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Compound Detail

CHEMBL203321

BRINCIDOFOVIR
💊 Approved Drug
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💊 Approved Drug
CCCCCCCCCCCCCCCCOCCCOP(=O)(O)CO[C@H](CO)Cn1ccc(N)nc1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL203321
Name BRINCIDOFOVIR
Phase Approved
Structure Type MOL
InChI Key WXJFKKQWPMNTIM-VWLOTQADSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL4594372

Known Names

Brincidofovir CMX 001 CMX-001 CMX001 Hdp-cidofovir Hexadecyloxypropyl cidofovir Hexadecyloxypropyl-cidofovir Tembexa
8
Targets
21
Activities
2
Assay Types
4
PK Parameters
20
Publications
8
Known Names
8
Indications
1
Mechanisms

Molecular Properties

561.7
MW (Da)
5.25
ALogP
9
HBA
3
HBD
146.1
PSA (Ų)
0.10
QED
2
Ro5 Violations
26
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2021
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Natural Product Prodrug
USAN Stem -vir
USAN Year 2013

Extended Properties

Molecular Formula C27H52N3O7P
MW 561.70
Aromatic Rings 1
Heavy Atoms 38
NP-Likeness 0.22

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA polymerase inhibitor INHIBITOR DNA polymerase ✓ ✓

Indications

Smallpox Virus Diseases Adenoviridae Infections Adenoviridae Infections Cytomegalovirus Infections Adenovirus Infections, Human Hemorrhagic Fever, Ebola Liver Diseases

ATC Classification

J05AB17
brincidofovir
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIVIRALS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

EC50 17 meas. best 9.05
IC50 4 meas. best 6.71

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Human betaherpesvirus 5
CHEMBL371
 EC50 9.05 9.05 0.9 2
Murid betaherpesvirus 1
CHEMBL613495
 EC50 9.05 9.05 0.9 1
Caviid betaherpesvirus 2
CHEMBL614682
 EC50 8.4 8.4 4.0 1
Cowpox virus
CHEMBL612672
 EC50 7.22 6.57 60.0 4
Vaccinia virus
CHEMBL613493
 EC50 7.1 6.5857 80.0 7
Ectromelia virus Moscow
CHEMBL612728
 EC50 6.9 6.9 125.0 1
Vaccinia virus
CHEMBL613493
 IC50 6.71 6.615 196.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.7 6.7 200.0 1
Human adenovirus 5
CHEMBL612237
 IC50 6.61 6.61 245.0 1
Cowpox virus
CHEMBL612672
 IC50 6.22 6.22 600.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 6.15 hr Homo sapiens
T1/2 32.7 hr Homo sapiens
T1/2 24.0 hr Homo sapiens
Tmax 7.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Murid betaherpesvirus 1 EC50 = 0.9 nM 9.05 Antiviral activity against MCMV Smith replication 16539388
Human betaherpesvirus 5 EC50 = 0.9 nM 9.05 Antiviral activity against Human cytomegalovirus AD169 infected in HFF cells ass... 21565516
Human betaherpesvirus 5 EC50 = 0.9 nM 9.05 Antiviral activity against HCMV AD-169 replication 16539388
Caviid betaherpesvirus 2 EC50 = 4.0 nM 8.4 Antiviral activity against Guinea pig cytomegalovirus strain 22122 infected guin... 21078944
Cowpox virus EC50 = 60.0 nM 7.22 Antiviral activity against Cowpox virus Brighton replication in HFF cells 16539388
Vaccinia virus EC50 = 80.0 nM 7.1 Antiviral activity against Vaccinia virus Copenhagen replication in HFF cells 16539388
Vaccinia virus EC50 = 80.0 nM 7.1 Antiviral activity against Vaccinia virus Copenhagen infected in human HFF cells... 21493074
Ectromelia virus Moscow EC50 = 125.0 nM 6.9 Antiviral activity against Ectromelia virus Moscow infected in african green mon... 21493074
Vaccinia virus EC50 = 130.0 nM 6.89 Antiviral activity against Vaccinia virus WR in HFF cells assessed as reduction ... 17724153
Vaccinia virus EC50 = 140.0 nM 6.85 Antiviral activity against Vaccinia virus Copenhagen in HFF cells assessed as re... 17724153
Vaccinia virus IC50 = 196.0 nM 6.71 Antiviral activity against VACV infected in Vero cells assessed as reduction in ... 37390509
NON-PROTEIN TARGET EC50 = 200.0 nM 6.7 Antiviral activity against Cowpox virus (Brighton Red) infected in human HFF cel... 21493074
Cowpox virus EC50 = 240.0 nM 6.62 Antiviral activity against Cowpox virus Brighton in HFF cells assessed as reduct... 17724153
Human adenovirus 5 IC50 = 245.0 nM 6.61 Antiviral activity against AdV5 infected in A549 cells assessed as reduction in ... 37390509
Vaccinia virus IC50 = 300.0 nM 6.52 Antiviral activity against VACV infected in A549 cells assessed as reduction in ... 37390509
Cowpox virus EC50 = 600.0 nM 6.22 Antiviral activity against Cowpox virus Brighton in HFF cells assessed as reduct... 17846137
Cowpox virus EC50 = 600.0 nM 6.22 Antiviral activity against Cowpox virus Brighton infected in Vero cells measured... 36961984
Cowpox virus IC50 = 600.0 nM 6.22 Antiviral activity against Cowpox virus 19112024
Vaccinia virus EC50 = 800.0 nM 6.1 Antiviral activity against Vaccinia virus Copenhagen in HFF cells assessed as re... 17846137
Vaccinia virus EC50 = 800.0 nM 6.1 Antiviral activity against Vaccinia virus infected in human HFF cells 36961984

Literature References

PubMed DOI Target Context # Activities
21078944 10.1128/aac.00971-10 Caviid betaherpesvirus 2 31
17724153 10.1128/aac.00762-07 Cowpox virus 18
21078944 10.1128/aac.00971-10 Cavia porcellus 12
21493074 10.1016/j.bmc.2011.03.034 Liver 7
37390509 10.1016/j.ejmech.2023.115601 ADMET 7
17846137 10.1128/aac.00184-07 Unchecked 3
17724153 10.1128/aac.00762-07 Unchecked 3
27559756 10.1021/acs.jmedchem.6b00523 ADMET 3
21493074 10.1016/j.bmc.2011.03.034 ADMET 3
21493074 10.1016/j.bmc.2011.03.034 Unchecked 3
17846137 10.1128/aac.00184-07 Vaccinia virus 2
17724153 10.1128/aac.00762-07 Vaccinia virus 2
37390509 10.1016/j.ejmech.2023.115601 Vaccinia virus 2
17846137 10.1128/aac.00184-07 HFF 1
19112024 10.1016/j.bmc.2008.11.075 Cowpox virus 1
37390509 10.1016/j.ejmech.2023.115601 Human adenovirus 5 1
17724153 10.1128/aac.00762-07 HFF 1
21078944 10.1128/aac.00971-10 ADMET 1
16539388 10.1021/jm050473m Vaccinia virus 1
16539388 10.1021/jm050473m Murid betaherpesvirus 1 1

Data from ChEMBL 36 via Core Engine