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K0600000

Ketoconazole

European Pharmacopoeia (EP) Reference Standard

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 MDL:
MFCD00058579
Code UNSPSC :
41116107
ID de substance PubChem :
329817121
Nomenclature NACRES :
NA.24

Qualité

pharmaceutical primary standard

Famille d'API

ketoconazole

Fabricant/nom de marque

EDQM

Application(s)

pharmaceutical (small molecule)

Format

neat

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

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Description générale

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.

Application

CYP3A4 inhibitor

Actions biochimiques/physiologiques

Antifungal agent

Conditionnement

The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.

Autres remarques

Sales restrictions may apply.

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

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Certificats d'analyse (COA)

Lot/Batch Number

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Sigma-Aldrich

Sigma-Aldrich

R7388

Milieu RPMI-1640

Masato Ohbuchi et al.
Antimicrobial agents and chemotherapy, 57(3), 1332-1338 (2013-01-01)
The antifungal efficacy of voriconazole (VRC) differs among host species, with potent efficacy in humans but less in rodents. We investigated the possible involvement of pregnane X receptor (PXR) and constitutive androstane receptor (CAR) in the species-specific efficacy of VRC
B Halama et al.
Clinical pharmacology and therapeutics, 93(6), 564-571 (2013-03-21)
The objective of the study was to establish an in vivo method for assessing cytochrome P450 3A (CYP3A) activity using therapeutically inert nanogram doses of midazolam. We administered four escalating single doses of oral midazolam (0.0001-3 mg) to 12 healthy participants
K-H Shin et al.
Clinical pharmacology and therapeutics, 94(5), 601-609 (2013-06-21)
This study aimed to evaluate endogenous metabolic markers of hepatic cytochrome P450 (CYP)3A activity in healthy subjects using a metabolomics approach. Twenty-four subjects received the following medication during the following three study periods: 1 mg of i.v. midazolam alone (control
Hao Li et al.
The Journal of biological chemistry, 288(19), 13655-13668 (2013-03-26)
Ketoconazole binds to and antagonizes pregnane X receptor (PXR) activation. Yeast high throughput screens of PXR mutants define a unique region for ketoconazole binding. Ketoconazole genetically interacts with specific PXR surface residues. A yeast-based genetic method to discover novel nuclear
J J Berwaerts et al.
Journal of the American Geriatrics Society, 46(7), 880-884 (1998-07-22)
Cushing's syndrome is a rare disorder. The corticotropin (ACTH)-dependent form of this syndrome generally results either from excessive ACTH secretion by a pituitary adenoma or ectopic secretion by a malignant tumor. Theoretically, the latter type can be assumed to occur
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