Telapristone

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MedKoo CAT#: 319801

CAS#: 198414-30-1

Description: 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

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Telapristone
CAS# 198414-30-1

Theoretical Analysis

MedKoo Cat#: 319801
Name: Telapristone
CAS#: 198414-30-1
Chemical Formula: C29H37NO4
Exact Mass: 463.27
Molecular Weight: 463.618
Elemental Analysis: C, 75.13; H, 8.04; N, 3.02; O, 13.80

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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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:

Biological target:
In vitro activity:
In vivo activity:

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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

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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.