YM-53601

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

MedKoo CAT#: 563462

CAS#: 182959-33-7

Description: YM-53601 is an inhibitor of squalene synthase activity that acts by lowering cholesterol as well as triglycerides.


Chemical Structure

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YM-53601
CAS# 182959-33-7

Theoretical Analysis

MedKoo Cat#: 563462
Name: YM-53601
CAS#: 182959-33-7
Chemical Formula: C21H22ClFN2O
Exact Mass: 372.1405
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

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: YM-53601; YM 53601; YM53601;

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

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

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1: 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. PubMed PMID: 26908642; PubMed Central PMCID: PMC4847613.

2: 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. PubMed PMID: 25473062; PubMed Central PMCID: PMC4338862.

3: 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. eCollection 2014. PubMed PMID: 25401046; PubMed Central PMCID: PMC4231203.

4: 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. PubMed PMID: 24690320.

5: 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. PubMed PMID: 21145825.

6: 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. PubMed PMID: 18593925.

7: 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. PubMed PMID: 12901918.

8: 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. PubMed PMID: 12746232; PubMed Central PMCID: PMC1573827.

9: 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. PubMed PMID: 12359639; PubMed Central PMCID: PMC1573526.

10: 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. PubMed PMID: 11906972; PubMed Central PMCID: PMC1573260.

11: 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. PubMed PMID: 10960070; PubMed Central PMCID: PMC1572301.