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MedKoo Cat#: 529181 | Name: Agisterol

Description:

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

Agisterol, also known as LY 295427, is a low-density lipoprotein (LDL) receptor up-regulator. LY295427 derepresses low-density lipoprotein receptor (LDL-R) expression in a cell-based model, was examined in hamsters. LY295427 acts to increase LDL-R may represent a novel approach in the pharmacotherapy for hypercholesterolemia. LY295427 reverses oxysterol-mediated suppression of SREBP processing. LY295427 increases expression of insulin-induced gene-1 (INSIG-1) and restores SREBP processing in cells treated with oxysterols.

Chemical Structure

Agisterol
Agisterol
CAS#152755-31-2

Theoretical Analysis

MedKoo Cat#: 529181

Name: Agisterol

CAS#: 152755-31-2

Chemical Formula: C30H52O

Exact Mass: 428.4018

Molecular Weight: 428.75

Elemental Analysis: C, 84.04; H, 12.23; O, 3.73

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
LY 295427; LY-295427; LY295427; Agisterol;
IUPAC/Chemical Name
Cholestan-3-ol, 4-(2-propenyl)-, (3alpha,4alpha,5alpha)-
InChi Key
GSFDFZOSYZNZOA-ROMNCUSUSA-N
InChi Code
InChI=1S/C30H52O/c1-7-9-23-26-13-12-22-25-15-14-24(21(4)11-8-10-20(2)3)29(25,5)18-16-27(22)30(26,6)19-17-28(23)31/h7,20-28,31H,1,8-19H2,2-6H3/t21-,22+,23+,24-,25+,26+,27+,28-,29-,30+/m1/s1
SMILES Code
CC(C)CCC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])[C@H](CC=C)[C@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 428.75 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: Bielska AA, Olsen BN, Gale SE, Mydock-McGrane L, Krishnan K, Baker NA, Schlesinger PH, Covey DF, Ory DS. Side-chain oxysterols modulate cholesterol accessibility through membrane remodeling. Biochemistry. 2014 May 13;53(18):3042-51. doi: 10.1021/bi5000096. Epub 2014 May 1. PubMed PMID: 24758724; PubMed Central PMCID: PMC4020583. 2: Bielska AA, Ory DS, Covey DF. Synthesis of the enantiomer of the oxysterol-antagonist LY295427. Steroids. 2011 Sep-Oct;76(10-11):986-90. doi: 10.1016/j.steroids.2011.03.008. Epub 2011 Apr 4. PubMed PMID: 21470559; PubMed Central PMCID: PMC3139699. 3: Nunomura S, Endo K, Makishima M, Ra C. Oxysterol represses high-affinity IgE receptor-stimulated mast cell activation in Liver X receptor-dependent and -independent manners. FEBS Lett. 2010 Mar 19;584(6):1143-8. doi: 10.1016/j.febslet.2010.02.006. Epub 2010 Feb 9. PubMed PMID: 20138879. 4: Borthwick F, Taylor JM, Bartholomew C, Graham A. Differential regulation of the STARD1 subfamily of START lipid trafficking proteins in human macrophages. FEBS Lett. 2009 Apr 2;583(7):1147-53. doi: 10.1016/j.febslet.2009.02.042. Epub 2009 Mar 10. PubMed PMID: 19272380. 5: Du X, Pham YH, Brown AJ. Effects of 25-hydroxycholesterol on cholesterol esterification and sterol regulatory element-binding protein processing are dissociable: implications for cholesterol movement to the regulatory pool in the endoplasmic reticulum. J Biol Chem. 2004 Nov 5;279(45):47010-6. Epub 2004 Aug 17. PubMed PMID: 15317807. 6: Hall AM, Krishnamoorthy L, Orlow SJ. 25-hydroxycholesterol acts in the Golgi compartment to induce degradation of tyrosinase. Pigment Cell Res. 2004 Aug;17(4):396-406. PubMed PMID: 15250942. 7: Janowski BA. The hypocholesterolemic agent LY295427 up-regulates INSIG-1, identifying the INSIG-1 protein as a mediator of cholesterol homeostasis through SREBP. Proc Natl Acad Sci U S A. 2002 Oct 1;99(20):12675-80. Epub 2002 Sep 19. PubMed PMID: 12242342; PubMed Central PMCID: PMC130519. 8: Janowski BA, Shan B, Russell DW. The hypocholesterolemic agent LY295427 reverses suppression of sterol regulatory element-binding protein processing mediated by oxysterols. J Biol Chem. 2001 Nov 30;276(48):45408-16. Epub 2001 Sep 27. PubMed PMID: 11577112. 9: Lin HS, Rampersaud AA, Richett ME, Harper RW, Beavers LS, McClure DB, Gardner AJ, Eacho PI, Foxworthy PS, Gadski RA. Synthesis and in vitro biological activity of 4alpha-(2-propenyl)-5alpha-cholest-24-en-3alpha-ol: a 24,25-dehydro analog of the hypocholesterolemic agent 4alpha-(2-propenyl)-5alpha-cholestan-3alpha-ol. Steroids. 1999 Mar;64(3):217-27. PubMed PMID: 10400383. 10: Bensch WR, Gadski RA, Bean JS, Beavers LS, Schmidt RJ, Perry DN, Murphy AT, McClure DB, Eacho PI, Breau AP, Archer RA, Kauffman RF. Effects of LY295427, a low-density lipoprotein (LDL) receptor up-regulator, on LDL receptor gene transcription and cholesterol metabolism in normal and hypercholesterolemic hamsters. J Pharmacol Exp Ther. 1999 Apr;289(1):85-92. PubMed PMID: 10086991. 11: Lin HS, Rampersaud AA, Richett ME, Beavers LS, McClure DB, Gadski RA. Synthesis of 4 alpha-(2-propenyl)-5,6-secocholestan-3 alpha-ol, a novel B-ring seco analog of the hypocholesterolemic agent 4 alpha-(2-propenyl)-5 alpha-cholestan-3 alpha-ol. Steroids. 1998 Apr;63(4):202-7. PubMed PMID: 9589554. 12: Bowling N, Matter WF, Gadski RA, McClure DB, Schreyer T, Dawson PA, Vlahos CJ. LY295427, a novel hypocholesterolemic agent, enhances [3H]25-hydroxycholesterol binding to liver cytosolic proteins. J Lipid Res. 1996 Dec;37(12):2586-98. PubMed PMID: 9017510.