Avasimibe
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MedKoo CAT#: 406842

CAS#: 166518-60-1 (free form)

Description: Avasimibe is an acyl coenzyme A: cholesterol acyltransferase (ACAT) inhibitor. Avasimibe can also reduce the synthesis and secretion of Apo B 100 in HepG2 cells. Avasimibe encapsulated in human serum albumin blocks cholesterol esterification for selective cancer treatment. Avasimibe could be an efficient therapy in the treatment of glioblastoma.

Chemical Structure

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Avasimibe
CAS# 166518-60-1 (free form)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 406842
Name: Avasimibe
CAS#: 166518-60-1 (free form)
Chemical Formula: C29H43NO4S
Exact Mass: 501.29
Molecular Weight: 501.720
Elemental Analysis: C, 69.42; H, 8.64; N, 2.79; O, 12.76; S, 6.39

Price and Availability

Size Price Availability Quantity
25mg USD 150 Ready to ship
50mg USD 250 Ready to ship
100mg USD 450 Ready to ship
200mg USD 750 Ready to ship
500mg USD 1450 2 Weeks
1g USD 2450 2 Weeks
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Related CAS #: 166518-61-2 (sodium)   166518-60-1 (free form)    

Synonym: CI-1011; CI 1011; CI1011; Avasimibe; Avasimibe sodium.

IUPAC/Chemical Name: ((2,4,6-Tris(1-methylethyl)phenyl)acetyl)sulfamic acid 2,6-bis(1-methylethyl)phenyl ester

InChi Key: PTQXTEKSNBVPQJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C29H43NO4S/c1-17(2)22-14-25(20(7)8)27(26(15-22)21(9)10)16-28(31)30-35(32,33)34-29-23(18(3)4)12-11-13-24(29)19(5)6/h11-15,17-21H,16H2,1-10H3,(H,30,31)

SMILES Code: c1(C(C)C)cc(cc(c1CC(NS(Oc1c(cccc1C(C)C)C(C)C)(=O)=O)=O)C(C)C)C(C)C

Appearance: White to off-white 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, not in water

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:

Biological target: Avasimibe is an oral inhibitor of acyl-Coenzyme A:cholesterol acyltransferase (ACAT) with IC50s of 24 and 9.2 µM for ACAT1 and ACAT2, respectively.
In vitro activity: LLC cells were treated with different avasimibe concentrations to inhibit ACAT-1, revealing a significant dose- and time-dependent suppression of proliferation as revealed using a CCK-8 assay (P<0.05; Fig. 1A and B). The cell viability rates in the blank group and the avasimibe (2.5, 5, 10 and 20 µM) groups were 100.00±0.00, 63.57±4.88, 45.47±5.35, 37.66±3.72 and 30.59±1.24%, respectively (Fig. 1A). In addition, the viability of the control group and the groups at 1, 2, 3 and 4 days were 100.00±0.00, 72.21±4.50, 58.60±5.25, 46.11±3.9 and 39.02±3.04%, respectively (Fig. 1B). These results therefore demonstrated that avasimbe inhibits LLC cell proliferation compared with the controls. Reference: Oncol Lett. 2019 Aug; 18(2): 1548–1556. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6607388/
In vivo activity: In vivo activity To explore the effect of avasimibe on glioma in vivo, a xenograft tumour assay was conducted. LN229 (1.0 × 107) cells treated with avasimibe or treated with avasimibe and transfected with linc00339 plasmid were subcutaneously injected into nude mice. The volume of the tumour was measured every week. Four weeks after injection, the mice were sacrificed, and the weight of the tumour was measured. By comparison, avasimibe could inhibit the volume and mass of tumours, and this inhibitory effect could be reversed with overexpression of linc00339 (Fig. 5A–C). Next, this study detected linc00339 expression in the three groups and found that avasimibe could suppress the expression of linc00339 in the model (Fig. 5D). Taken together, these results suggested that avasimibe inhibits glioma growth in vivo, and this regulation is related to linc00339 expression. Reference: Biomed Pharmacother. 2020 Oct;130:110508. https://pubmed.ncbi.nlm.nih.gov/32682982/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 47.5 94.75
DMSO:PBS (pH 7.2) (1:3) 0.3 0.50
DMF 5.0 9.97
Ethanol 8.7 17.36

Preparing Stock Solutions

The following data is based on the product molecular weight 501.72 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
Formulation protocol: 1. Gao Y, Xu D, Li H, Xu J, Pan Y, Liao X, Qian J, Hu Y, Yu G. Avasimibe Dampens Cholangiocarcinoma Progression by Inhibiting FoxM1-AKR1C1 Signaling. Front Oncol. 2021 May 28;11:677678. doi: 10.3389/fonc.2021.677678. PMID: 34127944; PMCID: PMC8195695. 2. Bi M, Qiao X, Zhang H, Wu H, Gao Z, Zhou H, Shi M, Wang Y, Yang J, Hu J, Liang W, Liu Y, Qiao X, Zhang S, Zhao Z. Effect of inhibiting ACAT-1 expression on the growth and metastasis of Lewis lung carcinoma. Oncol Lett. 2019 Aug;18(2):1548-1556. doi: 10.3892/ol.2019.10427. Epub 2019 May 31. PMID: 31423222; PMCID: PMC6607388. 3. Luo Y, Liu L, Li X, Shi Y. Avasimibe inhibits the proliferation, migration and invasion of glioma cells by suppressing linc00339. Biomed Pharmacother. 2020 Oct;130:110508. doi: 10.1016/j.biopha.2020.110508. Epub 2020 Jul 16. PMID: 32682982. 4. Liu JY, Fu WQ, Zheng XJ, Li W, Ren LW, Wang JH, Yang C, Du GH. Avasimibe exerts anticancer effects on human glioblastoma cells via inducing cell apoptosis and cell cycle arrest. Acta Pharmacol Sin. 2021 Jan;42(1):97-107. doi: 10.1038/s41401-020-0404-8. Epub 2020 May 25. PMID: 32451414; PMCID: PMC7921416.
In vitro protocol: 1. Gao Y, Xu D, Li H, Xu J, Pan Y, Liao X, Qian J, Hu Y, Yu G. Avasimibe Dampens Cholangiocarcinoma Progression by Inhibiting FoxM1-AKR1C1 Signaling. Front Oncol. 2021 May 28;11:677678. doi: 10.3389/fonc.2021.677678. PMID: 34127944; PMCID: PMC8195695. 2. Bi M, Qiao X, Zhang H, Wu H, Gao Z, Zhou H, Shi M, Wang Y, Yang J, Hu J, Liang W, Liu Y, Qiao X, Zhang S, Zhao Z. Effect of inhibiting ACAT-1 expression on the growth and metastasis of Lewis lung carcinoma. Oncol Lett. 2019 Aug;18(2):1548-1556. doi: 10.3892/ol.2019.10427. Epub 2019 May 31. PMID: 31423222; PMCID: PMC6607388.
In vivo protocol: 1. Luo Y, Liu L, Li X, Shi Y. Avasimibe inhibits the proliferation, migration and invasion of glioma cells by suppressing linc00339. Biomed Pharmacother. 2020 Oct;130:110508. doi: 10.1016/j.biopha.2020.110508. Epub 2020 Jul 16. PMID: 32682982. 2. Liu JY, Fu WQ, Zheng XJ, Li W, Ren LW, Wang JH, Yang C, Du GH. Avasimibe exerts anticancer effects on human glioblastoma cells via inducing cell apoptosis and cell cycle arrest. Acta Pharmacol Sin. 2021 Jan;42(1):97-107. doi: 10.1038/s41401-020-0404-8. Epub 2020 May 25. PMID: 32451414; PMCID: PMC7921416.

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1: Hasan MK, El Qaidi S, McDonald P, Roy A, Hardwidge PR. Repurposing Avasimibe to Inhibit Bacterial Glycosyltransferases. Pathogens. 2022 Mar 17;11(3):370. doi: 10.3390/pathogens11030370. PMID: 35335693; PMCID: PMC8953086.


2: Burnett JR, Huff MW. Avasimibe Pfizer. Curr Opin Investig Drugs. 2002 Sep;3(9):1328-33. PMID: 12498009.


3: Avasimibe. CI 1011. Drugs R D. 2002;3(3):173-4. doi: 10.2165/00126839-200203030-00005. PMID: 12099161.


4: Zhou Z, Liang S, Zhou Z, Liu J, Meng X, Zou F, Yu C, Cai S. Avasimibe Alleviates Disruption of the Airway Epithelial Barrier by Suppressing the Wnt/β-Catenin Signaling Pathway. Front Pharmacol. 2022 Feb 11;13:795934. doi: 10.3389/fphar.2022.795934. PMID: 35222024; PMCID: PMC8874122.


5: Gao Y, Xu D, Li H, Xu J, Pan Y, Liao X, Qian J, Hu Y, Yu G. Avasimibe Dampens Cholangiocarcinoma Progression by Inhibiting FoxM1-AKR1C1 Signaling. Front Oncol. 2021 May 28;11:677678. doi: 10.3389/fonc.2021.677678. PMID: 34127944; PMCID: PMC8195695.


6: Jiang Y, Sun A, Zhao Y, Ying W, Sun H, Yang X, Xing B, Sun W, Ren L, Hu B, Li C, Zhang L, Qin G, Zhang M, Chen N, Zhang M, Huang Y, Zhou J, Zhao Y, Liu M, Zhu X, Qiu Y, Sun Y, Huang C, Yan M, Wang M, Liu W, Tian F, Xu H, Zhou J, Wu Z, Shi T, Zhu W, Qin J, Xie L, Fan J, Qian X, He F; Chinese Human Proteome Project (CNHPP) Consortium. Proteomics identifies new therapeutic targets of early-stage hepatocellular carcinoma. Nature. 2019 Mar;567(7747):257-261. doi: 10.1038/s41586-019-0987-8. Epub 2019 Feb 27. PMID: 30814741.


7: Liu JY, Fu WQ, Zheng XJ, Li W, Ren LW, Wang JH, Yang C, Du GH. Avasimibe exerts anticancer effects on human glioblastoma cells via inducing cell apoptosis and cell cycle arrest. Acta Pharmacol Sin. 2021 Jan;42(1):97-107. doi: 10.1038/s41401-020-0404-8. Epub 2020 May 25. PMID: 32451414; PMCID: PMC7921416.


8: Luo Y, Liu L, Li X, Shi Y. Avasimibe inhibits the proliferation, migration and invasion of glioma cells by suppressing linc00339. Biomed Pharmacother. 2020 Oct;130:110508. doi: 10.1016/j.biopha.2020.110508. Epub 2020 Jul 16. PMID: 32682982.


9: Llaverías G, Laguna JC, Alegret M. Pharmacology of the ACAT inhibitor avasimibe (CI-1011). Cardiovasc Drug Rev. 2003 Spring;21(1):33-50. PMID: 12595916.


10: Avasimibe. CI 1011. Drugs R D. 1999 Jun;1(6):477-8. doi: 10.2165/00126839-199901060-00012. PMID: 10566087.


11: Yang W, Bai Y, Xiong Y, Zhang J, Chen S, Zheng X, Meng X, Li L, Wang J, Xu C, Yan C, Wang L, Chang CC, Chang TY, Zhang T, Zhou P, Song BL, Liu W, Sun SC, Liu X, Li BL, Xu C. Potentiating the antitumour response of CD8(+) T cells by modulating cholesterol metabolism. Nature. 2016 Mar 31;531(7596):651-5. doi: 10.1038/nature17412. Epub 2016 Mar 16. PMID: 26982734; PMCID: PMC4851431.


12: Xiong K, Wang G, Peng T, Zhou F, Chen S, Liu W, Ju L, Xiao Y, Qian K, Wang X. The cholesterol esterification inhibitor avasimibe suppresses tumour proliferation and metastasis via the E2F-1 signalling pathway in prostate cancer. Cancer Cell Int. 2021 Aug 30;21(1):461. doi: 10.1186/s12935-021-02175-5. PMID: 34461908; PMCID: PMC8407011.


13: Wang L, Liu Y, Yu G. Avasimibe inhibits tumor growth by targeting FoxM1-AKR1C1 in osteosarcoma. Onco Targets Ther. 2019 Jan 24;12:815-823. doi: 10.2147/OTT.S165647. PMID: 30774369; PMCID: PMC6353227.


14: Hu L, Li J, Cai H, Yao W, Xiao J, Li YP, Qiu X, Xia H, Peng T. Avasimibe: A novel hepatitis C virus inhibitor that targets the assembly of infectious viral particles. Antiviral Res. 2017 Dec;148:5-14. doi: 10.1016/j.antiviral.2017.10.016. Epub 2017 Oct 23. PMID: 29074218.


15: Lei J, Wang H, Zhu D, Wan Y, Yin L. Combined effects of avasimibe immunotherapy, doxorubicin chemotherapy, and metal-organic frameworks nanoparticles on breast cancer. J Cell Physiol. 2020 May;235(5):4814-4823. doi: 10.1002/jcp.29358. Epub 2019 Oct 29. PMID: 31663620.


16: Sahi J, Milad MA, Zheng X, Rose KA, Wang H, Stilgenbauer L, Gilbert D, Jolley S, Stern RH, LeCluyse EL. Avasimibe induces CYP3A4 and multiple drug resistance protein 1 gene expression through activation of the pregnane X receptor. J Pharmacol Exp Ther. 2003 Sep;306(3):1027-34. doi: 10.1124/jpet.103.050526. Epub 2003 May 23. PMID: 12766253.


17: Pan J, Zhang Q, Palen K, Wang L, Qiao L, Johnson B, Sei S, Shoemaker RH, Lubet RA, Wang Y, You M. Potentiation of Kras peptide cancer vaccine by avasimibe, a cholesterol modulator. EBioMedicine. 2019 Nov;49:72-81. doi: 10.1016/j.ebiom.2019.10.044. Epub 2019 Oct 31. PMID: 31680003; PMCID: PMC6945201.


18: Raal FJ, Marais AD, Klepack E, Lovalvo J, McLain R, Heinonen T. Avasimibe, an ACAT inhibitor, enhances the lipid lowering effect of atorvastatin in subjects with homozygous familial hypercholesterolemia. Atherosclerosis. 2003 Dec;171(2):273-9. doi: 10.1016/j.atherosclerosis.2003.07.011. PMID: 14644397.


19: Zhu Y, Gu L, Lin X, Zhou X, Lu B, Liu C, Li Y, Prochownik EV, Karin M, Wang F, Li Y. P53 deficiency affects cholesterol esterification to exacerbate hepatocarcinogenesis. Hepatology. 2023 May 1;77(5):1499-1511. doi: 10.1002/hep.32518. Epub 2023 Apr 17. PMID: 35398929.


20: Lee SS, Li J, Tai JN, Ratliff TL, Park K, Cheng JX. Avasimibe encapsulated in human serum albumin blocks cholesterol esterification for selective cancer treatment. ACS Nano. 2015 Mar 24;9(3):2420-32. doi: 10.1021/nn504025a. Epub 2015 Feb 16. PMID: 25662106; PMCID: PMC5909415.