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K1003

Ketoconazole

Name: Ketoconazole
Brand: SIGMA

99.0-101.0% (EP, titration), meets EP testing specifications

Synonyme(s) :

(±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine

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A propos de cet article

Formule empirique (notation de Hill) :

C₂₆H₂₈Cl₂N₄O₄

Numéro CAS:

65277-42-1

Poids moléculaire :

531.43

NACRES:

NA.85

PubChem Substance ID:

24278176

UNSPSC Code:

51101500

EC Number:

265-667-4

MDL number:

MFCD00058579

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Propriétés

Quality Segment

200

agency

meets EP testing specifications

description

Specific Optical Rotation (EP): (−0.10) ∼ +0.10 °

assay

99.0-101.0% (EP, titration)

form

powder

color

white to off-white

antibiotic activity spectrum

Gram-positive bacteria, fungi, yeast

mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

CC(=O)N1CCN(CC1)c2ccc(OC[C@H]3CO[C@@](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2

InChI

1S/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m0/s1

InChI key

XMAYWYJOQHXEEK-OZXSUGGESA-N

Gene Information

human ... ABCB1(5243), CYP11B1(1584), CYP11B2(1585), CYP17A1(1586), CYP19A1(1588), CYP1A2(1544), CYP24A1(1591), CYP26A1(1592), CYP3A4(1576), CYP51A1(1595), KCNH1(3756)
mouse ... Abcb1a(18671), Abcb1b(18669)
rat ... Alox5(25290), Cyp17a1(25146), Cyp51(25427), Cyp7a1(25428)

Description

General description

Chemical structure: imidazole

Application

Ketoconazole is a broad spectrum antifungal agent used to treat candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. It is used to identify p-glycoprotein/CYP3A-limited bioavailability in the monkey modelPMID 14744938, to study interleukin 1 mediated antitumor effectsPMID 2369744, and drug interactions in vivoPMID 8138941

CYP3A4 inhibitor

Biochem/physiol Actions

Antifungal agent

Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme that is necessary for the conversion of lanosterol to ergosterol. This interaction inhibits ergosterol synthesis and results in increased fungal cellular permeability. Other possible mechanisms of action are the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole inhibits the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone .

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pictograms

GHS06,GHS08,GHS09

signalword

Danger

hcodes

H301,H360F,H373,H410

pcodes

P202 - P260 - P264 - P273 - P280 - P301 + P310

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - STOT RE 2

Classe de stockage

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c