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MedKoo Cat#: 461057 | Name: Promegestone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Promegestone is a progestin medication which is used in menopausal hormone therapy and in the treatment of gynecological disorders.

Chemical Structure

Promegestone
Promegestone
CAS#34184-77-5

Theoretical Analysis

MedKoo Cat#: 461057

Name: Promegestone

CAS#: 34184-77-5

Chemical Formula: C22H30O2

Exact Mass: 326.2246

Molecular Weight: 326.48

Elemental Analysis: C, 80.94; H, 9.26; O, 9.80

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Promegestone; R 5020; R-5020; R5020; RU 5020; RU-5020; RU5020; Surgestone; U 56217; U-56217; U56217;
IUPAC/Chemical Name
(8S,13S,14S,17S)-13,17-dimethyl-17-propionyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
InChi Key
QFFCYTLOTYIJMR-XMGTWHOFSA-N
InChi Code
InChI=1S/C22H30O2/c1-4-20(24)22(3)12-10-19-18-7-5-14-13-15(23)6-8-16(14)17(18)9-11-21(19,22)2/h13,18-19H,4-12H2,1-3H3/t18-,19+,21+,22-/m1/s1
SMILES Code
C[C@@]12[C@](C(CC)=O)(C)CC[C@@]1([H])[C@]3([H])CCC4=CC(CCC4=C3CC2)=O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 326.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Uzan S, Denis C, Pomi V, Varin C. Double-blind trial of promegestone (R 5020) and lynestrenol in the treatment of benign breast disease. Eur J Obstet Gynecol Reprod Biol. 1992 Feb 28;43(3):219-27. PubMed PMID: 1563574. 2: Blanton MP, Xie Y, Dangott LJ, Cohen JB. The steroid promegestone is a noncompetitive antagonist of the Torpedo nicotinic acetylcholine receptor that interacts with the lipid-protein interface. Mol Pharmacol. 1999 Feb;55(2):269-78. PubMed PMID: 9927618. 3: Raynaud JP, Ojasoo T. [Promegestone, a new progestin]. J Gynecol Obstet Biol Reprod (Paris). 1983;12(7):697-710. French. PubMed PMID: 6366037. 4: Goswami D, Callaway C, Pascal BD, Kumar R, Edwards DP, Griffin PR. Influence of domain interactions on conformational mobility of the progesterone receptor detected by hydrogen/deuterium exchange mass spectrometry. Structure. 2014 Jul 8;22(7):961-73. doi: 10.1016/j.str.2014.04.013. Epub 2014 Jun 5. PubMed PMID: 24909783; PubMed Central PMCID: PMC4393884. 5: Speroni L, Whitt GS, Xylas J, Quinn KP, Jondeau-Cabaton A, Barnes C, Georgakoudi I, Sonnenschein C, Soto AM. Hormonal regulation of epithelial organization in a three-dimensional breast tissue culture model. Tissue Eng Part C Methods. 2014 Jan;20(1):42-51. doi: 10.1089/ten.TEC.2013.0054. Epub 2013 Jun 25. PubMed PMID: 23675751; PubMed Central PMCID: PMC3870574. 6: Tremollieres FA, Strong DD, Baylink DJ, Mohan S. Progesterone and promegestone stimulate human bone cell proliferation and insulin-like growth factor-2 production. Acta Endocrinol (Copenh). 1992 Apr;126(4):329-37. PubMed PMID: 1375800. 7: Taylor RN, Savouret JF, Vaisse C, Vigne JL, Ryan I, Hornung D, Seppälä M, Milgrom E. Promegestone (R5020) and mifepristone (RU486) both function as progestational agonists of human glycodelin gene expression in isolated human epithelial cells. J Clin Endocrinol Metab. 1998 Nov;83(11):4006-12. PubMed PMID: 9814484. 8: McFall T, Patki M, Rosati R, Ratnam M. Role of the short isoform of the progesterone receptor in breast cancer cell invasiveness at estrogen and progesterone levels in the pre- and post-menopausal ranges. Oncotarget. 2015 Oct 20;6(32):33146-64. doi: 10.18632/oncotarget.5082. PubMed PMID: 26356672; PubMed Central PMCID: PMC4741755. 9: Pasqualini JR, Maloche C, Maroni M, Chetrite G. Effect of the progestagen Promegestone (R-5020) on mRNA of the oestrone sulphatase in the MCF-7 human mammary cancer cells. Anticancer Res. 1994 Jul-Aug;14(4A):1589-93. PubMed PMID: 7979190. 10: Bashirelahi N, Ganesan S, Ekiko DB, Young JD Jr, Shida K, Yamanaka H, Takahashi E. Effect of 16 beta-ethyl-17 beta-hydroxy-4-estren-3-one (TSAA-291) on the binding of promegestone (R5020) and methyltrienolone (R1881) to hyperplastic and neoplastic human prostate. J Steroid Biochem. 1986 Sep;25(3):367-74. PubMed PMID: 2430141. 11: Chetrite G, Le Nestour E, Pasqualini JR. Human estrogen sulfotransferase (hEST1) activities and its mRNA in various breast cancer cell lines. Effect of the progestin, promegestone (R-5020). J Steroid Biochem Mol Biol. 1998 Sep;66(5-6):295-302. PubMed PMID: 9749835. 12: Sirett DA, Grant JK. Saturable binding of [3H]-promegestone in sheep liver cytosol is not to receptors for progesterone or glucocorticoids. J Steroid Biochem. 1982 Apr;16(4):553-5. PubMed PMID: 7201050. 13: Brun G, Dargent D, Pontonnier G, Petrescou L. [Clinical use of promegestone, a progestational agent with high specificity for receptors]. Rev Fr Gynecol Obstet. 1984 May;79(5):423-6. French. PubMed PMID: 6396815. 14: Kougioumtzi A, Tsaparas P, Magklara A. Deep sequencing reveals new aspects of progesterone receptor signaling in breast cancer cells. PLoS One. 2014 Jun 4;9(6):e98404. doi: 10.1371/journal.pone.0098404. eCollection 2014. PubMed PMID: 24897521; PubMed Central PMCID: PMC4045674. 15: Nguyen BL, Chetrite G, Pasqualini JR. Transformation of estrone and estradiol in hormone-dependent and hormone-independent human breast cancer cells. Effects of the antiestrogen ICI 164,384, danazol, and promegestone (R-5020). Breast Cancer Res Treat. 1995 May;34(2):139-46. PubMed PMID: 7647331. 16: Pasqualini JR, Varin C, Nguyen BL. Effect of the progestagen R5020 (promegestone) and of progesterone on the uptake and on the transformation of estrone sulfate in the MCF-7 and T-47d human mammary cancer cells: correlation with progesterone receptor levels. Cancer Lett. 1992 Sep 14;66(1):55-60. PubMed PMID: 1451096. 17: Joseph PJ, Couzinet B, Brailly S, Rigaud C, Raynaud JP, Schaison G. Interactions of oestradiol benzoate and promegestone upon basal and TRH-induced prolactin secretion in postmenopausal women. Clin Endocrinol (Oxf). 1986 May;24(5):497-503. PubMed PMID: 3098454. 18: Schneider W, Gauthier Y, Shyamala G. Effects of progesterone, promegestone and RU 486 on glucocorticoid receptor levels in primary cultures of mouse mammary epithelial cells. J Steroid Biochem. 1988 Jun;29(6):599-604. PubMed PMID: 3386227. 19: Bylander A, Lind K, Goksör M, Billig H, Larsson DG. The classical progesterone receptor mediates the rapid reduction of fallopian tube ciliary beat frequency by progesterone. Reprod Biol Endocrinol. 2013 May 8;11:33. doi: 10.1186/1477-7827-11-33. PubMed PMID: 23651709; PubMed Central PMCID: PMC3651731. 20: Chetrite G, Varin C, Delalonde L, Pasqualini JR. Effect of promegestone, tamoxifen, 4-hydroxytamoxifen and ICI 164,384 on the oestrone sulphatase activity of human breast cancer cells. Anticancer Res. 1993 Jul-Aug;13(4):931-4. PubMed PMID: 8352561.

View History

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