MedKoo Cat#: 528320 | Name: SIM-688

Description:

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

SIM-688, also known as WAY-204688, is an estrogen receptor agonist and NF-κB inhibitor potentially for the treatment of rheumatoid arthritis. Preservation of mucosal weight and prevention of histopathologic changes were observed with the administration of WAY-204688. Similar findings were observed in a cecal ligation and puncture model with WAY-204688 and a related compound WAY-169916. These results indicate that oral administration of these pathway-selective ER ligands preserved gastrointestinal barrier function and improve outcome in experimental models of systemic infection and inflammation. These agents may prove to be useful clinically as a novel treatment strategy for severe sepsis.

Chemical Structure

SIM-688
SIM-688
CAS#796854-35-8

Theoretical Analysis

MedKoo Cat#: 528320

Name: SIM-688

CAS#: 796854-35-8

Chemical Formula: C34H31F3N2O2

Exact Mass: 556.2338

Molecular Weight: 556.63

Elemental Analysis: C, 73.37; H, 5.61; F, 10.24; N, 5.03; O, 5.75

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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Synonym
SIM-688; SIM 688; SIM688; WAY-204688; WAY204688; WAY 204688
IUPAC/Chemical Name
(2S,3S)-3-(2-methoxyphenyl)-2-methyl-3-(naphthalen-1-yl)-2-(4-(3-(trifluoromethyl)phenyl)piperidine-1-carbonyl)propanenitrile
InChi Key
JZPONCMNBSEYQW-MOJIJOCKSA-N
InChi Code
InChI=1S/C34H31F3N2O2/c1-33(22-38,32(40)39-19-17-23(18-20-39)25-11-7-12-26(21-25)34(35,36)37)31(29-14-5-6-16-30(29)41-2)28-15-8-10-24-9-3-4-13-27(24)28/h3-16,21,23,31H,17-20H2,1-2H3/t31-,33?/m0/s1
SMILES Code
COC1=C(C=CC=C1)[C@H](C2=CC=CC3=CC=CC=C32)[C@](C(N4CCC(C5=CC=CC(C(F)(F)F)=C5)CC4)=O)(C#N)C
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
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 556.63 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: Caggiano TJ, Brazzale A, Ho DM, Kraml CM, Trybulski E, Chadwick CC, Chippari S, Borges-Marcucci L, Eckert A, Keith JC, Kenney T, Harnish DC. Estrogen receptor dependent inhibitors of NF-kappaB transcriptional activation-1 synthesis and biological evaluation of substituted 2-cyanopropanoic acid derivatives: pathway selective inhibitors of NF-kappaB, a potential treatment for rheumatoid arthritis. J Med Chem. 2007 Nov 1;50(22):5245-8. PubMed PMID: 17902637. 2: Opal SM, Palardy JE, Cristofaro P, Parejo N, Jhung JW, Keith JC Jr, Chippari S, Caggiano TJ, Steffan RJ, Chadwick CC, Harnish DC. The activity of pathway-selective estrogen receptor ligands in experimental septic shock. Shock. 2005 Dec;24(6):535-40. PubMed PMID: 16317384.