Omacetaxine mepesuccinate hydrochlorideProduct ingredient for Omacetaxine mepesuccinate
- Name
- Omacetaxine mepesuccinate hydrochloride
- Drug Entry
- Omacetaxine mepesuccinate
Omacetaxine mepesuccinate (formerly known as HHT or Homoharringtonine), is a cephalotaxine ester and protein synthesis inhibitor with established clinical activity as a single agent in hematological malignancies. Omacetaxine mepesuccinate is synthesized from cephalotaxine, which is an extract from the leaves of the plant, Cephalotaxus species. In October 2005, omacetaxine mepesuccinate received Orphan Drug designation from the EMEA for the treatment of chronic myeloid leukemia (CML). Then in March 2006, it received Orphan Drug status from the FDA for the treatment of CML. In November 2006, omacetaxine mepesuccinate, for the treatment of CML, was granted Fast Track designation by the FDA. Most recently, in October 2012, omacetaxine mepesuccinate was marketed under the brand name Synribo and FDA approved for patients who are intolerant and/or resistant to two or more tyrosine kinase inhibitors used to treat accelerated or chronic phase CML.
- Accession Number
- DBSALT001930
- Structure
- Synonyms
- Not Available
- UNII
- 563OX5661H
- CAS Number
- 457895-79-3
- Weight
- Average: 582.09
Monoisotopic: 581.2391596 - Chemical Formula
- C29H40ClNO9
- InChI Key
- RRNSZQVHVKGKOS-CALFFDBBSA-N
- InChI
- InChI=1S/C29H39NO9.ClH/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;1H/t24-,25-,28+,29-;/m1./s1
- IUPAC Name
- (2S,3S,6R)-4-methoxy-16,18-dioxa-10-azapentacyclo[11.7.0.0^{2,6}.0^{6,10}.0^{15,19}]icosa-1(20),4,13,15(19)-tetraen-3-yl 1-methyl (3R)-3-hydroxy-3-(4-hydroxy-4-methylpentyl)butanedioate hydrochloride
- SMILES
- Cl.COC(=O)C[C@](O)(CCCC(C)(C)O)C(=O)O[C@H]1[C@H]2C3=CC4=C(OCO4)C=C3CCN3CCC[C@]23C=C1OC
- External Links
- ChemSpider
- 8026977
- Predicted Properties
Property Value Source Water Solubility 0.108 mg/mL ALOGPS logP 2.09 ALOGPS logP 1.88 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 12.09 Chemaxon pKa (Strongest Basic) 9.42 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 123.99 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 142.07 m3·mol-1 Chemaxon Polarizability 57.63 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon