Synonym
RM133; RM 133; RM-133
IUPAC/Chemical Name
(4-((2S,3S,5S,8R,9S,10S,13S,14S,17R)-17-Ethynyl-3,17-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-2-yl)piperazin-1-yl)((S)-1-(quinoline-2-carbonyl)pyrrolidin-2-yl)methanone
InChi Key
HOUNMJYTCWEHQD-WGQHWTFVSA-N
InChi Code
InChI=1S/C40H52N4O4/c1-4-40(48)18-16-30-28-13-12-27-24-35(45)34(25-38(27,2)29(28)15-17-39(30,40)3)42-20-22-43(23-21-42)37(47)33-10-7-19-44(33)36(46)32-14-11-26-8-5-6-9-31(26)41-32/h1,5-6,8-9,11,14,27-30,33-35,45,48H,7,10,12-13,15-25H2,2-3H3/t27-,28+,29-,30-,33-,34-,35-,38-,39-,40-/m0/s1
SMILES Code
O=C(N1CCN([C@H]2C[C@]3(C)[C@@]4([H])CC[C@]5(C)[C@](O)(C#C)CC[C@@]5([H])[C@]4([H])CC[C@@]3([H])C[C@@H]2O)CC1)[C@H]6N(C(C7=NC8=CC=CC=C8C=C7)=O)CCC6
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
652.88
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: Perreault M, Maltais R, Roy J, Picard S, Popa I, Bertrand N, Poirier D. Induction of endoplasmic reticulum stress by aminosteroid derivative RM-581 leads to tumor regression in PANC-1 xenograft model. Invest New Drugs. 2018 Jul 30. doi: 10.1007/s10637-018-0643-4. [Epub ahead of print] PubMed PMID: 30062573.
2: Dutour R, Maltais R, Perreault M, Roy J, Poirier D. Parallel Solid-Phase Synthesis Using a New Diethylsilylacetylenic Linker and Leading to Mestranol Derivatives with Potent Antiproliferative Activities on Multiple Cancer Cell Lines. Anticancer Agents Med Chem. 2018 Mar 7. doi: 10.2174/1871520618666180307130158. [Epub ahead of print] PubMed PMID: 29521249.
3: Perreault M, Maltais R, Kenmogne LC, Létourneau D, LeHoux JG, Gobeil S, Poirier D. Implication of STARD5 and cholesterol homeostasis disturbance in the endoplasmic reticulum stress-related response induced by pro-apoptotic aminosteroid RM-133. Pharmacol Res. 2018 Feb;128:52-60. doi: 10.1016/j.phrs.2017.12.024. Epub 2017 Dec 26. PubMed PMID: 29287690.
4: Perreault M, Maltais R, Roy J, Dutour R, Poirier D. Design of a Mestranol 2-N-Piperazino-Substituted Derivative Showing Potent and Selective in vitro and in vivo Activities in MCF-7 Breast Cancer Models. ChemMedChem. 2017 Jan 20;12(2):177-182. doi: 10.1002/cmdc.201600482. Epub 2017 Jan 6. PubMed PMID: 28060448.
5: Perreault M, Maltais R, Dutour R, Poirier D. Explorative study on the anticancer activity, selectivity and metabolic stability of related analogs of aminosteroid RM-133. Steroids. 2016 Nov;115:105-113. doi: 10.1016/j.steroids.2016.08.015. Epub 2016 Aug 21. PubMed PMID: 27553727.
6: Kenmogne LC, Ayan D, Roy J, Maltais R, Poirier D. The Aminosteroid Derivative RM-133 Shows In Vitro and In Vivo Antitumor Activity in Human Ovarian and Pancreatic Cancers. PLoS One. 2015 Dec 14;10(12):e0144890. doi: 10.1371/journal.pone.0144890. eCollection 2015. PubMed PMID: 26660672; PubMed Central PMCID: PMC4682813.
7: Maltais R, Hospital A, Delhomme A, Roy J, Poirier D. Chemical synthesis, NMR analysis and evaluation on a cancer xenograft model (HL-60) of the aminosteroid derivative RM-133. Steroids. 2014 Apr;82:68-76. doi: 10.1016/j.steroids.2014.01.008. Epub 2014 Jan 30. PubMed PMID: 24486462.
8: Ayan D, Maltais R, Hospital A, Poirier D. Chemical synthesis, cytotoxicity, selectivity and bioavailability of 5α-androstane-3α,17β-diol derivatives. Bioorg Med Chem. 2014 Nov 1;22(21):5847-59. doi: 10.1016/j.bmc.2014.09.026. Epub 2014 Sep 19. PubMed PMID: 25300820.