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Substance Name: Omacetaxine mepesuccinate [USAN:INN]
RN: 26833-87-4
UNII: 6FG8041S5B
InChIKey: HYFHYPWGAURHIV-JFIAXGOJSA-N

Note

  • Alkaloid from Cephalotaxus harringtonia; FDA approved orphan drug status for Ceflatonin in the treatment of chronic myeloid leukemia due to being an inducer of apoptosis in myeloid cells and inhibitor of angiogenesis.

Molecular Formula

  • C29-H39-N-O9

Molecular Weight

  • 545.6251
 

Classification Codes

  • Angiogenesis Inhibitors
  • Angiogenesis Modulating Agents
  • Antineoplastic Agents
  • Antineoplastic Agents, Phytogenic
  • Drug / Therapeutic Agent
  • Growth Inhibitors
  • Growth Substances
  • Natural Product
  • Treatment of Acute Myeloid Leukemia
  • Treatment of Chronic Myeloid Leukemia
  • Treatment of Chronic Myeloid Leukemia, Acute Myeloid Leukemia and Myelodysplasia
  • Treatment of Myelodysplasia

Names and Synonyms

Name of Substance

  • Homoharringtonine
  • Omacetaxine mepesuccinate [USAN:INN]

Synonyms

  • 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
  • BRN 5687925
  • Ceflatonin
  • CGX-635
  • Homoharringtonine
  • Myelostat
  • NSC 141633
  • Omacetaxine mepesuccinate
  • Omapro
  • Synribo
  • UNII-6FG8041S5B

Systematic Names

  • Cephalotaxine, 4-methyl (2R)-2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester) (9CI)
  • Cephalotaxine, 4-methyl 2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester), (3(R))- (9CI)
  • Cephalotaxine, 4-methyl-, 2-hydroxy-2-(4-hydroxy-4-methylpentyl)butanedioate (ester)
  • Homoharringtonine (8CI)

Registry Numbers

CAS Registry Number

  • 26833-87-4

FDA UNII

  • 6FG8041S5B

System Generated Number

  • 0026833874

Structure Descriptors

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

InChIKey

HYFHYPWGAURHIV-JFIAXGOJSA-N

Smiles

COC(=O)C[C@](O)(CCCC(C)(C)O)C(=O)O[C@H]1[C@H]2c3cc4OCOc4cc3CCN5CCC[C@]25C=C1OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD10 intravenous 640ug/kg (0.64mg/kg) CARDIAC: CHANGE IN RATE

BEHAVIORAL: FOOD INTAKE (ANIMAL)

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
National Cancer Institute Report. Vol. AUG1982,
mouse LD50 intraperitoneal 3170ug/kg (3.17mg/kg)   Chinese Medical Journal Vol. 92, Pg. 175, 1979.
mouse LD50 intravenous 2400ug/kg (2.4mg/kg)   Journal of Ethnopharmacology. Vol. 24, Pg. 1, 1988.
mouse LD50 oral 7456ug/kg (7.456mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,
mouse LD50 subcutaneous 3948ug/kg (3.948mg/kg)   National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986,