[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine hydrochloride

• ChemBase ID: 73056
• Molecular Formular: C21H26ClN
• Molecular Mass: 327.89084
• Monoisotopic Mass: 327.17537752
• SMILES: c1cc2c(cc1)c(ccc2)CN(C/C=C/C#CC(C)(C)C)C.Cl
• Canonical SMILES: CN(Cc1cccc2c1cccc2)C/C=C/C#CC(C)(C)C.Cl
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine hydrochloride; (6,6-dimethylhept-2-en-4-yn-1-yl)(methyl)(naphthalen-1-ylmethyl)amine hydrochloride
• IUPAC Traditional name: terbinafine hydrochloride; lamisil hydrochloride
• Synonyms: Zabel; Corbinal; Zimig; Terbinafine hydrochloride; Lamisil; Sebifin; mycoCeaze; MycoVa; trans-N-(6,6-Dimethyl-2-hepten-4-ylyl)-N-methyl-1-naphthylmethylamine hydrochloride; Terbinafine hydrochloride; (E)-N,6,6-trimethyl-N-(naphthalen-1-ylmethyl)hept-2-en-4-yn-1-amine hydrochloride; Trebinafine hydrochloride; ({[(2E)-6,6-Dimethylhept-2-en-4-yn-1-yl](methyl)amino}methyl)naphthalene hydrochloride; N-[(2E)-6,6-Dimethyl-2-hepten-4-ynyl]-N-methyl-1-naphthalenemethanamine; trans-N-Methyl-N-(1-naphthylmethyl)-6,6-dimethylhept-2-en-4-ynyl-1-amine; Bramazil; Bramizil; Muzonal; Terbina; Terbine; trans-N-(6,6-Dimethyl-2-hepten-4-ylyl)-N-methyl-1-naphthylmethylamine 盐酸盐; Terbinafine 盐酸盐

Database IDs

• CAS Number: 78628-80-5
• MDL Number: MFCD00145430
• PubChem SID: 162037976
• PubChem CID: 5282481

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.3570302
• LogD (pH = 7.4): 3.9767735
• Log P: 5.527483
• Molar Refractivity: 98.0752 cm^3
• Polarizability: 38.508842 Å^3
• Polar Surface Area: 3.24 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid
• Melting Point: 195-198°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: Irritant
• RTECS: QJ8600100
• European Hazard Symbols: Nature polluting (N); Irritant (Xi)
• UN Number: 3077
• German water hazard class: 3
• Hazard Class: 9
• Packing Group: 3
• Risk Statements: 36/37/38-50/53
• Safety Statements: 26-60-61
• GHS Pictograms: GHS07; GHS09
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335-H410
• GHS Precautionary statements: P261-P273-P305 + P351 + P338-P501
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• RID/ADR: UN 3077 9/PG 3

Product Information

• Purity: ≥98%
• Salt Data: HCl; hydrochloride
• Empirical Formula (Hill Notation): C21H25N · HCl

DETAILS

Selleck Chemicals - S2513

Research Area: Infection
Biological Activity:
Terbinafine hydrochloride (Lamisil) is a hydrochloride salt of terbinafine that is a synthetic allylamine antifungal and a squalene epoxidase inhibitor with an IC50 of 30 nM for Candida albicans. Terbinafine hydrochloride (Lamisil) is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues. Like other allylamines, terbinafine hydrochloride (Lamisil) inhibits ergosterol synthesis by inhibiting squalene epoxidase, an enzyme that is part of the fungal cell membrane synthesis pathway. Because terbinafine hydrochloride (Lamisil) prevents conversion of squalene to lanosterol, ergosterol cannot be synthesized. This is thought to change cell membrane permeability, causing fungal cell lysis. At 90-120 µM, terbinafine exhibits antitumor and antiangiogenic activity by inducing cell cycle arrest at the G0/G1 stage in COLO 205 tumor cells and human vascular endothelia cells. [1][2][3]

Selleck Chemicals - S2557

Research Area: Infection
Biological Activity:
Terbinafine hydrochloride (Lamisil) is a hydrochloride salt of terbinafine that is a synthetic allylamine antifungal and a squalene epoxidase inhibitor with an IC50 of 30 nM for Candida albicans. Terbinafine hydrochloride (Lamisil) is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues. Like other allylamines, terbinafine hydrochloride (Lamisil) inhibits ergosterol synthesis by inhibiting squalene epoxidase, an enzyme that is part of the fungal cell membrane synthesis pathway. Because terbinafine hydrochloride (Lamisil) prevents conversion of squalene to lanosterol, ergosterol cannot be synthesized. This is thought to change cell membrane permeability, causing fungal cell lysis. At 90-120 µM, terbinafine exhibits antitumor and antiangiogenic activity by inducing cell cycle arrest at the G0/G1 stage in COLO 205 tumor cells and human vascular endothelia cells. [1][2][3]

Sigma Aldrich - T8826

Biochem/physiol Actions
Mode of Action: Inhibits squalene epoxidase, preventing biosynthesis of ergosterol.Antimicrobial spectrum: Antifungal and antimycotic. Fungicidal against dermatopytes and some yeasts; fungistatic against Candida albicans.
Terbinafine inhibits squalene monooxygenase thereby blocking the biosynthesis of ergosterol, which is an essential component of fungal cell membranes. The inhibition of squalene monooxygenase also results in the accumulation of squalene. Terbinafine hydrochloride is highly lipophilic and tends to accumulate in skin, nails, and fatty tissues1. It is antifungal and antimycotic. It is fungicidal against dermatopytes and some yeasts and is fungistatic against Candida albicans.
General description
Allylamine derivative.
Application
Terbinafine hydrochloride is a synthetic allylamine antifungal. It is used to treat dermatophyte infections of the toenail/fingernail, ringworm and jock itch1. It is used in adsorption, partition and stability studies2,3.

Toronto Research Chemicals - T107500

An orally active, antimycotic allylamine related to Naftifine. A specfic inhibitor of squalene epoxidase, a key enzyme in fungal ergosterol biosynthesis. Antifungal.

REFERENCES

• Lee WS et al. Int J Cancer. 2003 Aug 10;106(1)
• Ho PY et al. Int J Cancer. 2004 Aug 10; 111(1):51-9.
• Petranyi, G., et al.: Science, 224, 1239 (1984)
• Ryder, N.S., et al.: Antimicrob. Agents Chemother., 27, 252 (1984)
• Evans, E.G.V., et al.: Br. Med. J., 318, 1031 (1984)