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| SKU | Size | Availability |
Price | Qty |
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I426206-1ml
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1ml |
Available within 4-8 weeks(?)
Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience!
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$69.90
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Cytochrome p450 inhibitor
| Synonyms | 84625-61-6 | Itrizole | Canditral | Traconal | Triasporin | Itraconazolum [Latin] | ITRAZOLE | Itraconazole-d3 | 1-(Butan-2-yl)-4-{4-[4-(4-{[2-(2,4-dichlorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]phenyl}-4,5-dihydro-1H-1, |
|---|---|
| Specifications & Purity | Moligand™, 2mM in DMSO |
| Biochemical and Physiological Mechanisms | Cytochrome p450 CYP3A4 inhibitor (IC 50 = 16-26 nM for midazolam hydroxylation). Higher affinity for fungal enzymes over mammalian cytochrome p450. Limited ability to cross the blood-brain barrier. Antifungal activity. |
| Storage Temp | Store at -80°C |
| Shipped In |
Ice chest + Ice pads This product requires cold chain shipping. Ground and other economy services are not available. |
| Grade | Moligand™ |
| Product Description |
Itraconazole is a triazole antifungal agent. It inhibits the fungal CYP(cytochrome P450) oxidase-mediated synthesis of ergosterol. Itraconazole also acts as an effective hedgehog signaling inhibitor in a Ptch-independent manner, presumably by binding smoothened (Smo) at a site distinct from that targeted by cyclopamine and SAG. Itraconazole is an inhibitor of CYP3A4. |
Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Diazinanes |
| Subclass | Piperazines |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Phenylpiperazines |
| Alternative Parents | N-arylpiperazines Phenyl-1,2,4-triazoles Aminophenyl ethers Phenoxy compounds Aniline and substituted anilines Dichlorobenzenes Dialkylarylamines Alkyl aryl ethers Ketals Aryl chlorides 1,3-dioxolanes Heteroaromatic compounds Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Organic oxides Organochlorides Organopnictogen compounds |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Substituents | Phenylpiperazine - N-arylpiperazine - Phenyltriazole - Phenyl-1,2,4-triazole - Aminophenyl ether - Phenol ether - Phenoxy compound - Tertiary aliphatic/aromatic amine - 1,3-dichlorobenzene - Dialkylarylamine - Aniline or substituted anilines - Halobenzene - Alkyl aryl ether - Ketal - Chlorobenzene - Aryl halide - Benzenoid - Monocyclic benzene moiety - Aryl chloride - Azole - 1,2,4-triazole - Triazole - Meta-dioxolane - Heteroaromatic compound - Tertiary amine - Ether - Azacycle - Oxacycle - Acetal - Organochloride - Organohalogen compound - Organooxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Amine - Organic oxygen compound - Organonitrogen compound - Aromatic heteromonocyclic compound |
| Description | 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 | Not available |
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| ALogP | 5.7 |
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| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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| IUPAC Name | 2-butan-2-yl-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one |
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| INCHI | InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3 |
| InChIKey | VHVPQPYKVGDNFY-UHFFFAOYSA-N |
| Smiles | CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5COC(O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl |
| Isomeric SMILES | CCC(C)N1C(=O)N(C=N1)C2=CC=C(C=C2)N3CCN(CC3)C4=CC=C(C=C4)OCC5COC(O5)(CN6C=NC=N6)C7=C(C=C(C=C7)Cl)Cl |
| WGK Germany | 3 |
| RTECS | XZ5481000 |
| Molecular Weight | 705.63 |
| Reaxy-Rn | 4290027 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4290027&ln= |
| Sensitivity | Heat sensitive |
|---|---|
| Melt Point(°C) | 167.0 to 171.0 °C |
| Molecular Weight | 705.600 g/mol |
| XLogP3 | 5.700 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 9 |
| Rotatable Bond Count | 11 |
| Exact Mass | 704.239 Da |
| Monoisotopic Mass | 704.239 Da |
| Topological Polar Surface Area | 101.000 Ų |
| Heavy Atom Count | 49 |
| Formal Charge | 0 |
| Complexity | 1120.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 3 |
| 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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| 2. Xu Lingling, Zhao Yajuan, Zhao Changhao, Hu Tao, Wang Jing, Liu Yi, Tian Yong, Wang Xiufang. (2020) Controlled fabrication of orchid-like nitrogen-doped hierarchical porous carbon and hollow carbon nanospheres. JOURNAL OF MATERIALS SCIENCE, 55 (34): (16143-16157). |
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| 7. Heng Zhang, Yizheng Zhou, Hanmo Yang, Xinyi Tao, Yinping Chen, Fuqiang Dong, Yi Sun. (2025) In vitro interactions of berbamine hydrochloride and azoles against Aspergillus fumigatus. Microbiology Spectrum, |
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