Demegestone

Demegestone
Clinical data
Trade names	Lutionex
Other names	Dimegestone; R-2453; RU-2453; 17α-Methyl-δ9-19-norprogesterone; 17α-Methyl-19-norpregna-4,9-diene-3,20-dione
Routes of; administration	By mouth
Drug class	Progestogen; Progestin
ATC code	G03DB05 (WHO) ;
Pharmacokinetic data
Bioavailability	Good
Metabolism	Hydroxylation, others
Metabolites	• 21-Hydroxydemegestone; • Others
Excretion	Urine
Identifiers
	IUPAC name (8S,13S,14S,17S)-17-acetyl-13,17-dimethyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one;
CAS Number	10116-22-0;
PubChem CID	93057;
ChemSpider	84009;
UNII	6E89AM91SZ;
KEGG	D07223;
ChEBI	CHEBI:135339;
ChEMBL	ChEMBL2104231;
CompTox Dashboard (EPA)	DTXSID20878581 ;
ECHA InfoCard	100.030.278
Chemical and physical data
Formula	C21H28O2
Molar mass	312.453 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(=O)[C@]1(CC[C@@H]2[C@@]1(CCC3=C4CCC(=O)C=C4CC[C@@H]23)C)C;
	InChI InChI=1S/C21H28O2/c1-13(22)20(2)11-9-19-18-6-4-14-12-15(23)5-7-16(14)17(18)8-10-21(19,20)3/h12,18-19H,4-11H2,1-3H3/t18-,19+,20-,21+/m1/s1; Key:JWAHBTQSSMYISL-MHTWAQMVSA-N;

Demegestone, sold under the brand name Lutionex, is a progestin medication which was previously used to treat luteal insufficiency but is now no longer marketed.^[3]^[4]^[5]^[6]^[7] It is taken by mouth.^[2]^[1]

Demegestone is a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.^[6]^[2]^[8] It has no androgenic activity.^[2]

Demegestone was first described in 1966 and was introduced for medical use in France in 1974.^[3]^[4] It has only been marketed in France, and has since been discontinued in this country.^[5]^[4]

^ ^a ^b Iizuka R, Hayashi M, Kamouchi Y, Yamanaka K (1971). "Evaluation of a low-dose progestagen as a contraceptive". Nihon Funin Gakkai Zasshi. 16 (1): 68–82. PMID 12158578.
^ ^a ^b ^c ^d ^e ^f ^g ^h Cite error: The named reference RaynaudCousty1974 was invoked but never defined (see the help page).
^ ^a ^b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 356–. ISBN 978-1-4757-2085-3.
^ ^a ^b ^c William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 1215–. ISBN 978-0-8155-1856-3.
^ ^a ^b "Demegestone". Micromedex.: ^{[permanent dead link]}
^ ^a ^b Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.
^ Cite error: The named reference pmid3194612 was invoked but never defined (see the help page).
^ Lee DL, Kollman PA, Marsh FJ, Wolff ME (September 1977). "Quantitative relationships between steroid structure and binding to putative progesterone receptors". Journal of Medicinal Chemistry. 20 (9): 1139–1146. doi:10.1021/jm00219a006. PMID 926114.

[pmid12158578-1] Iizuka R, Hayashi M, Kamouchi Y, Yamanaka K (1971). "Evaluation of a low-dose progestagen as a contraceptive". Nihon Funin Gakkai Zasshi. 16 (1): 68–82. PMID 12158578.

[RaynaudCousty1974-2] ^ ^a ^b ^c ^d ^e ^f ^g ^h Cite error: The named reference RaynaudCousty1974 was invoked but never defined (see the help page).

[Elks2014-3] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 356–. ISBN 978-1-4757-2085-3.

[Publishing2013-4] William Andrew Publishing (22 October 2013). Pharmaceutical Manufacturing Encyclopedia (3rd ed.). Elsevier. pp. 1215–. ISBN 978-0-8155-1856-3.

[Micromedex-5] "Demegestone". Micromedex.: ^{[permanent dead link]}

[pmid16112947-6] Kuhl H (August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric. 8 (Suppl 1): 3–63. doi:10.1080/13697130500148875. PMID 16112947. S2CID 24616324.

[pmid3194612-7] Cite error: The named reference pmid3194612 was invoked but never defined (see the help page).

[pmid926114-8] Lee DL, Kollman PA, Marsh FJ, Wolff ME (September 1977). "Quantitative relationships between steroid structure and binding to putative progesterone receptors". Journal of Medicinal Chemistry. 20 (9): 1139–1146. doi:10.1021/jm00219a006. PMID 926114.

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Demegestone

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