Compound: aminoglutethimide
SMILES: O=C1NC(=O)CCC1(c2ccc(N)cc2)CC
InChIKey: ROBVIMPUHSLWNV-UHFFFAOYSA-N
Synonyms: aminoglutethimide, 125-84-8, dl-Aminoglutethimide, Cytadren, Orimeten, p-Aminoglutethimide, Elipten, 3-(4-aminophenyl)-3-ethylpiperidine-2,6-dione, Aminoglutetimida, 2,6-Piperidinedione, 3-(4-aminophenyl)-3-ethyl-, 3-(4-Aminophenyl)-3-ethyl-2,6-piperidinedione, Aminoglutethimidum, 2-(p-Aminophenyl)-2-ethylglutarimide, Ba-16038, Aminoglutetimide, 3-Ethyl-3-(p-aminophenyl)-2,6-dioxopiperidine, NSC-330915, DTXSID8022589, 0O54ZQ14I9, alpha-(p-Aminophenyl)-alpha-ethylglutarimide, CHEBI:2654, DTXCID202589, NSC330915, Aminoblastin, Mamomit, Orimenten, Orimetene, Rodazol, RefChem:57317, alpha-(4-Aminophenyl)-alpha-ethylglutarimide, 204-756-4, Glutethimide, para-amino, 3-(4-aminophenyl)-3-ethyl-piperidine-2,6-dione, MFCD00010122, AG-1, Glutarimide, 2-(p-aminophenyl)-2-ethyl-, CHEMBL488, (+/-)-p-AMINOGLUTETHIMIDE, .alpha.-(p-Aminophenyl)-.alpha.-ethylglutarimide, (RS)-2-(4-Amino-phenyl)-2-ethyl-glutarimide;(RS)-3-(4-Amino-phenyl)-3-ethyl-2,6-dioxo-piperidine, Aminoglutethimidum [INN-Latin], Aminoglutetimida [INN-Spanish], Ba 16038, Cytadren (TN), SMR000326785, C 16038-BA, CCRIS 7562, aminoglutethimide (AG), SR-01000075596, 3-(4-Aminophenyl)-3-ethyl-2,6-piperidindion, EINECS 204-756-4, BRN 0210656, Aminoglutethimide (USP/INN), UNII-0O54ZQ14I9, Cytadren;, Elipten;, HSDB 7494, 3-(p-Aminophenyl)-3-ethylpiperidine-2,6-dione, Aminoglutethimide [USP:INN:BAN], NCGC00016379-01, CAS-125-84-8, Prestwick_243, Spectrum_000040, (y)-p-Aminoglutethimide, Aminoglutethimide AG, 4, (?)-p-Aminoglutethimide, Prestwick0_000244, Prestwick1_000244, Prestwick2_000244, Prestwick3_000244, Spectrum2_000093, Spectrum3_000296, Spectrum4_000144, Spectrum5_000802, A 9657, SCHEMBL4306, Aminoglutethimide (Cytadren), Lopac0_000124, BSPBio_000028, BSPBio_001832, KBioGR_000588, KBioSS_000400, (A+/-)-p-Aminoglutethimide, MLS000859924, MLS001213216, AMINOGLUTETHIMIDE [MI], DivK1c_000884, SPECTRUM1500115, SPBio_000046, SPBio_002247, AMINOGLUTETHIMIDE [INN], BDBM9460, BPBio1_000032, GTPL7054, orb1309763, AMINOGLUTETHIMIDE [HSDB], AMINOGLUTETHIMIDE [VANDF], HMS502M06, KBio1_000884, KBio2_000400, KBio2_002968, KBio2_005536, KBio3_001332, AMINOGLUTETHIMIDE [MART.], NINDS_000884, AMINOGLUTETHIMIDE [WHO-DD], HMS1568B10, HMS1920C09, HMS2090I05, HMS2091I09, HMS2095B10, HMS2231M19, HMS3259H10, HMS3260I10, HMS3372M07, HMS3655O17, HMS3712B10, Pharmakon1600-01500115, HY-B0237, 2, 3-(4-aminophenyl)-3-ethyl-, Tox21_110406, Tox21_303497, Tox21_500124, BBL010961, CCG-38911, EBC-03739, NSC755868, SBB000711, STK802074, Aminoglutethimide - Bio-X trade mark, AKOS004120070, AKOS022060651, Tox21_110406_1, AMINOGLUTETHIMIDE [EP IMPURITY], AMINOGLUTETHIMIDE [ORANGE BOOK], DB00357, FA17754, LP00124, NC00714, NSC 330915, NSC 755868, NSC-755868, PB48252, SDCCGSBI-0050112.P005, AMINOGLUTETHIMIDE [EP MONOGRAPH], AMINOGLUTETHIMIDE [USP IMPURITY], IDI1_000884, SMP1_000017, NCGC00015110-02, NCGC00015110-03, NCGC00015110-04, NCGC00015110-05, NCGC00015110-06, NCGC00015110-07, NCGC00015110-09, NCGC00015110-12, NCGC00015110-21, NCGC00015110-24, NCGC00093615-01, NCGC00093615-02, NCGC00093615-03, NCGC00093615-04, NCGC00093615-05, NCGC00257263-01, NCGC00260809-01, AC-12456, AS-13282, BA164155, NCI60_002900, SBI-0050112.P004, DB-021640, DB-072002, DB-072275, A1947, AB00051935, EU-0100124, NS00010649, S1672, SW196550-3, ( inverted question mark)-p-Aminoglutethimide, EN300-53368, VU0243029-3, C07617, D00574, D88489, AB00051935-09, AB00051935-11, AB00051935_12, AB00051935_13, Q241150, 3-(4-aminophenyl)-3-ethylazaperhydroine-2,6-dione, SR-01000075596-1, SR-01000075596-4, SR-01000075596-6, BRD-A25234499-001-05-0, BRD-A25234499-001-09-2, BRD-A25234499-001-17-5, BRD-A25234499-001-18-3, BRD-A25234499-001-19-1, Z800191876, Aminoglutethimide, European Pharmacopoeia (EP) Reference Standard, Aminoglutethimide, United States Pharmacopeia (USP) Reference Standard
Theoretical properties:
molecular_formula: C13H16N2O2
molecular_weight: 232.28 g/mol
exact_mass: 232.121177757 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 2
heavy_atom_count: 17
topological_polar_surface_area: 72.2 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Cyrstals from methanol or ethyl acetate
color: Cyrstals from methanol or ethyl acetate
melting_point: 223-225
solubility: Practically insoluble in water
Descriptions:
{"pubchem": "Aminoglutethimide can cause developmental toxicity according to state or federal government labeling requirements.", "chebi": "A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.", "chembl": "AMINOGLUTETHIMIDE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Aminoglutethimide (AG), sold under the brand names Elipten, Cytadren, and Orimeten among others, is a medication which has been used in the treatment of seizures, Cushing's syndrome, breast cancer, and prostate cancer, among other indications. It has also been used by bodybuilders, athletes, and other men for muscle-building and performance- and physique-enhancing purposes. AG is taken by mouth three or four times per day.\nSide effects of AG include lethargy, somnolence, dizziness, headache, appetite loss, skin rash, hypertension, liver damage, and adrenal insufficiency, among others. AG is both an anticonvulsant and a steroidogenesis inhibitor. In terms of the latter property, it inhibits enzymes such as cholesterol side-chain cleavage enzyme (CYP11A1, P450scc) and aromatase (CYP19A1), thereby inhibiting the conversion of cholesterol into steroid hormones and blocking the production of androgens, estrogens, and glucocorticoids, among other endogenous steroids. As such, AG is an aromatase inhibitor and adrenal steroidogenesis inhibitor, including both an androgen synthesis inhibitor and a corticosteroid synthesis inhibitor.\nAG was introduced for medical use, as an anticonvulsant, in 1960. It was withdrawn in 1966 due to toxicity. Its steroidogenesis-inhibiting properties were discovered serendipitously and it was subsequently repurposed for use in the treatment of Cushing's syndrome, breast cancer, and prostate cancer from 1969 and thereafter. However, although used in the past, it has mostly been superseded by newer agents with better efficacy and lower toxicity such as ketoconazole, abiraterone acetate, and other aromatase inhibitors. It remains marketed only in a few countries.\n\n"}