Terbinafine hydrochloride

Base Information

• Chemical Name: Terbinafine hydrochloride
• CAS No.: 78628-80-5
• Molecular Formula: C21H26ClN
• Molecular Weight: 327.897
• Hs Code.: 29214990
• European Community (EC) Number: 616-640-4,691-642-6
• NSC Number: 759113
• UNII: 012C11ZU6G
• DSSTox Substance ID: DTXSID90229223
• Wikidata: Q27147212
• NCI Thesaurus Code: C29492
• RXCUI: 235838
• ChEMBL ID: CHEMBL1200832
• Mol file: 78628-80-5.mol

Synonyms:(E)-N-(6,6-dimethyl-2-heptenynyl)-N-methyl-1-naphthalenementhamin hydrochloride;DA 5505;Lamisil;SF 86 327;SF 86-327;SF 86327;SF-86-327;SF86327;TDT 067;TDT-067;TDT067;terbinafine;terbinafine hydrochloride;Terbinafine, (Z)-;terbinafine, (Z)-isomer

Chemical Property of Terbinafine hydrochloride

Chemical Property:

• Appearance/Colour: Crystalline powder
• Vapor Pressure: 3.42E-07mmHg at 25°C
• Melting Point: 204-208 °C
• Refractive Index: 1.586
• Boiling Point: 417.9 °C at 760 mmHg
• Flash Point: 183.7 °C
• PSA: 3.24000
• Density: 1.007g/cm3
• LogP: 5.67930
• Storage Temp.: -20°C Freezer
• Solubility.: methanol: soluble50mg/mL
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 327.1753775
• Heavy Atom Count: 23
• Complexity: 428

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

Terbinafine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi, N
• Hazard Codes: Xi,N
• Statements: 36/37/38-50/53
• Safety Statements: 26-36/37/39-61-60

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)C#CC=CCN(C)CC1=CC=CC2=CC=CC=C21.Cl
• Isomeric SMILES: CC(C)(C)C#C/C=C/CN(C)CC1=CC=CC2=CC=CC=C21.Cl
• Recent ClinicalTrials: SINGLE-APPLICATION TERBINAFINE HYDROCHLORIDE (1%) TOPICAL LIQUID SOLUTION VERSUS A SINGLE-APPLICATION BUTENAFINE HYDROCHLORIDE (1%) TOPICAL LIQUID SOLUTION FOR THE TREATMENT OF TINEA PEDIS
• Recent EU Clinical Trials: A multi-center, single-arm, open-label study to evaluate tolerability, safety, and efficacy of topical MOB015B solution in the treatment of mild to moderate distal subungual onychomycosis (DSO) in subjects aged 6-17 years
• Chemical Properties: Terbinafine hydrochloride is a synthetic antifungal drug. It is slightly soluble in water (3mg/ml) and highly permeable through the stomach. The λmax (maximum absorbance) of terbinafine hydrochloride in water is 283 nm.
• Mechanism of Action: Terbinafine hydrochloride irreversibly inhibits the enzyme squalene epoxidase in fungal ergosterol biosynthesis. This inhibition leads to intracellular squalene accumulation, compromising fungal cell wall integrity.
• Transdermal Properties: Terbinafine hydrochloride has poor skin penetration and high retention.
• Commercial Forms and Market Approval: Marketed in solid-state forms such as tablets, capsules, and oral granules. FDA approved terbinafine hydrochloride for the treatment of superficial skin and nail fungal infections on December 30, 1992. It is also approved for onychomycosis, a fungal infection of the nails.
• Difference between Terbinafine and Terbinafine Hydrochloride: Terbinafine is the active ingredient, while terbinafine hydrochloride is the salt form of terbinafine. Terbinafine hydrochloride is highly lipophilic and tends to accumulate in skin, nails, and fatty tissues.

Technology Process of Terbinafine hydrochloride

There total 16 articles about Terbinafine hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

N-methyl-1-naphthalenemethylamine (14489-75-9) + 1-chloro-6,6-dimethyl-hept-2-ene-4-yn (287471-30-1) → terbinafine hydrochloride (78628-80-5,176168-78-8)

Guidance literature:

N-methyl-1-naphthalenemethylamine; 1-chloro-6,6-dimethyl-hept-2-ene-4-yn; With potassium carbonate; In water; at 80 ℃; for 4h; Large scale;

With hydrogenchloride; In water; at 0 - 10 ℃; Large scale;

Reference yield: 89.0%

→ terbinafine hydrochloride (78628-80-5,176168-78-8)

Guidance literature:

Reference yield: 82.6%

N-(3-chloroallyl)-1-methyl-1-naphthylmethylamine (387383-30-4) + 3,3-Dimethylbut-1-yne (917-92-0) → terbinafine hydrochloride (78628-80-5,176168-78-8)

Guidance literature:

N-(3-chloroallyl)-1-methyl-1-naphthylmethylamine; 3,3-Dimethylbut-1-yne; With copper(l) iodide; N-butylamine; triphenylphosphine; palladium dichloride; at 60 - 65 ℃; for 20h;

With hydrogenchloride; In water; at 85 - 90 ℃; for 0.5h; Temperature;

upstream raw materials:

terbinafin

N-methyl-1-naphthalenemethylamine hydrochloride

(Z)-1-chloro-6,6-dimethylhept-2-en-4-yne

1-chloro-6,6-dimethyl-hept-2-ene-4-yn

Downstream raw materials:

terbinafin

(Z)-N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethanamine

Refernces

• 1、 -. "Preparation method for improving purity of terbinafine hydrochloride". Paragraph 0023-0037. . Retrieved 2019/11/21.
• 2、 -. "PROCESS FOR PREPARING TERBINAFINE". Page/Page column 17; 18. . Retrieved 2010/11/27.