Megestrol Acetate
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MedKoo CAT#: 100570

CAS#: 595-33-5

Description: 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.


Chemical Structure

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Megestrol Acetate
CAS# 595-33-5

Theoretical Analysis

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

Price and Availability

Size Price Availability Quantity
25.0mg USD 45.0 Same day
50.0mg USD 55.0 Same day
100.0mg USD 65.0 Same day
250.0mg USD 85.0 Same day
500.0mg USD 115.0 Same day
1.0g USD 150.0 Same day
2.0g USD 250.0 Same day
5.0g USD 450.0 2 Weeks
10.0g USD 650.0 2 Weeks
25.0g USD 950.0 2 Weeks
50.0g USD 1650.0 2 Weeks
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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

Appearance: White to off-white solid powder

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

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).

HS Tariff Code: 2934.99.9001

Product Data:

Certificate of Analysis:

Safety Data Sheet (SDS):

Biological target: Megestrol acetate is a synthetic progesteronal agent that downregulates autophagic catabolic pathway.
In vitro activity: The present study primarily investigated the involvement of megestrol acetate (MA), a progesterone analog, in the stimulation of ASCs, and identifies the target receptors underlying stimulation. Mitogenic and adipogenic effects of MA were investigated in vitro. Because MA acts as an agonist of diverse nuclear receptors (NRs), the mRNA expression of NRs was measured in ASCs with or without MA (10 μM) and progesterone (10 μM) treatment. Unexpectedly, PR was not expressed in ASCs (Fig. 2A). The mineralocorticoid receptor and AR were expressed at low levels, but GR was expressed at high levels (Fig. 2A; supplemental online Table 2). However, MA or progesterone treatment did not alter the expression of these receptors (supplemental online Table 2). In addition, MA (10 μM) and dexamethasone (1 μM, a positive control for GR phosphorylation) significantly increased the phosphorylation of GR in ASCs (Fig. 2B). Phosphorylated GR translocated to the nucleus after MA and dexamethasone treatment (Fig. 2C, green, phosphorylated GR; blue, 4′,6-diamidino-2-phenylindole). Collectively, these results suggest that MA might act as a GR agonist and stimulate ASCs via the GR. Magestrol acetate (MA) increases the proliferation, migration, and adipogenic differentiation of adipose-derived stem cells (ASCs) via glucocorticoid receptor phosphorylation. Therefore, MA can be applied to increase the production yield during expansion and can be used to facilitate adipogenic differentiation of ASCs. Reference: Stem Cells Transl Med. 2015 Jul; 4(7): 789–799. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4479629/
In vivo activity: The aim of the study is to investigate the effect of megestrol acetate, a synthetic progesteronal agent, on growth of HepG2 cells in vivo. As shown in Fig. 2⇓ , tumor volumes in nude mice were not affected by treatment of megestrol acetate in the first 5 weeks. However, from week 6 of megestrol treatment, a significant suppression of tumor growth was observed. The tumor volumes of the megestrol acetate-treated group regressed to 59% of controls at week 6 and to 41% of controls at week 13 (P < 0.05 compared with controls). The megestrol acetate-induced reductions of tumors are progressive during the period of treatment. Megestrol acetate was also demonstrated to have a beneficial effect on the weight gain of tumor-bearing nude mice, and the mean weight of the megestrol acetate-treated animals was higher than that of controls from week 4 of the treatment period, and the differences were statistically significant in week 5 and 6 (P < 0.05, compared with controls). No significant survival advantage was, however, demonstrated in the treatment group. This study showed that megestrol acetate inhibited the growth of HepG2 cells grown in vivo. These data provide useful information for clinical study of megestrol acetate for the treatment of HCC. Reference: Clin Cancer Res. 2004 Aug 1;10(15):5226-32. https://pubmed.ncbi.nlm.nih.gov/15297426/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 48.0 124.83

Preparing Stock Solutions

The following data is based on the product molecular weight 384.51 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Zhang K, 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. doi: 10.1158/1078-0432.CCR-04-0061. PMID: 15297426. 2. Sung JH, An HS, Jeong JH, Shin S, Song SY. Megestrol Acetate Increases the Proliferation, Migration, and Adipogenic Differentiation of Adipose-Derived Stem Cells via Glucocorticoid Receptor. Stem Cells Transl Med. 2015 Jul;4(7):789-99. doi: 10.5966/sctm.2015-0009. Epub 2015 May 13. PMID: 25972147; PMCID: PMC4479629. 3. Beck SA, Tisdale MJ. Effect of megestrol acetate on weight loss induced by tumour necrosis factor alpha and a cachexia-inducing tumour (MAC16) in NMRI mice. Br J Cancer. 1990 Sep;62(3):420-4. doi: 10.1038/bjc.1990.310. PMID: 2206950; PMCID: PMC1971439.
In vitro protocol: 1. Zhang K, 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. doi: 10.1158/1078-0432.CCR-04-0061. PMID: 15297426. 2. Sung JH, An HS, Jeong JH, Shin S, Song SY. Megestrol Acetate Increases the Proliferation, Migration, and Adipogenic Differentiation of Adipose-Derived Stem Cells via Glucocorticoid Receptor. Stem Cells Transl Med. 2015 Jul;4(7):789-99. doi: 10.5966/sctm.2015-0009. Epub 2015 May 13. PMID: 25972147; PMCID: PMC4479629.
In vivo protocol: 1. Zhang K, 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. doi: 10.1158/1078-0432.CCR-04-0061. PMID: 15297426. 2. Beck SA, Tisdale MJ. Effect of megestrol acetate on weight loss induced by tumour necrosis factor alpha and a cachexia-inducing tumour (MAC16) in NMRI mice. Br J Cancer. 1990 Sep;62(3):420-4. doi: 10.1038/bjc.1990.310. PMID: 2206950; PMCID: PMC1971439.

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1: Smith CS, Logomarsino JV. Using megestrol acetate to ameliorate protein-energy wasting in chronic kidney disease. J Ren Care. 2016 Mar;42(1):53-9. doi: 10.1111/jorc.12138. Epub 2015 Nov 5. Review. PubMed PMID: 26537025.

2: Ruiz Garcia V, López-Briz E, Carbonell Sanchis R, Gonzalvez Perales JL, Bort-Marti S. Megestrol acetate for treatment of anorexia-cachexia syndrome. Cochrane Database Syst Rev. 2013 Mar 28;3:CD004310. doi: 10.1002/14651858.CD004310.pub3. Review. PubMed PMID: 23543530.

3: Greenberg M, Lawler D, Zawistowski S, Jöchle W. Low-dose megestrol acetate revisited: a viable adjunct to surgical sterilization in free roaming cats? Vet J. 2013 Jun;196(3):304-8. doi: 10.1016/j.tvjl.2013.01.038. Epub 2013 Mar 14. Review. PubMed PMID: 23499239.

4: Argilés JM, Anguera A, Stemmler B. A new look at an old drug for the treatment of cancer cachexia: megestrol acetate. Clin Nutr. 2013 Jun;32(3):319-24. doi: 10.1016/j.clnu.2013.01.004. Epub 2013 Jan 22. Review. PubMed PMID: 23395103.

5: Fox CB, Treadway AK, Blaszczyk AT, Sleeper RB. Megestrol acetate and mirtazapine for the treatment of unplanned weight loss in the elderly. Pharmacotherapy. 2009 Apr;29(4):383-97. doi: 10.1592/phco.29.4.383. Review. PubMed PMID: 19323618.

6: Leśniak W, Bała M, Jaeschke R, Krzakowski M. Effects of megestrol acetate in patients with cancer anorexia-cachexia syndrome--a systematic review and meta-analysis. Pol Arch Med Wewn. 2008 Nov;118(11):636-44. Review. PubMed PMID: 19140567.

7: Yeh SS, Schuster MW. Megestrol acetate in cachexia and anorexia. Int J Nanomedicine. 2006;1(4):411-6. Review. PubMed PMID: 17722275; PubMed Central PMCID: PMC2676640.

8: Megestrol acetate NCD oral suspension -- Par Pharmaceutical: megestrol acetate nanocrystal dispersion oral suspension, PAR 100.2, PAR-100.2. Drugs R D. 2007;8(4):251-4. Review. Corrected and republished in: Drugs R D. 2007;8(6):403-6. PubMed PMID: 17596111.

9: Mateen F, Jatoi A. Megestrol acetate for the palliation of anorexia in advanced, incurable cancer patients. Clin Nutr. 2006 Oct;25(5):711-5. Epub 2006 Jul 25. Review. PubMed PMID: 16867306.

10: Femia RA, Goyette RE. The science of megestrol acetate delivery: potential to improve outcomes in cachexia. BioDrugs. 2005;19(3):179-87. Review. PubMed PMID: 15984902.

11: Berenstein EG, Ortiz Z. Megestrol acetate for the treatment of anorexia-cachexia syndrome. Cochrane Database Syst Rev. 2005 Apr 18;(2):CD004310. Review. Update in: Cochrane Database Syst Rev. 2013;3:CD004310. PubMed PMID: 15846706.

12: Pascual López A, Roqué i Figuls M, Urrútia Cuchi G, Berenstein EG, Almenar Pasies B, Balcells Alegre M, Herdman M. Systematic review of megestrol acetate in the treatment of anorexia-cachexia syndrome. J Pain Symptom Manage. 2004 Apr;27(4):360-9. Review. PubMed PMID: 15050664.

13: Thomas DR. Incidence of venous thromboembolism in megestrol acetate users. J Am Med Dir Assoc. 2004 Jan-Feb;5(1):65-6; author reply 66-7. Review. PubMed PMID: 14726802.

14: Ruiz-García V, Juan O, Pérez Hoyos S, Peiró R, Ramón N, Rosero MA, García MA. [Megestrol acetate: a systematic review usefulness about the weight gain in neoplastic patients with cachexia]. Med Clin (Barc). 2002 Jul 6;119(5):166-70. Review. Spanish. PubMed PMID: 12200017.

15: Karcic E, Philpot C, Morley JE. Treating malnutrition with megestrol acetate: literature review and review of our experience. J Nutr Health Aging. 2002 May;6(3):191-200. Review. PubMed PMID: 12152625.

16: Bonte J. Third generation aromatase inhibitors in metastatic breast cancer patients failing tamoxifen. Randomized comparisons with megestrol acetate: a critical review. Eur J Gynaecol Oncol. 2000;21(6):555-9. Review. PubMed PMID: 11214609.

17: Farrar DJ. Megestrol acetate: promises and pitfalls. AIDS Patient Care STDS. 1999 Mar;13(3):149-52. Review. PubMed PMID: 10375262.

18: Stockheim JA, Daaboul JJ, Yogev R, Scully SP, Binns HJ, Chadwick EG. Adrenal suppression in children with the human immunodeficiency virus treated with megestrol acetate. J Pediatr. 1999 Mar;134(3):368-70. Review. PubMed PMID: 10064680.

19: Mantovani G, Macciò A, Lai P, Massa E, Ghiani M, Santona MC. Cytokine involvement in cancer anorexia/cachexia: role of megestrol acetate and medroxyprogesterone acetate on cytokine downregulation and improvement of clinical symptoms. Crit Rev Oncog. 1998;9(2):99-106. Review. PubMed PMID: 9973244.

20: Chang AY. Megestrol acetate as a biomodulator. Semin Oncol. 1998 Apr;25(2 Suppl 6):58-61. Review. PubMed PMID: 9625385.



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.