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...

General Information

Structure

Molecular Formula

C₁₃H₁₆N₂O₂

Molecular Mass

232.27834

Exact Mass

232.12117776

Charge

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

Calculated Properties

JChem

LogD (pH = 7.4)

1.30

LogD (pH = 5.5)

1.27

Log P

1.30

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

4.28

Polar Surface Area

72.19

Polarizability

24.72

Molar Refractivity

65.35

LOG S

-2.12

Data Source

Names and Identifiers

Synonyms

3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dioneDL-AminoglutethimideDl-AminoglutethimideP-AminoglutethimideAminoglutethimideAminoglutethimide (Cytadren)(±)-p-AMINOGLUTETHIMIDE3-(4-aminophenyl)-3-ethylpiperidine-2,6-dioneCytadrenEliptenOrimetenAminoglutethimide3-Ethyl-3-(p-aminophenyl)-2,6-dioxopiperidinealpha-(p-Aminophenyl)-alpha-ethylglutarimideP-Aminoglutethimideaminoglutethimidep-Aminoglutethimide2-(p-Aminophenyl)-2-ethylglutarimideDL-Aminoglutethimide

IUPAC name

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

IUPAC Traditional name

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

Brand Name

CytadrenEliptenOrimeten

API Name

Aminoglutethimide

International Nonproprietary Name (INN)

aminoglutetimidaaminoglutethimideaminoglutethimidum

Names and Identifiers

Registration numbers

Chemspider ID

Wikipedia Title

CHEBI ID

KEGG ID

DrugBank ID

PubChem CID

Unique Ingredient Identifier

MDL Number

CAS Number

CHEMBL

Medline Plus

ATC CODE

PubChem SID

160963704242781424650606687322622

EC Number

204-756-4

BRENDA Database

1.14.15.181.14.15.151.14.14.141.17.3.21.14.15.6

SABIO-RK Database

3392

Beilstein Number

210656

KEGG DRUG Database

D00574

PubMed Citation Links

176026752435072711916226

Patent number

US2848455

Reaxys Registry

210656

BRENDA Ligand Database

124968

ACToR Database

125-84-8

MetaboLights Database

MTBLS2406MTBLS1918

CompTox Database

DTXSID8022589

BKMS React Database

124968

Drug Central Database

SureChEMBL Database

LINCS Database

HMDB Database

Registration numbers

Properties

Product Information

Certificate of Analysis

Download link

Application(s)

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

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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.

Molecule Details

References

PubChem Literature

From Data Sources

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

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

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

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

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

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

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

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

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

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

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

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

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

• 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)

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

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC name

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

IUPAC Traditional name

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

Brand Name

CytadrenEliptenOrimeten

API Name

Aminoglutethimide

International Nonproprietary Name (INN)

aminoglutetimidaaminoglutethimideaminoglutethimidum

Registration numbers

Chemspider ID

Wikipedia Title

CHEBI ID

KEGG ID

DrugBank ID

PubChem CID

Unique Ingredient Identifier

MDL Number

CAS Number

CHEMBL

Medline Plus

ATC CODE

PubChem SID

160963704242781424650606687322622

EC Number

204-756-4

BRENDA Database

1.14.15.181.14.15.151.14.14.141.17.3.21.14.15.6

SABIO-RK Database

3392

Beilstein Number

210656

KEGG DRUG Database

D00574

PubMed Citation Links

176026752435072711916226

Patent number

US2848455

Reaxys Registry

210656

BRENDA Ligand Database

124968

ACToR Database

125-84-8

MetaboLights Database

MTBLS2406MTBLS1918

CompTox Database

DTXSID8022589

BKMS React Database

124968

Drug Central Database

SureChEMBL Database

LINCS Database

HMDB Database

Molecule Details

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.

References

PubChem Literature

From Data Sources

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

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

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

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

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

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

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

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

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

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

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

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

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

• 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)

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

Bioactivity

PubChem BioAssay

Properties

Product Information

Certificate of Analysis

Download link

Application(s)

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

Molecule

ID:241