Compound: megestrol
SMILES: O=C1C=C2C(=C[C@H]3[C@H]4[C@]([C@@](O)(C(=O)C)CC4)(C)CC[C@@H]3[C@@]2(C)CC1)C
InChIKey: VXIMPSPISRVBPZ-NWUMPJBXSA-N
Synonyms: megestrol, 3562-63-8, Megestrolo, Pregna-4,6-diene-3,20-dione, 17-hydroxy-6-methyl-, Chronopil, Megestrolum, EA6LD1M70M, (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthren-3-one, DTXSID001009330, CHEBI:6722, (8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-6,10,13-trimethyl-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta(a)phenanthren-3-one, Compound 5071, RefChem:55564, G03AC05, G03DB02, L02AB01, DTXCID001436159, 222-628-6, 17-Hydroxy-6-methylpregna-4,6-diene-3,20-dione, Megestrol (INN), (8R,9S,10R,13S,14S,17R)-17-Acetyl-17-hydroxy-6,10,13-trimethyl-8,9,10,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one, Megestrol Acetate EP Impurity B, MEGESTROL [INN], Megestrol [INN:BAN], Megestrol (Acetate), Chronopil (TN), HSDB 3233, EINECS 222-628-6, UNII-EA6LD1M70M, VXIMPSPISRVBPZ-NWUMPJBXSA-N, Pregna-4,6-diene-3,20-dione, 17-hydroxy-6-methyl-; 17-Hydroxy-6-methylpregna-4,6-diene-3,20-dione; Megestrol; 6-Methyl-17-hydroxypregna-4,6-diene-3,20-dione, Megestrol (Standard), MEGESTROL [HSDB], MEGESTROL [VANDF], MEGESTROL [WHO-DD], SCHEMBL8942, GTPL9128, orb1705254, CHEMBL4071215, HY-B1834R, MSK8523, HY-B1834, MSK8523-100A, s5738, MSK8523-1000A, FH39644, AC-32473, MS-25250, CS-0013903, NS00014345, Megestrol Solution in Acetonitrile, 100ug/mL, C07120, D08167, Megestrol Solution in Acetonitrile, 1000ug/mL, F600899, MEGESTROL ACETATE IMPURITY B [EP IMPURITY], Q410513, Pregna-4,6-diene-3,20-dione, 17-hydroxy-6-methyl-, 6-Methyl-17-hydroxypregna-4,6-diene-3,20-dione, Megestrol, 17-Hydroxy-6-methylpregna-4,6-diene-3,20-dione
Theoretical properties:
molecular_formula: C22H30O3
molecular_weight: 342.5 g/mol
exact_mass: 342.21949481 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 1
heavy_atom_count: 25
topological_polar_surface_area: 54.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
odor: Odorless
solubility: WHITE OR ALMOST WHITE, CRYSTALLINE POWDER; SPARINGLY SOL IN ALC; SLIGHTLY SOL IN ETHER & FIXED OILS; SOL IN ACETONE; VERY SOL IN CHLOROFORM /ACETATE/
Descriptions:
{"pubchem": "Megestrol is a 3-oxo 4-steroid that is pregna-4,6-diene-3,20-dione substituted by a methyl group at position 6 and a hydroxy group at position 17. It has a role as an antineoplastic agent, a contraceptive drug, a synthetic oral contraceptive, an appetite enhancer and a progestin. It is a tertiary alpha-hydroxy ketone, a 17alpha-hydroxy steroid, a 20-oxo steroid and a 3-oxo-Delta(4) steroid.", "chebi": "A 3-oxo \u0394<small><sup>4</small></sup>-steroid that is pregna-4,6-diene-3,20-dione substituted by a methyl group at position 6 and a hydroxy group at position 17.", "chembl": "Unnamed Compound is a small molecule listed in the ChEMBL database but has not progressed to an approved clinical phase.", "wikipedia": "Megestrol acetate (MGA), sold under the brand name Megace among others, is a progestin medication which is used mainly as an appetite stimulant to treat wasting syndromes such as cachexia. It is also used to treat breast cancer and endometrial cancer, and has been used in birth control. Megestrol acetate is generally formulated alone, although it has been combined with estrogens in birth control formulations. It is usually taken by mouth.\nSide effects of megestrol acetate include increased appetite, weight gain, vaginal bleeding, nausea, edema, low sex hormone levels, sexual dysfunction, osteoporosis, cardiovascular complications, glucocorticoid effects, and others. Megestrol acetate is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone. It has weak partial androgenic activity, weak glucocorticoid activity, and no other important hormonal activity. Due to its progestogenic activity, megestrol acetate has antigonadotropic effects. The mechanism of action of the appetite stimulant effects of megestrol acetate is unknown.\nMegestrol acetate was discovered in 1959 and was introduced for medical use, specifically in birth control pills, in 1963. It may be considered a \"first-generation\" progestin. The medication was withdrawn in some countries in 1970 due to concerns about mammary toxicity observed in dogs, but this turned out not to apply to humans. Megestrol acetate was approved for the treatment of endometrial cancer in 1971 and wasting syndromes in 1993. It is marketed widely throughout the world. It is available as a generic medication.\n\n"}