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Compound Detail

CHEMBL849

TRICLOSAN
💊 Approved Drug
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💊 Approved Drug
Oc1cc(Cl)ccc1Oc1ccc(Cl)cc1Cl

Basic Information

ChEMBL ID CHEMBL849
Name TRICLOSAN
Phase Approved
Structure Type MOL
InChI Key XEFQLINVKFYRCS-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Aquasept CH 3565 CH-3565 Cloxifenol DNDI1246774 Gamophen Innoxa Manusept NSC-759151 Skinsan Stri-dex cleansing bar Tegusept +2 more
17
Targets
118
Activities
4
Assay Types
1
PK Parameters
20
Publications
14
Known Names
5
Indications
1
Mechanisms

Molecular Properties

289.6
MW (Da)
5.14
ALogP
2
HBA
1
HBD
29.5
PSA (Ų)
0.83
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1997
Availability Discontinued
Chirality Achiral

Routes of Administration

Topical

Flags

Natural Product
USAN Year 1972

Extended Properties

Molecular Formula C12H7Cl3O2
MW 289.55
Aromatic Rings 2
Heavy Atoms 17
NP-Likeness -0.33

Mechanism of Action

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

Indications

Gingivitis Hypersensitivity Mucositis Periodontal Diseases Periodontitis

ATC Classification

D08AE04
triclosan
Level 1: DERMATOLOGICALS
Level 2: ANTISEPTICS AND DISINFECTANTS
D09AA06
triclosan
Level 1: DERMATOLOGICALS
Level 2: MEDICATED DRESSINGS

Activity Summary

IC50 77 meas. best 8.3
Ki 27 meas. best 10.28
EC50 13 meas. best 5.81
Kd 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Enoyl-acyl-carrier protein reductase
CHEMBL4150
Ki 10.28 8.19 0.1 16
Enoyl-[acyl-carrier-protein] reductase [NADPH] FabI
CHEMBL3994
Ki 8.3 8.3 5.0 1
Enoyl-[acyl-carrier-protein] reductase [NADH] FabI
CHEMBL1857
IC50 8.3 6.772 5.0 5
Enoyl-acyl carrier reductase
CHEMBL1250368
IC50 7.82 7.82 15.0 2
Unchecked
CHEMBL612545
IC50 7.6 6.1736 25.0 22
Enoyl-[acyl-carrier-protein] reductase [NADH]
CHEMBL2150835
IC50 7.3 5.956 50.0 5
Unchecked
CHEMBL612545
Ki 7.3 6.965 50.0 2
Enoyl-[acyl-carrier-protein] reductase [NADPH] FabI
CHEMBL3994
IC50 7.23 6.6383 59.0 6
Carbonyl reductase [NADPH] 1
CHEMBL5586
Ki 7.22 7.22 60.0 1
Enoyl-acyl-carrier protein reductase
CHEMBL4150
IC50 7.18 7.095 66.0 8
Enoyl-[acyl-carrier-protein] reductase [NADH]
CHEMBL1849
Ki 6.7 6.692 200.0 5
Enoyl-[acyl-carrier-protein] reductase [NADH]
CHEMBL1849
IC50 6.7 5.8043 200.0 7
Carbonyl reductase [NADPH] 1
CHEMBL5586
IC50 6.4 6.4 400.0 1
Plasmodium falciparum
CHEMBL364
IC50 6.37 5.8292 424.4 12
Enoyl-[acyl-carrier-protein] reductase [NADH] FabI
CHEMBL1075044
IC50 6.3 6.3 500.0 1
Escherichia coli
CHEMBL354
IC50 6.12 6.12 750.0 1
Plasmodium falciparum
CHEMBL364
EC50 5.81 5.5167 1550.0 9
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.7 4.7 20000.0 1
Unchecked
CHEMBL612545
EC50 4.54 4.505 28570.0 2
Leishmania panamensis
CHEMBL612882
EC50 4.41 4.41 38610.0 1
Trypanosoma cruzi
CHEMBL368
EC50 4.31 4.31 48970.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.28 4.28 52960.0 1
Transthyretin
CHEMBL3194
IC50 4.27 4.27 53500.0 1
L6
CHEMBL614793
IC50 4.08 4.08 82250.0 1
Endoplasmic reticulum chaperone BiP
CHEMBL1781865
IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 10.8 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Enoyl-acyl-carrier protein reductase Ki = 0.05206 nM 10.28 Inhibition of Plasmodium falciparum ENR in presence of ECG by dilution assay 17263522
Enoyl-acyl-carrier protein reductase Ki = 0.109 nM 9.96 Inhibition of Plasmodium falciparum ENR in presence of EGC by dilution assay 17263522
Enoyl-acyl-carrier protein reductase Ki = 0.2806 nM 9.55 Inhibition of Plasmodium falciparum ENR in presence of quercetin by dilution ass... 17263522
Enoyl-acyl-carrier protein reductase Ki = 0.7983 nM 9.1 Inhibition of Plasmodium falciparum ENR in presence of butein by dilution assay 17263522
Enoyl-acyl-carrier protein reductase Ki = 1.0 nM 9.0 Inhibition of Plasmodium falciparum ENR in presence of EGCG 17263522
Enoyl-[acyl-carrier-protein] reductase [NADPH] FabI Ki = 5.0 nM 8.3 Inhibition of Staphylococcus aureus FabI in the presence of NADH using crotonyl ... 32883635
Enoyl-[acyl-carrier-protein] reductase [NADH] FabI IC50 = 5.0 nM 8.3 Inhibition of Escherichia coli FabI using 2-dodecenoyl-CoA as substrate at pH 8 23806111
Enoyl-acyl-carrier protein reductase Ki = 7.29 nM 8.14 Inhibition of Plasmodium falciparum ENR by fluorescence quenching in presence of... 17263522
Enoyl-acyl-carrier protein reductase Ki = 8.0 nM 8.1 Inhibition of Plasmodium falciparum ENR in presence of ECG 17263522
Enoyl-acyl-carrier protein reductase Ki = 8.25 nM 8.08 Inhibition of Plasmodium falciparum ENR in presence of EGC 17263522
Enoyl-acyl-carrier protein reductase Ki = 10.0 nM 8.0 Inhibition of Plasmodium falciparum ENR in presence of quercetin 17263522
Enoyl-acyl-carrier protein reductase Ki = 13.72 nM 7.86 Inhibition of Plasmodium falciparum ENR in presence of butein 17263522
Enoyl-acyl carrier reductase IC50 = 15.0 nM 7.82 Inhibition of Toxoplasma gondii enoyl reductase assessed as conversion of trans-... 23453069
Enoyl-acyl carrier reductase IC50 = 15.0 nM 7.82 Inhibition of Toxoplasma gondii enoyl acyl-carrier protein reductase 23664871
Unchecked IC50 = 25.0 nM 7.6 Inhibition of Staphylococcus aureus FabI using dodecenoyl ACP at pH 7.8 23806111
Enoyl-acyl-carrier protein reductase Ki = 28.31 nM 7.55 Inhibition of Plasmodium falciparum ENR by fluorescence quenching in presence of... 17263522
Enoyl-acyl-carrier protein reductase Ki = 30.54 nM 7.51 Inhibition of Plasmodium falciparum ENR by fluorescence quenching in presence of... 17263522
Unchecked Ki = 50.0 nM 7.3 Inhibition of Plasmodium falciparum FabI using crotonoyl-CoA as substrate by UV-... 24063369
Unchecked IC50 = 50.0 nM 7.3 Inhibition of Plasmodium falciparum FabI using crotonoyl-CoA as substrate preinc... 23806111
Enoyl-[acyl-carrier-protein] reductase [NADH] IC50 = 50.0 nM 7.3 Inhibition of Francisella tularensis SCHU S4 FabI R96G mutant using CrCoA as sub... 23815100

Literature References

PubMed DOI Target Context # Activities
18180352 10.1128/aac.01094-07 Proteus mirabilis 31
17263522 10.1021/jm061154d Enoyl-acyl-carrier protein reductase 15
33130290 10.1016/j.bmcl.2020.127651 Escherichia coli 14
30408748 10.1016/j.ejmech.2018.10.053 Unchecked 10
19223628 10.1128/aac.01293-08 Staphylococcus aureus 8
19933806 10.1128/aac.01152-09 Escherichia coli 8
30408748 10.1016/j.ejmech.2018.10.053 Staphylococcus aureus 8
30408748 10.1016/j.ejmech.2018.10.053 Escherichia coli 8
17060533 10.1128/aac.00808-06 Plasmodium falciparum 8
18694955 10.1128/aac.00661-08 NON-PROTEIN TARGET 7
17948976 10.1021/jm0700159 Transthyretin 7
19564371 10.1128/aac.00550-09 Mycobacterium tuberculosis 6
22285320 10.1016/j.bmcl.2012.01.025 Escherichia coli 6
17110371 10.1074/jbc.m608615200 Plasmodium falciparum 6
23815100 10.1021/jm4001242 Enoyl-[acyl-carrier-protein] reductase [NADH] 5
19097799 10.1016/j.bmc.2008.11.076 Carbonyl reductase [NADPH] 1 5
19933806 10.1128/aac.01152-09 Unchecked 5
22285320 10.1016/j.bmcl.2012.01.025 Staphylococcus epidermidis 4
19075064 10.1128/aac.00126-08 Unchecked 4
22285320 10.1016/j.bmcl.2012.01.025 Staphylococcus aureus 4

Data from ChEMBL 36 via Core Engine