Determine the necessary mass, volume, or concentration for preparing a solution.
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Moligand™, ≥98% Moligand™ for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Store at 2-8°C Ships Wet ice Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 35 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
Ketoconazole is an imidazole-containing small molecule inhibitor of cytochrome P-450-dependent steps in the biosynthesis of steroid hormones; also inhibits TXA Synthase (thromboxane synthetase) and 5-LO (5-lipoxygenase) activity. Ketoconazole exhibits antimetastatic, antineoplastic, and antipsoriatic activity. Inhibition of 5-LO (5-lipoxygenase) by Ketoconazole interrupts arachidonic acid -derived leukotriene production, which was correlated to a suppression of leukotriene-mediated anaphylactic bronchoconstriction in guinea pigs. Ketoconazole is described as reducing platelet cellular levels of thromboxane A2, suppressing thromboxane A2-mediated increase of microvascular permeability in response to ischemia insults. Ketoconazole produces an antiandrogen effect through inhibition of adrenocorticoid biosynthesis, suppressing the adrenal secretion of androgens and attenuating cortisol response. Ketoconazole is an inhibitor of CYP17A1, CYP3A4 and CYP3A5
An inhibitor of CYP proteins, thromboxane synthetase, and 5-LO
| Pubchem Sid | 504758897 |
|---|---|
| Pubchem Sid Url | https://pubchem.ncbi.nlm.nih.gov/substance/504758897 |
| Sonrisas canónicas | CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl |
| IUPAC Name | 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone |
| InChIKey | XMAYWYJOQHXEEK-OZXSUGGESA-N |
| 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 |
| Isómeros SMILES | CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl |
| WGK Alemania | 3 |
| RTECS | TK7912300 |
| Peso molecular | 531.43 |
| Reaxy-Rn | 634785 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=634785&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
Download SDS →Lot-specific quality data. Enter your lot number to retrieve the exact COA.
Look up COA →Full quality attributes and acceptance criteria for this grade.
View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Clase | Diazinanes |
| Subclass | Piperazines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenylpiperazines |
| Alternative Parents | N-arylpiperazines Aminophenyl ethers Phenoxy compounds Aniline and substituted anilines Dialkylarylamines Dichlorobenzenes Alkyl aryl ethers Ketals Aryl chlorides N-substituted imidazoles 1,3-dioxolanes Acetamides Tertiary carboxylic acid amides Heteroaromatic compounds Amino acids and derivatives Azacyclic compounds Oxacyclic compounds Organochlorides Organopnictogen compounds Carbonyl compounds Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Phenylpiperazine - N-arylpiperazine - Aminophenyl ether - 1,3-dichlorobenzene - Phenol ether - Tertiary aliphatic/aromatic amine - Phenoxy compound - Dialkylarylamine - Aniline or substituted anilines - Alkyl aryl ether - Ketal - Halobenzene - Chlorobenzene - Monocyclic benzene moiety - Aryl chloride - Aryl halide - N-substituted imidazole - Benzenoid - Meta-dioxolane - Heteroaromatic compound - Tertiary carboxylic acid amide - Imidazole - Azole - Acetamide - Carboxamide group - Amino acid or derivatives - Tertiary amine - Acetal - Oxacycle - Azacycle - Carboxylic acid derivative - Ether - Organooxygen compound - Carbonyl group - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Amine - Organonitrogen compound - Organochloride - Organopnictogen compound - Organohalogen compound - Aromatic heteromonocyclic compound |
| Descripción | This compound belongs to the class of organic compounds known as phenylpiperazines. These are compounds containing a phenylpiperazine skeleton, which consists of a piperazine bound to a phenyl group. |
| External Descriptors | 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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Find and download the COA for your product by matching the lot number on the packaging.
| Lot Number | Certificate Type | Fecha | Articulo |
|---|---|---|---|
| Certificate of Analysis | May 25, 2026 | K129737 | |
| Certificate of Analysis | May 20, 2026 | K129737 | |
| Certificate of Analysis | May 09, 2026 | K129737 | |
| Certificate of Analysis | Apr 24, 2026 | K129737 | |
| Certificate of Analysis | Feb 04, 2026 | K129737 | |
| Certificate of Analysis | Feb 04, 2026 | K129737 | |
| Certificate of Analysis | Feb 04, 2026 | K129737 | |
| Certificate of Analysis | Jan 05, 2026 | K129737 | |
| Certificate of Analysis | Jul 28, 2025 | K129737 | |
| Certificate of Analysis | Feb 27, 2025 | K129737 | |
| Certificate of Analysis | Jul 26, 2024 | K129737 | |
| Certificate of Analysis | Mar 25, 2024 | K129737 | |
| Certificate of Analysis | Mar 25, 2024 | K129737 | |
| Certificate of Analysis | Mar 25, 2024 | K129737 | |
| Certificate of Analysis | Apr 13, 2023 | K129737 | |
| Certificate of Analysis | Apr 13, 2023 | K129737 | |
| Certificate of Analysis | Apr 13, 2023 | K129737 | |
| Certificate of Analysis | Jun 15, 2022 | K129737 | |
| Certificate of Analysis | Jun 15, 2022 | K129737 | |
| Certificate of Analysis | Jun 15, 2022 | K129737 | |
| Certificate of Analysis | Jun 15, 2022 | K129737 | |
| Certificate of Analysis | Jun 15, 2022 | K129737 | |
| Certificate of Analysis | Jun 15, 2022 | K129737 | |
| Certificate of Analysis | Jun 15, 2022 | K129737 | |
| Certificate of Analysis | Jun 15, 2022 | K129737 |
| Solubilidad | Soluble in DMSO (20 mg/mL warm), ethanol (20 mg/mL warm), chloroform, water (<1 mg/mL), and methanol |
|---|---|
| Sensibilidad | heat sensitive |
| Punto de fusión (°C) | 150 °C |
| Peso molecular | 531.400 g/mol |
| XLogP3 | 4.300 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 7 |
| Exact Mass | 530.149 Da |
| Monoisotopic Mass | 530.149 Da |
| Topological Polar Surface Area | 69.100 Ų |
| Heavy Atom Count | 36 |
| Formal Charge | 0 |
| Complexity | 735.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
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| 3. Kun Ren, Xuanmeng Zhang, Ruijie Wang, Shumeng Ren, Huiming Hua, Dongmei Wang, Yingni Pan, Xiaoqiu Liu. (2023) The inhibitory effect of licorice on the hepatotoxicity induced by the metabolic activation of Euodiae Fructus. JOURNAL OF ETHNOPHARMACOLOGY, [PMID:37793580] [10.1016/j.jep.2023.117233] |
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| 16. Wei Zhang, Jingyan Guo, Dongmei Wang, Shumeng Ren, Huiming Hua, Toshio Morikawa, Yingni Pan, Xiaoqiu Liu. (2020) Effect of CYP3A inducer/inhibitor on pharmacokinetics of five alkaloids in Evodiae Fructus. CHEMICO-BIOLOGICAL INTERACTIONS, [PMID:32561335] [10.1016/j.cbi.2020.109146] |
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| 21. Y.W. Liu, Y. Chen, X.H. Chen, Z.N. Yang, Y. Xie, Z. Zhang. (2018) Study on adsorption behavior of ketoconazole on Q235 mild steel in 1.0 M HCl solution with electrochemical measurement. JOURNAL OF ALLOYS AND COMPOUNDS, [PMID:] [10.1016/j.jallcom.2018.05.107] |
| 22. Qingling Cui, Yingni Pan, Xiaowei Yan, Bao Qu, Xiaoqiu Liu, Wei Xiao. (2016) A metabolic way to investigate related hurdles causing poor bioavailability in oral delivery of isoacteoside in rats employing ultrahigh-performance liquid chromatography/quadrupole time-of-flight tandem mass spectrometry. RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 31 (4): (371-380). [PMID:27859774] [10.1002/rcm.7795] |
| 23. Lili Wu, Wanping Zhong, Junjin Liu, Weichao Han, Shilong Zhong, Qiang Wei, Shuwen Liu, Lan Tang. (2015) Human microsomal cyttrochrome P450-mediated reduction of oxysophocarpine, an active and highly toxic constituent derived from Sophora flavescens species, and its intestinal absorption and metabolism in rat. FITOTERAPIA, [PMID:26045316] [10.1016/j.fitote.2015.05.021] |
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