17-Hydroxy-6-methylpregna-4,6-dien-3,20-dion-17-acetat
S4 · MGA · Nia · 17alpha-acetoxy-6-methylpregna-4,6-diene-3,20-dione · MEGESTROL ACETATE-D3 · bdh1298 · sc10363 · 6-MethleneProgesterone Acetate
Identifikatoren & physikalische Daten
| CAS No. | 595-33-5 |
|---|---|
| Summenformel | C24H32O4 |
| Durchschnittliche Molmasse | 384,5 g/mol |
| Monoisotopische Masse | 384,2300595 g/mol |
| 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 |
| PubChem CID | 11683 |
| ChEMBL | CHEMBL1201139 |
| ChEBI | CHEBI:6723 |
| EC No. | 209-864-5 |
| DTXSID | DTXSID9040683 |
| Lokaler Name | 17-Hydroxy-6-methylpregna-4,6-dien-3,20-dion-17-acetat |
Chemische & physikalische Eigenschaften
| XLogP | 3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 60,4 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 4 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 28 |
| Formalladung | 0 |
| Komplexität | 820 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| Lipide | Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203] |
| Human Drugs | FDA approved drugs -> Active ingredient |
| Animal Drugs | Active Ingredients (Megestrol Acetate) -> FDA GreenbookPharmaceuticals -> Animal Drugs -> Approved in Taiwan |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Schmelzpunkt | 218.0-220.0 °C214°C |
| Collision Cross Section | 198.2 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID9040683]180.1 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards] |
| Siedepunkt | 431.17°C (rough estimate) |
| Dichte | 1.0474 (rough estimate) |
| Brechungsindex | 11 ° (C=2, CHCl3) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Löslichkeit | Practically insoluble in water, soluble in acetone, sparingly soluble in alcohol. |
| Aggregatzustand | Solid |
| Farbe | White |
| Merck | 14,5805 |
| BRN | 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 |
| CAS Datenbank | 595-33-5(CAS DataBase Reference) |
| NIST chemische Informationen | Megestrol acetate(595-33-5) |
| EPA chemische Informationen | Megestrol acetate (595-33-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH302 (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. |
|---|---|
| Regulatorische Informationen | Hazard Traits - CarcinogenicityDevelopmental ToxicityMegestrol acetate: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Pregna-4,6-diene-3,20-dione, 17-(acetyloxy)-6-methyl-: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (15.2%) |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)Megestrol acetateAmbiguous-DILI-concern1Adverse reactionsDOI:10.1016/j.drudis.2016.02.015 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29372390 |
| RTECS-Nr. | TU4075000 |
| R-Sätze (R) | 40-48 |
| Toxizität | LD50 intravenous in mouse: 56mg/kg |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 22-24/25 |
Anwendungen & Verwendung
Beschreibung
Megestrol 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.
Verwenden
Megestrol 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.