CAS 125-84-8|3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione|3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione|3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dione|DL-Aminoglutethimide|aminoglutethimide|Cytadren...

基本信息

化学结构

分子式

C₁₃H₁₆N₂O₂

分子量

232.27834

精确质量

232.12117776

电荷

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

Canonic Smiles

CCC1(CCC(=O)NC1=O)c1ccc(cc1)N

Isomeric Smiles

O=C1NC(=O)CCC1(CC)c1ccc(N)cc1

计算属性

JChem

LogD (pH = 7.4)

1.30

LogD (pH = 5.5)

1.27

Log P

1.30

可自由旋转的化学键

质子供体

质子受体

里宾斯基五规则

true

Acid pKa

4.28

极化表面积

72.19

极化性

24.72

摩尔折射率

65.35

LOG S

-2.12

数据来源

名称和标识

IUPAC标准名

3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione

别名

3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedioneDL-Aminoglutethimide3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dioneAminoglutethimideDl-AminoglutethimideP-AminoglutethimideAminoglutethimide (Cytadren)(±)-p-AMINOGLUTETHIMIDE3-(4-aminophenyl)-3-ethylpiperidine-2,6-dioneEliptenAminoglutethimideCytadrenOrimetenalpha-(p-Aminophenyl)-alpha-ethylglutarimide3-Ethyl-3-(p-aminophenyl)-2,6-dioxopiperidineP-Aminoglutethimide2-(p-Aminophenyl)-2-ethylglutarimideaminoglutethimidep-AminoglutethimideDL-Aminoglutethimide

IUPAC传统名

aminoglutethimide 3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione

商标名

CytadrenEliptenOrimeten

API名称

Aminoglutethimide

国际非专利药品(INN)

aminoglutetimidaaminoglutethimideaminoglutethimidum

名称和标识

数据登录号

Chemspider ID

维基百科标题

CHEBI ID

KEGG ID

DrugBank ID

PubChem CID

美国药典/FDA物质标识码

MDL号

CAS号

CHEMBL

Medline Plus

ATC码

PubChem SID

160963704242781424650606687322622

EC号

204-756-4

BRENDA数据库

1.14.15.181.14.15.151.14.14.141.17.3.21.14.15.6

SABIO-RK数据库

3392

Beilstein号

210656

KEGG DRUG Database

D00574

PubMed文献链接

176026752435072711916226

专利号

Reaxys Registry

BRENDA Ligand数据库

ACToR数据库

MetaboLights数据库

CompTox数据库

BKMS React数据库

Drug Central Database

SureChEMBL数据库

LINCS数据库

HMDB数据库

数据登录号

化合物性质

产品相关信息

质检报告

下载链接

应用领域

Now used as aromatase inhibitor for treatment of breast cancer in postmenopausal women and for treatment of secondary hyperaldosteronism and oedema

Originally used as anticonvulsant, withdrawn due to adrenotoxicity.

Inhibits adrenal corticosteroid synthesis

95%

Free Base

化合物性质

分子相关蛋白质

暂无数据

点击上传数据

分子图谱

暂无数据

点击上传数据

描述信息

DrugBank

DB00357

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]

MP Biomedicals

02153645

Inhibitor of cytochrome P-450-dependent hydroxylation reactions.

Wikipedia

Aminoglutethimide

Sigma Aldrich

A9657

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.

TRC

A609810

An aromatase inhibitor. Also blocks adrenal steroidogenesis.

ChEBI

CHEBI:2654

A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.

描述信息

参考文献

PubChem文献

数据源提供

• Havlin, K.A. and Trump, D.L.: Cancer Threat. Res., 39, 83 (1988)

• Santen, R.J. and Misbin, R.I.: Pharmacotherapy, 1, 95 (1981)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AKC600

• Santen, R.J. et al., Pharmanual (Basel), Vol. 2: A Comprehensive Guide to the Therapeutic Use of Aminoglutethimide, Karger, Basel, Switz., 1981, (book)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 454

• Aboul-Enein, H.Y. et al., J. Med. Chem., 1975, 18, 736, (synth, pharmacol)

• Aboul-Enein, H.Y., Anal. Profiles Drug Subst., 1986, 15, 35, (rev)

• Lee, C.M. et al., J.A.C.S., 1961, 83, 4586, (uv, ir)

• Chang, M.-Y. et al., Tet. Lett., 2000, 41, 10273-10276, (synth)

• Ruecker, G. et al., Arch. Pharm. (Weinheim, Ger.), 1969, 302, 204, (ms)

• Defay, N. et al., J. Pharm. Belg., 1972, 27, 335, (pmr)

• Van Roey, P. et al., Acta Cryst. C, 1991, 47, 829, (cryst struct, bibl)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 404A, (ir)

• Salhanick, H.A., Cancer Res., 1982, 42, 3315, (pharmacol)

• Bushell, S.M. et al., Tetrahedron, 1998, 54, 2269-2274, (synth, ir, pmr, cmr)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1456C, (nmr)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC标准名

3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione

别名

IUPAC传统名

aminoglutethimide 3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione

商标名

CytadrenEliptenOrimeten

API名称

Aminoglutethimide

国际非专利药品(INN)

aminoglutetimidaaminoglutethimideaminoglutethimidum

数据登录号

Chemspider ID

维基百科标题

CHEBI ID

KEGG ID

DrugBank ID

PubChem CID

美国药典/FDA物质标识码

MDL号

CAS号

CHEMBL

Medline Plus

ATC码

PubChem SID

160963704242781424650606687322622

EC号

204-756-4

BRENDA数据库

1.14.15.181.14.15.151.14.14.141.17.3.21.14.15.6

SABIO-RK数据库

3392

Beilstein号

210656

KEGG DRUG Database

D00574

PubMed文献链接

176026752435072711916226

专利号

Reaxys Registry

BRENDA Ligand数据库

ACToR数据库

MetaboLights数据库

CompTox数据库

BKMS React数据库

Drug Central Database

SureChEMBL数据库

LINCS数据库

HMDB数据库

描述信息

DB00357

Drug Groups

approved

Description

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

Toxicity

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]

MP Biomedicals

02153645

Inhibitor of cytochrome P-450-dependent hydroxylation reactions.

A9657

A609810

An aromatase inhibitor. Also blocks adrenal steroidogenesis.

ChEBI

CHEBI:2654

A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.

参考文献

PubChem文献

数据源提供

• Havlin, K.A. and Trump, D.L.: Cancer Threat. Res., 39, 83 (1988)

• Santen, R.J. and Misbin, R.I.: Pharmacotherapy, 1, 95 (1981)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, AKC600

• Santen, R.J. et al., Pharmanual (Basel), Vol. 2: A Comprehensive Guide to the Therapeutic Use of Aminoglutethimide, Karger, Basel, Switz., 1981, (book)

• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 454

• Aboul-Enein, H.Y. et al., J. Med. Chem., 1975, 18, 736, (synth, pharmacol)

• Aboul-Enein, H.Y., Anal. Profiles Drug Subst., 1986, 15, 35, (rev)

• Lee, C.M. et al., J.A.C.S., 1961, 83, 4586, (uv, ir)

• Chang, M.-Y. et al., Tet. Lett., 2000, 41, 10273-10276, (synth)

• Ruecker, G. et al., Arch. Pharm. (Weinheim, Ger.), 1969, 302, 204, (ms)

• Defay, N. et al., J. Pharm. Belg., 1972, 27, 335, (pmr)

• Van Roey, P. et al., Acta Cryst. C, 1991, 47, 829, (cryst struct, bibl)

• Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 404A, (ir)

• Salhanick, H.A., Cancer Res., 1982, 42, 3315, (pharmacol)

• Bushell, S.M. et al., Tetrahedron, 1998, 54, 2269-2274, (synth, ir, pmr, cmr)

• Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 2, 1456C, (nmr)

生物活性

PubChem BioAssay

化合物性质

产品相关信息

质检报告

下载链接

应用领域

Now used as aromatase inhibitor for treatment of breast cancer in postmenopausal women and for treatment of secondary hyperaldosteronism and oedema

Originally used as anticonvulsant, withdrawn due to adrenotoxicity.

Inhibits adrenal corticosteroid synthesis

95%

Free Base

化合物信息

ID:241