Homoharringtonine

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Structural formula
Structural formula of (-) - homoharringtonine
General
Non-proprietary name Omacetaxine mepesuccinate
other names

1-cephalotaxin-4-methyl [(2 S ) -2-hydroxy-2- (4-hydroxy-4-methylpentyl) butanedioate]

Molecular formula C 29 H 39 NO 9
External identifiers / databases
CAS number 26833-87-4
EC number 636-662-8
ECHA InfoCard 100.164.439
PubChem 285033
ChemSpider 65276
DrugBank DB04865
Wikidata Q7089373
Drug information
ATC code

L01 XX40

properties
Molar mass 545.63 g mol −1
Physical state

firmly

Melting point

144-146 ° C

safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
06 - Toxic or very toxic

danger

H and P phrases H: 300 + 310 + 330
P: 262-280-301 + 310 + 330-302 + 352 + 310-304 + 340 + 310
Toxicological data

7.456 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Homoharringtonine is an alkaloid from the group of the Cephalotaxus alkaloids .

Occurrence

Chinese head yew ( Cephalotaxus sinensis )

It comes in the cephalotaxus plants ( Cephalotaxaceae before), for example in Cephalotaxus fortunei , Cephalotaxus hainanensis or Cephalotaxus sinensis .

Extraction and presentation

Homoharringtonine is produced partially synthetically by acylation of cephalotaxine with a tetrahydropyrancarboxylic acid derivative and its subsequent ring opening.

properties

Homoharringtonine shows as well harringtonine antitumor activity. Furthermore, homoharringtonine inhibits the first elongation step in the translation of mRNA . It binds to the ribosomal acceptor site and prevents the correct positioning of the aminoacyl-tRNA .

use

In Chinese folk medicine , alcoholic extracts from the seeds of the Cephalotaxus sinensis were used to treat cancer.

In October 2012, the FDA approved homoharringtonine under the trade name Synribo for the treatment of patients with chronic myeloid leukemia (CML). It is administered subcutaneously .

Finished preparations

Synribo (USA)

Individual evidence

  1. ↑ a b c d e f Entry on omacetaxine mepesuccinate. In: Römpp Online . Georg Thieme Verlag, accessed on June 3, 2020.
  2. ↑ a b c Datasheet Homoharringtonine at Sigma-Aldrich , accessed on June 3, 2020 ( PDF ).