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K1003

Sigma-Aldrich

Ketoconazole

99.0-101.0% (EP, titration)

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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About This Item

Formule empirique (notation de Hill):
C26H28Cl2N4O4
Numéro CAS:
65277-42-1
Poids moléculaire :
531.43
Numéro CE :
265-667-4
Numéro MDL:
MFCD00058579
Code UNSPSC :
51101500
ID de substance PubChem :
24278176
Nomenclature NACRES :
NA.85

Description

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

Pureté

99.0-101.0% (EP, titration)

Forme

powder

Couleur

white to off-white

Spectre d'activité de l'antibiotique

Gram-positive bacteria
fungi
yeast

Mode d’action

enzyme | inhibits

Température de stockage

2-8°C

Chaîne SMILES 

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

Clé InChI

XMAYWYJOQHXEEK-OZXSUGGESA-N

Informations sur le gène

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)

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Description générale

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

Actions biochimiques/physiologiques

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

Application

Réf. du produit
Description
Tarif

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

UC280

Ketoconazole

Pictogrammes

Skull and crossbonesHealth hazardEnvironment
GHS06,GHS08,GHS09

Mention d'avertissement

Danger

Mentions de danger

H301,H360F,H373,H410

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Wendy W J van de Sande et al.
Antimicrobial agents and chemotherapy, 54(6), 2738-2740 (2010-03-31)
Eumycetoma caused by Madurella mycetomatis is treated surgically and with high doses of ketoconazole. Therapeutic responses are poor, and recurrent infections are common. In search of therapeutic alternatives in the treatment of mycetoma, we determined the in vitro susceptibilities of
Francisco M Garibotto et al.
Bioorganic & medicinal chemistry, 18(1), 158-167 (2009-12-05)
The synthesis, in vitro evaluation, and conformational study of a new series of small-size peptides acting as antifungal agents are reported. In a first step of our study we performed a conformational analysis using Molecular Mechanics calculations. The electronic study
L L von Moltke et al.
The Journal of pharmacology and experimental therapeutics, 268(3), 1278-1283 (1994-03-01)
Biotransformation of the tricyclic antidepressant desipramine (DMI) to its metabolite 2-hydroxy-desipramine (2-OH-DMI) was studied in vitro using microsomal preparations from human, monkey, mouse and rat liver. In all species 2-OH-DMI was the principal identified metabolite. Mean (+/- S.E.) reaction parameters
P G Braunschweiger et al.
Cancer research, 50(15), 4709-4717 (1990-08-01)
In the present studies, the regulatory role of adrenal hormones on the antitumor activity of recombinant human interleukin 1 alpha (IL-1 alpha) was investigated. Ketoconazole, a potent but transient inhibitor of adrenal steroid hormone biosynthesis, inhibited IL-1 alpha induced increases
Keith W Ward et al.
Drug metabolism and disposition: the biological fate of chemicals, 32(2), 172-177 (2004-01-28)
The effect of P-glycoprotein (Pgp) and/or CYP3A on the disposition of xenobiotics has been extensively investigated and is often of interest during drug discovery lead optimization. We have previously described a monkey pharmacokinetic screen to rapidly estimate absorption and first-pass
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Chromatograms

application for HPLC

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