Terbinafine (CED0003452)

Record Information
Version1.0
Creation Date2016-05-22 03:46:58 UTC
Update Date2026-08-21 19:08:53 UTC
Accession NumberCHEM016898
Identification
Common NameTerbinafine
ClassSmall Molecule
Description
Terbinafine is an organic compound with the chemical formula C21H25N and an average molecular weight of 291.43 g/mol. Terbinafine belongs to the naphthalenes, a class of benzenoids within the organic compounds. This compound has been identified in or released from 31 recorded sources across multiple sectors. These include aquatic systems and sediments, such as seawater, freshwater, surface water, and groundwater, as well as drinking water and water supply sources including bottled water, tap water, desalinated water, and drinking water. It is also found in wastewater, sanitation, and biosolids, specifically in wastewater, industrial wastewater, mine wastewater, and wastewater treatment effluent. Additional sources include marine, shipping, and aquaculture sectors, specifically bilge water and ballast water, and appliances, HVAC, and refrigerants, such as water heaters and water coolers. Furthermore, it is associated with electrical and electronic equipment, including antennas, adjustable resistors, communication cables or conductors, auxiliary devices, electric hearing aids, and three other sources, along with six additional sectors. Recorded routes of exposure for terbinafine include touch, topical, oral, and inhalation. At the molecular level, terbinafine is associated with two recorded protein targets. It acts as an inhibitor of squalene monooxygenase (SQLE) and targets squalene epoxidase ERG1.
Contaminant Type
  • PMT
Chemical Structure
Synonyms
ValueSource
(e)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamineChEBI
(e)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamineChEBI
TerbinafinaChEBI
TerbinafinumChEBI
LamasilKegg
(e)-N-(6,6-Dimethyl-2-heptenynyl)-N-methyl-1-naphthalenementhamin hydrochlorideHMDB
TDT-067HMDB
LamisilHMDB
Terbinafine hydrochlorideHMDB
Terbinafine, (Z)-isomerHMDB
TDT 067MeSH
Chemical FormulaC21H25N
Average Molecular Mass291.430 g/mol
Monoisotopic Mass291.199 g/mol
CAS Registry Number91161-71-6
IUPAC Name[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine
Traditional Nameterbinafine
SMILESCN(C\C=C\C#CC(C)(C)C)CC1=CC=CC2=CC=CC=C12
InChI IdentifierInChI=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+
InChI KeyDOMXUEMWDBAQBQ-WEVVVXLNSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as naphthalenes. Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
KingdomOrganic compounds
Super ClassBenzenoids
ClassNaphthalenes
Sub ClassNot Available
Direct ParentNaphthalenes
Alternative Parents
Substituents
  • Naphthalene
  • Aralkylamine
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.00074 g/LALOGPS
logP5.51ALOGPS
logP5.53ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.08 m³·mol⁻¹ChemAxon
Polarizability35.83 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-2930000000-c0f8480eb31fc7fbd935Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-3940000000-70d0c46dfa6b0976b000Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-1920000000-a7ec8e83df0d61d1f6b5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-21f09a1b44383f9e2f17Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-3a0933b844cbea414661Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-4fb92eeb2d5d7cba5249Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0390000000-e6fdb16d250e55ec779cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-2900000000-818d34136f53ffb9ada6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-ced135b5d1417f0bc5eaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0900000000-7680ead08d306856edb8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-1920000000-a169078200709f020b23Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0190000000-7397059642812e990049Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00dl-1970000000-73129fd49c2a85263415Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0ab9-2900000000-17448ff84bb8ba578229Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-392d0c026d7524f1ae01Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-006x-0790000000-a120321e1361129fa198Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-1900000000-4711e63dfba61da8256cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0490000000-2a7823026f61aa0613b1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-002f-1910000000-89ca4fa284b79895d70fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-5900000000-28d6b8e304157661d731Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-4f81054177f4676e3417Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0980000000-03245111efe9b36c1b3dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004l-3910000000-56e40a6f869979438c61Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
669.0Log mg/kg[380:1200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
3Irrigation waterAgriculture & land managementNot Available
19Indoor airAir, dust & atmospheric transportNot Available
27Water CoolersAppliances, HVAC & refrigerantsNot Available
43Water heatersAppliances, HVAC & refrigerantsNot Available
50GroundwaterAquatic systems & sedimentsNot Available
51Surface waterAquatic systems & sedimentsNot Available
52SeawaterAquatic systems & sedimentsNot Available
53FreshwaterAquatic systems & sedimentsNot Available
70Stormwater runoffAutomotive & urban infrastructureNot Available
88Waterproofing spraysBuilding & ConstructionNot Available
115Drinking waterDrinking water & water supplyNot Available
116Tap waterDrinking water & water supplyNot Available
117Bottled waterDrinking water & water supplyNot Available
118Desalinated waterDrinking water & water supplyNot Available
181Ballast waterMarine, shipping & aquacultureNot Available
182Bilge waterMarine, shipping & aquacultureNot Available
299Antifungals for dermatological useHealthcare, pharmaceuticals & veterinary productsNot Available
468Industrial wastewaterWastewater, sanitation & biosolidsNot Available
470Wastewater treatment effluentWastewater, sanitation & biosolidsNot Available
475Mine wastewaterWastewater, sanitation & biosolidsNot Available
477Wastewater, unspecifiedWastewater, sanitation & biosolidsNot Available
504Adjustable ResistorsElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
507Auxiliary DevicesElectrical & Electronic EquipmentNot Available
510Communication Cables Or ConductorsElectrical & Electronic EquipmentNot Available
516Electric Hearing AidsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
536Superconductive Or Hyperconductive Conductors Cables Or Transmission LinesElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
594Ship HullsMarine, shipping & aquacultureNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
619Manicure PedicurePersonal care & cosmeticsNot Available
638Decorating TextilesTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
653SewingTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)16.3483
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)46.9431
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)28.415
Sodium-dependent noradrenaline transporter structureClick to view 3D structureSodium-dependent noradrenaline transporterP23975HumansPredicted (SEA)27.1694
Click to view 3D structure4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming)Q2FDU6Staphylococcus aureus (strain USA300)Predicted (SEA)1.01204
Squalene monooxygenase structureClick to view 3D structureSqualene monooxygenaseQ14534HumansPredicted (SEA)0.233548
Click to view 3D structureSqualene epoxidase ERG1Q92206YeastPredicted (SEA)0.0778492
Click to view 3D structure4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming)O07855Staphylococcus aureus (strain Newman)Predicted (SEA)2.49118
Click to view 3D structure4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming)Q99R76Staphylococcus aureus (strain Mu50 / ATCC 700699)Predicted (SEA)2.41333
Click to view 3D structure4,4'-diapophytoene desaturase (4,4'-diaponeurosporene-forming)Q8NUQ6Staphylococcus aureus (strain MW2)Predicted (SEA)2.41333
Acetylcholinesterase structureClick to view 3D structureAcetylcholinesteraseP22303HumansPredicted (SEA)309.918
Listeriolysin regulatory protein structureClick to view 3D structureListeriolysin regulatory proteinP22262Listeria monocytogenes serovar 1/2a (strain ATCC BAA-679 / EGD-e)Predicted (SEA)1.24559
Interferon alpha/beta receptor 1 structureClick to view 3D structureInterferon alpha/beta receptor 1P17181HumansPredicted (SEA)2.64687
Sodium-dependent serotonin transporter structureClick to view 3D structureSodium-dependent serotonin transporterP31645HumansPredicted (SEA)719.872
Cytochrome P450 1A2 structureClick to view 3D structureCytochrome P450 1A2P05177HumansPredicted (SEA)2364.83
Click to view 3D structureChaperone protein dnaKC3TRK2Escherichia coliPredicted (SEA)34.2537
Voltage-gated inwardly rectifying potassium channel KCNH2 structureClick to view 3D structureVoltage-gated inwardly rectifying potassium channel KCNH2Q12809HumansPredicted (SEA)3900.17
Cytochrome P450 2C9 structureClick to view 3D structureCytochrome P450 2C9P11712HumansPredicted (SEA)4232.66
Click to view 3D structureCholine O-acetyltransferaseP32738Rattus norvegicusPredicted (SEA)1.47914
Click to view 3D structureC-8 sterol isomerase ERG2P32352Baker's yeastPredicted (SEA)36.5113
3-beta-hydroxysteroid-Delta(8),Delta(7)-isomerase structureClick to view 3D structure3-beta-hydroxysteroid-Delta(8),Delta(7)-isomeraseQ15125HumansPredicted (SEA)126.816
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)5452.79
Click to view 3D structureProtein arginine N-methyltransferase 1Q63009Rattus norvegicusPredicted (SEA)5.0602
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)2170.2
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)1747.79
Concentrations
Not Available
External Links
DrugBank IDDB00857
HMDB IDHMDB0014995
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-10571
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTerbinafine
Chemspider ID1266005
ChEBI ID9448
PubChem Compound ID1549008
Kegg Compound IDC08079
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Ryder NS: Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-7.
2. Birnbaum JE: Pharmacology of the allylamines. J Am Acad Dermatol. 1990 Oct;23(4 Pt 2):782-5.
3. McClellan KJ, Wiseman LR, Markham A: Terbinafine. An update of its use in superficial mycoses. Drugs. 1999 Jul;58(1):179-202.
4. Darkes MJ, Scott LJ, Goa KL: Terbinafine: a review of its use in onychomycosis in adults. Am J Clin Dermatol. 2003;4(1):39-65.
5. Klobucnikova V, Kohut P, Leber R, Fuchsbichler S, Schweighofer N, Turnowsky F, Hapala I: Terbinafine resistance in a pleiotropic yeast mutant is caused by a single point mutation in the ERG1 gene. Biochem Biophys Res Commun. 2003 Sep 26;309(3):666-71.
6. Korting HC, Kiencke P, Nelles S, Rychlik R: Comparable efficacy and safety of various topical formulations of terbinafine in tinea pedis irrespective of the treatment regimen: results of a meta-analysis. Am J Clin Dermatol. 2007;8(6):357-64.
7. Krishnan-Natesan S: Terbinafine: a pharmacological and clinical review. Expert Opin Pharmacother. 2009 Nov;10(16):2723-33. doi: 10.1517/14656560903307462.
8. Gianni C: Update on antifungal therapy with terbinafine. G Ital Dermatol Venereol. 2010 Jun;145(3):415-24.
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23750489
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23802806
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23841559
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23895037
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=24126579
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=24352873
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=24389279
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24410098
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24447130
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=24452843
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=24477462
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=24490976
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=24497012
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=24533442
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=24563892
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=24576265
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=24581620
26. https://www.ncbi.nlm.nih.gov/pubmed/?term=24588014