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Structure Database (LMSD)

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Common Name

Megestrol acetate

Systematic Name

17α-hydroxy-6-methylpregna-4,6-diene-3,20-dione acetate

Synonyms

LM ID

LMST02030118

Formula

C₂₄H₃₂O₄

Exact Mass

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384.23006

Sum Composition

ST 24:5;O4

Status

Curated

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Classification

Biological Context

Megestryl acetate is a synthetic progestogen and derivative of progesterone originally developed as a contraceptive.¹ It binds with high relative affinity to the progesterone , androgen, and glucocorticoid receptors in mammary cancer cells.² It increases neuropeptide Y by 90-140% and inhibits calcium channel currents in the rat hypothalamus.^3,4 Megestryl acetate decreases cytokine and serotonin production in patient-derived peripheral blood mononuclear cells (PBMCs).⁵ In rats, it increases food and water intake when administered at a dose of 50 mg/kg per day.³ Formulations containing megestryl acetate have been used in the treatment of endometriosis, hormone-related cancers, and as an appetite stimulant for cancer patients with anorexia and cachexia.⁶

This information has been provided by Cayman Chemical

References

1. Costa, A.-M., Spence, K.T., Plata-Salamán, C.R., et al. Residual Ca2+ channel current modulation by megestrol acetate via a G-protein αs-subunit in rat hypothalamic neurones. J. Physiol. 487(Pt 2), 291-303 (1995).

2. Mantovani, G., Macciò, A., Esu, S., et al. Medroxyprogesterone acetate reduces the in vitro production of cytokines and serotonin involved in anorexia/cachexia and emesis by peripheral blood mononuclear cells of cancer patients. Eur. J. Cancer 33(4), 602-607 (1997).

3. McCarthy, H.D., Crowder, R.E., Dryden, S., et al. Megestrol acetate stimulates food and water intake in the rat: Effects on regional hypothalamic neuropeptide Y concentrations. Eur. J. Pharmacol. 265(1-2), 99-102 (1994).

4. Østergaard, M.D. The oral progestational and anti-ovulatory properties of megestrol acetate and its therapeutic use in gynaecological disorders. J. Obstet. Gynaecol. Br. Emp. 72(1), 45-48 (1965).

5. Teulings, F.A., van Glise, H.A., Henkelman, M.S., et al. Estrogen, androgen, glucocorticoid, and progesterone receptors in progestin-induced regression of human breast cancer. Cancer Res. 40(7), 2557-2561 (1980).

6. Argilés, J.M., Anguera, A., and Stemmler, B. A new look at an old drug for the treatment of cancer cachexia: Megestrol acetate. Clin. Nutr. 32(3), 319-324 (2013).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

synthetic construct (#32630)

The oral progestational and anti-ovulatory properties of megestrol acetate and its therapeutic use in gynaecological disorders.,
J Obstet Gynaecol Br Emp, 1965

Pubmed ID: 12332461

String Representations

InChiKey (Click to copy)

RQZAXGRLVPAYTJ-GQFGMJRRSA-N

InChi (Click to copy)

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 (Click to copy)

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