From Wikipedia, the free encyclopedia
Chemical compound
This article is about a progestin compound. For the pharmaceutical drug, see
megestrol acetate .
Megestrol
ATC code
17-hydroxy-6-methylpregna-4,6-diene-3,20-dione
CAS Number
PubChem
CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (
EPA )
ECHA InfoCard
100.020.571
Formula C 22 H 30 O 3
Molar mass 342.479 g·mol−1 3D model (
JSmol )
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=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
N Y
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Megestrol (
INN Tooltip International Nonproprietary Name ,
BAN Tooltip 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
^
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, Chris; Nguyen, Hoang (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 .
PR Tooltip Progesterone receptor
Agonists
Testosterone derivatives: Progestins:
6,6-Difluoronorethisterone
6,6-Difluoronorethisterone acetate
17α-Allyl-19-nortestosterone
Allylestrenol
Altrenogest
Chloroethynylnorgestrel
Cingestol
Danazol
Desogestrel
Dienogest
Ethinylandrostenediol
Ethisterone
Ethynerone
Etonogestrel
Etynodiol
Etynodiol diacetate
Gestodene
Gestrinone
Levonorgestrel
Levonorgestrel esters (e.g.,
levonorgestrel butanoate )
Lynestrenol
Lynestrenol phenylpropionate
Metynodiol
Metynodiol diacetate
Norelgestromin
Norethisterone (norethindrone)
Norethisterone esters (e.g.,
norethisterone acetate ,
norethisterone enanthate )
Noretynodrel
Norgesterone
Norgestimate
Norgestrel
Norgestrienone
Norvinisterone
Oxendolone
Quingestanol
Quingestanol acetate
Tibolone
Tigestol
Tosagestin ; Anabolic–androgenic steroids:
11β-Methyl-19-nortestosterone
11β-Methyl-19-nortestosterone dodecylcarbonate
19-Nor-5-androstenediol
19-Nor-5-androstenedione
19-Nordehydroepiandrosterone
Bolandiol
Bolandiol dipropionate
Bolandione
Dimethisterone
Dienedione
Dienolone
Dimethandrolone
Dimethandrolone buciclate
Dimethandrolone dodecylcarbonate
Dimethandrolone undecanoate
Dimethyldienolone
Dimethyltrienolone
Ethyldienolone
Ethylestrenol (ethylnandrol)
Methyldienolone
Metribolone (R-1881)
Methoxydienone (methoxygonadiene)
Mibolerone
Nandrolone
Nandrolone esters (e.g.,
nandrolone decanoate ,
nandrolone phenylpropionate )
Norethandrolone
Normethandrone (methylestrenolone, normethandrolone, normethisterone)
RU-2309
Tetrahydrogestrinone
Trenbolone (trienolone)
Trenbolone esters (e.g.,
trenbolone acetate ,
trenbolone enanthate )
Trendione
Trestolone
Trestolone acetate
Mixed (
SPRMs Tooltip Selective progesterone receptor modulators ) Antagonists
mPR Tooltip Membrane progesterone receptor (
PAQR Tooltip Progestin and adipoQ receptor )