기본 정보
- CAS
595-33-5- 표준 SMILES
CC(=O)O[C@]1(C(C)=O)CC[C@H]2[C@@H]3C=C(C)C4=CC(=O)CC[C@]4(C)[C@H]3CC[C@@]21C- InChIKey
RQZAXGRLVPAYTJ-GQFGMJRRSA-N- 분자식
- C24H32O4
- 평균 분자량
- 384.5 g/mol
- 단동위원소 질량
- 384.2300595
개요
Megestrol Acetate can cause cancer and developmental toxicity according to state or federal government labeling requirements.
이름 및 식별자
- 우선 이름
- Megestrol Acetate
- IUPAC
- [(8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] acetate
- 현지명
- 메게스트롤아세테이트
- 영어명
- Megestrol acetate
- 분자식
- C24H32O4
- 분자량
- 384.51
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
595-33-5- PubChem CID
- 11683
- DTXSID
DTXSID9040683- ChEMBL
CHEMBL1201139- ChEBI
CHEBI:6723- UNII
- TJ2M0FR8ES
- EC Number
- 209-864-5
- Nikkaji
- J6.777F
물성
구조 계산 물성
- XLogP
- 3.1
- 극성 표면적
- 60.4 Ų
- 수소 결합 공여자 수
- 0
- 수소 결합 수용자 수
- 4
- 회전 가능 결합 수
- 3
- 무거운 원자 수
- 28
- 형식 전하
- 0
- 복잡도
- 820
실험 및 물리화학적 성질
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal Drugs
Active Ingredients (Megestrol Acetate) -> FDA Greenbook
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Collision Cross Section
198.2 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID9040683]
180.1 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
물리화학적 성질
- 녹는점
- 214 °C · 214°C
- 끓는 점
- 431.17 °C · 431.17°C (rough estimate)
- 밀도
- 1.0474 · 1.0474 (rough estimate)
- 굴절률
- 11 ° · 11 ° (C=2, CHCl3)
- 저장 조건
- Sealed in dry,Room Temperature
- 용해도
- 물에 거의 녹지 않으며, 아세톤에 녹고, 알코올에는 거의 녹지 않습니다.
- 물리적 상태
- Solid
- 색상
- 하얀색
- Merck
- 14 · 14,5805
- BRN
- 1917291 · 1917291
- InChIKey
- RQZAXGRLVPAYTJ-GQFGMJRRSA-N
- SMILES
- C1(=O)C=C2[C@](C)(CC1)[C@]1([H])[C@]([H])([C@@]3([H])[C@@](CC1)(C)[C@@](OC(C)=O)(C(=O)C)CC3)C=C2C
- NIST
- Megestrol acetate(595-33-5)
- EPA
- Megestrol acetate (595-33-5)
화학적 성질
Crystalline Solid
안전 및 규제
GHS 분류
GHS Classification
Danger
H302 (15.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P260, P261, P263, P264, P270, P271, P280, P301+P317, P302+P352, P304+P340, P317, P318, P319, P321, P330, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 125 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
유해성 정보
Regulatory Information
Hazard Traits - Carcinogenicity; Developmental Toxicity
Megestrol acetate: Does not have an individual approval but may be used under an appropriate group standard
독성 정보
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Megestrol acetate
Ambiguous-DILI-concern
1
Adverse reactions
DOI:10.1016/j.drudis.2016.02.015
안전 데이터
- wgk
- 3
- rtecs
- TU4075000
- 독성
- LD50 intravenous in mouse: 56mg/kg
- HS 번호
- 29372390
- risk_code
- 40-48
- hazard_code
- Xn
- safety_code
- 22-24/25
화학 및 산업
약리 정보
Pharmacodynamics
Megestrol is a synthetic progestin and has the same physiologic effects as natural progesterone. These effects include induction of secretory changes in the endometrium, increase in basal body temperature, pituitary inhibition, and production of withdrawal bleeding in the presence of estrogen. Mestrogel has slight glucocorticoid activity and very slight mineralocorticoid activity. This drug has no estrogenic, androgenic, or anabolic activity. The precise mechanism of megestrol’s antianorexic and anticachetic effects is unknown. Initially developed as a contraceptive, it was first evaluated in breast cancer treatment in 1967.
Mechanism of Action
The precise mechanism by which megestrol acetate produces effects in anorexia and cachexia is unknown at the present time, but its progestin antitumour activity may involve suppression of luteinizing hormone by inhibition of pituitary function. Studies also suggest that the megestrol's weight gain effect is related to its appetite-stimulant or metabolic effects rather than its glucocorticoid-like effects or the production of edema. It has also been suggested that megestrol may alter metabolic pathyways via interferences with the production or action of mediators such as cachectin, a hormone that inhibits adipocyte lipogenic enzymes.
Metabolism/Metabolites
Primarily hepatic. Megestrol metabolites which were identified in urine constituted 5% to 8% of the dose administered. Respiratory excretion as labeled carbon dioxide and fat storage may have accounted for at least part of the radioactivity not found in urine and feces. No active metabolites have been identified.
FDA Pharmacological Classification
MEGESTROL ACETATE
Progestin [EPC]; Progesterone Congeners [CS]
MeSH Pharmacological Classification
Antineoplastic agents that are used to treat hormone-sensitive tumors. Hormone-sensitive tumors may be hormone-dependent, hormone-responsive, or both. A hormone-dependent tumor regresses on removal of the hormonal stimulus, by surgery or pharmacological block. Hormone-responsive tumors may regress when pharmacologic amounts of hormones are administered regardless of whether previous signs of hormone sensitivity were observed. The major hormone-responsive cancers include carcinomas of the breast, prostate, and endometrium; lymphomas; and certain leukemias. (From AMA Drug Evaluations Annual 1994, p2079)
Agents that are used to stimulate appetite. These drugs are frequently used to treat anorexia associated with cancer and AIDS.
Absorption, Distribution and Excretion
Variable, but well absorbed orally.
The major route of drug elimination in humans is urine. Respiratory excretion as labeled carbon dioxide and fat storage may have accounted for at least part of the radioactivity not found in urine and feces.
용도 및 제조
Use Classification
Animal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
응용 분야
개요Megestrol Acetate is the acetate salt form of megestrol, a synthetic derivative of the naturally occurring female sex hormone progesterone with potential anti-estrogenic and antineoplastic activity. It is frequently used in the treatment of patients with metastatic breast cancer. It is generally well tolerated, except that it may cause undesirable weight gain. Subsequently, it was shown that megestrol acetate produced weight gain in a variety of cachectic cancer patients. Significant reduction inserum levels of IL-1a and b,IL-2,IL-6, and TNF-o were observed in cancer patientstreated with megestrol acetate which may bear on the mechanism of improved appetite and body weight gain.It has also been postulated that the effect is, at least in part,mediated by NPY,a potent central appetite stimulant.
용도Megestrol acetate (Megace), a semi-synthetic progestational steroid, is the most effective known appetite stimulant at present. Previously used in patients with cancer and acquired immunodeficiency syndrome, only a few studies have considered the applicability of this drug in malnourished older persons. Megestrol acetate is useful if profound anorexia is the main manifestation of cachexia and if expected survival is weeks to months. Megace has been shown to significantly increase appetite, but not survival. In patients with a shorter predicted survival, a brief course of corticosteroids may be useful to stimulate appetite and have positive effects on nausea, pain, and asthenia.
일반 설명Megestrol acetate, 17-hydroxy-6-methylpregna-4,6-diene-3,20-dione acetate(Megace), is a progestin used primarily for the palliativemanagement of recurrent, inoperable, or metastatic endometrialor breast carcinoma. Megestrol acetate has also beenindicated for appetite enhancement in patients with AIDS.The biochemical basis for this use of megestrol is unclear.
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