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Key Documents

UC280

Sigma-Aldrich

Ketoconazole

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:
Poids moléculaire :
531.43
Numéro CE :
Numéro MDL:
Code UNSPSC :
12161501
ID de substance PubChem :
Nomenclature NACRES :
NA.77

Pureté

≥99% (HPLC)

Forme

solid

Couleur

white to light yellow

Solubilité

DMSO: soluble

Spectre d'activité de l'antibiotique

fungi
yeast

Mode d’action

enzyme | inhibits

Auteur

Johnson & Johnson

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

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Application

Ketoconazole has been used as a cytochrome P450 (CYP) inhibitor to study its functions in embryonic testes of rats. Ketoconazole has also been used for the screening of antimicrobial agents against nonreplicating M. tuberculosis. Furthermore, studies have used ketoconazole for antifungal susceptibility testing and also as a standard antifungal agent.
CYP3A4 inhibitor

Actions biochimiques/physiologiques

Ketoconazole is an imidazole derivative. It plays an important role in inhibiting the conversion of lanosterol to ergosterol in the cell wall of fungi. Ketoconazole has therapeutic effects against dermatophytosis, superficial candidiasis, and paracoccidioidomycosis.
Antifungal agent

Caractéristiques et avantages

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Notes préparatoires

Ketoconazole is soluble in DMSO.

Pictogrammes

Skull and crossbonesHealth hazardEnvironment

Mention d'avertissement

Danger

Mentions de danger

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)

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Les clients ont également consulté

Ketoconazole.
Hay, R.
British Medical Journal (Clinical Research ed.), 285(6342), 584-584 (1982)
Ketoconazole and other imidazole derivatives as inhibitors of steroidogenesis.
D Feldman
Endocrine reviews, 7(4), 409-420 (1986-11-01)
Gökalp Işcan et al.
Journal of agricultural and food chemistry, 50(14), 3943-3946 (2002-06-27)
Essential oils of peppermint Mentha piperita L. (Lamiaceae), which are used in flavors, fragrances, and pharmaceuticals, were investigated for their antimicrobial properties against 21 human and plant pathogenic microorganisms. The bioactivity of the oils menthol and menthone was compared using
Ketoconazole and other imidazole derivatives as inhibitors of steroidogenesis
Feldman, David
Endocrine Reviews, 7(4), 409-420 (1986)
Po-Ren Hsueh et al.
Antimicrobial agents and chemotherapy, 49(2), 512-517 (2005-01-28)
The susceptibilities of nonduplicate isolates to six antifungal agents were determined for 391 blood isolates of seven Candida species, 70 clinical isolates (from blood or cerebrospinal fluid) of Cryptococcus neoformans, and 96 clinical isolates of four Aspergillus species, which were

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Chromatograms

application for HPLCapplication for HPLC

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