Avatrombopag free base

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

MedKoo CAT#: 200127

CAS#: 570406-98-3 (free base)

Description: Avatrombopag, also known as AKR-501, YM477, AS 1670542 or E5501, is a novel orally-active thrombopoietin (TPO) receptor agonist. AKR-501 specifically targeted the TPO receptor and stimulated megakaryocytopoiesis throughout the development and maturation of megakaryocytes just as rhTPO did. AKR-501 may be useful in the treatment of patients with thrombocytopenia.


Price and Availability

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Price

1g
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Size
Price

2g
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Size
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5g
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Avatrombopag free base is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200127
Name: Avatrombopag free base
CAS#: 570406-98-3 (free base)
Chemical Formula: C29H34Cl2N6O3S2
Exact Mass: 648.15109
Molecular Weight: 649.65
Elemental Analysis: C, 53.61; H, 5.28; Cl, 10.91; N, 12.94; O, 7.39; S, 9.87


Related CAS #: 677007-74-8 (maleate)   570406-98-3 (free base)    

Synonym: AKR501; AKR 501; AKR-501; YM477; YM-477; YM 477; E5501; AS 1670542; AS1670542; AS-1670542; Avatrombopag;

IUPAC/Chemical Name: (1-(3-chloro-5-((4-(4-chloro-2-thienyl)-5-(4-cyclohexylpiperazin-1-yl)thiazol-2-yl)carbamoyl)-2-pyridyl)piperidine-4-carboxylic acid)

InChi Key: OFZJKCQENFPZBH-UHFFFAOYSA-N

InChi Code: InChI=1S/C29H34Cl2N6O3S2/c30-20-15-23(41-17-20)24-27(37-12-10-35(11-13-37)21-4-2-1-3-5-21)42-29(33-24)34-26(38)19-14-22(31)25(32-16-19)36-8-6-18(7-9-36)28(39)40/h14-18,21H,1-13H2,(H,39,40)(H,33,34,38)

SMILES Code: O=C(C1CCN(C2=NC=C(C(NC3=NC(C4=CC(Cl)=CS4)=C(N5CCN(C6CCCCC6)CC5)S3)=O)C=C2Cl)CC1)O


Technical Data

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, not in water

Shelf Life:
>5 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).

Harmonized System Code:
2934990300


Additional Information

AKR-501, a novel, small-molecule thrombopoietin mimetic being investigated for the treatment of thrombocytopenia. AkaRx is now a wholly-owned subsidiary of Eisai Inc. and Eisai has the exclusive worldwide rights to develop, market and manufacture AKR-501. AKR-501 is an investigational thrombopoietin receptor agonist that, based on preclinical studies, increases platelet production by stimulating megakaryocytic proliferation and differentiation. Eisai is currently conducting Phase II clinical trials of AKR-501 in the United States as a potential treatment for idiopathic thrombocytopenic purpura (ITP) and thrombocytopenia associated with liver diseases (TLD), and has confirmed proof of concept in the clinical studies for ITP. In addition, Eisai will explore the compound's potential as a treatment for chemotherapy-induced thrombocytopenia (CIT).


 
 


References

1: Maan R, de Knegt RJ, Veldt BJ. Management of Thrombocytopenia in Chronic Liver Disease: Focus on Pharmacotherapeutic Strategies. Drugs. 2015 Nov;75(17):1981-92. doi: 10.1007/s40265-015-0480-0. PubMed PMID: 26501978; PubMed Central PMCID: PMC4642582.

2: Terrault NA, Hassanein T, Howell CD, Joshi S, Lake J, Sher L, Vargas H, McIntosh J, Tang S, Jenkins TM. Phase II study of avatrombopag in thrombocytopenic patients with cirrhosis undergoing an elective procedure. J Hepatol. 2014 Dec;61(6):1253-9. doi: 10.1016/j.jhep.2014.07.007. Epub 2014 Jul 15. PubMed PMID: 25048952.

3: Bussel JB, Kuter DJ, Aledort LM, Kessler CM, Cuker A, Pendergrass KB, Tang S, McIntosh J. A randomized trial of avatrombopag, an investigational thrombopoietin-receptor agonist, in persistent and chronic immune thrombocytopenia. Blood. 2014 Jun 19;123(25):3887-94. doi: 10.1182/blood-2013-07-514398. Epub 2014 May 6. PubMed PMID: 24802775.

4: Basciano PA, Bussel J, Hafeez Z, Christos PJ, Giannakakou P. The beta 1 tubulin R307H single nucleotide polymorphism is associated with treatment failures in immune thrombocytopenia (ITP). Br J Haematol. 2013 Jan;160(2):237-43. doi: 10.1111/bjh.12124. Epub 2012 Nov 15. PubMed PMID: 23157319; PubMed Central PMCID: PMC4001250.

5: Abe M, Suzuki K, Sakata C, Sugasawa K, Hirayama F, Koga Y, Kawasaki T, Naganuma S, Itoh H. Pharmacological profile of AS1670542, a novel orally-active human thrombopoietin receptor agonist. Eur J Pharmacol. 2011 Jan 10;650(1):58-63. doi: 10.1016/j.ejphar.2010.09.072. Epub 2010 Oct 13. PubMed PMID: 20950606.

6: Cohn CS, Bussel JB. Romiplostim: a second-generation thrombopoietin agonist. Drugs Today (Barc). 2009 Mar;45(3):175-88. doi: 10.1358/dot.2009.45.3.1343793. Review. PubMed PMID: 19436840.

7: Fukushima-Shintani M, Suzuki K, Iwatsuki Y, Abe M, Sugasawa K, Hirayama F, Kawasaki T, Nakahata T. AKR-501 (YM477) a novel orally-active thrombopoietin receptor agonist. Eur J Haematol. 2009 Apr;82(4):247-54. doi: 10.1111/j.1600-0609.2008.01198.x. Epub 2009 Jan 16. PubMed PMID: 19183407.

8: Fukushima-Shintani M, Suzuki K, Iwatsuki Y, Abe M, Sugasawa K, Hirayama F, Kawasaki T. AKR-501 (YM477) in combination with thrombopoietin enhances human megakaryocytopoiesis. Exp Hematol. 2008 Oct;36(10):1337-42. doi: 10.1016/j.exphem.2008.04.020. Epub 2008 Jul 10. PubMed PMID: 18619724.

(Last updated: 4/20/2016)