Megestrol acetate is the acetate ester of megestrol, a synthetic derivative of the naturally occurring female sex hormone progesterone, with progestogenic, antiestrogenic, and antineoplastic activities. Mimicking the action of progesterone, megestrol binds to and activates nuclear progesterone receptors (PRs) in the reproductive system and pituitary; ligand-receptor complexes are translocated to the nucleus where they bind to progesterone response elements (PREs) located on target genes.

MedKoo Cat#: 100570 Name: Megestrol Acetate CAS#: 595-33-5 Chemical Formula: C24H32O4 Exact Mass: 384.23006 Molecular Weight: 384.51 Elemental Analysis: C, 74.97; H, 8.39; O, 16.64

Synonym: BDH 1298; BDH1298; BDH-1298; Megace; Ovaban; Pallace. Maygace; Megestil; Niagestin.

IUPAC/Chemical Name: (8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate

InChi Key: RQZAXGRLVPAYTJ-GQFGMJRRSA-N

InChi Code: InChI=1S/C24H32O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h12-13,18-20H,6-11H2,1-5H3/t18-,19+,20+,22-,23+,24+/m1/s1

SMILES Code: CC(O[C@]1(C(C)=O)CC[C@@]2([H])[C@]3([H])C=C(C)C4=CC(CC[C@]4(C)[C@@]3([H])CC[C@]12C)=O)=O

Technical Data

Appearance: White to off-white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Certificate of Analysis: View CoA: current batch, Lot#TCI60212

Safety Data Sheet (MSDS): View Material Safety Data Sheet (MSDS)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code: 293490

Additional Information

  Megestrol is a progesterone derivative with antineoplastic properties used in the treatment of advanced carcinoma of the breast and endometrium. When given in relatively high doses, Megestrol can substantially increase appetite in most individuals, even those with advanced cancer. It is also used to boost appetite in individuals with other cancers or HIV/AIDS. Megestrol acetate oral suspension (a form of Megestrol) is used primarily as an appetite enhancer. The method of appetite enhancement is not known, but it can cause high blood sugar. Currently, it is manufactured under the trade name Megace. Little is known about the drug\'s chemical interactions. Doses range from 40 mg three times a day, 30 minutes before meals, to 800 mg once a day. Side effects may include diarrhea, rash, and impotence. Males may have some feminizing effects such as gynecomastia (breast development). It is a category X U.S. Food and Drug Administration drug, which means cannot be used in pregnancy as it crosses the placenta and malignantly affects the fetus. See: http://en.wikipedia.org/wiki/Megestrol_acetate .   DRUG DESCRIPTION Megace® ES (megestrol acetate) oral suspension contains megestrol acetate, a synthetic derivative of the naturally occurring steroid hormone, progesterone. Megestrol acetate is a white, crystalline solid chemically designated as 17-Hydroxy-6-methylpregna-4,6-diene-3,20-dione acetate. Solubility at 37° C in water is 2 µg per mL, solubility in plasma is 24 µg per mL. Its molecular weight is 384.52. The chemical formula is C24H32O4.  Megace® ES (megestrol acetate) is a concentrated formula supplied as an oral suspension containing 125 mg of megestrol acetate per mL. Megace® ES (megestrol acetate) oral suspension contains the following inactive ingredients: alcohol (max 0.06% v/v from flavor), artificial lime flavor, citric acid monohydrate, docusate sodium, hydroxypropyl methylcellulose (hypromellose), natural and artificial lemon flavor, purified water, sodium benzoate, sodium citrate dihydrate, and sucrose.    

References

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