Lonaprisan

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MedKoo CAT#: 205910

CAS#: 211254-73-8

Description: Lonaprisan is an orally bioavailable pentafluoroethyl derivative of a mifepristone-related steroid with antiprogestagenic activity. Lonaprisan is a pure, highly receptor-selective progesterone receptor (PR) antagonist; binding of this agent to PRs inhibits PR activation and the associated proliferative effects. Unlike many other antiprogestins such as mifepristone, this agent does not appear to convert to an agonist in the presence of protein kinase A (PKA) activators and shows high antiprogestagenic activity on both progesterone receptor (PR) isoforms PR-A and PR-B.


Chemical Structure

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Lonaprisan
CAS# 211254-73-8

Theoretical Analysis

MedKoo Cat#: 205910
Name: Lonaprisan
CAS#: 211254-73-8
Chemical Formula: C28H29F5O3
Exact Mass: 508.20369
Molecular Weight: 508.52
Elemental Analysis: C, 66.13; H, 5.75; F, 18.68; O, 9.44

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Synonym: Lonaprisan; ZK230211; ZK-230211; ZK 230211.

IUPAC/Chemical Name: (8S,11R,13S,14S,17S)-11-(4-acetylphenyl)-17-hydroxy-13-methyl-17-(perfluoroethyl)-6,7,8,11,12,13,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3(2H)-one

InChi Key: VHZPUDNSVGRVMB-RXDLHWJPSA-N

InChi Code: InChI=1S/C28H29F5O3/c1-15(34)16-3-5-17(6-4-16)22-14-25(2)23(11-12-26(25,36)27(29,30)28(31,32)33)21-9-7-18-13-19(35)8-10-20(18)24(21)22/h3-6,13,21-23,36H,7-12,14H2,1-2H3/t21-,22+,23-,25-,26-/m0/s1

SMILES Code: O=C1CCC2=C3[C@@H](C4=CC=C(C(C)=O)C=C4)C[C@]5(C)[C@@](C(F)(F)C(F)(F)F)(O)CC[C@@]5([H])[C@]3([H])CCC2=C1

Appearance: Solid powder

Purity: >98%

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: >5 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

Preparing Stock Solutions

The following data is based on the product molecular weight 508.52 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

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1: Busia L, Faus H, Hoffmann J, Haendler B. The antiprogestin Lonaprisan inhibits breast cancer cell proliferation by inducing p21 expression. Mol Cell Endocrinol. 2011 Feb 10;333(1):37-46. Epub 2010 Dec 5. PubMed PMID: 21138753.

2: Chakraborty A, Chatterjee S, Roy P. Progesterone receptor agonists and antagonists as anticancer agents. Mini Rev Med Chem. 2010 Jun;10(6):506-17. Review. PubMed PMID: 20370704.

3: Afhüppe W, Beekman JM, Otto C, Korr D, Hoffmann J, Fuhrmann U, Möller C. In vitro characterization of ZK 230211--A type III progesterone receptor antagonist with enhanced antiproliferative properties. J Steroid Biochem Mol Biol. 2010 Mar;119(1-2):45-55. Epub 2010 Jan 4. PubMed PMID: 20043998.

4: Heikinheimo O, Vani S, Carpén O, Tapper A, Härkki P, Rutanen EM, Critchley H. Intrauterine release of progesterone antagonist ZK230211 is feasible and results in novel endometrial effects: a pilot study. Hum Reprod. 2007 Sep;22(9):2515-22. Epub 2007 Jul 17. PubMed PMID: 17636280.

5: Nayak NR, Slayden OD, Mah K, Chwalisz K, Brenner RM. Antiprogestin-releasing intrauterine devices: a novel approach to endometrial contraception. Contraception. 2007 Jun;75(6 Suppl):S104-11. Epub 2007 Mar 21. Review. PubMed PMID: 17531599; PubMed Central PMCID: PMC1945229.

6: Slayden OD, Zelinski MB, Chwalisz K, Hess-Stumpp H, Brenner RM. Chronic progesterone antagonist-estradiol therapy suppresses breakthrough bleeding and endometrial proliferation in a menopausal macaque model. Hum Reprod. 2006 Dec;21(12):3081-90. Epub 2006 Aug 26. PubMed PMID: 16936297.

7: Slayden OD, Chwalisz K, Brenner RM. Reversible suppression of menstruation with progesterone antagonists in rhesus macaques. Hum Reprod. 2001 Aug;16(8):1562-74. PubMed PMID: 11473944.

8: Fuhrmann U, Hess-Stumpp H, Cleve A, Neef G, Schwede W, Hoffmann J, Fritzemeier KH, Chwalisz K. Synthesis and biological activity of a novel, highly potent progesterone receptor antagonist. J Med Chem. 2000 Dec 28;43(26):5010-6. PubMed PMID: 11150172.
  



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