Terbinafine hydrochlorideProduct ingredient for Terbinafine

Name
Terbinafine hydrochloride
Drug Entry
Terbinafine

Terbinafine hydrochloride (Lamisil) is a synthetic allylamine antifungal.10,11 It is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues.1 Like other allylamines, terbinafine inhibits ergosterol synthesis by inhibiting the fungal squalene monooxygenase (also called squalene epoxidase), an enzyme that is part of the fungal cell wall synthesis pathway.1,2,11

Terbinafine hydrochloride was granted FDA approval on 30 December 1992.9

Accession Number
DBSALT000470
Structure
Synonyms
Terbinafine HCl
External IDs
MOB015B
UNII
012C11ZU6G
CAS Number
78628-80-5
Weight
Average: 327.891
Monoisotopic: 327.175377544
Chemical Formula
C21H26ClN
InChI Key
BWMISRWJRUSYEX-SZKNIZGXSA-N
InChI
InChI=1S/C21H25N.ClH/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;1H/b9-5+;
IUPAC Name
[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)[(naphthalen-1-yl)methyl]amine hydrochloride
SMILES
Cl.[H]\C(CN(C)CC1=CC=CC2=CC=CC=C12)=C(\[H])C#CC(C)(C)C
PubChem Compound
5282481
ChemSpider
4445625
ChEBI
77614
ChEMBL
CHEMBL1200832
Wikipedia
Terbinafine
Predicted Properties
PropertyValueSource
Water Solubility0.000738 mg/mLALOGPS
logP5.51ALOGPS
logP5.53Chemaxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.86Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area3.24 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity98.08 m3·mol-1Chemaxon
Polarizability35.71 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon