UC280

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
• 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 : 12161501
• ID de substance PubChem : 24724652
• Nomenclature NACRES : NA.77

Propriétés

• 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
• 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)

Description

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.

Informations sur la sécurité

• Pictogrammes: GHS06,GHS08,GHS09
• Mention d'avertissement: Danger
• Mentions de danger: H301,H360F,H373,H410
• Conseils de prudence: P202 - P260 - P264 - P273 - P280 - P301 + P310
• 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