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Homoharringtonine

Synopsis, Chemistry

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Also known as: Homoharringtonine, Ceflatonin, Myelostat, 26833-87-4, Synribo, Cgx-635

Molecular Formula

C₂₉H₃₉NO₉

Molecular Weight

545.6 g/mol

InChI Key

HYFHYPWGAURHIV-JFIAXGOJSA-N

FDA UNII

6FG8041S5B

Semisynthetic derivative of harringtonine that acts as a protein synthesis inhibitor and induces APOPTOSIS in tumor cells. It is used in the treatment of MYELOID LEUKEMIA, CHRONIC.

1 2D Structure

Homoharringtonine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-O-[(2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-yl] 4-O-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate

2.1.2 InChI

InChI=1S/C29H39NO9/c1-27(2,33)8-5-10-29(34,16-23(31)36-4)26(32)39-25-22(35-3)15-28-9-6-11-30(28)12-7-18-13-20-21(38-17-37-20)14-19(18)24(25)28/h13-15,24-25,33-34H,5-12,16-17H2,1-4H3/t24-,25-,28+,29-/m1/s1

2.1.3 InChI Key

HYFHYPWGAURHIV-JFIAXGOJSA-N

2.1.4 Canonical SMILES

CC(C)(CCCC(CC(=O)OC)(C(=O)OC1C2C3=CC4=C(C=C3CCN5C2(CCC5)C=C1OC)OCO4)O)O

2.1.5 Isomeric SMILES

CC(C)(CCC[C@@](CC(=O)OC)(C(=O)O[C@H]1[C@H]2C3=CC4=C(C=C3CCN5[C@@]2(CCC5)C=C1OC)OCO4)O)O

2.2 Other Identifiers

2.2.1 UNII

6FG8041S5B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Ceflatonin

2. Cephalotaxine

3. Homoharringtonine

4. Homoharringtonine (3(r))-isomer

5. Omacetaxine

6. Synribo

2.3.2 Depositor-Supplied Synonyms

1. Homoharringtonine

2. Ceflatonin

3. Myelostat

4. 26833-87-4

5. Synribo

6. Cgx-635

7. Omapro

8. Homoharringtonin

9. (-)-homoharringtonine

10. Nsc-141633

11. C29h39no9

12. Chebi:71019

13. (2'r,3s,4s,5r)-(-)-homoharringtonine

14. Omacetaxine (homoharringtonine)

15. Omacetaxine Mepesuccinate [usan]

16. 6fg8041s5b

17. Nsc 141633

18. 1-o-[(2s,3s,6r)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.02,6.06,10.015,19]icosa-1(20),4,13,15(19)-tetraen-3-yl] 4-o-methyl (2r)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate

19. Cephalotaxine 4-methyl (2r)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate

20. Omacetaxine Mepesuccinate (usan)

21. Tekinex

22. Synribo (tn)

23. Cephalotaxine, 4-methyl (2r)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester)

24. Unii-6fg8041s5b

25. Nsc141633

26. Ncgc00025155-01

27. Omacetaxine Mepesuccinate [usan:inn]

28. Brn 5687925

29. Omacetaxini Mepesuccinas

30. Zj-c

31. Mepesuccinate D'omacetaxine

32. Mepesuccinato De Omacetaxina

33. Cephalotaxine 4-methyl (2r)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester)

34. Mls001424293

35. Chembl46286

36. Homoharringtonine [mi]

37. Cgx-635-14 (formulation)

38. Gtpl7454

39. Schembl12745687

40. Hms3267h22

41. Hms3414n05

42. Hms3678n03

43. Amy33459

44. Homoharringtonine, >=98% (hplc)

45. Bdbm50480293

46. Mfcd05618221

47. Nsc758253

48. S9015

49. Zinc26011099

50. Akos024456585

51. Ccg-269981

52. Db04865

53. Nc00395

54. Nsc-758253

55. Omacetaxine Mepesuccinate [inn]

56. Ncgc00025155-02

57. Ncgc00025155-03

58. Ncgc00025155-04

59. Ncgc00025155-07

60. Omacetaxine Mepesuccinate [mart.]

61. Omacetaxine Mepesuccinate [vandf]

62. Hy-14944

63. Nci60_000917

64. Omacetaxine Mepesuccinate [who-dd]

65. Smr000469230

66. H1775

67. N1504

68. D08956

69. Omacetaxine Mepesuccinate [orange Book]

70. Ab00642561-02

71. Sr-01000597562

72. Q7089373

73. Sr-01000597562-1

74. Brd-k76674262-001-01-7

75. Brd-k76674262-001-02-5

76. Cephalotaxine, 3-[4-methyl (2r)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate]

77. Cephalotaxine, 4-methyl-, 2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester)

78. (s)-1-((11bs,12s,14ar)-13-methoxy-2,3,5,6,11b,12-hexahydro-1h-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]cyclopenta[b]pyrrolo[1,2-a]azepin-12-yl) 4-methyl 2-hydroxy-2-(4-hydroxy-4-methylpentyl)succinate

79. 1-((1s,3ar,14bs)-2-methoxy-1,5,6,8,9,14b-hexahydro-4h- Cyclopenta(a)(1,3)dioxolo(4,5-h)pyrrolo(2,1-b)(3)benzazepin-1-yl) 4-methyl (2r)-2- Hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate

80. 1-((1s,3ar,14bs)-2-methoxy-1,5,6,8,9,14b-hexahydro-4h-cyclopenta(a)(1,3)dioxolo(4,5-h)pyrrolo(2,1-b)(3)benzazepin-1-yl) 4-methyl (2r)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate

81. Homoharringtonine; Cephalotaxine; [3(r)]-4-methyl 2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₉NO₉
Molecular Weight	545.6 g/mol
XLogP3	0.8
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	11
Exact Mass	545.26248182 g/mol
Monoisotopic Mass	545.26248182 g/mol
Topological Polar Surface Area	124 Å²
Heavy Atom Count	39
Formal Charge	0
Complexity	968
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Synribo
PubMed Health	Omacetaxine (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	SYNRIBO contains the active ingredient omacetaxine mepesuccinate, a cephalotaxine ester. It is a protein synthesis inhibitor. Omacetaxine mepesuccinate is prepared by a semi-synthetic process from cephalotaxine, an extract from the leaves of Cephalot...
Active Ingredient	Omacetaxine mepesuccinate
Dosage Form	Powder
Route	Subcutaneous
Strength	3.5mg/vial
Market Status	Prescription
Company	Ivax Intl

2 of 2
Drug Name	Synribo
PubMed Health	Omacetaxine (Injection)
Drug Classes	Antineoplastic Agent
Drug Label	SYNRIBO contains the active ingredient omacetaxine mepesuccinate, a cephalotaxine ester. It is a protein synthesis inhibitor. Omacetaxine mepesuccinate is prepared by a semi-synthetic process from cephalotaxine, an extract from the leaves of Cephalot...
Active Ingredient	Omacetaxine mepesuccinate
Dosage Form	Powder
Route	Subcutaneous
Strength	3.5mg/vial
Market Status	Prescription
Company	Ivax Intl

4.2 Drug Indication

Used in patients who are intolerant and/or resistant to two or more tyrosine kinase inhibitors used to treat accelerated or chronic phase CML.

FDA Label

Philadelphia chromosome positive chronic myeloid leukaemia in patients who have the T315I Bcr-Abl kinase domain mutation and who are resistant to prior imatinib therapy.

5 Pharmacology and Biochemistry

5.1 Pharmacology

The pharmacodynamics of homoharringtonine is not fully understood. It is known that homoharringtonine is involved with protein synthesis inhibition and this leads to its antineoplastic activity.

5.2 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

5.3 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XX - Other antineoplastic agents

L01XX40 - Omacetaxine mepesuccinate

5.4 Absorption, Distribution and Excretion

Absorption

Homoharringtonine absorption was not quantified, but maximum concentration is reached after about 30 mins.

Route of Elimination

The main route of elimination for homoharringtonine is still unknown, but renal elimination is less than 15%.

Volume of Distribution

Homoharringtonine has a steady state Vd of 141 93.4 L.

Clearance

Clearance for homoharringtonine was not quantified.

5.5 Metabolism/Metabolites

Homoharringtonine has undergoes little hepatic metabolism and is mostly metabolized to 4-DMHHT by plasma esterase hydrolysis.

5.6 Biological Half-Life

Homoharringtonine has a half life of about 6 hours after subcutaneous administration.

5.7 Mechanism of Action

Homoharringtonine inhibits protein synthesis by not directly binding to Bcr-Abl. It binds to the A-site cleft in the large ribosomal subunit, which affects chain elongation and prevents protein synthesis.