Aramchol | CAS#246529-22-6 | cholesterol solubilizer

MedKoo Cat#: 329609 | Name: Aramchol

Description:

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

Aramchol, also known as Arachidyl amido cholanoic acid, is a cholesterol solubilizer that prevents gallstone formation in inbred mice. Aramchol reduces liver fat content in patients with nonalcoholic fatty liver disease.

Chemical Structure

Aramchol

CAS#246529-22-6

Theoretical Analysis

MedKoo Cat#: 329609

Name: Aramchol

CAS#: 246529-22-6

Chemical Formula: C44H79NO5

Exact Mass: 701.5958

Molecular Weight: 702.12

Elemental Analysis: C, 75.27; H, 11.34; N, 1.99; O, 11.39

Price and Availability

Size	Price	Availability
5mg	USD 90.00	Ready to ship
10mg	USD 150.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
500mg	USD 2,450.00	Ready to ship
1g	USD 3,850.00	Ready to Ship
2g	USD 6,550.00	Ready to Ship

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Synonym

Aramchol; Arachidyl; amido cholanoic acid; Icomidocholic acid

IUPAC/Chemical Name

(R)-4-((3S,5S,7R,8R,9S,10S,12S,13R,14S,17R)-7,12-dihydroxy-3-icosanamido-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid

InChi Key

SHKXZIQNFMOPBS-OOMQYRRCSA-N

InChi Code

InChI=1S/C44H79NO5/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-40(48)45-34-27-28-43(3)33(29-34)30-38(46)42-36-25-24-35(32(2)23-26-41(49)50)44(36,4)39(47)31-37(42)43/h32-39,42,46-47H,5-31H2,1-4H3,(H,45,48)(H,49,50)/t32-,33+,34+,35-,36+,37+,38-,39+,42+,43+,44-/m1/s1

SMILES Code

CCCCCCCCCCCCCCCCCCCC(=O)N[C@H]1CC[C@]2([C@@H](C1)C[C@H]([C@@H]3[C@@H]2C[C@@H]([C@]4([C@H]3CC[C@@H]4[C@H](C)CCC(=O)O)C)O)O)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

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T9D10P25

View CoA: current batch, Lot#T9D08P29

View CoA: current batch, Lot#X7P05R22

QC Data

View QC data: current batch, Lot#T9D10P25

View QC data: current batch, Lot#T9D08P29

View QC data: current batch, Lot#X7P05R22

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Aramchol (C20-FABAC) could inhibit stearoyl coenzyme A desaturase 1 (SCD1) activity.

In vitro activity:

At 24 h of incubation, 10 μM Aramchol reduced the expression ACTA2, bPDGFR, and MMP2 mRNAs while it induced PPARG, which was sustained at 48 h (Fig. 1A); there was also reduction of ACTA2 and MMP2 at 48 h, along with COL1A1and SCD1 mRNAs (Fig. 1A). The effect of Aramchol (10 μM) was replicated in each of 3 patient-derived primary HSC isolates treated for up to 48 h, with similar downregulation in fibrogenic genes and SCD1 mRNA (Fig. 1B). Aramchol also induced PPARG mRNA at 48 h in phHSCs (Fig. 1B). Reference: JHEP Rep. 2021 Jun; 3(3): 100237. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8189934/

In vivo activity:

Mice given Aramchol displayed an improvement of liver histology, as indicated by hematoxylin and eosin histology (Fig. 4A). This was confirmed by Sudan III (1.5‐fold improvement compared to 0.1MCD‐fed mice administered Aramchol's vehicle; P < 0.05), F4/80 (3.2‐fold improvement compared to 0.1MCD‐fed mice administered Aramchol's vehicle; P < 0.05), CD64 (5‐fold improvement compared to 0.1MCD‐fed mice administered Aramchol's vehicle; P < 0.05), and Sirius Red (2.3‐fold improvement compared to 0.1MCD‐fed mice administered Aramchol's vehicle; P < 0.05) staining and measurement of COL1A1 protein by western blot (Fig. 4A,B,D). The content of COL1A1 in Aramchol‐treated mice decreased and did not differ significantly compared to mice fed a control diet (1.2‐fold 0.1MCD + Aramchol versus control diet). Feeding mice the 0.1MCD diet for 4 weeks caused a marked increase in serum liver enzymes (ALT and AST) (Fig. 4C). Reference: Hepatol Commun. 2017 Nov; 1(9): 911–927. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5691602/

	Solvent	mg/mL	mM
Solubility
	Ethanol	20.0	28.49

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 702.12 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.

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

Formulation protocol:

1. Bhattacharya D, Basta B, Mato JM, Craig A, Fernández-Ramos D, Lopitz-Otsoa F, Tsvirkun D, Hayardeny L, Chandar V, Schwartz RE, Villanueva A, Friedman SL. Aramchol downregulates stearoyl CoA-desaturase 1 in hepatic stellate cells to attenuate cellular fibrogenesis. JHEP Rep. 2021 Jan 28;3(3):100237. doi: 10.1016/j.jhepr.2021.100237. PMID: 34151243; PMCID: PMC8189934. 2. Fernández-Ramos D, Lopitz-Otsoa F, Delacruz-Villar L, Bilbao J, Pagano M, Mosca L, Bizkarguenaga M, Serrano-Macia M, Azkargorta M, Iruarrizaga-Lejarreta M, Sot J, Tsvirkun D, van Liempd SM, Goni FM, Alonso C, Martínez-Chantar ML, Elortza F, Hayardeny L, Lu SC, Mato JM. Arachidyl amido cholanoic acid improves liver glucose and lipid homeostasis in nonalcoholic steatohepatitis via AMPK and mTOR regulation. World J Gastroenterol. 2020 Sep 14;26(34):5101-5117. doi: 10.3748/wjg.v26.i34.5101. PMID: 32982112; PMCID: PMC7495035. 3. Fernández-Ramos D, Lopitz-Otsoa F, Delacruz-Villar L, Bilbao J, Pagano M, Mosca L, Bizkarguenaga M, Serrano-Macia M, Azkargorta M, Iruarrizaga-Lejarreta M, Sot J, Tsvirkun D, van Liempd SM, Goni FM, Alonso C, Martínez-Chantar ML, Elortza F, Hayardeny L, Lu SC, Mato JM. Arachidyl amido cholanoic acid improves liver glucose and lipid homeostasis in nonalcoholic steatohepatitis via AMPK and mTOR regulation. World J Gastroenterol. 2020 Sep 14;26(34):5101-5117. doi: 10.3748/wjg.v26.i34.5101. PMID: 32982112; PMCID: PMC7495035. 4. Iruarrizaga-Lejarreta M, Varela-Rey M, Fernández-Ramos D, Martínez-Arranz I, Delgado TC, Simon J, Juan VG, delaCruz-Villar L, Azkargorta M, Lavin JL, Mayo R, Van Liempd SM, Aurrekoetxea I, Buqué X, Cave DD, Peña A, Rodríguez-Cuesta J, Aransay AM, Elortza F, Falcón-Pérez JM, Aspichueta P, Hayardeny L, Noureddin M, Sanyal AJ, Alonso C, Anguita J, Martínez-Chantar ML, Lu SC, Mato JM. Role of Aramchol in steatohepatitis and fibrosis in mice. Hepatol Commun. 2017 Nov;1(9):911-927. doi: 10.1002/hep4.1107. Epub 2017 Oct 4. PMID: 29159325; PMCID: PMC5691602.

In vitro protocol:

In vivo protocol:

1. Fernández-Ramos D, Lopitz-Otsoa F, Delacruz-Villar L, Bilbao J, Pagano M, Mosca L, Bizkarguenaga M, Serrano-Macia M, Azkargorta M, Iruarrizaga-Lejarreta M, Sot J, Tsvirkun D, van Liempd SM, Goni FM, Alonso C, Martínez-Chantar ML, Elortza F, Hayardeny L, Lu SC, Mato JM. Arachidyl amido cholanoic acid improves liver glucose and lipid homeostasis in nonalcoholic steatohepatitis via AMPK and mTOR regulation. World J Gastroenterol. 2020 Sep 14;26(34):5101-5117. doi: 10.3748/wjg.v26.i34.5101. PMID: 32982112; PMCID: PMC7495035. 2. Iruarrizaga-Lejarreta M, Varela-Rey M, Fernández-Ramos D, Martínez-Arranz I, Delgado TC, Simon J, Juan VG, delaCruz-Villar L, Azkargorta M, Lavin JL, Mayo R, Van Liempd SM, Aurrekoetxea I, Buqué X, Cave DD, Peña A, Rodríguez-Cuesta J, Aransay AM, Elortza F, Falcón-Pérez JM, Aspichueta P, Hayardeny L, Noureddin M, Sanyal AJ, Alonso C, Anguita J, Martínez-Chantar ML, Lu SC, Mato JM. Role of Aramchol in steatohepatitis and fibrosis in mice. Hepatol Commun. 2017 Nov;1(9):911-927. doi: 10.1002/hep4.1107. Epub 2017 Oct 4. PMID: 29159325; PMCID: PMC5691602.

1: Ratziu V, de Guevara L, Safadi R, Poordad F, Fuster F, Flores-Figueroa J, Arrese M, Fracanzani AL, Ben Bashat D, Lackner K, Gorfine T, Kadosh S, Oren R, Halperin M, Hayardeny L, Loomba R, Friedman S; ARREST investigator study group; Sanyal AJ. Aramchol in patients with nonalcoholic steatohepatitis: a randomized, double-blind, placebo-controlled phase 2b trial. Nat Med. 2021 Oct;27(10):1825-1835. doi: 10.1038/s41591-021-01495-3. Epub 2021 Oct 7. PMID: 34621052. 2: Bhattacharya D, Basta B, Mato JM, Craig A, Fernández-Ramos D, Lopitz-Otsoa F, Tsvirkun D, Hayardeny L, Chandar V, Schwartz RE, Villanueva A, Friedman SL. Aramchol downregulates stearoyl CoA-desaturase 1 in hepatic stellate cells to attenuate cellular fibrogenesis. JHEP Rep. 2021 Jan 28;3(3):100237. doi: 10.1016/j.jhepr.2021.100237. PMID: 34151243; PMCID: PMC8189934. 3: Sumida Y, Yoneda M. Current and future pharmacological therapies for NAFLD/NASH. J Gastroenterol. 2018 Mar;53(3):362-376. doi: 10.1007/s00535-017-1415-1. Epub 2017 Dec 16. PMID: 29247356; PMCID: PMC5847174. 4: Fraile JM, Palliyil S, Barelle C, Porter AJ, Kovaleva M. Non-Alcoholic Steatohepatitis (NASH) - A Review of a Crowded Clinical Landscape, Driven by a Complex Disease. Drug Des Devel Ther. 2021 Sep 22;15:3997-4009. doi: 10.2147/DDDT.S315724. PMID: 34588764; PMCID: PMC8473845. 5: Rotman Y, Sanyal AJ. Current and upcoming pharmacotherapy for non-alcoholic fatty liver disease. Gut. 2017 Jan;66(1):180-190. doi: 10.1136/gutjnl-2016-312431. Epub 2016 Sep 19. PMID: 27646933. 6: Iruarrizaga-Lejarreta M, Varela-Rey M, Fernández-Ramos D, Martínez-Arranz I, Delgado TC, Simon J, Juan VG, delaCruz-Villar L, Azkargorta M, Lavin JL, Mayo R, Van Liempd SM, Aurrekoetxea I, Buqué X, Cave DD, Peña A, Rodríguez-Cuesta J, Aransay AM, Elortza F, Falcón-Pérez JM, Aspichueta P, Hayardeny L, Noureddin M, Sanyal AJ, Alonso C, Anguita J, Martínez-Chantar ML, Lu SC, Mato JM. Role of Aramchol in steatohepatitis and fibrosis in mice. Hepatol Commun. 2017 Nov;1(9):911-927. doi: 10.1002/hep4.1107. Epub 2017 Oct 4. PMID: 29159325; PMCID: PMC5691602. 7: Tacke F, Puengel T, Loomba R, Friedman SL. An integrated view of anti- inflammatory and antifibrotic targets for the treatment of NASH. J Hepatol. 2023 Apr 14:S0168-8278(23)00218-0. doi: 10.1016/j.jhep.2023.03.038. Epub ahead of print. PMID: 37061196. 8: Shen B, Lu LG. Efficacy and safety of drugs for nonalcoholic steatohepatitis. J Dig Dis. 2021 Feb;22(2):72-82. doi: 10.1111/1751-2980.12967. PMID: 33385317. 9: Malik A, Nadeem M, Amjad W, Malik MI, Javaid S, Farooq U, Naseem K, Khan A. Effects of Aramchol in patients with nonalcoholic fatty liver disease (NAFLD). A systematic review and meta-analysis. Prz Gastroenterol. 2023;18(1):67-75. doi: 10.5114/pg.2022.113573. Epub 2022 Feb 17. PMID: 37007760; PMCID: PMC10050975. 10: Chew NWS, Ng CH, Muthiah MD, Sanyal AJ. Comprehensive Review and Updates on Holistic Approach Towards Non-Alcoholic Fatty Liver Disease Management with Cardiovascular Disease. Curr Atheroscler Rep. 2022 Jul;24(7):515-532. doi: 10.1007/s11883-022-01027-5. Epub 2022 May 4. PMID: 35507280. 11: Safadi R, Konikoff FM, Mahamid M, Zelber-Sagi S, Halpern M, Gilat T, Oren R; FLORA Group. The fatty acid-bile acid conjugate Aramchol reduces liver fat content in patients with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2014 Dec;12(12):2085-91.e1. doi: 10.1016/j.cgh.2014.04.038. Epub 2014 May 9. PMID: 24815326. 12: Ratziu V. Novel Pharmacotherapy Options for NASH. Dig Dis Sci. 2016 May;61(5):1398-405. doi: 10.1007/s10620-016-4128-z. Epub 2016 Mar 22. PMID: 27003143. 13: Ajmera VH, Cachay E, Ramers C, Vodkin I, Bassirian S, Singh S, Mangla N, Bettencourt R, Aldous JL, Park D, Lee D, Blanchard J, Mamidipalli A, Boehringer A, Aslam S, Leinhard OD, Richards L, Sirlin C, Loomba R. MRI Assessment of Treatment Response in HIV-associated NAFLD: A Randomized Trial of a Stearoyl- Coenzyme-A-Desaturase-1 Inhibitor (ARRIVE Trial). Hepatology. 2019 Nov;70(5):1531-1545. doi: 10.1002/hep.30674. Epub 2019 Jun 18. PMID: 31013363; PMCID: PMC7164416. 14: Fernández-Ramos D, Lopitz-Otsoa F, Delacruz-Villar L, Bilbao J, Pagano M, Mosca L, Bizkarguenaga M, Serrano-Macia M, Azkargorta M, Iruarrizaga-Lejarreta M, Sot J, Tsvirkun D, van Liempd SM, Goni FM, Alonso C, Martínez-Chantar ML, Elortza F, Hayardeny L, Lu SC, Mato JM. Arachidyl amido cholanoic acid improves liver glucose and lipid homeostasis in nonalcoholic steatohepatitis via AMPK and mTOR regulation. World J Gastroenterol. 2020 Sep 14;26(34):5101-5117. doi: 10.3748/wjg.v26.i34.5101. PMID: 32982112; PMCID: PMC7495035. 15: Eshraghian A. Current and emerging pharmacological therapy for non-alcoholic fatty liver disease. World J Gastroenterol. 2017 Nov 14;23(42):7495-7504. doi: 10.3748/wjg.v23.i42.7495. PMID: 29204050; PMCID: PMC5698243. 16: Gilat T, Leikin-Frenkel A, Goldiner L, Laufer H, Halpern Z, Konikoff FM. Arachidyl amido cholanoic acid (Aramchol) is a cholesterol solubilizer and prevents the formation of cholesterol gallstones in inbred mice. Lipids. 2001 Oct;36(10):1135-40. doi: 10.1007/s11745-001-0824-3. PMID: 11768158. 17: Leikin-Frenkel A, Gonen A, Shaish A, Goldiner I, Leikin-Gobbi D, Konikoff FM, Harats D, Gilat T. Fatty acid bile acid conjugate inhibits hepatic stearoyl coenzyme A desaturase and is non-atherogenic. Arch Med Res. 2010 Aug;41(6):397-404. doi: 10.1016/j.arcmed.2010.09.001. PMID: 21044742. 18: Leikin-Frenkel A, Weinbroum AA, Leikin-Gobbi D, Krupitzky L, Goldiner I, Shafat L, Gilat T, Konikoff FM. Faecal sterol output is increased by arachidyl amido cholanoic acid (Aramchol) in rats. Biochem Soc Trans. 2004 Feb;32(Pt 1):131-3. doi: 10.1042/bst0320131. PMID: 14748731. 19: Goldiner I, van der Velde AE, Vandenberghe KE, van Wijland MA, Halpern Z, Gilat T, Konikoff FM, Veldman RJ, Groen AK. ABCA1-dependent but apoA-I- independent cholesterol efflux mediated by fatty acid-bile acid conjugates (FABACs). Biochem J. 2006 Jun 15;396(3):529-36. doi: 10.1042/BJ20051694. PMID: 16522192; PMCID: PMC1482810. 20: Huber Y, Galle PR, Schattenberg JM. Welches (ist das richtige) Target bei nichtalkoholischer Fettleber (NAFLD) [What is the (right) target for non- alcoholic fatty liver disease (NAFLD)?]. Z Gastroenterol. 2020 Jan;58(1):68-73. German. doi: 10.1055/a-1068-3981. Epub 2020 Jan 13. PMID: 31931543.