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K1003 Sigma-Aldrich

Ketoconazole

99.0-101.0% (EP, titration)

Synonym: (±)-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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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics G-M, Antifungal, Application Index,
Quality Level   300
description   Specific Optical Rotation (EP): (−0.10) ∼ +0.10 °
assay   99.0-101.0% (EP, titration)
color   white to off-white
mp   148-152 °C
solubility   methanol: soluble 40 mg/mL
Mode of action   enzyme | inhibits
antibiotic activity spectrum   Gram-positive bacteria
  fungi
  yeast
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 model, to study interleukin 1 mediated antitumor effects, and drug interactions in vivo

CYP3A4 inhibitor

Packaging

100 mg in glass bottle

Biochem/physiol Actions

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 .

Antifungal agent

Safety & Documentation

Safety Information

Symbol 
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN2811 - class 6.1 - PG 3 - EHS - Toxic solids, organic, n.o.s., HI: all
WGK Germany 
WGK 3
RTECS 
TK7912300
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Single- & multi-channel pipettes from BRAND
Protocols & Articles

Articles

HPLC Analysis of Triazole Antifungal Agent Enantiomers on Astec® CYCLOBOND® I 2000 HP-RSP

From our library of Articles, Sigma-Aldrich presents HPLC Analysis of Triazole Antifungal Agent Enantiomers on Astec® CYCLOBOND® I 2000 HP-RSP
Keywords: Antibiotics, Antifungals, Antimicrobials, Chromatography, High performance liquid chromatography, Pharmaceutical

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Peer-Reviewed Papers
15

References

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