Terbinafine

Terbinafine structural formula

UV- Vis Spectrum of Terbinafine λ max 220, 283 nm

 

CAS Number91161-71-6
Molecular FormulaC21H25N
Molecular Weight291.438
InChI KeyDOMXUEMWDBAQBQ-WEVVVXLNSA-N
LogP6.00
Synonyms
  • Terbinafine
  • (2E)-N,6,6-Trimethyl-N-[(naphthalen-1-yl)methyl]hept-2-en-4-yn-1-amine
  • 1-Naphthalenemethanamine, N-[(2E)-6,6-dimethyl-2-hepten-4-yn-1-yl]-N-methyl-
  • 91161-71-6
  • 1-Naphthalenemethanamine, N-[(2E)-6,6-dimethyl-2-hepten-4-ynyl]-N-methyl-
  • 1-Naphthalenemethanamine, N-(6,6-dimethyl-2-hepten-4-ynyl)-N-methyl-, (E)-
  • 1-Naphthalenemethanamine, N-[(2E)-6,6-dimethyl-2-hepten-4-yn-1-yl]-N-methyl-
  • Eksifine
  • Fungoterbin
  • Lamasil
  • Mycoterbin
  • BRN 4256376
  • (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamine
  • Lamisil Tablet
  • UNII-G7RIW8S0XP
  • (E)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine

Applications:

HPLC Method for Separation of a Mixture of Antifungal Agents on Primesep B Column

September 20, 2023

HPLC Method for Analysis of Antifungal Agents on Primesep B by SIELC Technologies

HPLC Method for Separation of a Mixture of Antifungal Agents on Primesep B Column
HPLC Method for Separation of a Mixture of Antifungal Agents on Newcrom R1 Column


Separation and Analysis of Antifungal Agents on a Primesep B Column Using Gradient HPLC Method

Antifungal agents are drugs used to treat fungal infections. Depending on their mechanism of action and chemical structure, antifungal agents can be categorized into several classes. Here are some of the main classes and examples of antifungal agents:

  1. Fluconazole: A triazole antifungal mainly used for the treatment and prevention of superficial and systemic fungal infections.
  2. Ketoconazole: An imidazole antifungal used to treat a wide variety of fungal infections, though its oral use has become less common due to potential side effects. It’s still frequently used topically.
  3. Climbazole: An imidazole antifungal primarily used in hair care products to treat dandruff.
  4. Clotrimazole: An imidazole antifungal used to treat various fungal infections including vaginal yeast infections, oral thrush, and ringworm.
  5. Itraconazole: A triazole antifungal used primarily to treat a variety of systemic fungal infections.
  6. Terbinafine: This compound belongs to the allylamine class. It’s mainly used to treat fungal infections of the nails and skin, like athlete’s foot and ringworm.
  7. Econazole: An imidazole antifungal used mainly for skin infections such as athlete’s foot and ringworm.
  8. Miconazole: An imidazole antifungal with a broad spectrum of activity. It’s used for a variety of skin infections and also as a vaginal cream for yeast infections.
  9. Triclosan: This is a broad-spectrum antimicrobial agent. While it has some antifungal activity, it’s more commonly known for its antibacterial properties. Due to concerns regarding its safety and potential contribution to antibiotic resistance, its use in hand soaps and some other personal care products has been phased out in several regions.

Of these, fluconazole, itraconazole, ketoconazole, climbazole, clotrimazole, econazole, and miconazole belong to the azole class, which primarily acts by inhibiting the fungal enzyme lanosterol 14α-demethylase. This enzyme is crucial for ergosterol synthesis, a vital component of fungal cell membranes. Terbinafine, on the other hand, inhibits squalene epoxidase, another enzyme important in ergosterol synthesis. Triclosan works through a different mechanism, targeting bacterial and fungal fatty acid synthesis.

Antifungal Agents can be separated, retained, and analyzed on a Primesep B mix mode phase column using an gradient analytical method with a simple mobile phase of water, Acetonitrile (MeCN), and sulfuric acid as a buffer. This analysis method can be detected in the UV 200 nm.

ColumnPrimesep B, 4.6 x 150 mm, 5 µm, 100 A
Mobile PhaseGradient MeCN – 10-60%, 20 min
BufferH2SO4 – 0.2%
Flow Rate1.0 ml/min
DetectionUV, 200 nm
Class of Compounds
Antifungal Agents
Analyzing CompoundsFluconazole, Ketoconazole, Climbazole, Clotrimazole, Itraconazole, Terbinafine, Econazole, Miconazole

Application Column

Primesep B

Column Diameter: 4.6 mm
Column Length: 150 mm
Particle Size: 5 µm
Pore Size: 100 A

Add to cart
Application Analytes:
Climbazole
Clotrimazole
Econazole
Fluconazole
Itraconazole
Ketoconazole
Miconazole
Terbinafine

Application Detection:
UV Detection
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

HPLC Method for Separation of a Mixture of Antifungal Agents on Newcrom R1 Column

September 20, 2023

HPLC Method for Analysis of Antifungal Agents on Newcrom R1 by SIELC Technologies

HPLC Method for Separation of a Mixture of Antifungal Agents on Newcrom R1 Column
HPLC Method for Separation of a Mixture of Antifungal Agents on Newcrom R1 Column


Separation and Analysis of Antifungal Agents on a Newcrom R1 Reverse Phase Column Using Gradient HPLC Method

Antifungal agents are drugs used to treat fungal infections. Depending on their mechanism of action and chemical structure, antifungal agents can be categorized into several classes. Here are some of the main classes and examples of antifungal agents:

  1. Fluconazole: A triazole antifungal mainly used for the treatment and prevention of superficial and systemic fungal infections.
  2. Ketoconazole: An imidazole antifungal used to treat a wide variety of fungal infections, though its oral use has become less common due to potential side effects. It’s still frequently used topically.
  3. Climbazole: An imidazole antifungal primarily used in hair care products to treat dandruff.
  4. Clotrimazole: An imidazole antifungal used to treat various fungal infections including vaginal yeast infections, oral thrush, and ringworm.
  5. Itraconazole: A triazole antifungal used primarily to treat a variety of systemic fungal infections.
  6. Terbinafine: This compound belongs to the allylamine class. It’s mainly used to treat fungal infections of the nails and skin, like athlete’s foot and ringworm.
  7. Econazole: An imidazole antifungal used mainly for skin infections such as athlete’s foot and ringworm.
  8. Miconazole: An imidazole antifungal with a broad spectrum of activity. It’s used for a variety of skin infections and also as a vaginal cream for yeast infections.
  9. Triclosan: This is a broad-spectrum antimicrobial agent. While it has some antifungal activity, it’s more commonly known for its antibacterial properties. Due to concerns regarding its safety and potential contribution to antibiotic resistance, its use in hand soaps and some other personal care products has been phased out in several regions.

Of these, fluconazole, itraconazole, ketoconazole, climbazole, clotrimazole, econazole, and miconazole belong to the azole class, which primarily acts by inhibiting the fungal enzyme lanosterol 14α-demethylase. This enzyme is crucial for ergosterol synthesis, a vital component of fungal cell membranes. Terbinafine, on the other hand, inhibits squalene epoxidase, another enzyme important in ergosterol synthesis. Triclosan works through a different mechanism, targeting bacterial and fungal fatty acid synthesis.

Antifungal agents can be separated, retained, and analyzed on a Newcrom R1 reverse phase column using an gradient analytical method with a simple mobile phase of water, Acetonitrile (MeCN), and sulfuric acid as a buffer. This analysis method can be detected in the UV 200 nm.

ColumnNewcrom R1, 4.6 x 150 mm, 5 µm, 100 A
Mobile PhaseGradient MeCN – 40-90%, 10 min, hold 2 min
BufferH2SO4 – 0.2%
Flow Rate1.0 ml/min
DetectionUV, 200 nm
Class of Compounds
Antifungal Agents
Analyzing CompoundsFluconazole, Ketoconazole, Climbazole, Clotrimazole, Itraconazole, Terbinafine, Econazole, Miconazole, Triclosan

Application Column

Newcrom R1

Column Diameter: 4.6 mm
Column Length: 150 mm
Particle Size: 5 µm
Pore Size: 100 A

Add to cart
Application Analytes:
Climbazole
Clotrimazole
Econazole
Fluconazole
Itraconazole
Ketoconazole
Miconazole
Terbinafine
Triclosan

Application Detection:
UV Detection
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

HPLC – MS Method for Analysis of Terbinafine on Primesep B Column

September 13, 2023

HPLC Method for Analysis of Terbinafine on Primesep B by SIELC Technologies

HPLC - MS Method for Analysis of Terbinafine on Primesep B Column  by SIELC Technologies


 High Performance Liquid Chromatography (HPLC) Method for Analysis of  Terbinafine

Terbinafine is an antifungal medication commonly used to treat fungal infections, particularly those caused by dermatophytes. Here are some key points about terbinafine:

Mechanism of Action: Terbinafine is classified as an allylamine antifungal. It works by inhibiting the enzyme squalene epoxidase, which is important in the fungal ergosterol synthesis pathway. This disruption results in a deficiency of ergosterol in the fungal cell membrane and an accumulation of squalene, which is toxic to the fungus.

Terbinafine can be retained, and analyzed on a Primesep B mixed-mode stationary phase column using an isocratic analytical method with a simple mobile phase of water, Acetonitrile (MeCN), and a ammonium format as a buffer. This analysis method can be detected using UV at 283 nm, an Evaporative Light Scattering Detector (ELSD), or any other evaporative detection method (CAD, ESI-MS)

ColumnPrimesep B, 2.1 x 100 mm, 5 µm, 100 A
Mobile PhaseGradient MeCN – 20-50%, 8 min
BufferAmmonium Formate pH 3.0-20 mM
Flow Rate0.2 ml/min
DetectionUV, 282 nm, SIM 292+
Class of Compounds
Allylamines
Analyzing CompoundsTerbinafine

Application Column

Primesep B

Column Diameter: 2.1 mm
Column Length: 100 mm
Particle Size: 5 µm
Pore Size: 100 A

Add to cart
Application Analytes:
Terbinafine

Application Detection:
UV Detection
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

HPLC Method for Analysis of Terbinafine on Primesep B Column

September 1, 2023

HPLC Method for Analysis of Terbinafine on Primesep B by SIELC Technologies

HPLC Method for Analysis of Terbinafine on Primesep B Column by SIELC Technologies


 High Performance Liquid Chromatography (HPLC) Method for Analysis of  Terbinafine

Terbinafine is an antifungal medication primarily used to treat fungal infections of the skin and nails. It belongs to the allylamine class of antifungals.

Terbinafine is classified as an allylamine antifungal agent.

The allylamines are a class of antifungal drugs that inhibit the enzyme squalene epoxidase, which is an essential component of fungal cell membrane synthesis. By inhibiting this enzyme, terbinafine prevents the fungi from synthesizing ergosterol, a vital component of their cell membranes. This leads to an accumulation of squalene and results in fungal cell death.

Terbinafine is commonly prescribed for the treatment of fungal infections of the skin, hair, and nails, such as tinea pedis (athlete’s foot), tinea cruris (jock itch), tinea corporis (ringworm), and onychomycosis (fungal infection of the nails).

Here are some key aspects and indications for terbinafine:

  1. Mechanism of Action: Terbinafine works by inhibiting squalene epoxidase, an enzyme crucial to the biosynthesis of ergosterol in fungi. Ergosterol is an essential component of the fungal cell membrane. By interfering with its production, terbinafine disrupts the cell membrane’s integrity, leading to fungal cell death.

Terbinafin can be retained, and analyzed on a Primesep B mixed-mode stationary phase column using an isocratic analytical method with a simple mobile phase of water, Acetonitrile (MeCN), and a ammonium format a buffer. This analysis method can be detected in the UV 270 nm.

ColumnPrimesep B, 2.1 x 100 mm, 5 µm, 100 A
Mobile PhaseGradient MeCN – 20-50%, 10 min
BufferAmmonium Formate pH 4.0-20 mM
Flow Rate0.2 ml/min
DetectionUV, 282 nm
Sample concentration0.5 mg/ml
Injection volume1 µl
LOD 8 ppb
Class of Compounds
Allylamines
Analyzing CompoundsTerbinafine

Application Column

Primesep B

Column Diameter: 2.1 mm
Column Length: 100 mm
Particle Size: 5 µm
Pore Size: 100 A

Add to cart
Application Analytes:
Terbinafine

Application Detection:
UV Detection
SIELC Technologies usually develops more than one method for each compound. Therefore, this particular method may not be the best available method from our portfolio for your specific application. Before you decide to implement this method in your research, please send us an email to research@sielc.com so we can ensure you get optimal results for your compound/s of interest.

Separation of Terbinafine on Newcrom R1 HPLC column

February 16, 2018
Separation of Terbinafine on Newcrom C18 HPLC column

Terbinafine can be analyzed by this reverse phase (RP) HPLC method with simple conditions. The mobile phase contains an acetonitrile (MeCN), water, and phosphoric acid. For Mass-Spec (MS) compatible applications the phosphoric acid needs to be replaced with formic acid. Smaller 3 µm particles columns available for fast UPLC applications. This liquid chromatography method is scalable and can be used for isolation impurities in preparative separation. It also suitable for pharmacokinetics.

Application Column

Newcrom R1

The Newcrom columns are a family of reverse-phase-based columns. Newcrom A, AH, B, and BH are all mixed-mode columns with either positive or negative ion-pairing groups attached to either short (25 Å) or long (100 Å) ligand chains. Newcrom R1 is a special reverse-phase column with low silanol activity.

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Application Analytes:
Terbinafine
The result was obtained by a proprietary SIELC algorithm. It may deviate from the actual experimental data. The experimental data are available upon request. Contact us by e-mail: support@sielc.com or by phone: 847-229-2629.