Ketoconazole N-​Oxide

CAS: 254912-65-7

Ref. TR-K186005

Product Information

• Name: Ketoconazole N-​Oxide
• Synonyms: Ethanone, 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-oxido-1-piperazinyl]-, rel-, Piperazine, 1-acetyl-4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, 4-oxide, rel- (9CI), R 053165

Description

Applications Ketoconazole N-​Oxide is an impure analogue of Ketoconazole (K186000) which inhibits cytochrome P-450 dependent steps in the biosynthesis of steroid hormones in vivo. Antimetastatic and antineoplastic activity. Orally active 5-lipoxygenase and thromboxane synthase inhibitor.
References Lambert, A., et al.: Biochem. Pharmacol., 35, 3999 (1986), Van Wauwe, J.P. and Janssen, P.A.J., J. Med. Chem., 32, 2231 (1989), Nardone, P.A., et al.: . Surg. Res., 44, 425 (1988), Tucker, W.F.G., et al.: Br. Med. J., 293, 882 (1986)

• Brand: TRC

Chemical properties

• Molecular weight: 547.43
• Formula: C₂₆H₂₈Cl₂N₄O₅
• Color/Form: Off-White
• InChI: InChI=1S/C26H28Cl2N4O5/c1-19(33)31-10-12-32(34,13-11-31)21-3-5-22(6-4-21)35-15-23-16-36-26(37-23,17-30-9-8-29-18-30)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: InChIKey=TVMVVRYAPWZNJP-OZXSUGGESA-N
• SMILES: CC(=O)N1CC[N+]([O-])(c2ccc(OC[C@H]3CO[C@](Cn4ccnc4)(c4ccc(Cl)cc4Cl)O3)cc2)CC1