Megestrol

This article is about a progestin compound. For the pharmaceutical drug, see megestrol acetate.

Megestrol (INNTooltip International Nonproprietary Name, BANTooltip British Approved Name) is a progestin of the 17α-hydroxyprogesterone group which was, until recently, never marketed or used clinically.^[1][2] It is now used for treatments of disease-related weight loss, endometrial cancer, and breast cancer.^[3] Its acylated derivative megestrol acetate is also a progestogen, which, in contrast to megestrol itself, has been extensively used as a pharmaceutical drug.^[1][2]

Megestrol

Clinical data
ATC code	G03AC05
Identifiers
IUPAC name 17-hydroxy-6-methylpregna-4,6-diene-3,20-dione
CAS Number	3562-63-8 Y
PubChem CID	1909019090
ChemSpider	18023 Y
UNII	EA6LD1M70M
ChEBI	CHEBI:6722 N
CompTox Dashboard (EPA)	DTXSID001009330
ECHA InfoCard	100.020.571
Chemical and physical data
Formula	C22H30O3
Molar mass	342.479 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C4\C=C3\C(=C/[C@@H]1[C@H](CC[C@@]2([C@@](O)(C(=O)C)CC[C@@H]12)C)[C@@]3(C)CC4)C
InChI InChI=1S/C22H30O3/c1-13-11-16-17(20(3)8-5-15(24)12-19(13)20)6-9-21(4)18(16)7-10-22(21,25)14(2)23/h11-12,16-18,25H,5-10H2,1-4H3/t16-,17+,18+,20-,21+,22+/m1/s1 Y Key:VXIMPSPISRVBPZ-NWUMPJBXSA-N Y
NY (what is this?)  (verify)

Medical Use

As of June 2023, megestrol is being used to treat significant weight loss in HIV/AIDS patients, and as a palliative treatment of endometrial and breast cancers. It can be administered in both tablet and oral suspension forms, with dosages ranging from 100 mg/day to 1600 mg/day depending on the condition being treated.^[3]

Synthesis

Megestrol synthesis:^[4] U.S. patent 2,891,079

See also

• Megestrol acetate
• Medroxyprogesterone
• Medroxyprogesterone acetate