Ombrabulin was an experimental drug candidate discovered by Ajinomoto and further developed by Sanofi-Aventis .[ 1] combretastatin A-4 derivative that exerts its antitumor effect by disrupting the formation of blood vessels needed for tumor growth.[ 2] [ 3]
Quick facts Names, Identifiers ...
Ombrabulin
Names
IUPAC name
N 1 -{2-Methoxy-5-[(Z )-2-(3,4,5-trimethoxyphenyl)ethen-1-yl]phenyl}-L -serinamide
Systematic IUPAC name
(2S )-2-Amino-3-hydroxy-N -{{#parsoidfragment:0}}{2-methoxy-5-[(Z )-2-(3,4,5-trimethoxyphenyl)ethen-1-yl]phenyl}propanamide
Other names
AVE-8062; AVE-8062A; AC7700; CS-39-L-Ser.HCl
Identifiers
ChemSpider
UNII
InChI=1S/C21H26N2O6/c1-26-17-8-7-13(9-16(17)23-21(25)15(22)12-24)5-6-14-10-18(27-2)20(29-4)19(11-14)28-3/h5-11,15,24H,12,22H2,1-4H3,(H,23,25)/b6-5-/t15-/m0/s1 N
Key: IXWNTLSTOZFSCM-YVACAVLKSA-N N
InChI=1/C21H26N2O6/c1-26-17-8-7-13(9-16(17)23-21(25)15(22)12-24)5-6-14-10-18(27-2)20(29-4)19(11-14)28-3/h5-11,15,24H,12,22H2,1-4H3,(H,23,25)/b6-5-/t15-/m0/s1
Key: IXWNTLSTOZFSCM-YVACAVLKBS
COC1=C(C=C(C=C1)/C=C\C2=CC(=C(C(=C2)OC)OC)OC)NC(=O)[C@H](CO)N
Properties
C 21 H 26 N 2 O 6
Molar mass g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25
°C [77
°F], 100
kPa).
Close
It was granted orphan drug status by the European Medicines Agency in April 2011.[ 4]
In January 2013, Sanofi said it discontinued development of ombrabulin after disappointing results from phase III clinical trials.[ 5]
