Megestrol

Megestrol
Clinical data
ATC code
Identifiers
IUPAC name
  • 17-hydroxy-6-methylpregna-4,6-diene-3,20-dione
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
ECHA InfoCard100.020.571
Chemical and physical data
FormulaC22H30O3
Molar mass342.479 g·mol−1
3D model (JSmol)
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 checkY
  • Key:VXIMPSPISRVBPZ-NWUMPJBXSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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]

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

References

  1. ^ a b Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1267. ISBN 978-0-412-46630-4. Retrieved 12 May 2012.
  2. ^ a b Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 641. ISBN 978-3-88763-075-1. Retrieved 28 May 2012.
  3. ^ a b Manikkuttiyil C, Nguyen H (2024). "Megestrol". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 32644631. Retrieved 2024-04-25.
  4. ^ Ringold HJ, Ruelas JP, Batres E, Djerassi C (1959). "Steroids. CXVIII.16-Methyl Derivatives of 17α-Hydroxyprogesterone and of Reichstein's Substance "S"". Journal of the American Chemical Society. 81 (14): 3712–3716. Bibcode:1959JAChS..81.3712R. doi:10.1021/ja01523a055.
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