Aminoglutethimide
- CAS No.
- 125-84-8
- Chemical Name:
- Aminoglutethimide
- Synonyms
- 3-(4-AMINOPHENYL)-3-ETHYLPIPERIDINE-2,6-DIONE;Cytadren;AMINOGLUTETHAMIDE;DL-AMINOGLUTETHIMIDE;Elipten;Ba-16038;ORIMETEN;NSC-330915;AKOS NCG1-0032;AMINOGLUTETHIMIDE
- CBNumber:
- CB5131691
- Molecular Formula:
- C13H16N2O2
- Molecular Weight:
- 232.28
- MOL File:
- 125-84-8.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/7/2 8:55:10
| Melting point | 152-154 °C(lit.) |
|---|---|
| Boiling point | 374.44°C (rough estimate) |
| Density | 1.1099 (rough estimate) |
| refractive index | 1.6450 (estimate) |
| storage temp. | 2-8°C |
| solubility | H2O: 0.2 mg/mL, slightly soluble |
| form | Solid |
| pka | 11.60±0.40(Predicted) |
| color | white |
| 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. |
| Merck | 14,440 |
| CAS DataBase Reference | 125-84-8(CAS DataBase Reference) |
| NIST Chemistry Reference | Aminoglutethimide(125-84-8) |
| EPA Substance Registry System | Aminoglutethimide (125-84-8) |
SAFETY
Risk and Safety Statements
| Symbol(GHS) |  GHS07 |
|||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Signal word | Warning | |||||||||
| Hazard statements | H315-H319-H335 | |||||||||
| Precautionary statements | P261-P264-P271-P280-P302+P352-P305+P351+P338 | |||||||||
| Hazard Codes | Xi | |||||||||
| Risk Statements | 36/37/38 | |||||||||
| Safety Statements | 26-36 | |||||||||
| RIDADR | 3249 | |||||||||
| WGK Germany | 3 | |||||||||
| RTECS | MA4026950 | |||||||||
| HazardClass | 6.1(b) | |||||||||
| PackingGroup | III | |||||||||
| HS Code | 2925190100 | |||||||||
| NFPA 704 |
|
Aminoglutethimide price More Price(7)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich(India) | A9657 | DL-Aminoglutethimide | 125-84-8 | 100MG | ₹15523.05 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | PHR3173 | Aminoglutethimide pharmaceutical secondary standard, certified reference material | 125-84-8 | 500MG | ₹24572.75 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A9657 | DL-Aminoglutethimide | 125-84-8 | 500MG | ₹49675.93 | 2022-06-14 | Buy |
| Sigma-Aldrich(India) | A9657 | DL-Aminoglutethimide | 125-84-8 | 1G | ₹88321.18 | 2022-06-14 | Buy |
| ALFA India | ALF-J62182-14 | DL-Aminoglutethimide, 99% | 125-84-8 | 25g | ₹30418 | 2022-05-26 | Buy |
Aminoglutethimide Chemical Properties,Uses,Production
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.
Chemical Properties
White Solid
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.
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.
Definition
ChEBI: A dicarboximide that is a six-membered cyclic compound having ethyl and 4-aminophenyl substituents at the 3-position.
World Health Organization (WHO)
Aminoglutethimide, a weak anticonvulsant, was introduced in 1960 for use in the treatment of epilepsy. However, its adrenocortical suppressant activity gave rise to serious adverse effects. The FDA decision in 1966 was taken in respect of a preparation indicated in epilepsy. In 1980 preparations containing aminoglutethimide were reintroduced in the USA exclusively for the treatment of Cushing's disease. In 1986 they were also registered in Saudi Arabia for use in Cushing's syndrome and for the treatment of breast cancer. In some other countries these preparations are additionally approved for carcinoma of the prostate.
General Description
Aminoglutethimide, 3-(4-aminophenyl)-3-ethyl-2,6-piperidinedione, is mainly usedto treat Cushing syndrome, a condition of adrenal steroidexcess, a use in which the P450scc inhibition of thiscompound is exploited rather than its aromatase inhibition.Aminoglutethimide is a weak inhibitor of aromataseand has been used successfully in the treatment of estrogen-dependent breast cancer. Because of the developmentof more selective aromatase inhibitors, the use ofaminoglutethimide for its ability to inhibit aromatase is notsupported.
Mechanism of action
This drug blocks the transformation of cholesterol into pregnenolone, and androgens into estrogens in the adrenal glands, thus completely suppressing the production of all steroid hormones. Aminoglutethimide is used for palliative treatment of prostate carcinomas and post-menopausal breast carcinomas. Synonyms of aminoglutethimide are orimeten, citadren and others.
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.
Side effects
Such a medical adrenalectomy is an efficacious treatment for metastatic breast and prostate cancer, since it diminishes the levels of circulating sex hormones. Glucocorticoids are administered concomitantly to suppress enhanced corticotrophin release. Cortisol is preferable to dexamethasone in this situation because aminoglutethimide markedly enhances the hepatic microsomal metabolism of dexamethasone. Hepatic enzyme induction may be responsible for the development of tolerance to the side effects of aminoglutethimide, such as ataxia, lethargy, dizziness, and rashes.
Metabolic pathway
Following administration of a single oral dose of 14C- aminoglutethimide to rats, guinea pigs, rabbits, and man, more than 89% of the dose is excreted in urine and feces within 72h, and dogs eliminate only 51% in this time. Extensive metabolism occurs in all species, with N-acetylaminoglutethimide being the major metabolite except for dogs and man. In the latter two species, the unchanged drug is the main product excreted. As shown in the pathways, it appears that aminoglutethimide is metabolized by several pathways in man and, of the ten metabolites, only two are present in any quantity, namely N-acetylaminoglutethimide and N-hydroxyaminoglutethimide, the latter increasing during the course of treatment.
Aminoglutethimide Preparation Products And Raw materials
Raw materials
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chevron_rightPreparation Products
| Supplier | Tel | Country | ProdList | Advantage | Inquiry |
|---|---|---|---|---|---|
| TCI Chemicals (India) Pvt. Ltd. | 1800 425 7889 | New Delhi, India | 6778 | 58 | Inquiry |
| CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
| A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
| Alfa Aesar | 1 800 209 7001 | Maharashtra, India | 6913 | 58 | Inquiry |
| Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
| ChemGenix Laboratories Pvt. Ltd. | 91-6305240004 | Hyderabad, India | 14 | 58 | Inquiry |
| Clearsynth Labs | 91-22-45045900 | Maharashtra, India | 3889 | 58 | Inquiry |
| Merit International | 91-22-40150081 | Maharashtra, India | 226 | 58 | Inquiry |
| Pharma Affiliates | 172-5066494 | Haryana, India | 6761 | 58 | Inquiry |
| Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | China | 21676 | 55 | Inquiry |
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