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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號碼:
265-667-4
MDL號碼:
MFCD00058579
分類程式碼代碼:
51101500
PubChem物質ID:
24278176
NACRES:
NA.85

描述

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

品質等級

200

化驗

99.0-101.0% (EP, titration)

形狀

powder

顏色

white to off-white

抗生素活性譜

Gram-positive bacteria
fungi
yeast

作用方式

enzyme | inhibits

儲存溫度

2-8°C

SMILES 字串

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 密鑰

XMAYWYJOQHXEEK-OZXSUGGESA-N

基因資訊

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

一般說明

化学结构：咪唑

應用

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

訊號詞

Danger

危險分類

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

儲存類別代碼

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

水污染物質分類（WGK）

WGK 3

閃點（°F）

Not applicable

閃點（°C）

Not applicable

個人防護裝備

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

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Wendy W J van de Sande et al.
Antimicrobial agents and chemotherapy, 54(6), 2738-2740 (2010-03-31)
Eumycetoma caused by Madurella mycetomatis is treated surgically and with high doses of ketoconazole. Therapeutic responses are poor, and recurrent infections are common. In search of therapeutic alternatives in the treatment of mycetoma, we determined the in vitro susceptibilities of
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
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
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
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