Eltrombopag free base
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MedKoo CAT#: 201240

CAS#: 496775-61-2 (free base)

Description: Eltrombopag is a small-molecule, nonpeptide thrombopoietin receptor agonist with megakaryopoiesis-stimulating activity. Eltrombopag binds to and stimulates the transmembrane domain of the platelet thrombopoietin receptor (TPO-R or CD110), a member of the hematopoietin receptor superfamily. Activation of TPO-R leads to the proliferation and differentiation of cells in the megakaryocytic lineage and an increase in platelet production. Eltrombopag was approved by FDA in November 20, 2008.


Chemical Structure

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Eltrombopag free base
CAS# 496775-61-2 (free base)

Theoretical Analysis

MedKoo Cat#: 201240
Name: Eltrombopag free base
CAS#: 496775-61-2 (free base)
Chemical Formula: C25H22N4O4
Exact Mass: 442.16411
Molecular Weight: 442.47
Elemental Analysis: C, 67.86; H, 5.01; N, 12.66; O, 14.46

Price and Availability

Size Price Availability Quantity
100.0mg USD 120.0 Ready to ship
200.0mg USD 190.0 Ready to ship
500.0mg USD 350.0 Ready to ship
1.0g USD 550.0 Ready to ship
2.0g USD 950.0 Ready to ship
5.0g USD 1850.0 Ready to ship
10.0g USD 3250.0 Ready to ship
20.0g USD 5250.0 Ready to ship
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Related CAS #: 496775-61-2 (free base)   496775-62-3 (olamine)    

Synonym: SB497115; SB-497115; SB 497115; SB497115GR; Eltrombopag; Brand name: PROMACTA

IUPAC/Chemical Name: 3'-[2-[(2Z)-1-(3,4-Dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazinyl]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid

InChi Key: XDXWLKQMMKQXPV-QYQHSDTDSA-N

InChi Code: InChI=1S/C25H22N4O4/c1-14-10-11-19(12-15(14)2)29-24(31)22(16(3)28-29)27-26-21-9-5-8-20(23(21)30)17-6-4-7-18(13-17)25(32)33/h4-13,26,30H,1-3H3,(H,32,33)/b27-22-

SMILES Code: O=C(C1=CC(C2=CC=CC(N/N=C3C(C)=NN(C4=CC=C(C)C(C)=C4)C/3=O)=C2O)=CC=C1)O

Appearance: Red 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

Biological target: Eltrombopag is a thrombopoietin (TPO) receptor agonist.
In vitro activity: Eltrombopag's cell toxicity to five cancer cell lines and one macrophage cell line (4T1, A549, H1299, LLC, SMMC7721 and RAW264.7) was evaluated. As shown in Fig. 3A, eltrombopag could inhibit the in vitro cell viability of all the detected cell lines. Reference: Acta Pharm Sin B. 2020 Aug;10(8):1414-1425. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7488360/
In vivo activity: To detect the in vivo anti-tumor effect of eltrombopag, mice bearing allografts with 4T1 cell lines were used. Over the course of the experiment, eltrombopag was well tolerated, and no signs of acute toxicity were observed (Fig. 3B and Supporting Information Fig. S2). Obvious anti-tumor effects of eltrombopag were observed for the 75 mg/kg dose (P < 0.01) and 150 mg/kg dose (P < 0.01) (Fig. 3C and D). Reference: Acta Pharm Sin B. 2020 Aug;10(8):1414-1425. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7488360/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 22.44 50.72
DMF 1.0 2.26
DMF:PBS (pH 7.2) (1:3) 0.25 0.57
Ethanol 0.1 0.23

Preparing Stock Solutions

The following data is based on the product molecular weight 442.47 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. Zhu Y, Yang L, Xu J, Yang X, Luan P, Cui Q, Zhang P, Wang F, Li R, Ding X, Jiang L, Lin G, Zhang J. Discovery of the anti-angiogenesis effect of eltrombopag in breast cancer through targeting of HuR protein. Acta Pharm Sin B. 2020 Aug;10(8):1414-1425. doi: 10.1016/j.apsb.2020.02.007. Epub 2020 Feb 24. PMID: 32963940; PMCID: PMC7488360. 2. Di Paola A, Palumbo G, Merli P, Argenziano M, Tortora C, Strocchio L, Roberti D, Santoro C, Perrotta S, Rossi F. Effects of Eltrombopag on In Vitro Macrophage Polarization in Pediatric Immune Thrombocytopenia. Int J Mol Sci. 2020 Dec 24;22(1):97. doi: 10.3390/ijms22010097. PMID: 33374151; PMCID: PMC7796119.
In vitro protocol: 1. Zhu Y, Yang L, Xu J, Yang X, Luan P, Cui Q, Zhang P, Wang F, Li R, Ding X, Jiang L, Lin G, Zhang J. Discovery of the anti-angiogenesis effect of eltrombopag in breast cancer through targeting of HuR protein. Acta Pharm Sin B. 2020 Aug;10(8):1414-1425. doi: 10.1016/j.apsb.2020.02.007. Epub 2020 Feb 24. PMID: 32963940; PMCID: PMC7488360. 2. Di Paola A, Palumbo G, Merli P, Argenziano M, Tortora C, Strocchio L, Roberti D, Santoro C, Perrotta S, Rossi F. Effects of Eltrombopag on In Vitro Macrophage Polarization in Pediatric Immune Thrombocytopenia. Int J Mol Sci. 2020 Dec 24;22(1):97. doi: 10.3390/ijms22010097. PMID: 33374151; PMCID: PMC7796119.
In vivo protocol: 1. Zhu Y, Yang L, Xu J, Yang X, Luan P, Cui Q, Zhang P, Wang F, Li R, Ding X, Jiang L, Lin G, Zhang J. Discovery of the anti-angiogenesis effect of eltrombopag in breast cancer through targeting of HuR protein. Acta Pharm Sin B. 2020 Aug;10(8):1414-1425. doi: 10.1016/j.apsb.2020.02.007. Epub 2020 Feb 24. PMID: 32963940; PMCID: PMC7488360. 2. Di Paola A, Palumbo G, Merli P, Argenziano M, Tortora C, Strocchio L, Roberti D, Santoro C, Perrotta S, Rossi F. Effects of Eltrombopag on In Vitro Macrophage Polarization in Pediatric Immune Thrombocytopenia. Int J Mol Sci. 2020 Dec 24;22(1):97. doi: 10.3390/ijms22010097. PMID: 33374151; PMCID: PMC7796119.

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Spitz AZ, Zacharioudakis E, Reyna DE, Garner TP, Gavathiotis E. Eltrombopag directly inhibits BAX and prevents cell death. Nat Commun. 2021 Feb 18;12(1):1134. doi: 10.1038/s41467-021-21224-1. PMID: 33602934; PMCID: PMC7892824.

1: Eltrombopag Olamine (Revolade) [Internet]. Ottawa (ON): Canadian Agency for Drugs and Technologies in Health; 2015 Aug. Available from http://www.ncbi.nlm.nih.gov/books/NBK362529/ PubMed PMID: 27227203.

2: Merli P, Strocchio L, Vinti L, Palumbo G, Locatelli F. Eltrombopag for treatment of thrombocytopenia-associated disorders. Expert Opin Pharmacother. 2015;16(14):2243-56. doi: 10.1517/14656566.2015.1085512. Review. PubMed PMID: 26364898.

3: McCormack PL. Eltrombopag: a review of its use in patients with severe aplastic anaemia. Drugs. 2015 Apr;75(5):525-31. doi: 10.1007/s40265-015-0363-4. Review. PubMed PMID: 25700916.

4: Desmond R, Townsley DM, Dunbar C, Young NS. Eltrombopag in aplastic anemia. Semin Hematol. 2015 Jan;52(1):31-7. doi: 10.1053/j.seminhematol.2014.10.002. Epub 2014 Oct 31. Review. PubMed PMID: 25578417; PubMed Central PMCID: PMC4293077.

5: Burness CB. Eltrombopag: a review of its use in the treatment of thrombocytopenia in patients with chronic hepatitis C. Drugs. 2014 Oct;74(16):1961-71. doi: 10.1007/s40265-014-0312-7. Review. PubMed PMID: 25331767.

6: Mihăilă RG, Cipăian RC. Eltrombopag in chronic hepatitis C. World J Gastroenterol. 2014 Sep 21;20(35):12517-21. doi: 10.3748/wjg.v20.i35.12517. Review. PubMed PMID: 25253952; PubMed Central PMCID: PMC4168085.

7: Pathak S, Roth M, Verma A, Steidl U. Eltrombopag for the treatment of thrombocytopenia in patients with malignant and non-malignant hematologic disorders. Expert Opin Drug Metab Toxicol. 2013 Dec;9(12):1667-75. doi: 10.1517/17425255.2013.858119. Epub 2013 Nov 12. Review. PubMed PMID: 24215532.

8: Giannini EG, Afdhal NH. Eltrombopag in patients with chronic liver disease. Expert Opin Pharmacother. 2013 Apr;14(5):669-78. doi: 10.1517/14656566.2013.775249. Epub 2013 Mar 4. Review. PubMed PMID: 23452139.

9: Danish FI, Yasmin S. The role of eltrombopag in the management of hepatitis C virus-related thrombocytopenia. Hepat Med. 2013 Mar 15;5:17-30. doi: 10.2147/HMER.S27100. eCollection 2013. Review. PubMed PMID: 24696622; PubMed Central PMCID: PMC3953736.

10: Cooper KL, Fitzgerald P, Dillingham K, Helme K, Akehurst R. Romiplostim and eltrombopag for immune thrombocytopenia: methods for indirect comparison. Int J Technol Assess Health Care. 2012 Jul;28(3):249-58. doi: 10.1017/S0266462312000414. Review. PubMed PMID: 22980701.

11: Sharma V, Randhawa H, Sharma A, Aggarwal S. Eltrombopag--an oral thrombopoietin agonist. Eur Rev Med Pharmacol Sci. 2012 Jun;16(6):743-6. Review. PubMed PMID: 22913204.

12: Boyers D, Jia X, Crowther M, Jenkinson D, Fraser C, Mowatt G. Eltrombopag for the treatment of chronic idiopathic (immune) thrombocytopenic purpura (ITP). Health Technol Assess. 2011 May;15 Suppl 1:23-32. doi: 10.3310/hta15suppl1/03. Review. PubMed PMID: 21609650.

13: Boyers D, Jia X, Jenkinson D, Mowatt G. Eltrombopag for the treatment of chronic immune or idiopathic thrombocytopenic purpura: a NICE single technology appraisal. Pharmacoeconomics. 2012 Jun 1;30(6):483-95. doi: 10.2165/11591550-000000000-00000. Review. PubMed PMID: 22480381.

14: Zhang Y, Kolesar JM. Eltrombopag: an oral thrombopoietin receptor agonist for the treatment of idiopathic thrombocytopenic purpura. Clin Ther. 2011 Nov;33(11):1560-76. doi: 10.1016/j.clinthera.2011.10.004. Epub 2011 Nov 4. Review. PubMed PMID: 22054810.

15: Garnock-Jones KP. Spotlight on eltrombopag in treatment-refractory chronic primary immune thrombocytopenia. BioDrugs. 2011 Dec 1;25(6):401-4. doi: 10.2165/11207620-000000000-00000. Review. PubMed PMID: 22050343.

16: Garnock-Jones KP. Eltrombopag: a review of its use in treatment-refractory chronic primary immune thrombocytopenia. Drugs. 2011 Jul 9;71(10):1333-53. doi: 10.2165/11207390-000000000-00000. Review. PubMed PMID: 21770480.

17: Nieto M, Calvo G, Hudson I, Feldschreiber P, Brown D, Lee CC, Lay G, Valeri A, Abadie E, Thomas A, Pignatti F. The European Medicines Agency review of eltrombopag (Revolade) for the treatment of adult chronic immune (idiopathic) thrombocytopenic purpura: summary of the scientific assessment of the Committee for Medicinal Products for Human Use. Haematologica. 2011 Sep;96(9):e33-40. doi: 10.3324/haematol.2011.048819. Epub 2011 Jun 28. Review. PubMed PMID: 21712542; PubMed Central PMCID: PMC3166089.

18: Bussel JB, Pinheiro MP. Eltrombopag. Cancer Treat Res. 2011;157:289-303. doi: 10.1007/978-1-4419-7073-2_17. Review. PubMed PMID: 21052963.

19: Cook L, Cooper N. Eltrombopag--a novel approach for the treatment of chronic immune thrombocytopenic purpura: review and safety considerations. Drug Des Devel Ther. 2010 Jul 21;4:139-45. Review. PubMed PMID: 20689640; PubMed Central PMCID: PMC2915538.

20: Chouhan JD, Herrington JD. Treatment options for chronic refractory idiopathic thrombocytopenic purpura in adults: focus on romiplostim and eltrombopag. Pharmacotherapy. 2010 Jul;30(7):666-83. doi: 10.1592/phco.30.7.666. Review. PubMed PMID: 20575632.



Additional Information

Related CAS#
496775-61-2 (Eltrombopag free base);
496775-62-3 (Eltrombopag olamine).