Structure Database (LMSD)

Common Name
Megestrol acetate
Systematic Name
17α-hydroxy-6-methylpregna-4,6-diene-3,20-dione acetate
Synonyms
LM ID
LMST02030118
Formula
Exact Mass
Calculate m/z
384.230061
Sum Composition
Status
Curated

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

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

Other Databases

Wikipedia
KEGG ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 28
Rings 4
Aromatic Rings 0
Rotatable Bonds 3
Van der Waals Molecular Volume 396.28
Topological Polar Surface Area 60.44
Hydrogen Bond Donors 0
Hydrogen Bond Acceptors 4
logP 4.86
Molar Refractivity 106.92

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Created at
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Updated at
1st Jun 2022