Megestrol acetate
- CAS No.
- 595-33-5
- Chemical Name:
- Megestrol acetate
- Synonyms
- S4;17alpha-acetoxy-6-methylpregna-4,6-diene-3,20-dione;Nia;MGA;bdh1298;sc10363;MEGESTROL ACETATE-D3;6-MethleneProgesterone Acetate;5071;MGA-d3
- CBNumber:
- CB9434253
- Molecular Formula:
- C24H32O4
- Molecular Weight:
- 384.51
- MDL Number:
- MFCD00056470
- MOL File:
- 595-33-5.mol
| Melting point | 214°C |
|---|---|
| alpha | D24 +5° (chloroform) |
| Boiling point | 431.17°C (rough estimate) |
| Density | 1.0474 (rough estimate) |
| refractive index | 11 ° (C=2, CHCl3) |
| storage temp. | Sealed in dry,Room Temperature |
| solubility | Practically insoluble in water, soluble in acetone, sparingly soluble in alcohol. |
| form | Solid |
| color | 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 DataBase Reference | 595-33-5(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| NCI Dictionary of Cancer Terms | megestrol acetate |
| FDA UNII | TJ2M0FR8ES |
| NCI Drug Dictionary | megestrol acetate |
| Proposition 65 List | Megestrol Acetate |
| NIST Chemistry Reference | Megestrol acetate(595-33-5) |
| EPA Substance Registry System | Megestrol acetate (595-33-5) |
Megestrol acetate price More Price(41)
| Manufacturer | Product number | Product description | CAS number | Packaging | Price | Updated | Buy |
|---|---|---|---|---|---|---|---|
| Sigma-Aldrich | 1379106 | Megestrol acetate United States Pharmacopeia (USP) Reference Standard | 595-33-5 | 250mg | $436 | 2024-03-01 | Buy |
| Sigma-Aldrich | M0513 | Megestrol acetate analytical standard, for drug analysis | 595-33-5 | 1g | $137 | 2022-05-15 | Buy |
| TCI Chemical | M1949 | Megestrol Acetate >96.0%(HPLC) | 595-33-5 | 1g | $93 | 2024-03-01 | Buy |
| TCI Chemical | M1949 | Megestrol Acetate >96.0%(HPLC) | 595-33-5 | 5g | $278 | 2024-03-01 | Buy |
| Cayman Chemical | 21749 | Megestryl Acetate ≥98% | 595-33-5 | 1g | $73 | 2024-03-01 | Buy |
Megestrol acetate Chemical Properties,Uses,Production
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.
Chemical Properties
Crystalline Solid
Originator
Megestat,Bristol,W. Germany,1964
Uses
Megestrol acetate USP (Megace) is used to treat Carcinoma of the breast or endorometrium.
Uses
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.
Definition
ChEBI: Megestrol acetate is a steroid ester resulting from the formal condensation of the hydroxy group of megestrol with the carboxy group of acetic acid. It is an appetite stimulant used for the treatment of anorexia and cachexia. Also used for birth control and for the treatment of breast cancer. It has a role as an antineoplastic agent, an appetite enhancer, a contraceptive drug, a progestin and a synthetic oral contraceptive. It is a steroid ester, an acetate ester, a 20-oxo steroid and a 3-oxo-Delta(4) steroid. It derives from a megestrol.
Manufacturing Process
The following preparation is given in US Patent 3,356,573. 17α-Acetoxy-3βhydroxy-6-methylpregn-5-ene-20-one (1 g), aluminum tert-butoxide (1 g) and p-benzoquinone (6 g) were dissolved in dry benzene (100 ml) and the mixture was heated under reflux for 30 minutes. The reaction mixture was cooled and washed with potassium hydroxide solution until the benzene layer was colorless. The benzene was washed with water, dried and evaporated to dryness under reduced pressure. The residue crystallized from aqueous methanol to give 17α-acetoxy-6-methylpregna-4,6-diene-3,20-dione, needles, MP 214° to 216°C.
brand name
Megace (Bristol-Myers Squibb); Megace (Par).
Therapeutic Function
Cancer chemotherapy
General Description
Megestrol 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.
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.
Safety Profile
Suspected carcinogen with experimental carcinogenic and teratogenic data. Poison by intravenous route. Human reproductive effects bp ingestion and implant routes: effects on ovaries and fallopian tubes, menstrual cycle changes, and female fertility index changes. Mutation data reported. Experimental reproductive effects. When heated to decomposition it emits acrid smoke and irritating fumes. An FDA proprietary drug used to treat endometriosis and breast cancer. A steroid.
Veterinary Drugs and Treatments
Megestrol acetate (Ovaban?—Schering) is approved by FDA for use
in dogs only for the postponement of estrus and the alleviation of
false pregnancy. In male dogs, it has been used for benign prostatic
hypertrophy. It is used clinically for many dermatologic and behavior-
related conditions, primarily in the cat. See the Dosage section
for specific indications and dosages for both dogs and cats.
Megestrol acetate is indicated in humans for the palliative treatment
of advanced carcinoma of the breast or endometrium.
Metabolism
Less than 10% of an oral dose undergoes metabolism. Several major metabolites appear in the urine (e.g., 2-hydroxy and 6-hydroxymethyl megestrol and their glucuronide conjugates).
storage
Store at RT
References
[1] zhang k1, chow pk. the effect of megestrol acetate on growth of hepg2 cells in vitro and in vivo. clin cancer res. 2004 aug 1; 10(15):5226-32.
Megestrol acetate Preparation Products And Raw materials
Raw materials
Preparation Products
| Supplier | Tel | Country | ProdList | Advantage | |
|---|---|---|---|---|---|
| Hebei Bonster Technology Co.,Limited | +8613315996897 | bsterltd.wendy@gmail.com | China | 792 | 58 |
| Pharmaceuticals Group Corp., Ltd. | +8613004379774 | wu@jiaerke.com | China | 33 | 58 |
| Wuhan Han Sheng New Material Technology Co.，Ltd | +8617798174412 | admin01@hsnm.com.cn | China | 2097 | 58 |
| Hebei Yanxi Chemical Co., Ltd. | +8617531190177 | peter@yan-xi.com | China | 5857 | 58 |
| Wuhan Fortuna Chemical Co., Ltd | +86-027-59207850 | info@fortunachem.com | China | 5978 | 58 |
| Hong Kong Excellence Biotechnology Co., Ltd. | ada@sh-teruiop.com | China | 875 | 58 | |
| Wuhan Haorong Biotechnology Co.,ltd | +86-18565342920; +8618565342920 | sales@chembj.net | China | 289 | 58 |
| Zibo Hangyu Biotechnology Development Co., Ltd | +86-0533-2185556 +8617865335152 | Mandy@hangyubiotech.com | China | 10986 | 58 |
| Shaanxi Haibo Biotechnology Co., Ltd | +undefined18602966907 | qinhe02@xaltbio.com | China | 997 | 58 |
| Nantong Guangyuan Chemicl Co,Ltd | +undefined17712220823 | admin@guyunchem.com | China | 615 | 58 |
View Lastest Price from Megestrol acetate manufacturers
| Image | Update time | Product | Price | Min. Order | Purity | Supply Ability | Manufacturer | |
|---|---|---|---|---|---|---|---|---|
 |
2024-11-22 | Megestrol acetate
595-33-5
|
US $0.00 / Kg/Bag | 1KG | 97.0～103.0%; USP42 | 2000kg/month | WUHAN FORTUNA CHEMICAL CO., LTD | |
 |
2024-11-19 | Megestrol acetate
595-33-5
|
US $45.00 / mg | 99.72% | 10g | TargetMol Chemicals Inc. | ||
 |
2024-11-19 | Megestrol acetate
595-33-5
|
US $45.00 / mg | 99.72% | 10g | TargetMol Chemicals Inc. |
-
- Megestrol acetate
595-33-5
- US $0.00 / Kg/Bag
- 97.0～103.0%; USP42
- WUHAN FORTUNA CHEMICAL CO., LTD
-
- Megestrol acetate
595-33-5
- US $45.00 / mg
- 99.72%
- TargetMol Chemicals Inc.
-
- Megestrol acetate
595-33-5
- US $45.00 / mg
- 99.72%
- TargetMol Chemicals Inc.