Aminoglutethimide

Base Information

• Chemical Name: Aminoglutethimide
• CAS No.: 125-84-8
• Molecular Formula: C13H16N2O2
• Molecular Weight: 232.282
• Hs Code.: 2925190100
• European Community (EC) Number: 204-756-4
• NSC Number: 755868,330915
• UNII: 0O54ZQ14I9
• DSSTox Substance ID: DTXSID8022589
• Nikkaji Number: J5.378C
• Wikipedia: Aminoglutethimide
• Wikidata: Q241150
• NCI Thesaurus Code: C233
• Pharos Ligand ID: 9DBHHYR7P7DA
• Metabolomics Workbench ID: 138657
• ChEMBL ID: CHEMBL488
• Mol file: 125-84-8.mol

Synonyms:Aminoglutethimide;Cytadren;Orimeten

Chemical Property of Aminoglutethimide

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 1.5E-08mmHg at 25°C
• Melting Point: 152-154 °C(lit.)
• Refractive Index: 1.566
• Boiling Point: 457.4 °C at 760 mmHg
• PKA: 11.60±0.40(Predicted)
• Flash Point: 230.4 °C
• PSA: 72.19000
• Density: 1.173 g/cm³
• LogP: 2.26320
• Storage Temp.: 2-8°C
• Solubility.: H2O: 0.2 mg/mL, slightly soluble
• Water Solubility.: Soluble in water (2 mg/ml at 20°C), methanol (50 mg/ml), ethanol (7 mg/ml at 25°C), DMSO (20 mg/ml at 25°C), and chloroform.
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 232.121177757
• Heavy Atom Count: 17
• Complexity: 321

Purity/Quality:

99.9% ^*data from raw suppliers

Aminoglutethimide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1(CCC(=O)NC1=O)C2=CC=C(C=C2)N
• Recent ClinicalTrials: Randomized Study Comparing Tamoxifen vs. Tamoxifen + Aminoglutethimide in Postmenopausal Receptor-positive Patients
• Description: Aminoglutethimide is an aromatase inhibitor (IC50 = 7.5 μM). Aromatase inhibitors, including aminoglutethimide, inhibit estrogen synthesis via aromatase, suppressing estrogen levels in post-menopausal women. Formulations containing aromatase inhibitors have been used to treat estrogen receptor-positive breast cancer in post-menopausal women.
• Uses: Aminoglutethimide is used to decrease the production of sex hormones and suppress the growth of tumors that need sex hormones to grow. It blocks the production of steroids derived from cholesterol and is clinically used in the treatment of Cushing's syndrome and metastatic breast cancer. It is also a drug of abuse by body builders. An aromatase inhibitor. Also blocks adrenal steroidogenesis aromatase inhibitor, antineoplastic, testosterone suppressant
• Indications: Aminoglutethimide (Cytadren) is a competitive inhibitor of desmolase, the enzyme that catalyzes the conversion of cholesterol to pregnenolone; it also inhibits 11-hydroxylase activity.This drug also reduces estrogen production by inhibiting the aromatase enzyme complex in peripheral (skin, muscle, fat) and steroid target tissues.
• Therapeutic Function: Cytostatic
• Clinical Use: Aminoglutethimide is suitable for use in Cushing’s syndrome that results from adrenal carcinoma and in congenital adrenal hyperplasia, in which it protects the patient from excessive secretion of endogenous androgens. The drug is not curative, and relapse occurs when treatment is terminated. Since aminoglutethimide therapy is frequently associated with mineralocorticoid deficiency, mineralocorticoid supplements may be needed. Aminoglutethimide and metyrapone are frequently used in combination at lower doses of both drugs as an adjunct to radiation or surgical therapy.

Technology Process of Aminoglutethimide

There total 17 articles about Aminoglutethimide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

dimethyl 2-(1-((4-(3-ethyl-2,6-dioxopiperidin-3-yl)phenyl)amino)hex-5-yn-1-ylidene)malonate → aminoglutethimide (125-84-8)

Guidance literature:

With acetic acid; at 20 ℃; for 1h;

DOI:10.1002/chem.201902699

Reference yield: 95.0%

rac-3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione (38527-73-0) → aminoglutethimide (125-84-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 1h; under 760 Torr;

DOI:10.1016/S0040-4039(99)00590-0

Reference yield: 81.0%

→ 3-ethyl-3-(4-{(Z)-[(2-oxo-2,3-dihydro-1H-pyrrolo[3,2-f]quinolin-1-ylidene)methyl]amino}phenyl)-2,6-piperidinedione (297756-95-7) + aminoglutethimide (125-84-8)

Guidance literature:

upstream raw materials:

rac-3-ethyl-3-(4-nitrophenyl)piperidine-2,6-dione

1-hydroxy-3-ethyl-3-(4-aminophenyl)piperidine-2,6-dione

2-(4-Nitrophenyl)-buttersaeureethylester

nitrobenzene

Downstream raw materials:

p-amino-m-hydroxyglutethimide

3-(4-amino-3-iodo-phenyl)-3-ethyl-piperidine-2,6-dione

3-Ethyl-3-(4-{(Z)-[(7-oxo-6,7-dihydro-8H-[1,3]thiazolo[5,4-e]indol-8-ylidene)methyl]amino}phenyl)-2,6-piperidinedione

3-ethyl-3-(4-{(Z)-[(2-oxo-2,3-dihydro-1H-pyrrolo[3,2-f]quinolin-1-ylidene)methyl]amino}phenyl)-2,6-piperidinedione

Refernces

• 1、 Flaih, Nazar,Pham-Huy, Chuong,Galons, Herve. "An expeditious synthesis of cyclic imides". . p. 3697 - 3698. Retrieved 1999.
• 2、 Bushell, Simon M.,Crump, J. Paul,Lawrence, Nicholas J.,Pineau, Guillaume. "The synthesis of (±)-aminoglutethimide via vicarious nucleophilic aromatic substitution of hydrogen". . p. 2269 - 2274. Retrieved 2007/10/03.