Promegestone

Names

[ Name ]:
Promegestone

[Synonym ]:
R5020
(8S,13S,14S,17S)-13,17-dimethyl-17-propanoyl-1,2,6,7,8,11,12,14,15,16-decahydrocyclopenta[a]phenanthren-3-one
Promegestona
Promegestone
17,21-dimethyl-19-nor-4,9-pregnadiene-3,20-dione
RU5020
Promegestonum
promegestrone

Biological Activity

[Description]:

Promegestone (R-5020), a progestin, is a potent progesterone receptor (PR) agonist. Promegestone has the potential for endocrine regulation and cancer research[1].

[Related Catalog]:

Signaling Pathways >> Others >> Progesterone Receptor

Research Areas >> Cancer

Research Areas >> Endocrinology

[In Vitro]

Promegestone (R-5020; 1 nM) is efficient ligand with a full agonist response profile and a low EC50 of 0.33 nM) in HELN-hPR while it only partially induced luciferase activity in U2OS-zfPR (EC50=1.93 nM)[1]. Promegestone is inactive in HELN cells that express luciferase but no functional receptor[1]. Promegestone (10 nM) robustly stimulates SLC37A2 expression in cells expressing SUMO-deficient PR, but not in cells expressing WT PR in T47D cell models[3].

[In Vivo]

Promegestone (R-5020; 8 mg/kg; intramuscularly)-treated pregnant mice on day 18 postbreeding has the least deterioration in extracellular collagen (lowest OD) and highest cell density compared to other groups on the day before birth[2].

[References]

[1]. Clémentine Garoche, et al. Human and Zebrafish Nuclear Progesterone Receptors Are Differently Activated by Manifold Progestins. Environ Sci Technol. 2020 Aug 4;54(15):9510-9518.

[2]. Michael A Kirby, et al. Progesterone Receptor-Mediated Actions Regulate Remodeling of the Cervix in Preparation for Preterm Parturition. Reprod Sci. 2016 Nov;23(11):1473-1483.

[3]. Todd P Knutson, et al. Posttranslationally modified progesterone receptors direct ligand-specific expression of breast cancer stem cell-associated gene programs. J Hematol Oncol. 2017 Apr 17;10(1):89.

Chemical & Physical Properties

[ Density]:
1.09 g/cm3

[ Boiling Point ]:
486.8ºC at 760 mmHg

[ Melting Point ]:
152°

[ Molecular Formula ]:
C₂₂H₃₀O₂

[ Molecular Weight ]:
326.47200

[ Flash Point ]:
180.4ºC

[ Exact Mass ]:
326.22500

[ PSA ]:
34.14000

[ LogP ]:
5.17780

[ Index of Refraction ]:
1.553

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: KG2965000

CHEMICAL NAME :: Estra-4,9-dien-3-one, 17-alpha-methyl-17-propionyl-

CAS REGISTRY NUMBER :: 34184-77-5

LAST UPDATED :: 199209

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C22-H30-O2

MOLECULAR WEIGHT :: 326.52

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

TYPE OF TEST :: Unscheduled DNA synthesis

TEST SYSTEM :: Rodent - rat Liver

DOSE/DURATION :: 20 umol/L

REFERENCE :: CRNGDP Carcinogenesis (London). (Oxford Univ. Press, Pinkhill House, Southfield Road, Eynsham, Oxford OX8 1JJ, UK) V.1- 1980- Volume(issue)/page/year: 13,373,1992

Related Compounds

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