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
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.
| 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: 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.
