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Compound Detail

CHEMBL496

HEXACHLOROPHENE
💊 Approved Drug
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💊 Approved Drug
Oc1c(Cl)cc(Cl)c(Cl)c1Cc1c(O)c(Cl)cc(Cl)c1Cl

Basic Information

ChEMBL ID CHEMBL496
Name HEXACHLOROPHENE
Phase Approved
Structure Type MOL
InChI Key ACGUYXCXAPNIKK-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

"germa-medica ""mg""" Dial E-z scrub Gamophen Germa-medica Germa-medica "mg" Hexa-germ Hexachlorophene Hexaclorofeno Hexascrub NSC-49115 Phiso-scrub +8 more
51
Targets
93
Activities
3
Assay Types
0
PK Parameters
20
Publications
20
Known Names
1
Mechanisms

Molecular Properties

406.9
MW (Da)
6.61
ALogP
2
HBA
2
HBD
40.5
PSA (Ų)
0.55
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1949
Availability Prescription
Chirality Achiral

Routes of Administration

Topical

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C13H6Cl6O2
MW 406.91
Aromatic Rings 2
Heavy Atoms 21
NP-Likeness -0.01

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Bacterial enoyl-[acyl-carrier-protein] reductase inhibitor INHIBITOR Enoyl-[acyl-carrier-protein] reductase [NADH] FabI

ATC Classification

D08AE01
hexachlorophene
Level 1: DERMATOLOGICALS
Level 2: ANTISEPTICS AND DISINFECTANTS

Drug Warnings

Withdrawn
dermatological toxicity
teratogenicity, embryotoxicity, neurotoxicity, photosensitizing and allergic potential
Country: Union of Soviet Socialist Republics   Year: 1988
Withdrawn
teratogenicity
teratogenicity, embryotoxicity, neurotoxicity, photosensitizing and allergic potential
Country: Union of Soviet Socialist Republics   Year: 1988
Withdrawn
dermatological toxicity
teratogenicity, embryotoxicity, neurotoxicity, photosensitizing and allergic potential
Country: Union of Soviet Socialist Republics   Year: 1988
Withdrawn
neurotoxicity
teratogenicity, embryotoxicity, neurotoxicity, photosensitizing and allergic potential
Country: Union of Soviet Socialist Republics   Year: 1988
Withdrawn
immune system toxicity
teratogenicity, embryotoxicity, neurotoxicity, photosensitizing and allergic potential
Country: Union of Soviet Socialist Republics   Year: 1988

Activity Summary

IC50 72 meas. best 8.52
EC50 11 meas. best 6.7
Ki 10 meas. best 6.44

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 8.52 5.7987 3.0 23
Mitogen-activated protein kinase 14
CHEMBL260
IC50 7.06 7.06 87.6 1
Estrogen receptor beta
CHEMBL242
IC50 7.01 7.01 98.3 1
Mitogen-activated protein kinase 1
CHEMBL4040
IC50 6.71 6.71 196.0 1
Streptokinase A
CHEMBL1293228
EC50 6.7 6.7 202.0 1
Streptococcus sp. 'group A'
CHEMBL612389
EC50 6.61 6.61 244.0 1
Streptococcus
CHEMBL612313
EC50 6.58 6.58 262.0 1
Adenosine receptor A3
CHEMBL256
Ki 6.44 6.44 361.1 1
Adenosine receptor A3
CHEMBL256
IC50 6.2 6.2 638.9 1
Prostaglandin G/H synthase 2
CHEMBL230
IC50 6.19 6.19 644.3 1
Epidermal growth factor receptor
CHEMBL203
IC50 6.13 6.13 748.6 1
SARS-CoV-2
CHEMBL4303835
IC50 6.05 6.05 900.0 1
Adenosine receptor A2a
CHEMBL251
Ki 6.04 6.04 906.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 5.99 5.99 1013.5 1
Cytochrome P450 2C19
CHEMBL3622
IC50 5.91 5.91 1226.5 1
HSP60/HSP10
CHEMBL4106131
IC50 5.89 5.89 1300.0 1
Cytochrome P450 1A2
CHEMBL3356
IC50 5.88 5.88 1313.3 1
Substance-K receptor
CHEMBL2327
Ki 5.86 5.86 1379.7 1
GroEL/GroES
CHEMBL4106139
IC50 5.85 5.59 1400.0 2
N-acyl-phosphatidylethanolamine-hydrolyzing phospholipase D
CHEMBL4630839
IC50 5.8 5.8 1600.0 1
Adenosine receptor A2a
CHEMBL251
IC50 5.79 5.79 1613.8 1
ATP-dependent molecular chaperone HSP82
CHEMBL1293251
EC50 5.76 5.76 1725.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.69 5.69 2061.2 1
Estrogen receptor
CHEMBL206
IC50 5.67 5.67 2161.6 1
Sodium-dependent serotonin transporter
CHEMBL228
Ki 5.64 5.64 2310.6 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 5.62 5.62 2411.7 1
Mitogen-activated protein kinase 3
CHEMBL3385
IC50 5.61 5.61 2484.4 1
Tyrosine-protein kinase Lck
CHEMBL258
IC50 5.61 5.61 2432.5 1
Acetylcholinesterase
CHEMBL220
IC50 5.52 5.52 3014.9 1
Thromboxane-A synthase
CHEMBL1835
IC50 5.51 5.51 3087.0 1
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
IC50 5.48 5.48 3318.8 1
Androgen receptor
CHEMBL3072
Ki 5.48 5.48 3316.9 1
Tyrosine-protein kinase Fyn
CHEMBL1841
IC50 5.46 5.46 3478.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 5.44 5.44 3623.9 1
Calpain-2 catalytic subunit
CHEMBL4143
IC50 5.43 5.43 3733.6 1
Plasmodium yoelii
CHEMBL612889
IC50 5.4 5.4 4000.0 1
Substance-K receptor
CHEMBL2327
IC50 5.38 5.38 4139.2 1
Sodium-dependent serotonin transporter
CHEMBL228
IC50 5.36 5.36 4349.4 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 5.34 5.34 4604.2 1
ClpP1P2
CHEMBL4662931
IC50 5.31 5.31 4900.0 1
Androgen receptor
CHEMBL3072
IC50 5.3 5.3 4975.3 1
Candida albicans
CHEMBL366
IC50 5.29 5.29 5100.0 1
Transitional endoplasmic reticulum ATPase
CHEMBL1075145
IC50 5.26 5.26 5488.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.26 5.26 5496.5 1
Macrophage migration inhibitory factor
CHEMBL2085
Ki 5.26 5.26 5550.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 5.25 5.25 5694.7 1
Macrophage migration inhibitory factor
CHEMBL2085
IC50 5.22 5.22 6000.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.16 5.16 6975.4 1
Protein RecA
CHEMBL1741171
EC50 5.14 5.14 7270.0 1
Envelope glycoprotein gp160
CHEMBL1293311
IC50 5.14 5.14 7260.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 3.0 nM 8.52 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 15.7 nM 7.8 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 31.21 nM 7.51 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 32.0 nM 7.5 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 57.2 nM 7.24 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Mitogen-activated protein kinase 14 IC50 = 87.6 nM 7.06 DRUGMATRIX: Protein Serine/Threonine Kinase, p38alpha enzyme inhibition (substra... -
Estrogen receptor beta IC50 = 98.27 nM 7.01 PUBCHEM_BIOASSAY: Estrogen Receptor-beta Coactivator Binding Inhibitors ELISA Se... -
Unchecked IC50 = 108.5 nM 6.96 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Mitogen-activated protein kinase 1 IC50 = 196.0 nM 6.71 DRUGMATRIX: Protein Serine/Threonine Kinase, ERK2 enzyme inhibition (substrate: ... -
Streptokinase A EC50 = 202.0 nM 6.7 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptococcus sp. 'group A' EC50 = 244.0 nM 6.61 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Streptococcus EC50 = 262.0 nM 6.58 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -
Adenosine receptor A3 Ki = 361.1 nM 6.44 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Unchecked IC50 = 405.0 nM 6.39 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Unchecked IC50 = 459.6 nM 6.34 PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Adenosine receptor A3 IC50 = 638.9 nM 6.2 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Prostaglandin G/H synthase 2 IC50 = 644.3 nM 6.19 DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) -
Epidermal growth factor receptor IC50 = 748.6 nM 6.13 DRUGMATRIX: Protein Tyrosine Kinase, EGF Receptor enzyme inhibition (substrate: ... -
SARS-CoV-2 IC50 = 900.0 nM 6.05 Antiviral activity against SARS-CoV-2 (viral titer) measured by plaque assay in ... -
Adenosine receptor A2a Ki = 906.0 nM 6.04 DRUGMATRIX: Adenosine A2A radioligand binding (ligand: AB-MECA) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
31129054 10.1016/j.bmcl.2019.05.041 HCT-116 10
31129054 10.1016/j.bmcl.2019.05.041 Endoplasmic reticulum chaperone BiP 8
19223628 10.1128/aac.01293-08 Staphylococcus aureus 8
7288822 10.1021/jm00141a011 Staphylococcus aureus 6
30852084 10.1016/j.bmcl.2019.02.028 Unchecked 5
26789657 10.1021/acs.jmedchem.5b01696 Lanosterol 14-alpha demethylase 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 4
6802973 10.1021/jm00345a016 No relevant target 3
19734050 10.1016/j.bmc.2009.07.073 NAD-dependent protein deacetylase HST2 3
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
23643898 10.1016/j.bmc.2013.04.012 Unchecked 2
31129054 10.1016/j.bmcl.2019.05.041 Unchecked 2
28051303 10.1021/acs.jmedchem.6b01203 Candida albicans 2
19633659 10.1038/nchembio.192 Granzyme B 2
29812929 10.1021/acs.jmedchem.8b00589 Macrophage migration inhibitory factor 2
6802973 10.1021/jm00345a016 Bacillus subtilis 2

Data from ChEMBL 36 via Core Engine