TERBINAFINE

Search structure
Trade Names:
Synonyms:
Status: Approved (1992)
Entry Type: Small molecule
Molecule Category: Parent
ATC: D01AE15
UNII: G7RIW8S0XP

Structure
InChI Key DOMXUEMWDBAQBQ-WEVVVXLNSA-N
Smile CN(C/C=C/C#CC(C)(C)C)Cc1cccc2ccccc12
InChI
InChI=1S/C21H25N/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,16-17H2,1-4H3/b9-5+

Physicochemical Descriptors

Property Name Value
Molecular Formula C21H25N
Molecular Weight 291.44
AlogP 4.88
Hydrogen Bond Acceptor 1.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 4.0
Polar Surface Area 3.24
Molecular species BASE
Aromatic Rings 2.0
Heavy Atoms 22.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Squalene monooxygenase inhibitor FDA
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 6000 - 30 -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Tinea Pedis 3 D014008 ClinicalTrials
Colitis, Ulcerative 2 D003093 ClinicalTrials
Mycoses 1 D009181 ClinicalTrials

Related Entries

Scaffolds

Salt

Side Effects from Label

Side effects Relative Frequency (%) Labels
Gastrointestinal disorders Dyspepsia 22.0
Gastrointestinal disorders Gastritis 22.0
Nervous system disorders Headache 12.9
Infections and infestations Nasopharyngitis 11.0
Gastrointestinal disorders Nausea 11.0
Gastrointestinal disorders Vomiting 11.0
Gastrointestinal disorders Diarrhoea 10.0
Musculoskeletal and connective tissue disorders Muscle spasms 10.0
Infections and infestations Nasopharyngitis 10.0
Nervous system disorders Headache
Skin and subcutaneous tissue disorders Dermatitis 9.0
Skin and subcutaneous tissue disorders Erythema 9.0
Nervous system disorders Headache 9.0
Skin and subcutaneous tissue disorders Rash 9.0
Nervous system disorders Headache 8.0
Investigations Body temperature increased 7.0
Nervous system disorders Headache 7.0
Investigations Body temperature increased 6.0
Respiratory, thoracic and mediastinal disorders Cough 6.0
Skin and subcutaneous tissue disorders Dermatitis 6.0
Gastrointestinal disorders Diarrhoea 6.0
Skin and subcutaneous tissue disorders Rash 6.0
Skin and subcutaneous tissue disorders Dermatitis 5.6
Gastrointestinal disorders Diarrhoea 5.6
Skin and subcutaneous tissue disorders Rash 5.6
Respiratory, thoracic and mediastinal disorders Cough 5.0
Infections and infestations Upper respiratory tract infection 5.0
Immune system disorders Urticaria 5.0
Gastrointestinal disorders Vomiting 5.0
Gastrointestinal disorders Dyspepsia 4.3
Gastrointestinal disorders Abdominal pain upper 4.0
Gastrointestinal disorders Diarrhoea 4.0
Gastrointestinal disorders Dyspepsia 4.0
Skin and subcutaneous tissue disorders Pruritus 4.0
General disorders and administration site conditions Asthenia 3.0
Gastrointestinal disorders Diarrhoea 3.0
General disorders and administration site conditions Fatigue 3.0
Gastrointestinal disorders Nausea 3.0
Skin and subcutaneous tissue disorders Pruritus 3.0
Gastrointestinal disorders Diarrhoea
Gastrointestinal disorders Diarrhoea 2.9
Gastrointestinal disorders Dyspepsia
Gastrointestinal disorders Dyspepsia 2.9
Gastrointestinal disorders Nausea
Gastrointestinal disorders Nausea 2.9
Gastrointestinal disorders Dysgeusia 2.8
Skin and subcutaneous tissue disorders Pruritus 2.8
Gastrointestinal disorders Nausea 2.6
Gastrointestinal disorders Abdominal pain 2.4
Gastrointestinal disorders Gastrointestinal pain 2.4
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 2.2
Gastrointestinal disorders Dyspepsia 2.2
Gastrointestinal disorders Flatulence
Gastrointestinal disorders Flatulence 2.2
Gastrointestinal disorders Gastritis 2.2
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 2.2
Gastrointestinal disorders Abdominal pain 2.0
Skin and subcutaneous tissue disorders Dermatitis 2.0
Gastrointestinal disorders Gastrointestinal pain 2.0
Infections and infestations Influenza 2.0
Respiratory, thoracic and mediastinal disorders Laryngeal pain 2.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 2.0
Infections and infestations Nasopharyngitis 2.0
Gastrointestinal disorders Nausea 2.0
Skin and subcutaneous tissue disorders Rash 2.0
Respiratory, thoracic and mediastinal disorders Rhinorrhoea 2.0
Skin and subcutaneous tissue disorders Skin disorder 1.9
Gastrointestinal disorders Abdominal pain
Gastrointestinal disorders Abdominal pain 1.5
Gastrointestinal disorders Gastrointestinal pain
Gastrointestinal disorders Gastrointestinal pain 1.5
Skin and subcutaneous tissue disorders Pruritus
Skin and subcutaneous tissue disorders Pruritus 1.5
Eye disorders Visual impairment
Eye disorders Visual impairment 1.5
Gastrointestinal disorders Nausea 1.1
Skin and subcutaneous tissue disorders Pruritus 1.1
Immune system disorders Urticaria 1.1
Eye disorders Visual impairment 1.1
Gastrointestinal disorders Vomiting 1.1
Gastrointestinal disorders Abdominal pain 1.0
Gastrointestinal disorders Diarrhoea 1.0
Gastrointestinal disorders Dry mouth 1.0
Skin and subcutaneous tissue disorders Eczema 1.0
Gastrointestinal disorders Gastrointestinal pain 1.0
Investigations Hepatic enzyme increased 1.0
Endocrine disorders Hypoglycaemia 1.0
Infections and infestations Influenza 1.0
General disorders and administration site conditions Malaise 1.0
Musculoskeletal and connective tissue disorders Muscle spasms 1.0
Respiratory, thoracic and mediastinal disorders Nasal congestion 1.0
General disorders and administration site conditions Pain 1.0
Skin and subcutaneous tissue disorders Pruritus 1.0
Skin and subcutaneous tissue disorders Skin exfoliation 1.0
Gastrointestinal disorders Toothache 1.0
Immune system disorders Urticaria 1.0
Skin and subcutaneous tissue disorders Dermatitis 0.9
Skin and subcutaneous tissue disorders Erythema 0.9
Nervous system disorders Headache 0.9
Skin and subcutaneous tissue disorders Rash 0.9
Skin and subcutaneous tissue disorders Rash erythematous 0.9
Eye disorders Visual impairment 0.9
Skin and subcutaneous tissue disorders Dermatitis
Skin and subcutaneous tissue disorders Dermatitis 0.7
Gastrointestinal disorders Dysgeusia
Gastrointestinal disorders Dysgeusia 0.7
Skin and subcutaneous tissue disorders Rash
Skin and subcutaneous tissue disorders Rash 0.7
Gastrointestinal disorders Diarrhoea 0.6
Immune system disorders Urticaria 0.5
Gastrointestinal disorders Abdominal pain 0.4
Gastrointestinal disorders Dyspepsia 0.4
Gastrointestinal disorders Gastrointestinal pain 0.4
Skin and subcutaneous tissue disorders Pruritus 0.4
General disorders and administration site conditions Asthenia 0.3
General disorders and administration site conditions Fatigue 0.3
Gastrointestinal disorders Dysgeusia 0.2
Nervous system disorders Headache 0.2
Gastrointestinal disorders Nausea 0.2
Skin and subcutaneous tissue disorders Pruritus 0.2
Gastrointestinal disorders Dry mouth 0.1
Skin and subcutaneous tissue disorders Eczema 0.1
Investigations Hepatic enzyme increased 0.1
Endocrine disorders Hypoglycaemia 0.1
General disorders and administration site conditions Malaise 0.1
General disorders and administration site conditions Pain 0.1

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
50.0
Injury, poisoning and procedural complications
40.0
Product issues
10.0

Cross References

Resources Reference
CAS NUMBER 91161-71-6
ChEBI 9448
ChEMBL CHEMBL822
DrugBank DB00857
DrugCentral 2597
EPA CompTox DTXSID2023640
FDA SRS G7RIW8S0XP
Human Metabolome Database HMDB0014995
KEGG C08079
PharmGKB PA451614
PubChem 1549008
SureChEMBL SCHEMBL36794
ZINC ZINC000001530981
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