4
20014752 10.1021/tx900326k Hepatotoxicity 3
11677126 10.1016/s0960-894x(01)00589-3 Vero 3
2754699 10.1021/jm00128a012 Mus musculus 3
- 10.1016/S0960-894X(97)00422-8 HepG2 3
17438061 10.1128/aac.01284-06 Macacine alphaherpesvirus 1 3
10891113 10.1021/jm990543n CCRF-CEM 2
3040998 10.1021/jm00392a020 Vero 2
- 10.6019/CHEMBL3301361 No relevant target 2
17438061 10.1128/aac.01284-06 Thymidine kinase 2
19445515 10.1021/jm900403j Homo sapiens 2
2848125 10.1021/jm00120a010 Oryctolagus cuniculus 2

Data from ChEMBL 36 via Core Engine