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MedKoo Cat#: 563462 | Name: YM53601 HCl
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Description:

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

YM-53601 is an inhibitor of squalene synthase activity that acts by lowering cholesterol as well as triglycerides. YM53601 selectively depletes SQS from mammalian cells upon UV irradiation. YM-53601 suppresses lipogenic biosynthesis and lipid secretion in rodents. the decrease in plasma total cholesterol and triglyceride after the treatment with YM-53601 is due to its enhancement of the clearance rate of LDL and VLDL, respectively. Moreover, YM-53601 may be effective in decreasing plasma triglyceride levels early in the course of treatment of hypertriglyceridaemia in humans.

Chemical Structure

YM53601 HCl
YM53601 HCl
CAS#182959-33-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 563462

Name: YM53601 HCl

CAS#: 182959-33-7 (HCl)

Chemical Formula: C21H22ClFN2O

Exact Mass: 0.0000

Molecular Weight: 372.86

Elemental Analysis: C, 67.65; H, 5.95; Cl, 9.51; F, 5.10; N, 7.51; O, 4.29

Price and Availability

Size Price Availability Quantity
5mg USD 1,950.00 2 Weeks
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Related CAS #
182959-28-0 (free base) 182959-33-7 (HCl)
Synonym
YM-53601; YM 53601; YM53601; YM53601 HCl; YM53601 hydrochloride;
IUPAC/Chemical Name
(E)-2-[2-(1-Azabicyclo[2.2.2]octan-3-ylidene)-2-fluoroethoxy]-9H-carbazole hydrochloride
InChi Key
JWXYVHMBPISIJQ-TVWXOORISA-N
InChi Code
InChI=1S/C21H21FN2O.ClH/c22-19(18-12-24-9-7-14(18)8-10-24)13-25-15-5-6-17-16-3-1-2-4-20(16)23-21(17)11-15;/h1-6,11,14,23H,7-10,12-13H2;1H/b19-18-;
SMILES Code
F/C(COC1=CC(NC2=C3C=CC=C2)=C3C=C1)=C4CN5CCC/4CC5.[H]Cl
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 372.86 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: Kang J, Lee D, Lee KJ, Yoon JE, Kwon JH, Seo Y, Kim J, Chang SY, Park J, Kang EA, Park SJ, Park JJ, Cheon JH, Kim TI. Tumor-Suppressive Effect of Metformin via the Regulation of M2 Macrophages and Myeloid-Derived Suppressor Cells in the Tumor Microenvironment of Colorectal Cancer. Cancers (Basel). 2022 Jun 10;14(12):2881. doi: 10.3390/cancers14122881. PMID: 35740547; PMCID: PMC9220791. 2: Seo Y, Kim J, Park SJ, Park JJ, Cheon JH, Kim WH, Kim TI. Metformin Suppresses Cancer Stem Cells through AMPK Activation and Inhibition of Protein Prenylation of the Mevalonate Pathway in Colorectal Cancer. Cancers (Basel). 2020 Sep 8;12(9):2554. doi: 10.3390/cancers12092554. PMID: 32911743; PMCID: PMC7563617. 3: Takemoto Y, Mao D, Punzalan LL, Götze S, Sato SI, Uesugi M. Discovery of a Small-Molecule-Dependent Photolytic Peptide. J Am Chem Soc. 2020 Jan 22;142(3):1142-1146. doi: 10.1021/jacs.9b09178. Epub 2020 Jan 8. PMID: 31899620. 4: Alarcon VB, Marikawa Y. Statins inhibit blastocyst formation by preventing geranylgeranylation. Mol Hum Reprod. 2016 May;22(5):350-63. doi: 10.1093/molehr/gaw011. Epub 2016 Feb 7. PMID: 26908642; PMCID: PMC4847613. 5: Saito K, Shirasago Y, Suzuki T, Aizaki H, Hanada K, Wakita T, Nishijima M, Fukasawa M. Targeting cellular squalene synthase, an enzyme essential for cholesterol biosynthesis, is a potential antiviral strategy against hepatitis C virus. J Virol. 2015 Feb;89(4):2220-32. doi: 10.1128/JVI.03385-14. Epub 2014 Dec 3. PMID: 25473062; PMCID: PMC4338862. 6: Benakanakere I, Johnson T, Sleightholm R, Villeda V, Arya M, Bobba R, Freter C, Huang C. Targeting cholesterol synthesis increases chemoimmuno-sensitivity in chronic lymphocytic leukemia cells. Exp Hematol Oncol. 2014 Sep 26;3:24. doi: 10.1186/2162-3619-3-24. PMID: 25401046; PMCID: PMC4231203. 7: Park EM, Nguyen LN, Lim YS, Hwang SB. Farnesyl-diphosphate farnesyltransferase 1 regulates hepatitis C virus propagation. FEBS Lett. 2014 May 2;588(9):1813-20. doi: 10.1016/j.febslet.2014.03.043. Epub 2014 Mar 29. PMID: 24690320. 8: Llacuna L, Fernández A, Montfort CV, Matías N, Martínez L, Caballero F, Rimola A, Elena M, Morales A, Fernández-Checa JC, García-Ruiz C. Targeting cholesterol at different levels in the mevalonate pathway protects fatty liver against ischemia-reperfusion injury. J Hepatol. 2011 May;54(5):1002-10. doi: 10.1016/j.jhep.2010.08.031. Epub 2010 Oct 29. PMID: 21145825. 9: Montero J, Morales A, Llacuna L, Lluis JM, Terrones O, Basañez G, Antonsson B, Prieto J, García-Ruiz C, Colell A, Fernández-Checa JC. Mitochondrial cholesterol contributes to chemotherapy resistance in hepatocellular carcinoma. Cancer Res. 2008 Jul 1;68(13):5246-56. doi: 10.1158/0008-5472.CAN-07-6161. PMID: 18593925. 10: Ishihara T, Kakuta H, Moritani H, Ugawa T, Sakamoto S, Tsukamoto Si, Yanagisawa I. Syntheses of 3-ethylidenequinuclidine derivatives as squalene synthase inhibitors. Part 2: enzyme inhibition and effects on plasma lipid levels. Bioorg Med Chem. 2003 Aug 15;11(17):3735-45. doi: 10.1016/s0968-0896(03)00336-5. PMID: 12901918. 11: Ugawa T, Kakuta H, Moritani H, Inagaki O, Shikama H. YM-53601, a novel squalene synthase inhibitor, suppresses lipogenic biosynthesis and lipid secretion in rodents. Br J Pharmacol. 2003 May;139(1):140-6. doi: 10.1038/sj.bjp.0705229. PMID: 12746232; PMCID: PMC1573827. 12: Ugawa T, Kakuta H, Moritani H, Inagaki O. Effect of YM-53601, a novel squalene synthase inhibitor, on the clearance rate of plasma LDL and VLDL in hamsters. Br J Pharmacol. 2002 Oct;137(4):561-9. doi: 10.1038/sj.bjp.0704906. PMID: 12359639; PMCID: PMC1573526. 13: Ugawa T, Kakuta H, Moritani H, Shikama H. Experimental model of escape phenomenon in hamsters and the effectiveness of YM-53601 in the model. Br J Pharmacol. 2002 Mar;135(6):1572-8. doi: 10.1038/sj.bjp.0704595. PMID: 11906972; PMCID: PMC1573260. 14: Ugawa T, Kakuta H, Moritani H, Matsuda K, Ishihara T, Yamaguchi M, Naganuma S, Iizumi Y, Shikama H. YM-53601, a novel squalene synthase inhibitor, reduces plasma cholesterol and triglyceride levels in several animal species. Br J Pharmacol. 2000 Sep;131(1):63-70. doi: 10.1038/sj.bjp.0703545. PMID: 10960070; PMCID: PMC1572301.

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