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HomeProduct name listKP 103

KP 103

Synonym(s):(αR,βR)-, α-(2,4-Difluorophenyl)-β-methyl-4-methylene-α-(1H-1,2,4-triazol-1-ylmethyl)-1-piperidineethanol;(2R,3R)-2-(2,4-Difluorophenyl)-3-(4-methylenepiperidin-1-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;KP-103

  • CAS NO.:164650-44-6
  • Empirical Formula: C18H22F2N4O
  • Molecular Weight: 348.39
  • MDL number: MFCD00936406
  • EINECS: 813-597-5
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-10-31 18:15:48
KP 103 Structural

What is KP 103?

Description

In October 2013, efinaconazole (also known as KP-103) was approved in Canada as a 10% topical solution for the treatment of onychomycosis. Like other azole antifungal agents, efinaconazole acts by disrupting fungal cell membranes through inhibition of sterol 14α-demethylase, an enzyme involved in the biosynthesis of ergosterol, which is a key component of the fungal cell membrane. Efinaconazole has potent antifungal activity against clinical isolates of dermatophytes, including Trichophyton mentagrophyes (MIC80 =0.125 μg/mL) and Trichophyton rubrum (MIC80 =0.25 μg/mL), as well as against Candida and Malassezia species. Unlike other antifungal agents, efinaconazole retains activity in the presence of keratin, indicating that more unbound drug is available at the site of action. Efinaconazole is efficacious in guinea-pig models of fungal infection. Efinaconazole is prepared by reaction of an epoxide intermediate with 4-methylenepiperidine.

Description

Efinaconazole is a broad-spectrum triazole antifungal agent with activity against Acremonium, Aspergillus, Candida, Cryptococcus, Epidermophyton, Fusarium, Microsporum, Paecilomyces, Pseudallescheria, Scopulariopsis, Trichophyton, and Trichosporon. It inhibits the growth of T. rubrum and T. mentagrophytes clinical isolates with MIC values ranging from ≤2.0 to 60 ng/ml and of C. albicans isolates with MIC values ranging from ≤0.5 to >250 ng/ml. Efinaconazole inhibits sterol 14α-demethylase, which arrests ergosterol biosynthesis at the fungal membrane. It inhibits ergosterol biosynthesis in T. mentagrophytes and C. albicans with IC50 values of 7.0 and 0.40 ng/ml, respectfully. Topical formulations containing efinaconazole have been used for the treatment of onychomycosis.

Originator

Kaken Pharmaceuticals (Japan)

The Uses of KP 103

Efinaconazole has been used as:

  • a topical anti-onychomycosis drug to determine its effects on Trichophyton rubrum and Trichophyton interdigitale
  • as an anti-fungal agent to study its permeability into the nail lysates
  • as an anti-fungal agent to study its effects on Candida africana and Candida dubliniensis

Indications

Indicated in the treatment of fungal infection of the nail, known as onychomycosis.

Background

Efinaconazole is a 14 alpha-demethylase inhibitor indicated in the treatment of fungal infection of the nail, known as onychomycosis. It was approved for use in Canada and the USA in 2014 and is marketed by Valeant Pharmaceuticals North America LLC under the name Jublia.

Definition

ChEBI: A member of the class of triazoles that is butan-2-ol which is substituted at positions 1, 2, and 3 by 1,2,4-triazol-1-yl, 2,4-difluorophenyl, and 4-methylenepiperidin-1-yl groups, respectively (the 2R,3R stereoisomer). It is an antifungal drug used for the topical treatment of onychomycosis (a nail infection caused mainly by dermatophytes).

brand name

Jublia

Biochem/physiol Actions

Efinaconazole is a triazole antifungal drug approved clinically for the treatment of nail fungus (Onychomycosis). It inhibits sterol biosynthesis by inhibition of cytochrome P450 14α-demethylase, an enzyme in the sterol biosynthesis pathway that leads from lanosterol to ergosterol. Efinaconazole has better nail penetration, so is more effective than other topical agents and as effective as oral medication for nail fungus.

Pharmacokinetics

mean ± SD plasma Cmax on Day 28 of treatment: 0.67 ± 0.37 ng/mL. mean ± SD AUC was 12.15 ± 6.91 ng*h/mL.

Synthesis

Commercially available (R)-methyl lactate (55) was first converted to THP protected alcohol 57 in 4 steps and 78% yield via morpholino amide 56. Grignard displacement of the morpholine afforded ketone 58 in 81% yield. Next, ketone 58 was epoxidized by means of the Corey ylide followed by ring-opening of the epoxide by triazole which had been activated by exposure to sodium tbutoxide. Finally, subjection to methanesulfonic acid furnished diol 59 in 51% yield as the corresponding mesylate salt. Diol 59 was then converted to epoxide 60 through the use of mesyl chloride and triethylamine in 78% yield and >99% ee. Finally, treatment of epoxide 60 with 4-methylene piperidine¨CHBr in the presence of lithium hydroxide afforded efinaconazole (VIII) in 87% yield.

Synthesis_164650-44-6

Metabolism

Not Available

Properties of KP 103

Melting point: 192-195°C
Boiling point: 512.2±60.0 °C(Predicted)
Density  1.26±0.1 g/cm3(Predicted)
storage temp.  -20°C
solubility  Chloroform (Slightly), Methanol (Slightly)
form  powder
pka 12.11±0.29(Predicted)
color  white to beige
optical activity [α]/D -85 to -95°, c = 1 in chloroform

Safety information for KP 103

Signal word Warning
Pictogram(s)
ghs
Health Hazard
GHS08
GHS Hazard Statements H361:Reproductive toxicity
Precautionary Statement Codes P201:Obtain special instructions before use.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for KP 103

Abamectin manufacturer

Metrochem API Private Limited

1Y
Phone:+91-4069069999
product: Efinaconazole 98%
Inquiry

Lupin Ltd

1Y
Phone:+91-8019896181
Whatsapp: +91 8019896181
product: Efinaconazole 99%
Inquiry

Glenmark Pharmaceuticals Limited

1Y
Phone:+912240189999
product: Efinaconazole 164650-44-6 98%
Inquiry

Hetero Drugs Limited

1Y
Phone:+91-4023704923
product: 164650-44-6 Efinaconazole 98%
Inquiry

Honour Lab Limited

1Y
Phone:+919845977466
Whatsapp: +91-9845977466
product: 164650-44-6 98%
Inquiry

Virupaksha Organics Pvt Ltd

1Y
Phone:+91-9848648601
Whatsapp: +91-9848648601
product: Efinaconazole 98%
Inquiry

Solara Active Pharma Sciences Ltd

1Y
Phone:+91-7075706520
Whatsapp: +91 7075706520
product: Efinaconazole 164650-44-6 98%
Inquiry

BDR Pharmaceuticals International Pvt Ltd

1Y
Phone:+917718884418
Whatsapp: +91-7718884418
product: 164650-44-6 Efinaconazole 98%
Inquiry

Turtle Pharma Private Limited

1Y
Phone:+91-9850998504
Whatsapp: +91-9850998504
product: Efinaconazole 164650-44-6 98%
Inquiry

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