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K0600000

Ketoconazole

European Pharmacopoeia (EP) Reference Standard

Synonym(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

Empirical Formula (Hill Notation):
C26H28Cl2N4O4
CAS Number:
65277-42-1
Molecular Weight:
531.43
MDL number:
MFCD00058579
UNSPSC Code:
41116107
PubChem Substance ID:
329817121
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

ketoconazole

manufacturer/tradename

EDQM

application(s)

pharmaceutical (small molecule)

format

neat

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

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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.

Application

CYP3A4 inhibitor

Biochem/physiol Actions

Antifungal agent

Packaging

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

Other Notes

Sales restrictions may apply.

Signal Word

Danger

Hazard Statements

H301,H360F,H373,H410

Hazard Classifications

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

Storage Class Code

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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Certificates of Analysis (COA)

Lot/Batch Number

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Sigma-Aldrich

Sigma-Aldrich

R7388

RPMI-1640 Medium

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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
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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
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