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Compound Detail

CHEMBL1465

PHENPROCOUMON
💊 Approved Drug
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💊 Approved Drug
CCC(c1ccccc1)c1c(O)c2ccccc2oc1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1465
Name PHENPROCOUMON
Phase Approved
Structure Type MOL
InChI Key DQDAYGNAKTZFIW-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

BS-7565 Fencumar Fenprocumon Liquamar Marcoumar Marcumar Phenprocoumarol Phenprocoumarole Phenprocoumon Phenprocoumone Phenprocumone RO-1-4849
4
Targets
11
Activities
2
Assay Types
0
PK Parameters
20
Publications
12
Known Names
4
Indications
1
Mechanisms

Molecular Properties

280.3
MW (Da)
4.04
ALogP
3
HBA
1
HBD
50.4
PSA (Ų)
0.74
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1957
Availability Discontinued
Chirality Racemic

Routes of Administration

Oral

Flags

Natural Product
USAN Year 1961

Extended Properties

Molecular Formula C18H16O3
MW 280.32
Aromatic Rings 3
Heavy Atoms 21
NP-Likeness 0.25

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Vitamin k epoxide reductase complex subunit 1 isoform 1 inhibitor INHIBITOR Vitamin K epoxide reductase complex subunit 1 ✓ ✓

Indications

Thrombosis Venous Thrombosis Venous Thrombosis Melanoma

ATC Classification

B01AA04
phenprocoumon
Level 1: BLOOD AND BLOOD FORMING ORGANS
Level 2: ANTITHROMBOTIC AGENTS

Activity Summary

Ki 7 meas. best 6.7
IC50 4 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vitamin K epoxide reductase complex subunit 1
CHEMBL4105870
 Ki 6.7 6.7 200.0 1
Human immunodeficiency virus type 1 protease
CHEMBL243
 Ki 6.1 6.025 800.0 4
Human immunodeficiency virus type 1 protease
CHEMBL243
 IC50 6.0 6.0 1000.0 1
Unchecked
CHEMBL612545
 Ki 6.0 6.0 1000.0 1
Unchecked
CHEMBL612545
 IC50 5.75 5.75 1800.0 1
Human immunodeficiency virus
CHEMBL613758
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vitamin K epoxide reductase complex subunit 1 Ki = 200.0 nM 6.7 Inhibition of VKORC1 in rat liver microsomes in presence of 0.003 to 0.2 mM vita... 28254487
Human immunodeficiency virus type 1 protease Ki = 800.0 nM 6.1 Binding affinity towards HIV protease was determined 8831779
Human immunodeficiency virus type 1 protease IC50 = 1000.0 nM 6.0 Inhibitory concentration against human immunodeficiency virus 1 protease in MT-4... 15923115
Human immunodeficiency virus type 1 protease Ki = 1000.0 nM 6.0 Tested for inhibition of HIV protease 8893827
Human immunodeficiency virus type 1 protease Ki = 1000.0 nM 6.0 Tested for the HIV Protease inhibitory activity of the compound 7932546
Unchecked Ki = 1000.0 nM 6.0 Binding affinity to HIV protease assessed as inhibition constant 27484512
Human immunodeficiency virus type 1 protease Ki = 1000.0 nM 6.0 Inhibition of HIV-1 protease 37393791
Unchecked IC50 = 1800.0 nM 5.75 Inhibition of rat microsomal VKER 17275317
Human immunodeficiency virus IC50 = 100000.0 nM 4.0 Antiviral activity against HIV 37393791

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
28254487 10.1016/j.bmcl.2017.02.017 Rattus norvegicus 2
28254487 10.1016/j.bmcl.2017.02.017 Liver 2
16610785 10.1021/jm0508538 Cytochrome P450 2D6 1
37393791 10.1016/j.ejmech.2023.115586 Human immunodeficiency virus type 1 protease 1
20020916 10.1080/15376510701857262 Phospholipidosis 1
17275317 10.1016/j.bmc.2007.01.014 Unchecked 1
7381857 10.1021/jm00179a017 No relevant target 1
15923115 10.1016/j.bmcl.2005.04.057 Human immunodeficiency virus type 1 protease 1
7932546 10.1021/jm00046a002 ADMET 1
7932546 10.1021/jm00046a002 Human immunodeficiency virus type 1 protease 1
8831779 10.1021/jm960296c Human immunodeficiency virus type 1 protease 1
9089336 10.1021/jm960441m Human immunodeficiency virus type 1 protease 1
8893827 10.1021/jm960541s Human immunodeficiency virus type 1 protease 1
7381857 10.1021/jm00179a017 Cavia porcellus 1
7381857 10.1021/jm00179a017 Albumin 1

Data from ChEMBL 36 via Core Engine