CAS 83374-59-8

trans-Ketoconazole

Description:

Trans-Ketoconazole is an antifungal agent belonging to the imidazole class of compounds, primarily used in the treatment of various fungal infections. It exhibits a broad spectrum of antifungal activity by inhibiting the synthesis of ergosterol, a crucial component of fungal cell membranes. The substance is characterized by its relatively low solubility in water, which can affect its bioavailability and absorption when administered. Trans-Ketoconazole is typically formulated in topical preparations, but it can also be found in oral forms. Its chemical structure includes a chiral center, leading to the existence of different stereoisomers, with the trans configuration being the more therapeutically relevant form. The compound is known for its potential side effects, including hepatotoxicity and endocrine disruptions, necessitating careful monitoring during treatment. Additionally, it may interact with various medications due to its effects on liver enzymes, particularly cytochrome P450. Overall, trans-Ketoconazole serves as an important therapeutic agent in the management of fungal infections, albeit with considerations for its safety profile.

Formula: C₂₆H₂₈Cl₂N₄O₄

InChI: InChI=1/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+/s2

InChI key: InChIKey=XMAYWYJOQHXEEK-NQJIZXJYNA-N

SMILES: C([C@]1(O[C@H](COC2=CC=C(C=C2)N3CCN(C(C)=O)CC3)CO1)C4=C(Cl)C=C(Cl)C=C4)N5C=CN=C5

Synonyms:

• RS 36745
• Piperazine, 1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, trans-
• rel-1-Acetyl-4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine
• Piperazine, 1-acetyl-4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, rel-
• R 44319

Ketoconazole Impurity C

CAS: 83374-59-8

Formula: C26H28Cl2N4O4

Molecular weight: 531.4

Ref: 3W-CS-P-00435

Ketoconazole EP Impurity C

CAS: 83374-59-8

Formula: C₂₆H₂₈Cl₂N₄O₄

Color and Shape: White To Off-White Solid

Molecular weight: 531.43

Ref: 4Z-K-015

rac-trans-Ketoconazole

Controlled Product

CAS: 83374-59-8

Impurity Ketoconazole EP Impurity C
Applications rac-trans-Ketoconazole (Ketoconazole EP Impurity C) is a Ketoconazole (K186000) analog. The trans isomer of Ketoconazole.
References Kan, P.B., et al.: J. Steroid Biochem., 23, 1023 (1985),

Formula: C₂₆H₂₈Cl₂N₄O₄

Color and Shape: Off-White

Molecular weight: 531.43

Ref: TR-K186010

Ketoconazole EP Impurity C

CAS: 83374-59-8

Formula: C₂₆H₂₈Cl₂N₄O₄

Molecular weight: 531.43

Ref: ST-EA-CP-K2003

rac-trans-ketoconazole

CAS: 83374-59-8

Rac-trans-ketoconazole is a synthetic derivative of ketoconazole, an antifungal drug. It inhibits the growth of fungi by inhibiting mitochondrial cytochrome P450 enzymes, which are involved in the synthesis of ergosterol, a component of fungal cell membranes. Rac-trans-ketoconazole has also been shown to have potential antineoplastic activity and is used as an antifungal agent. This drug is not active against bacteria and has been found to be free of impurities when synthesized using ammonium formate and electrospray techniques.

Formula: C₂₆H₂₈Cl₂N₄O₄

Purity: Min. 95%

Color and Shape: Off-white solid.

Molecular weight: 531.43 g/mol

Ref: 3D-FR27664