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Compound Detail

CHEMBL822

TERBINAFINE
💊 Approved Drug
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💊 Approved Drug
CN(C/C=C/C#CC(C)(C)C)Cc1cccc2ccccc12

Basic Information

ChEMBL ID CHEMBL822
Name TERBINAFINE
Phase Approved
Structure Type MOL
InChI Key DOMXUEMWDBAQBQ-WEVVVXLNSA-N
Therapeutic ✓ Yes

Known Names

Lamasil Lamisil Lamisil at SF 86-327 SF-86-327 TDT-067 Terbinafina Terbinafine Terbinafine component of osurnia
27
Targets
57
Activities
2
Assay Types
4
PK Parameters
20
Publications
9
Known Names
8
Indications
1
Mechanisms

Molecular Properties

291.4
MW (Da)
4.88
ALogP
1
HBA
0
HBD
3.2
PSA (Ų)
0.73
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1992
Availability OTC
Chirality Achiral

Routes of Administration

Oral Topical

Flags

Natural Product
USAN Year 1987

Extended Properties

Molecular Formula C21H25N
MW 291.44
Aromatic Rings 2
Heavy Atoms 22
NP-Likeness -0.03

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Squalene monooxygenase inhibitor INHIBITOR Squalene monooxygenase

Indications

Onychomycosis Onychomycosis Tinea Tinea Pedis Colitis, Ulcerative Crohn Disease Hepatitis B, Chronic Mycoses

ATC Classification

D01AE15
terbinafine
Level 1: DERMATOLOGICALS
Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE
D01BA02
terbinafine
Level 1: DERMATOLOGICALS
Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE

Activity Summary

IC50 51 meas. best 8.0
Ki 6 meas. best 7.66

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Trichophyton quinckeanum
CHEMBL612334
IC50 8.0 8.0 10.0 1
Unchecked
CHEMBL612545
Ki 7.66 6.775 21.8 2
Trichophyton rubrum
CHEMBL612649
IC50 7.52 6.6867 30.0 3
Squalene monooxygenase
CHEMBL3592
Ki 7.52 7.52 30.0 1
Unchecked
CHEMBL612545
IC50 7.45 6.65 35.4 2
Trichophyton mentagrophytes
CHEMBL613162
IC50 7.22 7.22 60.0 1
Microsporum canis
CHEMBL612335
IC50 7.0 7.0 100.0 1
Cytochrome P450 2D6
CHEMBL289
IC50 6.7 6.7 200.0 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
Ki 6.63 6.63 235.4 1
Aspergillus flavus
CHEMBL614955
IC50 6.52 6.52 300.0 1
Candida parapsilosis
CHEMBL612868
IC50 6.4 6.4 400.0 1
Cryptococcus neoformans
CHEMBL365
IC50 6.4 6.35 400.0 2
Sigma non-opioid intracellular receptor 1
CHEMBL287
IC50 6.25 6.25 560.2 1
Aspergillus niger
CHEMBL358
IC50 6.16 6.16 700.0 1
Aspergillus fumigatus
CHEMBL363
IC50 6.0 5.98 1000.0 2
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.67 5.67 2138.6 1
Candida albicans
CHEMBL366
IC50 5.58 5.0988 2600.0 8
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.39 5.39 4095.4 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.38 5.38 4129.5 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.24 5.24 5702.9 1
Squalene monooxygenase
CHEMBL3592
IC50 5.22 5.22 6000.0 1
Kluyveromyces marxianus
CHEMBL612842
IC50 5.2 5.2 6330.0 1
Plasmodium falciparum
CHEMBL364
IC50 5.11 5.11 7720.0 1
Trypanosoma cruzi
CHEMBL368
IC50 4.77 4.5044 17100.0 9
Leishmania donovani
CHEMBL367
IC50 4.64 4.4 23000.0 2
Nakaseomyces glabratus
CHEMBL612647
IC50 4.51 4.51 30660.0 1
Candida tropicalis
CHEMBL612870
IC50 4.34 4.34 45400.0 1
NON-PROTEIN TARGET
CHEMBL3879801
IC50 4.33 4.33 46970.0 1
Pichia kudriavzevii
CHEMBL612841
IC50 4.19 4.19 64000.0 1
J774
CHEMBL614123
IC50 4.06 4.06 88000.0 2
Squalene monooxygenase
CHEMBL4241
IC50 4.03 4.03 93000.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 4.02 4.02 95150.0 1

Pharmacokinetic Data

Parameter Value Units Species
Cmax 205.87 nM Cavia porcellus
F 49.0 % Homo sapiens
T1/2 6.6 hr Cavia porcellus
Tmax 0.7 hr Cavia porcellus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Trichophyton quinckeanum IC50 = 10.0 nM 8.0 Antifungal activity against 5 x 10'6 CFU/ml Trichophyton quinckeanum B68683 by r... 20805398
Unchecked Ki = 21.8 nM 7.66 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
Squalene monooxygenase Ki = 30.0 nM 7.52 Inhibitory activity against Candida albicans Squalene Epoxidase 2769687
Trichophyton rubrum IC50 = 30.0 nM 7.52 Antifungal activity against 5 x 10'6 CFU/ml Trichophyton rubrum J941704 by resaz... 20805398
Unchecked IC50 = 35.4 nM 7.45 DRUGMATRIX: Sigma2 radioligand binding (ligand: [3H] Ifenprodil) -
Trichophyton mentagrophytes IC50 = 60.0 nM 7.22 Antifungal activity against 5 x 10'6 CFU/ml Trichophyton mentagrophytes B70554 b... 20805398
Trichophyton rubrum IC50 = 70.0 nM 7.16 Antifungal activity against 5 x 10'6 CFU/ml Trichophyton rubrum B68183 by resazu... 20805398
Microsporum canis IC50 = 100.0 nM 7.0 Antifungal activity against 5 x 10'6 CFU/ml Microsporum canis B68128 by resazuri... 20805398
Cytochrome P450 2D6 IC50 = 200.0 nM 6.7 DRUGMATRIX: CYP450, 2D6 enzyme inhibition (substrate: 3-Cyano-7-ethoxycoumarin) -
Sigma non-opioid intracellular receptor 1 Ki = 235.4 nM 6.63 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Aspergillus flavus IC50 = 300.0 nM 6.52 Antifungal activity against Aspergillus flavus ATCC 204304 after 5 days by CLSI ... 18458131
Candida parapsilosis IC50 = 400.0 nM 6.4 Antifungal activity against Candida parapsilosis ATCC 22019 after 48 hrs by CLSI... 18458131
Cryptococcus neoformans IC50 = 400.0 nM 6.4 Antifungal activity against Cryptococcus neoformans ATCC 66031 after 72 hrs by C... 18458131
Cryptococcus neoformans IC50 = 500.0 nM 6.3 Antifungal activity against Cryptococcus neoformans ATCC 90113 after 72 hrs by C... 18458131
Sigma non-opioid intracellular receptor 1 IC50 = 560.2 nM 6.25 DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) -
Aspergillus niger IC50 = 700.0 nM 6.16 Antifungal activity against Aspergillus niger ATCC 16404 after 5 days by CLSI me... 18458131
Aspergillus fumigatus IC50 = 1000.0 nM 6.0 Antifungal activity against Aspergillus fumigatus ATCC 90906 after 5 days by CLS... 18458131
Aspergillus fumigatus IC50 = 1100.0 nM 5.96 Antifungal activity against Aspergillus fumigatus ATCC 204305 after 5 days by CL... 18458131
Unchecked Ki = 1279.5 nM 5.89 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -
Unchecked IC50 = 1402.6 nM 5.85 DRUGMATRIX: Sodium Channel, Site 2 radioligand binding (ligand: [3H] Batrachotox... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1414
- 10.6019/CHEMBL3885881 Rattus norvegicus 269
- 10.5281/zenodo.13943903 ADMET 73
18212093 10.1128/aac.00942-07 NON-PROTEIN TARGET 28
19635955 10.1128/aac.00585-09 Aspergillus tubingensis 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
18458131 10.1128/aac.01297-07 Candida albicans 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
19635955 10.1128/aac.00585-09 Aspergillus niger 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
30765301 10.1016/j.bmc.2019.02.009 Candida albicans 9
22411894 10.1002/ps.3263 Zymoseptoria tritici 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
18458131 10.1128/aac.01297-07 Trichophyton rubrum 6
18458131 10.1128/aac.01297-07 Trichophyton mentagrophytes 6
18458131 10.1128/aac.01297-07 Aspergillus fumigatus 6
17049255 10.1016/j.bmc.2006.09.038 Trichophyton rubrum 6
18458131 10.1128/aac.01297-07 Cryptococcus neoformans 6
19171801 10.1128/aac.01467-08 Molecular identity unknown 6
18752959 10.1016/j.bmc.2008.07.079 Trichophyton mentagrophytes 6

Data from ChEMBL 36 via Core Engine