Basic information
- CAS
78628-80-5- Standard SMILES
CN(C/C=C/C#CC(C)(C)C)Cc1cccc2ccccc12.Cl- InChIKey
BWMISRWJRUSYEX-SZKNIZGXSA-N- Molecular formula
- C21H26ClN
- Average molar mass
- 327.9 g/mol
- Monoisotopic mass
- 327.1753775
Names & identifiers
- Preferred name
- Terbinafine Hydrochloride
- IUPAC
- (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine;hydrochloride
- English name
- Terbinafine Hydrochloride
- Molecular formula
- C21H26ClN
- Molecular weight
- 327.89
Names & synonyms
Terbinafine hydrochloride78628-80-5Terbinafine HClLamisil ATBramazilBramizilMuzonalTerbinaTerbineNSC-759113Terbinafine (as hydrochloride)012C11ZU6G
Show more names
LAMISILlamosilDacronin hydrochlorideTerbisilmethylamin hclAfoganD02219Brican
(E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine hydrochlorideCHEBI:77614DTXSID90229223(2E)-N,6,6-TRIMETHYL-N-(NAPHTHALEN-1-YLMETHYL)HEPT-2-EN-4-YN-1-AMINE HYDROCHLORIDEShopriteCuristSilkaLamisil once
Database identifiers
- CAS
78628-80-5- PubChem CID
- 5282481
- DTXSID
DTXSID90229223- ChEMBL
CHEMBL1200832- ChEBI
CHEBI:77614- UNII
- 012C11ZU6G
- EC Number
- 616-640-4、691-642-6
Properties
Computed structural properties
- Topological polar surface area
- 3.2 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 5
- Heavy atoms
- 23
- Formal charge
- 0
- Complexity
- 428
Experimental & physicochemical properties
Collision Cross Section185.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 204 · 204-208°C
- storage temp.
- 15 · 15-25°C
- solubility
- 50 mg/mL · methanol: soluble50mg/mL
- form
- powder
- color
- white
- Merck
- 14 · 14,9156
- BCS Class
- 1 · 1
- Major Application
- pharmaceuticalpharmaceutical small molecule
- 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+;
- InChIKey
- BWMISRWJRUSYEX-SZKNIZGXSA-N
- SMILES
- C12C=CC=CC1=CC=CC=2CN(C)C/C=C/C#CC(C)(C)C.Cl
- CAS DataBase Reference
- 78628 · 78628-80-5(CAS DataBase Reference)
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 0.6% (1 of 179) of reports.
Warning
H315 (46.4%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (46.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H335 (46.4%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]；H400 (87.2%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410 (95.5%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]
P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 179 reports by companies from 22 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 179 reports by companies.；There are 21 notifications provided by 178 of 179 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
Hazard information
Regulatory Information
Status: Active Update: 13-08-2014 https://echa.europa.eu/registration-dossier/-/registered-dossier/12149
Terbinafine hydrochloride: Does not have an individual approval but may be used under an appropriate group standard
Hazard Classes and CategoriesSkin Irrit. 2 (46.4%)；Eye Irrit. 2 (46.4%)；STOT SE 3 (46.4%)；Aquatic Acute 1 (87.2%)；Aquatic Chronic 1 (95.5%)
Toxicology
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
TERBINAFINE HYDROCHLORIDE
Allylamine [CS]; Allylamine Antifungal [EPC]
TERBINAFINE TABLETS 250 MG
Allylamine Antifungal [EPC]; Allylamine [CS]
MeSH Pharmacological Classification
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Applications
DescriptionTerbinafine hydrochloride is the first orally active allylamine antifungal with 30-fold greater antifungal activity than naftifine. The compound is indicated for the treatment of ringworm and fungal nail infections. Terbinatine hydrochloride acts on a single fungal enzyme, squalene epoxidase, interfering with the biosynthesis of ergosterols in cell membranes. Unlike other antifungal agents, it does not inhibit cytochrome P450 enzymes.
UsesAn orally active, antimycotic allylamine related to Naftifine. A specfic inhibitor of squalene epoxidase, a key enzyme in fungal ergosterol biosynthesis. Antifungal.
UsesTerbinafine hydrochloride may be used as a pharmaceutical reference standard for the determination of the analyte in drug dosage forms by UV spectrophotometry and high-performance thin layer chromatography (HPTLC).
General DescriptionTerbinafine Hydrochloride is a synthetic allylamine derivative structurally related to naftifine, antifungal Terbinafine Hydrochloride blocks ergosterol biosynthesis by inhibition of squalene epoxidase, part of the sterol synthesis pathway for the fungal cell membrane.
Upstream & downstream products
Upstream raw materials
Related reactions
16 records
Compound notes
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