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125-84-8 分子结构
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3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione

ChemBase编号:241
分子式:C13H16N2O2
平均质量:232.27834
单一同位素质量:232.12117776
SMILES和InChIs

SMILES:
O=C1NC(=O)CCC1(CC)c1ccc(N)cc1
Canonical SMILES:
CCC1(CCC(=O)NC1=O)c1ccc(cc1)N
InChI:
InChI=1S/C13H16N2O2/c1-2-13(8-7-11(16)15-12(13)17)9-3-5-10(14)6-4-9/h3-6H,2,7-8,14H2,1H3,(H,15,16,17)
InChIKey:
ROBVIMPUHSLWNV-UHFFFAOYSA-N

引用这个纪录

CBID:241 http://www.chembase.cn/molecule-241.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione
IUPAC传统名
3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione
aminoglutethimide
商标名
Cytadren
Elipten
Orimeten
别名
Cytadren
Elipten
Orimeten
Aminoglutethimide
DL-Aminoglutethimide
3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione
3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dione
(±)-p-AMINOGLUTETHIMIDE
3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione
Aminoglutethimide (Cytadren)
Dl-Aminoglutethimide
P-Aminoglutethimide
Aminoglutethimide
CAS号
125-84-8
EC号
204-756-4
MDL号
MFCD00010122
PubChem SID
160963704
24278142
46506066
PubChem CID
2145
CHEBI ID
2654
ATC码
L02BG01
CHEMBL
488
Chemspider ID
2060
DrugBank ID
DB00357
KEGG ID
D00574
美国药典/FDA物质标识码
0O54ZQ14I9
维基百科标题
Aminoglutethimide
Medline Plus
a604039

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 11.691995  质子受体
质子供体 LogD (pH = 5.5) 1.2744231 
LogD (pH = 7.4) 1.2991968  Log P 1.2995443 
摩尔折射率 65.3543 cm3 极化性 24.911802 Å3
极化表面积 72.19 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.49  LOG S -2.8 
溶解度 3.71e-01 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
0.1 M HCl: soluble expand 查看数据来源
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble1.2 mg/mL expand 查看数据来源
acetonitrile: soluble expand 查看数据来源
Chloroform expand 查看数据来源
Dichloromethane expand 查看数据来源
DMSO expand 查看数据来源
Ethyl Acetate expand 查看数据来源
H2O: slightly soluble0.2 mg/mL expand 查看数据来源
Hexane expand 查看数据来源
methanol: soluble expand 查看数据来源
Practically insoluble in water expand 查看数据来源
外观
white expand 查看数据来源
White to Off-White Solid expand 查看数据来源
熔点
149-150°C expand 查看数据来源
152 - 154°C expand 查看数据来源
152-154 °C(lit.) expand 查看数据来源
疏水性(logP)
0.766 expand 查看数据来源
1.3 expand 查看数据来源
保存条件
-20°C Freezer expand 查看数据来源
Room Temperature (15-30°C) expand 查看数据来源
RTECS编号
MA4026950 expand 查看数据来源
欧盟危险性物质标志
刺激性(Irritant) 刺激性(Irritant) (Xi) expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
3 expand 查看数据来源
危险公开号
36/37/38 expand 查看数据来源
安全公开号
26-36 expand 查看数据来源
GHS危险品标识
GHS07 expand 查看数据来源
GHS警示词
Warning expand 查看数据来源
GHS危险声明
H315-H319-H335 expand 查看数据来源
GHS警示性声明
P261-P305 + P351 + P338 expand 查看数据来源
个人保护装置
dust mask type N95 (US), Eyeshields, Gloves expand 查看数据来源
作用靶点
Aromatase expand 查看数据来源
给药途径
Oral expand 查看数据来源
生物利用度
>95% expand 查看数据来源
排泄
Renal expand 查看数据来源
半衰期
12.5 ± 1.6 hours expand 查看数据来源
代谢
Hepatic expand 查看数据来源
妊娠期药物分类
D (Australia) expand 查看数据来源
D (US) expand 查看数据来源
相关基因信息
human ... CYP17A1(1586), CYP19A1(1588)rat ... Cyp19a1(25147) expand 查看数据来源
生物活性机理
Androgen synthesis inhibitor expand 查看数据来源
Aromatase inhibitor expand 查看数据来源
Cholesterol desmolase inhibitor expand 查看数据来源
Corticosteroid antagonist expand 查看数据来源
Corticosteroid synthesis inhibitor expand 查看数据来源
Inhibits hydroxylations required for aromatization of androgens to estrogens expand 查看数据来源
Mineralocorticoid synthesis inhibitor expand 查看数据来源
纯度
95% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
应用领域
Inhibits adrenal corticosteroid synthesis expand 查看数据来源
Now used as aromatase inhibitor for treatment of breast cancer in postmenopausal women and for treatment of secondary hyperaldosteronism and oedema expand 查看数据来源
Originally used as anticonvulsant, withdrawn due to adrenotoxicity. expand 查看数据来源

详细说明

详细说明

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals -  02153645 external link
Inhibitor of cytochrome P-450-dependent hydroxylation reactions.
DrugBank -  DB00357 external link
Item Information
Drug Groups approved
Description An aromatase inhibitor that produces a state of "medical" adrenalectomy by blocking the production of adrenal steroids. It also blocks the conversion of androgens to estrogens. Aminoglutethimide has been used in the treatment of advanced breast and prostate cancer. It was formerly used for its weak anticonvulsant properties. (From Martindale, The Extra Pharmacopoeia, 30th ed, p454)
Indication For the suppression of adrenal function in selected patients with Cushing's syndrome, malignant neoplasm of the female breast, and carcinoma in situ of the breast.
Pharmacology Aminoglutethimide inhibits the enzymatic conversion of cholesterol to D5-pregnenolone, resulting in a decrease in the production of adrenal glucocorticoids, mineralocorticoids, estrogens, and androgens.
Toxicity Oral LD50s (mg/kg): rats, 1800; dogs, >100. Intravenous LD50s (mg/kg): rats, 156; dogs, >100. Symptoms of overdose include respiratory depression, hypoventilation, hypotension, hypovolemic shock due to dehydration, somnolence, lethargy, coma, ataxia, dizziness, fatigue, nausea, and vomiting.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. 34-54% of the administered dose is excreted in the urine as unchanged drug during the first 48 hours, and an additional fraction as an N-acetyl derivative.
Absorption Rapidly and completely absorbed from gastrointestinal tract. The bioavailability of tablets is equivalent to equal doses given as a solution.
Half Life 12.5 ± 1.6 hours
Protein Binding 21-25%
Elimination After ingestion of a single oral dose, 34%-54% is excreted in the urine as unchanged drug during the first 48 hours, and an additional fraction as the N-acetyl derivative.
External Links
Wikipedia
RxList
Drugs.com
Sigma Aldrich -  A9657 external link
Biochem/physiol Actions
DL-Aminoglutethimide is a derivative of the sedative glutethimide. Originally introduced as an anticonvulsant, it was found to cause adrenal insufficiency. Blocks adrenal steroidogenesis by inhibiting the enzymatic conversion of cholesterol to pregnenolone. It also blocks the peripheral conversion (aromatization) of androgenic precursors to estrogens. The D-isomer is 30 times more potent at inhibiting aromatase activity, whereas the L-isomer is more potent at inhibiting cholesterol side-chain cleavage (steroidogenesis).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. A9657.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals -  A609810 external link
An aromatase inhibitor. Also blocks adrenal steroidogenesis.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Santen, R.J. and Misbin, R.I.: Pharmacotherapy, 1, 95 (1981)
  • Havlin, K.A. and Trump, D.L.: Cancer Threat. Res., 39, 83 (1988)
  • Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 404A, (ir)
  • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1456C, (nmr)
  • Lee, C.M. et al., J.A.C.S., 1961, 83, 4586, (uv, ir)
  • Ruecker, G. et al., Arch. Pharm. (Weinheim, Ger.), 1969, 302, 204, (ms)
  • Defay, N. et al., J. Pharm. Belg., 1972, 27, 335, (pmr)
  • Aboul-Enein, H.Y. et al., J. Med. Chem., 1975, 18, 736, (synth, pharmacol)
  • Santen, R.J. et al., Pharmanual (Basel), Vol. 2: A Comprehensive Guide to the Therapeutic Use of Aminoglutethimide, Karger, Basel, Switz., 1981, (book)
  • Salhanick, H.A., Cancer Res., 1982, 42, 3315, (pharmacol)
  • Aboul-Enein, H.Y., Anal. Profiles Drug Subst., 1986, 15, 35, (rev)
  • Van Roey, P. et al., Acta Cryst. C, 1991, 47, 829, (cryst struct, bibl)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 454
  • Bushell, S.M. et al., Tetrahedron, 1998, 54, 2269-2274, (synth, ir, pmr, cmr)
  • Chang, M.-Y. et al., Tet. Lett., 2000, 41, 10273-10276, (synth)
  • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AKC600
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