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
3D model of Megestrol acetate
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
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
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
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
Admin
Created at
-
Updated at
1st Jun 2022