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Merck

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
NACRES:
NA.24
PubChem Substance ID:
329817121
UNSPSC Code:
41116107
MDL number:
MFCD00058579

Nom du produit

Ketoconazole, European Pharmacopoeia (EP) Reference Standard

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

SMILES string

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

InChI key

XMAYWYJOQHXEEK-OZXSUGGESA-N

grade

pharmaceutical primary standard

API family

ketoconazole

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

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Catégories apparentées

Application

CYP3A4 inhibitor

Biochem/physiol Actions

Antifungal agent

General description

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.

Other Notes

Sales restrictions may apply.

Packaging

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

signalword

Danger

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

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number

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Consulter la Bibliothèque de documents

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
Jan Faergemann et al.
Expert opinion on pharmacotherapy, 8(9), 1365-1371 (2007-06-15)
Seborrhoeic dermatitis (SD) is a chronic, inflammatory skin disorder, affecting areas of the head and body where sebaceous glands are most prominent and active. The disorder commonly affects hair-bearing areas of the head, including the scalp. Involvement on the face
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