Demegestone

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Chemical compound

title: "Demegestone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["abandoned-drugs", "antiandrogens", "conjugated-dienes", "diketones", "enones", "norpregnanes", "progestogens"] description: "Chemical compound" topic_path: "arts/music" source: "https://en.wikipedia.org/wiki/Demegestone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

::data[format=table title="Infobox drug"]

Field	Value
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
image	Demegestone.svg
image_class	skin-invert-image
width	215px
alt	Skeletal formula of demegestone
image2	Demegestone 3D ball.png
image_class2	bg-transparent
width2	225px
alt2	Ball-and-stick model of the demegestone molecule
tradename	Lutionex
pregnancy_AU
pregnancy_US
legal_AU
legal_CA
legal_UK
legal_US
routes_of_administration	By mouth
class	Progestogen; Progestin
bioavailability	Good
metabolism	Hydroxylation, others
metabolites	• 21-Hydroxydemegestone
• Others
excretion	Urine
CAS_number	10116-22-0
ATC_prefix	G03
ATC_suffix	DB05
PubChem	93057
ChemSpiderID	84009
UNII_Ref
UNII	6E89AM91SZ
ChEBI	135339
ChEMBL	2104231
KEGG	D07223
synonyms	Dimegestone; R-2453; RU-2453; 17α-Methyl-δ9-19-norprogesterone; 17α-Methyl-19-norpregna-4,9-diene-3,20-dione
C	21
SMILES	CC(=O)[C@]1(CC[C@@H]2[C@@]1(CCC3=C4CCC(=O)C=C4CC[C@@H]23)C)C
StdInChI	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
StdInChIKey	JWAHBTQSSMYISL-MHTWAQMVSA-N
::

| C=21 | H=28 | O=2 | SMILES = CC(=O)[C@]1(CC[C@@H]2[C@@]1(CCC3=C4CCC(=O)C=C4CC[C@@H]23)C)C | StdInChI = 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 | StdInChIKey = 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. It is taken by mouth.

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

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

Medical uses

Demegestone has been used to treat luteal insufficiency. It has also been studied in combination with estrogens, such as moxestrol, as an oral contraceptive and treatment for infertility.

Side effects

Pharmacology

Pharmacodynamics

Demegestone is a progestogen, and hence is an agonist of the progesterone receptor (PR). It is a highly potent progestogen, showing 50 times the potency of progesterone in the Clauberg test. The ovulation-inbhiting dosage of demegestone is 2.5 mg/day, while the endometrial transformation dosage is 100 mg per cycle. The medication is devoid of androgenic activity, and instead has some antiandrogenic activity. Demegestone has low affinity for the glucocorticoid receptor. In a particular bioassay, both demegestone and progesterone showed antiglucocorticoid rather than glucocorticoid activity. The major metabolite of demegestone, a 21-hydroxylated metabolite, is a moderately potent progestogen (4 times the potency of progesterone) and a weak mineralocorticoid (2% of the potency of deoxycorticosterone).

::data[format=table title="class="nowrap" | Relative affinities (%) of demegestone"] | Compound || || || || || || || | |---| | Demegestone | | Notes: Values are percentages (%). Reference ligands (100%) were progesterone for the , testosterone for the , E2 for the , for the , aldosterone for the , for , and cortisol for . Sources: | ::

Pharmacokinetics

Demegestone has good bioavailability. The initial volume of distribution of demegestone is 31 L. Demegestone is metabolized by hydroxylation at the C21, C1, C2, and C11 positions, which is eventually followed by A-ring aromatization after 1,2-dehydration. The major metabolite of demegestone is a 21-hydroxy derivative. The metabolic clearance rate of demegestone is 20 L/h. Its biological half-lives are 2.39 and 0.24 hours with intravenous injection. Demegestone and/or its metabolites are excreted, at least in part, in urine.

Chemistry

Demegestone, also known as 17α-methyl-δ9-19-norprogesterone or as 17α-methyl-19-norpregna-4,9-diene-3,20-dione, is a synthetic norpregnane steroid and a derivative of progesterone. It is specifically a combined derivative of 17α-methylprogesterone and 19-norprogesterone, or of 17α-methyl-19-norprogesterone. Related derivatives of 17α-methyl-19-norprogesterone include promegestone and trimegestone.

History

Demegestone was first described in the literature in 1964 and was introduced for medical use in 1974 in France. It was developed by Roussel Uclaf.

Society and culture

Generic names

Demegestone is the generic name of the drug and its . It is also known by its developmental code name R-2453 or RU-2453.

Brand names

Demegestone was marketed under the brand name Lutionex.

Availability

Demegestone is no longer marketed and hence is no longer available in any country. It was previously available in France.

References

(14 November 2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer.
William Andrew Publishing. (22 October 2013). "Pharmaceutical Manufacturing Encyclopedia". Elsevier.
(July 2019). "Demegestone". Micromedex}}: {{Dead link.
(August 2005). "Pharmacology of estrogens and progestogens: influence of different routes of administration". Climacteric.
(1971). "Evaluation of a low-dose progestagen as a contraceptive". Nihon Funin Gakkai Zasshi.
(September 1977). "Quantitative relationships between steroid structure and binding to putative progesterone receptors". Journal of Medicinal Chemistry.
(1988). "[Luteal insufficiency and elevation of sex-binding proteins by demegestone]". Revue Française de Gynécologie et d'Obstétrique.
(1970). "[Clinical observation on oral contraceptive effect by R-2453 (Abstracts of Papers Presented at Showa 44 in the field of gynecology]).". Japanese Journal of Obstetrics and Gynecology-Acta Obstetrica et Gynaecologica Japonica.
(January 1979). "Treatment of Ovarian Sterility with Combined Moxestrol-Demegestone Preparation.". Masson Editeur.
(1974). "121. Metabolic studies of R2453, a highly potent progestin". Journal of Steroid Biochemistry.
(October 2011). "Oral Contraceptive Pills: Combinations, Dosages and the Rationale behind 50 Years or Oral Hormonal Contraceptive Development". Journal für Reproduktionsmedizinund Endokrinologie.
(1981). "Mechanisms of Steroid Action". Macmillan Education UK.
(September 1977). "The relationship between glucocorticoid structure and effects upon thymocytes". Molecular Pharmacology.
(January 1980). "Steroid flexibility and receptor specificity". Journal of Steroid Biochemistry.
(January 1980). "Steroid hormone receptors and pharmacology". Journal of Steroid Biochemistry.
(January 1994). "Affiliations among steroid receptors as revealed by multivariate analysis of steroid binding data". The Journal of Steroid Biochemistry and Molecular Biology.
(November 1978). "Unique steroid congeners for receptor studies". Cancer Research.

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