MedKoo Cat#: 319801 | Name: Telapristone

Description:

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

Telapristone, is the active metabolite of telapristone acetate (also known as CDB-4124). Telapristone is a selective progesterone receptor modulator (SPRM) being studied for the treatment of certain progesterone-sensitive conditions.

Chemical Structure

Telapristone
Telapristone
CAS#198414-30-1

Theoretical Analysis

MedKoo Cat#: 319801

Name: Telapristone

CAS#: 198414-30-1

Chemical Formula: C29H37NO4

Exact Mass: 463.2723

Molecular Weight: 463.62

Elemental Analysis: C, 75.13; H, 8.04; N, 3.02; O, 13.80

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 #
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Synonym
Telapristone; metabolite of telapristone acetate (CDB-4124).
IUPAC/Chemical Name
(8S,11R,13S,14S,17R)-11-(4-(dimethylamino)phenyl)-17-hydroxy-17-(2-methoxyacetyl)-13-methyl-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one
InChi Key
BHERMCLNVOVDPU-DQFOBABISA-N
InChi Code
InChI=1S/C29H37NO4/c1-28-16-24(18-5-8-20(9-6-18)30(2)3)27-22-12-10-21(31)15-19(22)7-11-23(27)25(28)13-14-29(28,33)26(32)17-34-4/h5-6,8-9,15,23-25,33H,7,10-14,16-17H2,1-4H3/t23-,24+,25-,28-,29-/m0/s1
SMILES Code
C[C@@]12[C@](C(COC)=O)(O)CC[C@@]1([H])[C@]3([H])CCC4=CC(CCC4=C3[C@@H](C5=CC=C(N(C)C)C=C5)C2)=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, not in water
Shelf Life
>2 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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 463.62 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: Lee O, Ivancic D, Allu S, Shidfar A, Kenney K, Helenowski I, Sullivan ME, Muzzio M, Scholtens D, Chatterton RT Jr, Bethke KP, Hansen NM, Khan SA. Local transdermal therapy to the breast for breast cancer prevention and DCIS therapy: preclinical and clinical evaluation. Cancer Chemother Pharmacol. 2015 Dec;76(6):1235-46. doi: 10.1007/s00280-015-2848-y. Epub 2015 Nov 11. PubMed PMID: 26560487. 2: Gamarra-Luques CD, Hapon MB, Goyeneche AA, Telleria CM. Resistance to cisplatin and paclitaxel does not affect the sensitivity of human ovarian cancer cells to antiprogestin-induced cytotoxicity. J Ovarian Res. 2014 Apr 27;7:45. doi: 10.1186/1757-2215-7-45. eCollection 2014. PubMed PMID: 24795781; PubMed Central PMCID: PMC4007005. 3: Uphouse L, Hiegel C. Allopregnanolone's attenuation of the lordosis-inhibiting effects of restraint is blocked by the antiprogestin, CDB-4124. Pharmacol Biochem Behav. 2014 Jul;122:16-9. doi: 10.1016/j.pbb.2014.03.012. Epub 2014 Mar 18. PubMed PMID: 24650591; PubMed Central PMCID: PMC4099060. 4: Brazert M, Korman MP, Pawelczyk LA. [Applicability of selective progesterone receptor modulators in the treatment of uterine leiomyomata and their future role in the field of gynecology]. Ginekol Pol. 2013 Sep;84(9):794-800. Review. Polish. PubMed PMID: 24191519. 5: Uphouse L, Hiegel C. An antiprogestin, CDB4124, blocks progesterone's attenuation of the negative effects of a mild stress on sexual behavior. Behav Brain Res. 2013 Mar 1;240:21-5. doi: 10.1016/j.bbr.2012.11.002. Epub 2012 Nov 12. PubMed PMID: 23153933; PubMed Central PMCID: PMC3538906. 6: Gupta A, Mehta R, Alimirah F, Peng X, Murillo G, Wiehle R, Mehta RG. Efficacy and mechanism of action of Proellex, an antiprogestin in aromatase overexpressing and Letrozole resistant T47D breast cancer cells. J Steroid Biochem Mol Biol. 2013 Jan;133:30-42. doi: 10.1016/j.jsbmb.2012.08.004. Epub 2012 Aug 23. PubMed PMID: 22939887. 7: Talaulikar VS, Manyonda I. Progesterone and progesterone receptor modulators in the management of symptomatic uterine fibroids. Eur J Obstet Gynecol Reprod Biol. 2012 Dec;165(2):135-40. doi: 10.1016/j.ejogrb.2012.07.023. Epub 2012 Aug 15. Review. PubMed PMID: 22901974. 8: Morris D, Podolski J, Kirsch A, Wiehle R, Fleckenstein L. Population pharmacokinetics of telapristone (CDB-4124) and its active monodemethylated metabolite CDB-4453, with a mixture model for total clearance. AAPS J. 2011 Dec;13(4):665-73. doi: 10.1208/s12248-011-9304-7. Epub 2011 Oct 25. PubMed PMID: 22028249; PubMed Central PMCID: PMC3221841. 9: Bouchard P, Chabbert-Buffet N, Fauser BC. Selective progesterone receptor modulators in reproductive medicine: pharmacology, clinical efficacy and safety. Fertil Steril. 2011 Nov;96(5):1175-89. doi: 10.1016/j.fertnstert.2011.08.021. Epub 2011 Sep 23. PubMed PMID: 21944187. 10: Roeder H, Jayes F, Feng L, Leppert PC. CDB-4124 does not cause apoptosis in cultured fibroid cells. Reprod Sci. 2011 Sep;18(9):850-7. doi: 10.1177/1933719111399929. Epub 2011 Mar 21. PubMed PMID: 21422050. 11: Beckley EH, Scibelli AC, Finn DA. Progesterone receptor antagonist CDB-4124 increases depression-like behavior in mice without affecting locomotor ability. Psychoneuroendocrinology. 2011 Jul;36(6):824-33. doi: 10.1016/j.psyneuen.2010.11.004. Epub 2010 Dec 15. PubMed PMID: 21163582; PubMed Central PMCID: PMC3081939. 12: Wiehle R, Lantvit D, Yamada T, Christov K. CDB-4124, a progesterone receptor modulator, inhibits mammary carcinogenesis by suppressing cell proliferation and inducing apoptosis. Cancer Prev Res (Phila). 2011 Mar;4(3):414-24. doi: 10.1158/1940-6207.CAPR-10-0244. Epub 2010 Nov 30. PubMed PMID: 21119048. 13: Luo X, Yin P, Coon V JS, Cheng YH, Wiehle RD, Bulun SE. The selective progesterone receptor modulator CDB4124 inhibits proliferation and induces apoptosis in uterine leiomyoma cells. Fertil Steril. 2010 May 15;93(8):2668-73. doi: 10.1016/j.fertnstert.2009.11.031. Epub 2010 Jan 8. PubMed PMID: 20056218; PubMed Central PMCID: PMC2872031. 14: Spitz IM. Clinical utility of progesterone receptor modulators and their effect on the endometrium. Curr Opin Obstet Gynecol. 2009 Aug;21(4):318-24. doi: 10.1097/GCO.0b013e32832e07e8. Review. PubMed PMID: 19602929. 15: Ioffe OB, Zaino RJ, Mutter GL. Endometrial changes from short-term therapy with CDB-4124, a selective progesterone receptor modulator. Mod Pathol. 2009 Mar;22(3):450-9. doi: 10.1038/modpathol.2008.204. Epub 2009 Jan 9. PubMed PMID: 19136935. 16: Leo JC, Lin VC. The activities of progesterone receptor isoform A and B are differentially modulated by their ligands in a gene-selective manner. Int J Cancer. 2008 Jan 1;122(1):230-43. PubMed PMID: 17893877. 17: Wiehle RD, Christov K, Mehta R. Anti-progestins suppress the growth of established tumors induced by 7,12-dimethylbenz(a)anthracene: comparison between RU486 and a new 21-substituted-19-nor-progestin. Oncol Rep. 2007 Jul;18(1):167-74. PubMed PMID: 17549364. 18: Attardi BJ, Burgenson J, Hild SA, Reel JR. In vitro antiprogestational/antiglucocorticoid activity and progestin and glucocorticoid receptor binding of the putative metabolites and synthetic derivatives of CDB-2914, CDB-4124, and mifepristone. J Steroid Biochem Mol Biol. 2004 Mar;88(3):277-88. PubMed PMID: 15120421. 19: Attardi BJ, Burgenson J, Hild SA, Reel JR, Blye RP. CDB-4124 and its putative monodemethylated metabolite, CDB-4453, are potent antiprogestins with reduced antiglucocorticoid activity: in vitro comparison to mifepristone and CDB-2914. Mol Cell Endocrinol. 2002 Feb 25;188(1-2):111-23. PubMed PMID: 11911951.