91161-71-6 Usage
Originator
Lamisil,Novartis,UK
Uses
Terbinafine (Lamisil) is a second-generation allylamine that is related to naftifine; however, it is 10 to 100 times more potent in vitro. It is fungicidal, whereas griseofulvin, ketoconazole, itraconazole, and other azole derivatives are all fungistatic. Because it is fungicidal, duration of therapy is shorter, and relapse rates are less than with other oral or topical therapies. Terbinafine acts by inhibiting squalene epoxidase and thereby decreasing synthesis of ergosterol, an essential component of fungal cell membranes. It is highly lipophilic and concentrates in the stratum corneum, sebum, and hair follicles. Slightly better cure rates are attained with b.i.d. than with daily dosing.
Definition
ChEBI: A tertiary amine that is N-methyl-1-naphthalenemethylamine in which the amino hydrogen is replaced by a 3-(tertbutylethynyl)allyl group. An antifungal agent administered orally (generally as the hydrochloride salt) for the t
eatment of skin and nail infections.
Indications
Terbinafine (Lamisil) is a second-generation allylamine that is related to
naftifine; however, it is 10 to 100 times more potent in vitro. It is fungicidal,
whereas griseofulvin, ketoconazole, itraconazole, and other azole derivatives
are all fungistatic. Because it is fungicidal, duration of therapy is shorter, and
relapse rates are less than with other oral or topical therapies.
Terbinafine acts by inhibiting squalene epoxidase and thereby decreasing
synthesis of ergosterol, an essential component of fungal cell membranes.
It is highly lipophilic and concentrates in the stratum corneum, sebum, and
hair follicles. Slightly better cure rates are attained with b.i.d. than with daily
dosing.
Therapeutic Function
Antifungal
Synthesis Reference(s)
Tetrahedron Letters, 29, p. 1509, 1988 DOI: 10.1016/S0040-4039(00)80338-X
Antimicrobial activity
Terbinafine is active against a wide range of pathogenic fungi,
including dermatophytes (Epidermophyton, Microsporum and
Trichophyton spp.), various Candida spp., Aspergillus spp.,
some dimorphic fungi (Blastomyces dermatitidis, Histoplasma
capsulatum and Sporothrix schenckii) and many dematiaceous
fungi.
Acquired resistance
Resistance has not been reported.
Pharmaceutical Applications
A synthetic allylamine available as the hydrochloride for oral
and topical administration.
Pharmacokinetics
Oral absorption: 70–80%
Cmax 250 mg oral: c. 1 mg/L after 2 h
Plasma half-life: c. 17 h
Volume of distribution: 1000 L
Plasma protein binding: >99%
Blood concentrations increase in proportion to dosage. It is
lipophilic and is rapidly and extensively distributed to body
tissues. It reaches the stratum corneum by diffusion through
the dermis and epidermis, and secretion in sebum. Diffusion
from the nail bed is the major factor in its rapid penetration
of nails. It is metabolized by the liver and the inactive metabolites
are mostly excreted in the urine. The elimination half-life
is prolonged in patients with hepatic or renal impairment.
Clinical Use
Terbinafine hydrochloride can be used in Tinea pedis, tinea corporis, tinea cruris, tinea capitis, Onychomycosis caused by dermatophytes.
Side effects
These include abdominal discomfort, loss of appetite,
nausea, diarrhea, headache, impairment of taste, rash
and urticaria. Serious skin reactions, including Stevens–
Johnson syndrome, and rare hepatotoxic reactions, including
jaundice, cholestasis and hepatitis, are occasionally
encountered.
Drug interactions
Potentially hazardous interactions with other drugs
Antibacterials: concentration reduced by rifampicin.
Metabolism
Terbinafine undergoes extensive first pass loss. It is
hepatically metabolised to two major inactive metabolites,
80% of which are renally excreted.
Check Digit Verification of cas no
The CAS Registry Mumber 91161-71-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,1,1,6 and 1 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 91161-71:
(7*9)+(6*1)+(5*1)+(4*6)+(3*1)+(2*7)+(1*1)=116
116 % 10 = 6
So 91161-71-6 is a valid CAS Registry Number.
InChI:InChI=1/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+
91161-71-6Relevant articles and documents
Amine compound as well as preparation method and application thereof
-
, (2021/08/21)
The invention discloses an amine compound containing allyl or benzyl as well as a preparation method and application of the amine compound. The preparation method comprises the steps of sequentially adding a raw material 1, amine, a catalyst and an additive into a reaction solvent, and stirring and reacting for 12-24 hours in an air atmosphere at the temperature of 50-120 DEG C to obtain a reaction solution, wherein the raw material 1 is allyl alcohol or benzyl alcohol, and the molar volume ratio of the raw material 1 to the amine to the catalyst to the additive to the reaction solvent is (0.2 to 8) mmol: (0.4 to 12) mmol: (0.01 to 0.4) mmol: (0.01 to 0.4) mmol: (2 to 40) mL; and removing the reaction solvent of the reaction solution, and then carrying out purification through thin layer chromatography/column chromatography, wherein a developing solvent system is petroleum ether/ethyl acetate, and the amine compound containing allyl or benzyl is obtained. The amine compound can be applied to preparation of framework of biological and pharmaceutical active molecules. The preparation method disclosed by the invention is wide in applicable substrate range, convenient to operate, green and environment-friendly.
Removal of heavy metals from organic reaction mixtures: Preparation and application of functionalized resins
Barbaras, Damien,Brozio, Joerg,Johannsen, Ib,Allmendinger, Thomas
scheme or table, p. 1068 - 1079 (2010/04/22)
Using a toolbox, sulfur and amine ligands are attached to a variety of hydrophobic and hydrophilic resins, and the combinations were tested for the removal of heavy metals from a number of products, prepared by metal-catalyzed reactions. As a result, cheap combinations of silica resins and simple polyamines proved to be among the most effective metal scavengers particularly in apolar solvents such as cyclohexane. Expensive cyclic polyamines are not suitable, owing to kinetic retardation of complexation. Functionalized PEGbased polymers, originally designed for solid phase synthesis, show promising performance as metal scavengers. The results are discussed and compared to alternative approaches for purification such as salt-formation and chemical downstream transformation.
IMPROVED PROCESS FOR THE PREPARATION OF TERBINAFINE HYDROCHLORIDE AND NOVEL CRYSTALLINE FORM OF TERBINAFINE
-
Page/Page column 22-23, (2010/11/28)
Improved process for the preparation of Terbinafme Hydrochloride compound of formula (I): substantially free of Genotoxic impurity compound of formula (II) and Novel crystalline form of Terbinafine.
