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MedKoo Cat#: 575257 | Name: F-1394

Description:

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

F-1394 is an acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor. F-1394 both prevents the formation of atherosclerosis and accelerates its regression without affecting the serum TC level, indicating that F-1394 acts directly on the arterial wall. F-1394 significantly reduced neointimal thickening and the extent of macrophages in lesions without affecting serum cholesterol levels. In vitro, F-1394 attenuated foam cell formation in mouse peritoneal macrophages.

Chemical Structure

F-1394
F-1394
CAS#162490-89-3

Theoretical Analysis

MedKoo Cat#: 575257

Name: F-1394

CAS#: 162490-89-3

Chemical Formula: C33H61N3O6

Exact Mass: 595.4560

Molecular Weight: 595.87

Elemental Analysis: C, 66.52; H, 10.32; N, 7.05; O, 16.11

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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Related CAS #
No Data
Synonym
F 1394; F-1394; F1394
IUPAC/Chemical Name
(1S,2S)-2-(3-neopentyl-3-nonylureido)cyclohexyl 3-((R)-2,2,5,5-tetramethyl-1,3-dioxane-4-carboxamido)propanoate
InChi Key
NWLFOBZKYXKBOF-NSVAZKTRSA-N
InChi Code
InChI=1S/C33H61N3O6/c1-9-10-11-12-13-14-17-22-36(23-31(2,3)4)30(39)35-25-18-15-16-19-26(25)41-27(37)20-21-34-29(38)28-32(5,6)24-40-33(7,8)42-28/h25-26,28H,9-24H2,1-8H3,(H,34,38)(H,35,39)/t25-,26-,28-/m0/s1
SMILES Code
CCCCCCCCCN(CC(C)(C)C)C(=O)N[C@H]1CCCC[C@@H]1OC(=O)CCNC(=O)[C@@H]2OC(C)(C)OCC2(C)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
>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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 595.87 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: Amengual J, Ogando Y, Nikain C, Quezada A, Qian K, Vaisar T, Fisher EA. Short-Term Acyl-CoA:Cholesterol Acyltransferase Inhibition, Combined with Apoprotein A1 Overexpression, Promotes Atherosclerosis Inflammation Resolution in Mice. Mol Pharmacol. 2021 Mar;99(3):175-183. doi: 10.1124/molpharm.120.000108. Epub 2020 Dec 31. PMID: 33384285; PMCID: PMC7883010. 2: Rong JX, Blachford C, Feig JE, Bander I, Mayne J, Kusunoki J, Miller C, Davis M, Wilson M, Dehn S, Thorp E, Tabas I, Taubman MB, Rudel LL, Fisher EA. ACAT inhibition reduces the progression of preexisting, advanced atherosclerotic mouse lesions without plaque or systemic toxicity. Arterioscler Thromb Vasc Biol. 2013 Jan;33(1):4-12. doi: 10.1161/ATVBAHA.112.252056. Epub 2012 Nov 8. PMID: 23139293; PMCID: PMC3617493. 3: Duriez P, Fruchart JC. Post-statin approaches to hyperlipidaemia. Expert Opin Investig Drugs. 1998 Dec;7(12):1997-2009. doi: 10.1517/13543784.7.12.1997. PMID: 15991942. 4: Rong JX, Kusunoki J, Oelkers P, Sturley SL, Fisher EA. Acyl-coenzymeA (CoA):cholesterol acyltransferase inhibition in rat and human aortic smooth muscle cells is nontoxic and retards foam cell formation. Arterioscler Thromb Vasc Biol. 2005 Jan;25(1):122-7. doi: 10.1161/01.ATV.0000148202.49842.3b. Epub 2004 Oct 21. PMID: 15499046. 5: Hirakawa Y, Shimokawa H. [Lipid-lowering drugs]. Nihon Yakurigaku Zasshi. 2001 Dec;118(6):389-95. Japanese. doi: 10.1254/fpj.118.389. PMID: 11778457. 6: Aragane K, Kojima K, Fujinami K, Kamei J, Kusunoki J. Effect of F-1394, an acyl-CoA:cholesterol acyltransferase inhibitor, on atherosclerosis induced by high cholesterol diet in rabbits. Atherosclerosis. 2001 Sep;158(1):139-45. doi: 10.1016/s0021-9150(01)00441-5. PMID: 11500184. 7: Chiwata T, Aragane K, Fujinami K, Kojima K, Ishibashi S, Yamada N, Kusunoki J. Direct effect of an acyl-CoA:cholesterol acyltransferase inhibitor, F-1394, on atherosclerosis in apolipoprotein E and low density lipoprotein receptor double knockout mice. Br J Pharmacol. 2001 Aug;133(7):1005-12. doi: 10.1038/sj.bjp.0704160. PMID: 11487509; PMCID: PMC1572866. 8: Kusunoki J, Hansoty DK, Aragane K, Fallon JT, Badimon JJ, Fisher EA. Acyl- CoA:cholesterol acyltransferase inhibition reduces atherosclerosis in apolipoprotein E-deficient mice. Circulation. 2001 May 29;103(21):2604-9. doi: 10.1161/01.cir.103.21.2604. PMID: 11382731. 9: Miyazaki A, Horiuchi S. [ACAT inhibitors]. Nihon Rinsho. 2001 Mar;59 Suppl 3:675-80. Japanese. PMID: 11347152. 10: Aragane K, Fujinami K, Kojima K, Kusunoki J. ACAT inhibitor F-1394 prevents intimal hyperplasia induced by balloon injury in rabbits. J Lipid Res. 2001 Apr;42(4):480-8. PMID: 11290819. 11: Kusunoki J, Aragane K, Kitamine T, Kozono H, Kano K, Fujinami K, Kojima K, Chiwata T, Sekine Y. Postprandial hyperlipidemia in streptozotocin-induced diabetic rats is due to abnormal increase in intestinal acyl coenzyme A:cholesterol acyltransferase activity. Arterioscler Thromb Vasc Biol. 2000 Jan;20(1):171-8. doi: 10.1161/01.atv.20.1.171. PMID: 10634814. 12: Aragane K, Kusunoki J, Kitamine T, Yamaura T, Ohnishi H. Effects of F-1394, an acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor, on ACAT activity in HepG2 cells and on hepatic secretion of lipids in Triton WR-1339-induced hyperlipidemic rats: possible role of hepatic ACAT in very low density lipoprotein secretion. Jpn J Pharmacol. 1998 Mar;76(3):309-12. doi: 10.1254/jjp.76.309. PMID: 9593225. 13: Kusunoki J, Aragane K, Kitamine T, Yamaura T, Ohnishi H. [Effect of F-1394, a potent and selective inhibitor of acyl-CoA:cholesterol acyltransferase (ACAT), on esterification of cholesterol and basolateral secretion of cholesteryl ester in Caco-2 cells]. Nihon Yakurigaku Zasshi. 1997 Dec;110(6):357-65. Japanese. doi: 10.1254/fpj.110.357. PMID: 9503394. 14: Kusunoki J, Aragane K, Kitamine T, Yamaura T, Ohnishi H. [Hypolipidemic action of F-1394, an acyl-CoA: cholesterol acyltransferase (ACAT) inhibitor, in high-fat diet fed beagle dogs]. Yakugaku Zasshi. 1997 Apr;117(4):233-41. Japanese. doi: 10.1248/yakushi1947.117.4_233. PMID: 9167444. 15: Kusunoki J, Aragane K, Kitamine T, Higashinakagawa S, Kase N, Yamaura T, Ohnishi H. Hypocholesterolemic action and prevention of cholesterol absorption via the gut by F-1394, a potent acyl-CoA:cholesterol acyltransferase (ACAT) inhibitor, in cholesterol diet-fed rats. Jpn J Pharmacol. 1995 Sep;69(1):53-60. doi: 10.1254/jjp.69.53. PMID: 8847832. 16: Kusunoki J, Aragane K, Yamaura T, Ohnishi H. Studies on acyl-CoA: cholesterol acyltransferase (ACAT) inhibitory effects and enzyme selectivity of F-1394, a pantotheic acid derivative. Jpn J Pharmacol. 1995 Mar;67(3):195-203. doi: 10.1254/jjp.67.195. PMID: 7630037.

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