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Itraconazole

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Catalog No.
B2104
抗真菌剂
组合的产品项目
规格价格库存 数量
10mM (in 1mL DMSO)
¥ 600.00
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100mg
¥ 500.00
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200mg
¥ 850.00
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1g
¥ 2,500.00
现货

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Background

Itraconazole is a potent inhibitor of CYP3A4 which can be used as a triazole antifungal agent [1].

Cytochrome P450 3A4, abbreviated CYP3A4, is an important enzymethat oxidizessmall foreign organic molecules (xenobiotics).

In vitro: Itraconazole was metabolized into hydroxy-itraconazole (OH-ITZ), a known in vivo metabolite of ITZ, and two new metabolites: keto-itraconazole (keto-ITZ) and N-desalkyl-itraconazole (ND-ITZ). Itraconazole was a substrate for CYP3A and to characterize the metabolites generated. Itraconazole exhibited an unbound Km of 3.9 nM for CYP3A. Itraconazole metabolites are as potent as or more potent CYP3A4 inhibitors than ITZ itself [1]. Itraconazole was pharmacologically distinct from other azole antifungal agents. Itraconazole has been shown to inhibit both the hedgehog signaling pathway and angiogenesis [2] Itraconazole was active against 60 clinical isolates of Aspergillus spp. with geometric mean (GM) MICs of 0.25 mg/mL [3]. Itraconazoleshowed an affinity for mammalian cytochrome P-450 enzymes as well as for fungal P-450-dependent enzyme, and thus has the potential for clinically important interactions [4].

In vivo: Oral Administration of itraconazole (200 mg) once daily for 4 days increased the area under the midazolam concentration-time curve from 10 to 15 times (p < 0.001) and mean peak concentrations three to four times (p < 0.001) compared with the placebo phase [5].

References:
[1]. Isoherranen N1,Kunze KL,Allen KE,Nelson WL,Thummel KE. Role of itraconazole metabolites in CYP3A4 inhibition.Drug Metab Dispos.2004 Oct;32(10):1121-31. Epub 2004 Jul 8.
[2]. Kim J1,Tang JY,Gong R,Kim J,Lee JJ,Clemons KV,Chong CR, et al. Itraconazole, a commonly used antifungal that inhibits Hedgehog pathway activity and cancer growth.Cancer Cell.2010 Apr 13;17(4):388-99. doi: 10.1016/j.ccr.2010.02.027.
[3]. Oakley KL1,Moore CB,Denning DW. In vitro activity of SCH-56592 and comparison with activities of amphotericin B and itraconazole against Aspergillus spp.Antimicrob Agents Chemother.1997 May;41(5):1124-6.
[4]. Leyden J1. Pharmacokinetics and pharmacology of terbinafine and itraconazole.J Am Acad Dermatol.1998 May;38(5 Pt 3):S42-7.
[5]. Olkkola, K.T., J.T. Backman, and P.J. Neuvonen, Midazolam should be avoided in patients receiving the systemic antimycotics ketoconazole or itraconazole. Clinical Pharmacology & Therapeutics, 1994. 55(5): p. 481-485.

Chemical Properties

Physical AppearanceA solid
StorageStore at -20°C
M.Wt705.63
Cas No.84625-61-6
FormulaC35H38Cl2N8O4
Solubility≥8.83mg/mL in DMSO
Chemical Name2-butan-2-yl-4-[4-[4-[4-[[(2R,4S)-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
SDFDownload SDF
Canonical SMILESCCC(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
运输条件试用装:蓝冰运输。 其他可选规格:常温运输或根据您的要求用蓝冰运输。
一般建议为了使其更好的溶解,请用37℃加热试管并在超声波水浴中震动片刻。不同厂家不同批次产品溶解度各有差异,仅做参考。若实验所需浓度过大至产品溶解极限,请添加助溶剂助溶或自行调整浓度。

试验操作

细胞实验 [1]:

细胞系

C. glabrata,C. kefyr

溶解方法

该化合物在DMSO中的溶解度大于8.8 mg/mL。若获取更高浓度的溶液,可在37℃下孵育10分钟,随后在超声波浴中摇匀。-20℃以下可储存数月。

反应条件

0.016 μg/ml

应用

Itraconazole对玻璃青光眼206种分离株具有抗真菌活性。对于144个分离株,从数据库中可以寻找到两个或更多个重复测试结果。在五个重复测试中,在C.kefyr的两个生物测定菌株SA和ATCC 46764中,Itraconazole的IC50为0.016 mg/L。

动物实验 [2]:

动物模型

传播性念珠菌病CD1小鼠模型

给药剂量

5 mg/kg,每天两次,持续5天

应用

ITZ治疗导致每克肾脏CFU数量降低。在用ITZ处理的小鼠中,在10只用菌株Sr和分离物B接种的小鼠中,7只小鼠存活。

注意事项

由于实验环境的不同,实际溶解度可能与理论值略有不同,请测试室内所有化合物的溶解度。

References:

[1]. Odds F C, Bossche H V. Antifungal activity of itraconazole compared with hydroxy-itraconazole in vitro[J]. Journal of Antimicrobial Chemotherapy, 2000, 45(3): 371-373.

[2]. Valentin A, Le Guennec R, Rodriguez E, et al. Comparative resistance of Candida albicans clinical isolates to fluconazole and itraconazole in vitro and in vivo in a murine model[J]. Antimicrobial agents and chemotherapy, 1996, 40(6): 1342-1345.

质量控制

化学结构

Itraconazole