Megestrol

Megestrol
Clinical data
ATC code	G03AC05 ;
Identifiers
	IUPAC name 17-hydroxy-6-methylpregna-4,6-diene-3,20-dione;
CAS Number	3562-63-8 ;
PubChem CID	1909019090;
ChemSpider	18023 ;
UNII	EA6LD1M70M;
ChEBI	CHEBI:6722 ;
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 ; Key:VXIMPSPISRVBPZ-NWUMPJBXSA-N ;
	(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

References

^ ^a ^b Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1267. ISBN 978-0-412-46630-4. Retrieved 12 May 2012.
^ ^a ^b Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 641. ISBN 978-3-88763-075-1. Retrieved 28 May 2012.
^ ^a ^b Manikkuttiyil C, Nguyen H (2024). "Megestrol". StatPearls. Treasure Island (FL): StatPearls Publishing. PMID 32644631. Retrieved 2024-04-25.
^ 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. doi:10.1021/ja01523a055.

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[Macdonald1997-1] Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1267. ISBN 978-0-412-46630-4. Retrieved 12 May 2012.

[Index_Nominum_2000:_International_Drug_Directory-2] Index Nominum 2000: International Drug Directory. Taylor & Francis US. 2000. p. 641. ISBN 978-3-88763-075-1. Retrieved 28 May 2012.

[:0-3] 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. doi:10.1021/ja01523a055.

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[2]

[3]

[4]

Megestrol

Contents

Medical Use

Synthesis

See also

References

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)