Efinaconazole - ≥99% , Lanosterol 14-alpha demethylase inhibitor, CAS No.164650-44-6, Lanosterol 14-alpha demethylase inhibitor

CAS: 164650-44-6 Cat. No.: E413214 Molecular Weight: 348.39 EC Number: 813-597-5

GRADE & PURITY ≥99%

Synonyms

KP103 | KP-103 | NCGC00390702-02 | HY-15660 | CCG-268012 | (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidine-1-yl)-1-(1H-1,2,4-triazole-1-yl)butane-2-ol | EFINACONAZOLE | MFCD00936406 | D01AC19 | NCGC00390702-01 | Efinaconazole [USAN:INN] | EFINACON

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Information

Efinaconazole Efinaconazole (KP-103) is an inhibitor of 14 alpha-demethylase which is involved in the biosynthesis of ergosterol, a constituent of fungal cell membranes.

Targets

14 alpha-demethylase

In vitro

In in vitro antifungal susceptibility tests, efinaconazole shows lower minimum inhibitory concentration (MIC) than terbinafine, ciclopirox, itraconazole and amorolfine.

In vivo

Efinaconazole is a topical antifungal, so it has relatively low systemic accumulation. The plasma half-life after 10 days of administration is 29.9 h. It has high plasma protein-binding affinity from 95.8 to 96.5%; primarily to albumin, a1-acid glycoprotein and γ-globulin. Efinaconazole is metabolized extensively through oxidative and reductive processes resulting in a sole H3 metabolite. It may also undergo glucuronidation. Efinaconazole does not have significant interactions with CYP450 enzymes in the liver. CYP2C8, CYP2C9, CYP2C19 and CYP3A4 are inhibited by efinaconazole at concentrations higher than the systemic concentrations achieved clinically.

Specifications

Synonyms

KP103 | KP-103 | NCGC00390702-02 | HY-15660 | CCG-268012 | (2R, 3R)-2-(2, 4-difluorophenyl)-3-(4-methylenepiperidine-1-yl)-1-(1H-1, 2, 4-triazole-1-yl)butane-2-ol | EFINACONAZOLE | MFCD00936406 | D01AC19 | NCGC00390702-01 | Efinaconazole [USAN:INN] | EFINACON

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Efinaconazole (KP-103) is an inhibitor of 14 alpha-demethylase which is involved in the biosynthesis of ergosterol, a constituent of fungal cell membranes.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

Lanosterol 14-alpha demethylase inhibitor

Purity

≥99%

Product Properties

• ALogP: 2

Names and Identifiers

• Pubchem Sid: 504758943
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758943
• Canonical Smiles: CC(C(CN1C=NC=N1)(C2=C(C=C(C=C2)F)F)O)N3CCC(=C)CC3
• IUPAC Name: (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylidenepiperidin-1-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol
• InChIKey: NFEZZTICAUWDHU-RDTXWAMCSA-N
• INCHI: 1S/C18H22F2N4O/c1-13-5-7-23(8-6-13)14(2)18(25,10-24-12-21-11-22-24)16-4-3-15(19)9-17(16)20/h3-4,9,11-12,14,25H,1,5-8,10H2,2H3/t14-,18-/m1/s1
• Isomeric SMILES: C[C@H]([C@](CN1C=NC=N1)(C2=C(C=C(C=C2)F)F)O)N3CCC(=C)CC3
• Molecular Weight: 348.39
• Reaxy-Rn: 13491930
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=13491930&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Phenethylamines

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Phenethylamines
• Intermediate Tree Nodes: Not available
• Direct Parent: Amphetamines and derivatives
• Alternative Parents: Phenylpropanes Fluorobenzenes Aralkylamines Piperidines Aryl fluorides Triazoles Tertiary alcohols Heteroaromatic compounds Trialkylamines 1,2-aminoalcohols Azacyclic compounds Organopnictogen compounds Organofluorides Hydrocarbon derivatives Aromatic alcohols
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Amphetamine or derivatives - Phenylpropane - Fluorobenzene - Halobenzene - Aralkylamine - Aryl fluoride - Aryl halide - Piperidine - Azole - Heteroaromatic compound - Tertiary alcohol - 1,2,4-triazole - Tertiary aliphatic amine - Tertiary amine - 1,2-aminoalcohol - Organoheterocyclic compound - Azacycle - Aromatic alcohol - Organofluoride - Organohalogen compound - Alcohol - Hydrocarbon derivative - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organooxygen compound - Amine - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
• External Descriptors: piperidines - organofluorine compound - tertiary alcohol - tertiary amino compound - triazole antifungal drug - conazole antifungal drug - olefinic compound

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

Discover Target: Hdac6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Nakaseomyces glabratus (9108 Activities)

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Trichophyton rubrum (3646 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solubility (25°C) In vitro DMSO: 69 mg/mL (198.05 mM); Ethanol: 69 mg/mL (198.05 mM); Water: Insoluble
• Specific Rotation[α]: [α]/D -85 to -95°, c = 1 in chloroform
• Molecular Weight: 348.400 g/mol
• XLogP3: 2.000
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 348.176 Da
• Monoisotopic Mass: 348.176 Da
• Topological Polar Surface Area: 54.200 Ų
• Heavy Atom Count: 25
• Formal Charge: 0
• Complexity: 470.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 2
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1