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Eltrombopag

Eltrombopag

Synopsis, Chemistry

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TABLET;ORAL - EQ 100MG ACID **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET;ORAL - EQ 12.5MG ACID, TABLET;ORAL - EQ 25MG ACID, TABLET;ORAL - EQ 50MG ACID, TABLET;ORAL - EQ 75MG ACID

TABLET;ORAL - EQ 100MG ACID **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET;ORAL - EQ 12.5MG ACID
TABLET;ORAL - EQ 25MG ACID
TABLET;ORAL - EQ 50MG ACID
TABLET;ORAL - EQ 75MG ACID

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Also known as: 496775-62-3, Revolade, Promacta, Eltrombopag (olamine), Unii-4u07f515lg, Sb-497115-gr

Molecular Formula

C₂₉H₃₆N₆O₆

Molecular Weight

564.6 g/mol

InChI Key

DJMJHIKGMVJYCW-UHFFFAOYSA-N

FDA UNII

4U07F515LG

Eltrombopag Olamine is the orally active ethanolamine salt of eltrombopag, 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.

1 2D Structure

Eltrombopag

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-aminoethanol;3-[3-[[2-(3,4-dimethylphenyl)-5-methyl-3-oxo-1H-pyrazol-4-yl]diazenyl]-2-hydroxyphenyl]benzoic acid

2.1.2 InChI

InChI=1S/C25H22N4O4.2C2H7NO/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;2*3-1-2-4/h4-13,28,30H,1-3H3,(H,32,33);2*4H,1-3H2

2.1.3 InChI Key

DJMJHIKGMVJYCW-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(C=C(C=C1)N2C(=O)C(=C(N2)C)N=NC3=CC=CC(=C3O)C4=CC(=CC=C4)C(=O)O)C.C(CO)N.C(CO)N

2.2 Other Identifiers

2.2.1 UNII

4U07F515LG

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (1,1'-biphenyl)-3-carboxylic Acid, 3'-((2z)-(1-(3,4-dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4h-pyrazol-4-ylidene)hydrazino)-2'-hydroxy-

2. Ddl-701

3. Eltrombopag

4. Promacta

5. Revolade

6. Sb-497 115

7. Sb-497-115

8. Sb497115

2.3.2 Depositor-Supplied Synonyms

1. 496775-62-3

2. Revolade

3. Promacta

4. Eltrombopag (olamine)

5. Unii-4u07f515lg

6. Sb-497115-gr

7. Eltrombopag Diethanolamine Salt

8. 496775-62-3 (olamine)

9. Eltrombopag (as Olamine)

10. 4u07f515lg

11. Sb-497115gr

12. Eltrombopag Compd With 2-aminoethanol (1:2)

13. Eltrombopag Diethanolamine Salt;sb-497115gr

14. (z)-3'-(2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-4h-pyrazol-4-ylidene)hydrazinyl)-2'-hydroxy-[1,1'-biphenyl]-3-carboxyiic Acid;2-aminoethan-1-ol (1:2)

15. 3'-((2z)-2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-4h-pyrazol-4-ylidene)diazanyl)-2'-hydroxybiphenyl-3-carboxylic Acid Compound With 2-aminoethanol (1:2)

16. Promacta Olamine

17. Eltrombopagolamine

18. Eltrombopag Olamine [usan:jan]

19. Promacta (tn)

20. Sb 497115gr

21. Schembl210183

22. Amy267

23. Chembl3989691

24. Schembl16207741

25. Schembl23458316

26. Eltrombopag Olamine (jan/usan)

27. Eltrombopag Olamine [jan]

28. Eltrombopag Olamine [usan]

29. Bcp07055

30. Eltrombopag Olamine [mart.]

31. Eltrombopag Olamine [who-dd]

32. Hy-15306a

33. Mfcd22380664

34. S2229

35. Akos025396658

36. Akos037515856

37. Ccg-270074

38. Cs-1566

39. Sb19102

40. Eltrombopag Olamine [orange Book]

41. 2-aminoethan-1-ol Hemi((e)-3'-(2-(2-(3,4-dimethylphenyl)-5-methyl-3-oxo-2,3-dihydro-1h-pyrazol-4-yl)hydrazono)-2'-oxo-2',3'-dihydro-[1,1'-biphenyl]-3-carboxylate)

42. Ac-26286

43. Bs-17370

44. Ft-0773802

45. D03978

46. A904098

47. Q27260489

48. Eltrombopag Compd With 2-aminoethanol (1:2) [mi]

49. (1,1'-biphenyl)-3-carboxylic Acid, 3'-((2z)-(1-(3,4-dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4h-pyrazol-4-ylidene)hydrazino)-2'-hydroxy, Compound With 2-aminoethanol (1:2)

50. (1,1'-biphenyl)-3-carboxylic Acid, 3'-((2z)-(1-(3,4-dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4h-pyrazol-4-ylidene)hydrazino)-2'-hydroxy-, Compound With 2-aminoethanol (1:2)

51. (1,1'-biphenyl)-3-carboxylic Acid, 3'-(2-(1-(3,4-dimethylphenyl)-4,5-dihydro-3-methyl-5-oxo-1h-pyrazol-4-yl)diazenyl)-2'-hydroxy-, Compd. With 2-aminoethanol (1:2)

52. 2-aminoethan-1-ol Hemi((z)-3'-(2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-4h-pyrazol-4-ylidene)hydrazinyl)-2'-hydroxy-[1,1'-biphenyl]-3-carboxylate)

53. 2-aminoethanol (e)-3'-(2-(1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1h-pyrazol-4(5h)-ylidene)hydrazinyl)-2'-hydroxy-[1,1'-biphenyl]-3-carboxylate

54. 2-aminoethanol;3-[3-[[2-(3,4-dimethylphenyl)-5-methyl-3-oxo-1h-pyrazol-4-yl]diazenyl]-2-hydroxyphenyl]benzoic Acid

55. 3'-[(2z)-[1-(3,4-dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4h-pyrazol-4-ylidene]hydrazino]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic Acid Bis-(monoethanolamine)

56. 3'-[(2z)-[1-(3,4-dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4h-pyrazol4-ylidene]hydrazino]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic Acid Bis-(monoethanolamine)

57. 3'-{(2z)-2-[1-(3,4-dimethylphenyl)-3-methyl-5-oxo-1,5-dihydro-4h-pyrazol-4-ylidene]hydrazino}-2'-hydroxy-3-biphenylcarboxylic Acid 2-aminoethanol (1:2)

2.4 Create Date

2019-01-15

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₆N₆O₆
Molecular Weight	564.6 g/mol
Hydrogen Bond Donor Count	7
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	7
Exact Mass	564.26963289 g/mol
Monoisotopic Mass	564.26963289 g/mol
Topological Polar Surface Area	207 Å²
Heavy Atom Count	41
Formal Charge	0
Complexity	822
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Drug Indication

Revolade is indicated for the treatment of adult patients with primary immune thrombocytopenia (ITP) who are refractory to other treatments (e. g. corticosteroids, immunoglobulins) (see sections 4. 2 and 5. 1).

Revolade is indicated for the treatment of paediatric patients aged 1 year and above with primary immune thrombocytopenia (ITP) lasting 6 months or longer from diagnosis and who are refractory to other treatments (e. g. corticosteroids, immunoglobulins) (see sections 4. 2 and 5. 1).

Revolade is indicated in adult patients with chronic hepatitis C virus (HCV) infection for the treatment of thrombocytopenia, where the degree of thrombocytopenia is the main factor preventing the initiation or limiting the ability to maintain optimal interferon-based therapy (see sections 4. 4 and 5. 1).

Revolade is indicated in adult patients with acquired severe aplastic anaemia (SAA) who were either refractory to prior immunosuppressive therapy or heavily pretreated and are unsuitable for haematopoietic stem cell transplantation (see section 5. 1).

5 Pharmacology and Biochemistry

5.1 FDA Pharmacological Classification

5.1.1 Pharmacological Classes

Increased Megakaryocyte Maturation [PE]; Increased Platelet Production [PE]; Organic Anion Transporting Polypeptide 1B1 Inhibitors [MoA]; Thrombopoietin Receptor Agonist [EPC]; Thrombopoietin Receptor Agonists [MoA]; UGT1A1 Inhibitors [MoA]; UGT1A3 Inhibitors [MoA]; UGT1A4 Inhibitors [MoA]; UGT1A6 Inhibitors [MoA]; UGT1A9 Inhibitors [MoA]; UGT2B15 Inhibitors [MoA]; UGT2B7 Inhibitors [MoA]; Breast Cancer Resistance Protein Inhibitors [MoA]

5.2 ATC Code

B02BX05

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