acetic acid [(17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] ester

Base Information

• Chemical Name: acetic acid [(17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] ester
• CAS No.: 595-33-5
• Molecular Formula: C24H32O4
• Molecular Weight: 384.516
• Hs Code.: 29372390
• NSC Number: 757097
• Wikidata: Q27163477
• Mol file: 595-33-5.mol

Synonyms:Spectrum2_001271;Spectrum3_000489;Spectrum4_000963;Spectrum5_001839;BSPBio_001957;KBioGR_001305;SPECTRUM1500381;SPBio_001262;SCHEMBL12998544;CHEBI:91652;KBio3_001457;HMS1920L03;HMS2091B14;Pharmakon1600-01500381;BBL033969;CCG-40073;NSC757097;STL377947;AKOS024319484;NSC-757097;NCGC00018279-02;VS-12352;SBI-0206695.P002;AB01562936_01;SR-05000001666;SR-05000001666-1;BRD-A35989968-001-02-6;BRD-A35989968-001-03-4;Q27163477;6-METHYL-3,20-DIOXOPREGNA-4,6-DIEN-17-ALPHA-YL ACETATE;(1R)-1-acetyl-5,9a,11a-trimethyl-7-oxo-1H,2H,3H,3aH,3bH,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl acetate;acetic acid [(17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] ester

Chemical Property of acetic acid [(17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] ester

Chemical Property:

• Appearance/Colour: Crystalline Solid
• Vapor Pressure: 2.59E-10mmHg at 25°C
• Melting Point: 214 °C
• Refractive Index: 11 ° (C=2, CHCl3)
• Boiling Point: 507.1 °C at 760 mmHg
• Flash Point: 218.5 °C
• PSA: 60.44000
• Density: 1.15 g/cm³
• LogP: 4.57530
• Storage Temp.: Refrigerator
• Solubility.: Practically insoluble in water, soluble in acetone, sparingly soluble in alcohol.
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 384.23005950
• Heavy Atom Count: 28
• Complexity: 821

Purity/Quality:

99.00% ^*data from raw suppliers

Megestrol acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 40-48
• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1=CC2C(CCC3(C2CCC3(C(=O)C)OC(=O)C)C)C4(C1=CC(=O)CC4)C
• Isomeric SMILES: CC1=CC2C3CC[C@@](C3(CCC2C4(C1=CC(=O)CC4)C)C)(C(=O)C)OC(=O)C
• Description: 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.
• Uses: Megestrol acetate USP (Megace) is used to treat Carcinoma of the breast or endorometrium. 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.
• Therapeutic Function: Cancer chemotherapy
• Clinical Use: Progestin activity is further enhanced when a double bond is introduced between positions 6 and 7, as is found in megestrol acetate. Megestrol is used primarily in the treatment of breast and endometrial carcinomas and in postmenopausal women with advanced hormone-dependent carcinoma.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: metabolism of progestogens accelerated by griseofulvin and rifamycins. Anticoagulants: progestogens antagonise anticoagulant effect of phenindione; may enhance or reduce anticoagulant effect of coumarins. Antiepileptics: metabolism accelerated by carbamazepine, eslicarbazepine, fosphenytoin, oxcarbazepine, phenobarbital, phenytoin, primidone, rufinamide and topiramate; concentration of lamotrigine reduced; concentration reduced by high dose perampanel. Antivirals: metabolism accelerated by nevirapine. Ciclosporin: progestogens inhibit metabolism of ciclosporin (increased plasma concentration). Dopaminergics: concentration of selegiline increased - avoid.

Technology Process of acetic acid [(17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] ester

There total 20 articles about acetic acid [(17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-17-yl] ester 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: 69.8%

methyl bromide (74-83-9) + C27H38O7 → Megestrol acetate (595-33-5)

Guidance literature:

methyl bromide; C₂₇H₃₈O₇; With magnesium; In tetrahydrofuran; at 30 - 55 ℃; Inert atmosphere;

With hydrogenchloride; In water; at 60 - 65 ℃;

Reference yield: 51.0%

methoxymethyl acetate (4382-76-7) + hydroxyprogesterone acetate (4134-58-1,17308-02-0,41460-93-9,41460-97-3,630-56-8,302-23-8) → Megestrol acetate (595-33-5)

Guidance literature:

With sodium acetate; trichlorophosphate; In chloroform; at 70 ℃; for 0.166667h;

Reference yield:

17α-Acetoxy-6-methylene-pregn-4-ene-3,20-dione (32634-95-0) → Megestrol acetate (595-33-5)

Guidance literature:

With sodium acetate; palladium on activated charcoal; 4-methylcyclohexene; In ethanol; Heating / reflux;

upstream raw materials:

Medroxyprogesterone acetate

chloranil

acetic acid

ethyl acetate

Downstream raw materials:

17α-Acetoxy-6α-methyl-pregna-4,7-dien-3,20-dion

6-methylpregna-4,6-diene-3β,17α-diol-20-one 17-acetate

17-acetoxy-6-methyl-pregna-1,4,6-triene-3,20-dione

megestrol

Refernces

• 1、 -. "THERAPEUTIC FOR HEPATIC CANCER". . . Retrieved 2011/02/18.
• 2、 -. "PROCESS FOR PREPARING 17ALPHA-ACETOXY-6-METHYLENEPREGN-4-ENE-3,20-DIONE, MEDROXYPROGESTERONE ACETATE AND MEGESTROL ACETATE". Page/Page column 3. . Retrieved 2009/01/24.