Aminoglutethimide
3-(4-AMINOPHENYL)-3-ETHYLPIPERIDINE-2,6-DIONE · Cytadren · AMINOGLUTETHAMIDE · DL-AMINOGLUTETHIMIDE · Elipten · Ba-16038 · ORIMETEN · NSC-330915
식별자 및 물리적 특성
| CAS No. | 125-84-8 |
|---|---|
| 분자식 | C13H16N2O2 |
| 평균 분자량 | 232.28 g/mol |
| 단동위원소 질량 | 232.12117775 g/mol |
| SMILES | CCC1(c2ccc(N)cc2)CCC(=O)NC1=O |
| InChIKey | ROBVIMPUHSLWNV-UHFFFAOYSA-N |
| PubChem CID | 2145 |
| ChEMBL | CHEMBL488 |
| ChEBI | CHEBI:2654 |
| EC No. | 204-756-4 |
| DTXSID | DTXSID8022589 |
화학 및 물리적 성질
| XLogP | 1.2 |
|---|---|
| 극성 표면적 | 72.2 |
| 수소 결합 공여자 수 | 2 |
| 수소 결합 수용자 수 | 3 |
| 회전 가능 결합 수 | 2 |
| 무거운 원자 수 | 17 |
| 형식 전하 | 0 |
| 복잡도 | 321 |
| LogP(분배 계수) | 1.30.6 |
| Color/Form | Cyrstals from methanol or ethyl acetateFine, white or creamy white crystalline powder |
| 용해도 | Practically insoluble in waterFreely soluble in most organic solventspoorly soluble in ethyl acetate, 0.1N hydrochloric acid and absolute alcoholreadily soluble in acetone and 100% acetic acid. Practically insoluble in water.3.71e-01 g/L>34.8 [ug/mL] (The mean of the results at pH 7.4)H2O: 0.2 mg/mL, 약간 용해됨 |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomposition it emits toxic fumes of /nitrogen oxides/. |
| 녹는점 | 223-225159-150 °C149 - 150 °C152-154 °C(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 158.8 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID8022589]164.8 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]153.69 Ų [M+K]+ [CCS Type: TW |
| Other Experimental Properties | Hydroxyl radical reaction rate constant = 1.54X10-10 cu cm/molec-sec at 25 °C |
| 끓는 점 | 374.44°C (rough estimate) |
| 밀도 | 1.1099 (rough estimate) |
| 굴절률 | 1.6450 (estimate) |
| 저장 조건 | 2-8°C |
| pKa(산도 계수) | 11.60±0.40(Predicted) |
| 물리적 상태 | Solid |
| 색상 | 하얀색 |
| 생물학적 소스 | synthetic |
| 용해도 | 물(20°C에서 2mg/ml), 메탄올(50mg/ml), 에탄올(25°C에서 7mg/ml), DMSO(25°C에서 20mg/ml) 및 클로로포름에 용해됩니다. |
| Merck | 14,440 |
| 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 |
| SMILES | CCC1(CCC(=O)NC1=O)c2ccc(N)cc2 |
| NIST | Aminoglutethimide(125-84-8) |
| EPA | Aminoglutethimide (125-84-8) |
화학적 성질
White Solid
안전 및 규제
| GHS 분류 | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 42 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 규제 정보 | Hazard Traits - Developmental Toxicity |
| 기타 안전 정보 | IMAP assessments - 2,6-Piperidinedione, 3-(4-aminophenyl)-3-ethyl-: Environment tier I assessment |
| FDA 요건 | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl aminoglutethimide, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| 보관 조건 | Protect from light. Do not store above 30 °F (86 °C). Dispense in tight, light resistant container. |
| 처리 방법 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| 상호 작용 | Aminoglutethimide may inhibit the adrenal response to ACTHthis may interfere with the therapeutic response to ACTH./Upon concomitant administration of/ CNS depression-producing medications, additive CNS depression may occur.Hyponatremia may occur /with concomitant administration of/ diuretics.Cytadren accelerates the metabolism of dexamethasone...For more Interactions (Complete) data for AMINOGLUTETHIMIDE (12 total), please visit the HSDB record page. |
| 노출 경로 | Rapidly and completely absorbed from gastrointestinal tract. The bioavailability of tablets is equivalent to equal doses given as a solution. |
| 독성 요약 | Aminoglutethimide reduces the production of D5-pregnenolone and blocks several other steps in steroid synthesis, including the C-11, C-18, and C-21 hydroxylations and the hydroxylations required for the aromatization of androgens to estrogens, mediated through the binding of aminoglutethimide to cytochrome P-450 complexes. Specifically, the drug binds to and inhibits aromatase which is essential for the generation of estrogens from androstenedione and testosterone. A decrease in adrenal secretion of cortisol is followed by an increased secretion of pituitary adrenocorticotropic hormone (ACTH), which will overcome the blockade of adrenocortical steroid synthesis by aminoglutethimide. The compensatory increase in ACTH secretion can be suppressed by the simultaneous administration of hydrocortisone. Since aminoglutethimide increases the rate of metabolism of dexamethasone but not that of hydrocortisone, the latter is preferred as the adrenal glucocorticoid replacement. Although aminoglutethimide inhibits the synthesis of thyroxine by the thyroid gland, the compensatory increase in thyroid-stimulating hormone (TSH) is frequently of sufficient magnitude to overcome the inhibition of thyroid synthesis due to aminoglutethimide. In spite of an increase in TSH, aminoglutethimide has not been associated with increased prolactin secretion. |
용도
개요
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.
용도
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.
일반 설명
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.