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125-84-8 molecular structure
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3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione

ChemBase ID: 241
Molecular Formular: C13H16N2O2
Molecular Mass: 232.27834
Monoisotopic Mass: 232.12117776
SMILES and 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

Cite this record

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

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione
IUPAC Traditional name
3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione
aminoglutethimide
Brand Name
Cytadren
Elipten
Orimeten
Synonyms
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 Number
125-84-8
EC Number
204-756-4
MDL Number
MFCD00010122
PubChem SID
46506066
24278142
160963704
PubChem CID
2145
CHEBI ID
2654
ATC CODE
L02BG01
CHEMBL
488
Chemspider ID
2060
DrugBank ID
DB00357
KEGG ID
D00574
Unique Ingredient Identifier
0O54ZQ14I9
Wikipedia Title
Aminoglutethimide
Medline Plus
a604039

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 11.691995  H Acceptors
H Donor LogD (pH = 5.5) 1.2744231 
LogD (pH = 7.4) 1.2991968  Log P 1.2995443 
Molar Refractivity 65.3543 cm3 Polarizability 24.911802 Å3
Polar Surface Area 72.19 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.49  LOG S -2.8 
Solubility (Water) 3.71e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.1 M HCl: soluble expand Show data source
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble1.2 mg/mL expand Show data source
acetonitrile: soluble expand Show data source
Chloroform expand Show data source
Dichloromethane expand Show data source
DMSO expand Show data source
Ethyl Acetate expand Show data source
H2O: slightly soluble0.2 mg/mL expand Show data source
Hexane expand Show data source
methanol: soluble expand Show data source
Practically insoluble in water expand Show data source
Apperance
white expand Show data source
White to Off-White Solid expand Show data source
Melting Point
149-150°C expand Show data source
152 - 154°C expand Show data source
152-154 °C(lit.) expand Show data source
Hydrophobicity(logP)
0.766 expand Show data source
1.3 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
MA4026950 expand Show data source
European Hazard Symbols
Irritant Irritant (Xi) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
36/37/38 expand Show data source
Safety Statements
26-36 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H315-H319-H335 expand Show data source
GHS Precautionary statements
P261-P305 + P351 + P338 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Target
Aromatase expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
>95% expand Show data source
Excretion
Renal expand Show data source
Half Life
12.5 ± 1.6 hours expand Show data source
Metabolism
Hepatic expand Show data source
Pregnancy Category
D (Australia) expand Show data source
D (US) expand Show data source
Gene Information
human ... CYP17A1(1586), CYP19A1(1588)rat ... Cyp19a1(25147) expand Show data source
Mechanism of Action
Androgen synthesis inhibitor expand Show data source
Aromatase inhibitor expand Show data source
Cholesterol desmolase inhibitor expand Show data source
Corticosteroid antagonist expand Show data source
Corticosteroid synthesis inhibitor expand Show data source
Inhibits hydroxylations required for aromatization of androgens to estrogens expand Show data source
Mineralocorticoid synthesis inhibitor expand Show data source
Purity
95% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Inhibits adrenal corticosteroid synthesis expand Show data source
Now used as aromatase inhibitor for treatment of breast cancer in postmenopausal women and for treatment of secondary hyperaldosteronism and oedema expand Show data source
Originally used as anticonvulsant, withdrawn due to adrenotoxicity. expand Show data source

DETAILS

DETAILS

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.

REFERENCES

REFERENCES

From Suppliers 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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PATENTS

PATENTS

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