Determine the necessary mass, volume, or concentration for preparing a solution.
Activity Type | Activity Value -log(M) | Mechanism of Action | Activity Reference | Publications (PubMed IDs) |
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SKU | Size | Availability | Price | Qty |
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K129737-1g | 1g | In stock | $128.90 | |
K129737-5g | 5g | In stock | $441.90 | |
K129737-10g | 10g | Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience! | $795.90 | |
K129737-25g | 25g | Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience! | $1,790.90 | |
K129737-100g | 100g | In stock | $6,444.90 | |
K129737-500g | 500g | Available within 4-8 weeks(?) Items will be manufactured post-order and can take 4-8 weeks. Thank you for your patience! | $28,999.90 |
Potent cytochrome P450 inhibitor. Antifungal agent.
Synonyms | HMS3678J17 | Ketoconazole (k) | KTZ | MLS002222255 | N-(1,3,4-Trihydroxyoctadecan-2-yl)octadecanimidic acid | NCGC00025000-08 | SW196888-4 | ketoconazole | Opera_ID_397 | Prestwick0_000389 | NCGC00253967-01 | 1-acetyl-4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl) |
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Specifications & Purity | Moligand™, ≥98% |
Biochemical and Physiological Mechanisms | Potent cytochrome P450 inhibitor (K i values are 26.7 and 109 nM at CYP3A4 and CYP3A5, respectively). Antifungal agent. Additionally, shows activity at human androgen receptors. |
Storage Temp | Store at 2-8°C |
Shipped In | Wet ice |
Grade | Moligand™ |
Action Type | CHANNEL BLOCKER, INHIBITOR |
Mechanism of action | Inhibitor of CYP3A4;Channel blocker of K v1.8 |
Note | Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details. |
Product Description | 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 |
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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 |
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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 |
InChi Key | XMAYWYJOQHXEEK-OZXSUGGESA-N |
Canonical SMILES | CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl |
Isomeric 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 Germany | 3 |
RTECS | TK7912300 |
PubChem CID | 456201 |
Molecular Weight | 531.43 |
Reaxy-Rn | 5488107 |
PubChem CID | 3823 |
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ChEBI | CHEBI:48339 |
BindingDB Ligand | 8610 |
DrugBank Ligand | DB01026 |
Wikipedia | Ketoconazole |
CAS Registry No. | 65277-42-1 |
ChEMBL Ligand | CHEMBL157101 |
DrugCentral Ligand | 1527 |
Enter Lot Number to search for COA:
Find and download the COA for your product by matching the lot number on the packaging.
Lot Number | Certificate Type | Date | Item |
---|---|---|---|
G2423154 | Certificate of Analysis | Jul 26, 2024 | K129737 |
G2227239 | Certificate of Analysis | May 20, 2024 | K129737 |
G2227241 | Certificate of Analysis | May 20, 2024 | K129737 |
G2227242 | Certificate of Analysis | May 20, 2024 | K129737 |
G2227270 | Certificate of Analysis | May 20, 2024 | K129737 |
G2227240 | Certificate of Analysis | May 13, 2024 | K129737 |
G2425490 | Certificate of Analysis | Mar 25, 2024 | K129737 |
G2425489 | Certificate of Analysis | Mar 25, 2024 | K129737 |
G2425488 | Certificate of Analysis | Mar 25, 2024 | K129737 |
D2422220 | Certificate of Analysis | Mar 25, 2024 | K129737 |
F2125353 | Certificate of Analysis | Apr 13, 2023 | K129737 |
F2125352 | Certificate of Analysis | Apr 13, 2023 | K129737 |
F2125354 | Certificate of Analysis | Apr 13, 2023 | K129737 |
H2005074 | Certificate of Analysis | Jun 17, 2022 | K129737 |
G2311055 | Certificate of Analysis | Jun 15, 2022 | K129737 |
H2311033 | Certificate of Analysis | Jun 15, 2022 | K129737 |
I2311025 | Certificate of Analysis | Jun 15, 2022 | K129737 |
Solubility | Soluble in DMSO (20 mg/mL warm), ethanol (20 mg/mL warm), chloroform, water (<1 mg/mL), and methanol |
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Sensitivity | heat sensitive |
Melt Point(°C) | 150 °C |
Pictogram(s) | GHS06, GHS08, GHS09 |
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Signal | Danger |
Hazard Statements | H301:Toxic if swallowed H373:Causes damage to organs through prolonged or repeated exposure H400:Very toxic to aquatic life H410:Very toxic to aquatic life with long lasting effects H360F:May damage fertility |
Precautionary Statements | P273:Avoid release to the environment. P280:Wear protective gloves/protective clothing/eye protection/face protection. P321:Specific treatment (see ... on this label). P405:Store locked up. P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P260:Do not breathe dust/fume/gas/mist/vapors/spray. P270:Do not eat, drink or smoke when using this product. P391:Collect spillage. P330:Rinse mouth. P203:Obtain, read and follow all safety instructions before use. P301+P316:IF SWALLOWED: Get emergency medical help immediately. P318:if exposed or concerned, get medical advice. P319:Get medical help if you feel unwell. |
WGK Germany | 3 |
RTECS | TK7912300 |
Reaxy-Rn | 5488107 |
Merck Index | 5302 |
1. Chao Meng, Lingye Zhou, Lin Huang, Qi Gu, Xinyue Du, Cheng Wang, Fanglan Liu, Chunhua Xia. (2024) Chlorogenic acid regulates the expression of NPC1L1 and HMGCR through PXR and SREBP2 signaling pathways and their interactions with HSP90 to maintain cholesterol homeostasis. PHYTOMEDICINE, 123 (155271). [PMID:38103317] |
2. Yanxiong Gan, Yaxin Xu, Xue Zhang, Huiling Hu, Wenke Xiao, Zheng Yu, Tao Sun, Jinming Zhang, Chuanbiao Wen, Shichao Zheng. (2023) Revisiting Supersaturation of a Biopharmaceutical Classification System IIB Drug: Evaluation via a Multi-Cup Dissolution Approach and Molecular Dynamic Simulation. MOLECULES, 28 (19): (6962). [PMID:37836805] |
3. Kun Ren, Xuanmeng Zhang, Ruijie Wang, Shumeng Ren, Huiming Hua, Dongmei Wang, Yingni Pan, Xiaoqiu Liu. (2024) The inhibitory effect of licorice on the hepatotoxicity induced by the metabolic activation of Euodiae Fructus. JOURNAL OF ETHNOPHARMACOLOGY, 319 (29): (117233). [PMID:37793580] |
4. Mengming Xia, Xueyi Song, Zebei Lu, Yu Wang, Quan Zhou, Peiwu Geng, Shuanghu Wang, Yunfang Zhou, Qingjun Wu, Aixia Han. (2023) Evaluation of the inhibitory effect of azoles on pharmacokinetics of lenvatinib in rats both in vivo and in vitro by UPLC-MS/MS. Thoracic Cancer, 14 (33): (3331-3341). [PMID:37771131] |
5. Hudie Fu, Li Kang, Lanjun Yu, Yanping Fu, Zhijie Wen, Shengpeng Zhu, Mohan Zhao, Yuqing Wang, Qi Chen, Qinxiong Lin, Xinzhou Yang, Yan Hu. (2023) A sustained-release gel film based on chitosan for treating cutaneous candidiasis. JOURNAL OF APPLIED POLYMER SCIENCE, (9): (e54665). [PMID:19448668] |
6. Luyao Ma, Fangjun Yu, Di He, Lianxia Guo, Yu Yang, Wangchun Li, Tianpeng Zhang. (2023) Role of circadian clock in the chronoefficacy and chronotoxicity of clopidogrel. BRITISH JOURNAL OF PHARMACOLOGY, [PMID:37403641] |
7. Shuhang Wang, Jingxin Gou, Yue Wang, Xinyi Tan, Linxuan Zhao, Xiangqun Jin, Xing Tang. (2023) Synergistic Antitumor Efficacy Mediated by Liposomal Co-Delivery of Polymeric Micelles of Vinorelbine and Cisplatin in Non-Small Cell Lung Cancer. International Journal of Nanomedicine, [PMID:33790554] |
8. Yufen Liao, Xin Wang, Guangyun Ran, Shiyu Zhang, Chutian Wu, Rong Tan, Ying Liu, Yan He, Ting Liu, Zhongxiu Wu, Ying Peng, Weiwei Li, Jiang Zheng. (2023) DNA damage and up-regulation of PARP-1 induced by columbin in vitro and in vivo. TOXICOLOGY LETTERS, 379 (20). [PMID:36905973] |
9. Yuan Liang, Qiuyan Jiang, Yiyao Gong, Yifan Yu, Haoyang Zou, Jingqi Zhao, Tiehua Zhang, Jie Zhang. (2023) In vitro and in silico assessment of endocrine disrupting effects of food contaminants through pregnane X receptor. FOOD AND CHEMICAL TOXICOLOGY, 175 (113711). [PMID:36893891] |
10. Wei Fan, Yao Zhang, Yanli Sun, Shujuan Wang, Cong Zhang, Xichen Yu, Weiting Wang, Kai Dong. (2023) Durable antibacterial and temperature regulated core-spun yarns for textile health and comfort applications. CHEMICAL ENGINEERING JOURNAL, 455 (140917). [PMID:] |
11. Kun Ren, Ruijie Wang, Shinuo Fang, Shumeng Ren, Huiming Hua, Dongmei Wang, Yingni Pan, Xiaoqiu Liu. (2023) Effect of CYP3A inducer/inhibitor and licorice on hepatotoxicity and in vivo metabolism of main alkaloids of Euodiae Fructus based on UPLC-Q-Exactive-MS. JOURNAL OF ETHNOPHARMACOLOGY, 303 (116005). [PMID:36516906] |
12. Yangjie LI, Jiaying HUANG, Jihui FANG, Zhiye HUANG. (2022) [Fast screening and confirmation of 73 common prohibited compounds in cosmetics by ultra performance liquid chromatography-quadrupole-time-of-flight high resolution mass spectrometry].. Chinese Journal of Chromatography, 40 (5): (433-442). [PMID:35478002] |
13. Shiyu Zhang, Ying Liu, Ting Liu, Jie Pan, Rong Tan, Zixia Hu, Bowen Gong, Yufen Liao, Peng Luo, Qibing Zeng, Weiwei Li, Jiang Zheng. (2022) DNA damage by reactive oxygen species resulting from metabolic activation of 8-epidiosbulbin E acetate in vitro and in vivo. TOXICOLOGY AND APPLIED PHARMACOLOGY, 443 (116007). [PMID:35367474] |
14. Hang Xue,Liangcong Hu,Yuan Xiong,Xiangwei Zhu,Congying Wei,Faqi Cao,Wu Zhou,Yun Sun,Yori Endo,Mengfei Liu,Yi Liu,Jing Liu,Abudula Abududilibaier,Lang Chen,Chenchen Yan,Bobin Mi,Guohui Liu. (2019-10-05) Quaternized chitosan-Matrigel-polyacrylamide hydrogels as wound dressing for wound repair and regeneration.. Carbohydrate polymers, 226 (115302-115302). [PMID:31582049] |
1. Islam M et al.. (2018) Microfluidic cell sorting by stiffness to examine heterogenic responses of cancer cells to chemotherapy.. Cell Death Dis, 9 (2): (239). [PMID:29445159] |
2. Chao Meng, Lingye Zhou, Lin Huang, Qi Gu, Xinyue Du, Cheng Wang, Fanglan Liu, Chunhua Xia. (2024) Chlorogenic acid regulates the expression of NPC1L1 and HMGCR through PXR and SREBP2 signaling pathways and their interactions with HSP90 to maintain cholesterol homeostasis. PHYTOMEDICINE, 123 (155271). [PMID:38103317] |
3. Yanxiong Gan, Yaxin Xu, Xue Zhang, Huiling Hu, Wenke Xiao, Zheng Yu, Tao Sun, Jinming Zhang, Chuanbiao Wen, Shichao Zheng. (2023) Revisiting Supersaturation of a Biopharmaceutical Classification System IIB Drug: Evaluation via a Multi-Cup Dissolution Approach and Molecular Dynamic Simulation. MOLECULES, 28 (19): (6962). [PMID:37836805] |
4. Kun Ren, Xuanmeng Zhang, Ruijie Wang, Shumeng Ren, Huiming Hua, Dongmei Wang, Yingni Pan, Xiaoqiu Liu. (2024) The inhibitory effect of licorice on the hepatotoxicity induced by the metabolic activation of Euodiae Fructus. JOURNAL OF ETHNOPHARMACOLOGY, 319 (29): (117233). [PMID:37793580] |
5. Mengming Xia, Xueyi Song, Zebei Lu, Yu Wang, Quan Zhou, Peiwu Geng, Shuanghu Wang, Yunfang Zhou, Qingjun Wu, Aixia Han. (2023) Evaluation of the inhibitory effect of azoles on pharmacokinetics of lenvatinib in rats both in vivo and in vitro by UPLC-MS/MS. Thoracic Cancer, 14 (33): (3331-3341). [PMID:37771131] |
6. Hudie Fu, Li Kang, Lanjun Yu, Yanping Fu, Zhijie Wen, Shengpeng Zhu, Mohan Zhao, Yuqing Wang, Qi Chen, Qinxiong Lin, Xinzhou Yang, Yan Hu. (2023) A sustained-release gel film based on chitosan for treating cutaneous candidiasis. JOURNAL OF APPLIED POLYMER SCIENCE, (9): (e54665). [PMID:19448668] |
7. Luyao Ma, Fangjun Yu, Di He, Lianxia Guo, Yu Yang, Wangchun Li, Tianpeng Zhang. (2023) Role of circadian clock in the chronoefficacy and chronotoxicity of clopidogrel. BRITISH JOURNAL OF PHARMACOLOGY, [PMID:37403641] |
8. Shuhang Wang, Jingxin Gou, Yue Wang, Xinyi Tan, Linxuan Zhao, Xiangqun Jin, Xing Tang. (2023) Synergistic Antitumor Efficacy Mediated by Liposomal Co-Delivery of Polymeric Micelles of Vinorelbine and Cisplatin in Non-Small Cell Lung Cancer. International Journal of Nanomedicine, [PMID:33790554] |
9. Yufen Liao, Xin Wang, Guangyun Ran, Shiyu Zhang, Chutian Wu, Rong Tan, Ying Liu, Yan He, Ting Liu, Zhongxiu Wu, Ying Peng, Weiwei Li, Jiang Zheng. (2023) DNA damage and up-regulation of PARP-1 induced by columbin in vitro and in vivo. TOXICOLOGY LETTERS, 379 (20). [PMID:36905973] |
10. Yuan Liang, Qiuyan Jiang, Yiyao Gong, Yifan Yu, Haoyang Zou, Jingqi Zhao, Tiehua Zhang, Jie Zhang. (2023) In vitro and in silico assessment of endocrine disrupting effects of food contaminants through pregnane X receptor. FOOD AND CHEMICAL TOXICOLOGY, 175 (113711). [PMID:36893891] |
11. Wei Fan, Yao Zhang, Yanli Sun, Shujuan Wang, Cong Zhang, Xichen Yu, Weiting Wang, Kai Dong. (2023) Durable antibacterial and temperature regulated core-spun yarns for textile health and comfort applications. CHEMICAL ENGINEERING JOURNAL, 455 (140917). [PMID:] |
12. Kun Ren, Ruijie Wang, Shinuo Fang, Shumeng Ren, Huiming Hua, Dongmei Wang, Yingni Pan, Xiaoqiu Liu. (2023) Effect of CYP3A inducer/inhibitor and licorice on hepatotoxicity and in vivo metabolism of main alkaloids of Euodiae Fructus based on UPLC-Q-Exactive-MS. JOURNAL OF ETHNOPHARMACOLOGY, 303 (116005). [PMID:36516906] |
13. Yangjie LI, Jiaying HUANG, Jihui FANG, Zhiye HUANG. (2022) [Fast screening and confirmation of 73 common prohibited compounds in cosmetics by ultra performance liquid chromatography-quadrupole-time-of-flight high resolution mass spectrometry].. Chinese Journal of Chromatography, 40 (5): (433-442). [PMID:35478002] |
14. Shiyu Zhang, Ying Liu, Ting Liu, Jie Pan, Rong Tan, Zixia Hu, Bowen Gong, Yufen Liao, Peng Luo, Qibing Zeng, Weiwei Li, Jiang Zheng. (2022) DNA damage by reactive oxygen species resulting from metabolic activation of 8-epidiosbulbin E acetate in vitro and in vivo. TOXICOLOGY AND APPLIED PHARMACOLOGY, 443 (116007). [PMID:35367474] |
15. Hang Xue,Liangcong Hu,Yuan Xiong,Xiangwei Zhu,Congying Wei,Faqi Cao,Wu Zhou,Yun Sun,Yori Endo,Mengfei Liu,Yi Liu,Jing Liu,Abudula Abududilibaier,Lang Chen,Chenchen Yan,Bobin Mi,Guohui Liu. (2019-10-05) Quaternized chitosan-Matrigel-polyacrylamide hydrogels as wound dressing for wound repair and regeneration.. Carbohydrate polymers, 226 (115302-115302). [PMID:31582049] |