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
ChemSpider
8026977
Predicted Properties
PropertyValueSource
Water Solubility0.108 mg/mLALOGPS
logP2.09ALOGPS
logP1.88Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)12.09Chemaxon
pKa (Strongest Basic)9.42Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area123.99 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity142.07 m3·mol-1Chemaxon
Polarizability57.63 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon