1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

• ChemBase ID: 72632
• Molecular Formular: C26H28Cl2N4O4
• Molecular Mass: 531.43092
• Monoisotopic Mass: 530.14876076
• SMILES: c1(ccc(cc1)OC[C@@H]1O[C@@](OC1)(Cn1ccnc1)c1ccc(cc1Cl)Cl)N1CCN(CC1)C(=O)C
• Canonical SMILES: Clc1ccc(c(c1)Cl)[C@]1(OC[C@@H](O1)COc1ccc(cc1)N1CCN(CC1)C(=O)C)Cn1cncc1
• InChI: 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
• InChIKey: XMAYWYJOQHXEEK-OZXSUGGESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one
• IUPAC Traditional name: (2R,4S)-ketoconazole
• Synonyms: Nizoral; Extina; Xolegel; Kuric; Ketoconazole; (±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine; Ketoconazole; rel-1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]ethanone; cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine; (+/-)-Ketoconazole; Brizoral; Fungarest; Fungoral; Ketoderm; Ketoisdin; Ketozoral; Nizral; Onofin K; Orifungal M; Panfungol; R 41400

Database IDs

• CAS Number: 65277-42-1
• EC Number: 265-667-4
• MDL Number: MFCD00058579
• PubChem SID: 162037557; 24278176; 24724652
• PubChem CID: 456201

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 3.6516862
• LogD (pH = 7.4): 4.128518
• Log P: 4.191598
• Molar Refractivity: 138.0672 cm^3
• Polarizability: 53.26531 Å^3
• Polar Surface Area: 69.06 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; DMSO
• Apperance: White Solid; white to light yellow
• Melting Point: 144-146°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: TK7912300
• European Hazard Symbols: Nature polluting (N); Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 60-25-48/22-50/53
• Safety Statements: 53-45-60-61
• GHS Pictograms: GHS06; GHS08; GHS09
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H360F-H373-H410
• GHS Precautionary statements: P201-P273-P301 + P310-P308 + P313-P501
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: P450
• Gene Information: 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)

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: Free Base
• Quality Level: PREMIUM
• Empirical Formula (Hill Notation): C26H28Cl2N4O4

DETAILS

Selleck Chemicals - S1353

Research Area: Infection
Biological Activity:
Ketoconazole is a synthetic antifungal drug used to prevent and treat skin and fungal infections, especially in immunocompromised patients such as those with AIDS. ketoconazole is structurally similar to imidazole and interferes with the fungal synthesis of ergosterol, a constituent of fungal cell membranes, as well as certain enzymes. [1] 

Sigma Aldrich - UC280

Application
CYP3A4 inhibitor
Biochem/physiol Actions
Antifungal agent

Sigma Aldrich - K1003

Application
CYP3A4 inhibitor
Ketoconazole is a broad spectrum antifungal agent used to treat candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. It is used to identify p-glycoprotein/CYP3A-limited bioavailability in the monkey model1, to study interleukin 1 mediated antitumor effects2, and drug interactions in vivo3
Biochem/physiol Actions
Antifungal agent
Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme that is necessary for the conversion of lanosterol to ergosterol. This interaction inhibits ergosterol synthesis and results in increased fungal cellular permeability. Other possible mechanisms of action are the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole inhibits the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone .
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Toronto Research Chemicals - K186000

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

• http://en.wikipedia.org/wiki/Ketoconazole
• Lambert, A., et al.: Biochem. Pharmacol., 35, 3999 (1986)
• Van Wauwe, J.P. and Janssen, P.A.J., J. Med. Chem., 32, 2231 (1986)
• Nardone, P.A., et al.: . Surg. Res., 44, 425 (1986)
• Tucker, W.F.G., et al.: Br. Med. J., 293, 882 (1986)