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Merck
CN
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文件

K1003

Sigma-Aldrich

酮康唑

99.0-101.0% (EP, titration)

别名:

(±)-顺-1-乙酰基-4-(4-[(2-[2,4-二氯苯基]-2-[1H-咪唑-1-基甲基]-1,3-二氧戊环-4-基)-甲氧基]苯基)哌嗪

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About This Item

经验公式（希尔记法）:
C26H28Cl2N4O4
CAS号:
65277-42-1
分子量:
531.43
EC 号:
265-667-4
MDL编号:
MFCD00058579
UNSPSC代码:
51101500
PubChem化学物质编号:
24278176
NACRES:
NA.85

描述

Specific Optical Rotation (EP): (−0.10) ∼ +0.10 °

质量水平

200

检测方案

99.0-101.0% (EP, titration)

形式

powder

颜色

white to off-white

抗生素抗菌谱

Gram-positive bacteria
fungi
yeast

作用机制

enzyme | inhibits

储存温度

2-8°C

SMILES字符串

CC(=O)N1CCN(CC1)c2ccc(OC[C@H]3CO[C@@](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2

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

基因信息

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)

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相关类别

一般描述

化学结构：咪唑

应用

酮康唑是一种广谱抗真菌药，可用于治疗念珠菌病、慢性粘膜皮肤念珠菌病、口腔鹅口疮、念珠菌、芽生菌病、球孢子菌病、组织胞浆菌病、色素霉菌病和副球菌病。 它被用于鉴定猴模型中p-糖蛋白/CYP3A限制的生物利用度，研究白细胞介素1介导的抗肿瘤作用以及 体内药物相互作用
CYP3A4抑制剂

生化/生理作用

酮康唑能够与14-α去甲基化酶发生相互作用，这是一种细胞色素P-450酶，是羊毛甾醇转化为麦角甾醇所必需的酶。这种相互作用抑制了麦角甾醇合成并导致真菌细胞渗透性增强。其他可能的作用机制是抑制内源性呼吸、与膜磷脂的相互作用、抑制酵母转化为菌丝体形式、抑制嘌呤摄取以及破坏甘油三酯和/或磷脂生物合成。酮康唑可抑制血栓素和甾醇的合成，如醛固酮、皮质醇和睾酮。
抗真菌剂

警示用语：

Danger

危险分类

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - STOT RE 2

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

个人防护装备

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Flor Soriano-Agatón et al.
Journal of natural products, 68(11), 1581-1587 (2005-11-29)
Zanthoxylum chiloperone var. angustifolium was investigated. Alkaloids 1-3 from the canthin-6-one series were characterized. Derivatives 7-28 were prepared by hemisynthesis or total synthesis. All compounds were tested for in vitro antifungal activities against five pathogenic fungal strains. Analogues of canthin-6-one
Keith W Ward et al.
Drug metabolism and disposition: the biological fate of chemicals, 32(2), 172-177 (2004-01-28)
The effect of P-glycoprotein (Pgp) and/or CYP3A on the disposition of xenobiotics has been extensively investigated and is often of interest during drug discovery lead optimization. We have previously described a monkey pharmacokinetic screen to rapidly estimate absorption and first-pass
P G Braunschweiger et al.
Cancer research, 50(15), 4709-4717 (1990-08-01)
In the present studies, the regulatory role of adrenal hormones on the antitumor activity of recombinant human interleukin 1 alpha (IL-1 alpha) was investigated. Ketoconazole, a potent but transient inhibitor of adrenal steroid hormone biosynthesis, inhibited IL-1 alpha induced increases
Francisco M Garibotto et al.
Bioorganic & medicinal chemistry, 18(1), 158-167 (2009-12-05)
The synthesis, in vitro evaluation, and conformational study of a new series of small-size peptides acting as antifungal agents are reported. In a first step of our study we performed a conformational analysis using Molecular Mechanics calculations. The electronic study
L L von Moltke et al.
The Journal of pharmacology and experimental therapeutics, 268(3), 1278-1283 (1994-03-01)
Biotransformation of the tricyclic antidepressant desipramine (DMI) to its metabolite 2-hydroxy-desipramine (2-OH-DMI) was studied in vitro using microsomal preparations from human, monkey, mouse and rat liver. In all species 2-OH-DMI was the principal identified metabolite. Mean (+/- S.E.) reaction parameters
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