Ombrabulin

Ombrabulin was an experimental drug candidate discovered by Ajinomoto and further developed by Sanofi-Aventis.^[1] Ombrabulin is a combretastatin A-4 derivative that exerts its antitumor effect by disrupting the formation of blood vessels needed for tumor growth.^[2][3]

Ombrabulin

Names
IUPAC name N1-{2-Methoxy-5-[(Z)-2-(3,4,5-trimethoxyphenyl)ethen-1-yl]phenyl}-L-serinamide
Systematic IUPAC name (2S)-2-Amino-3-hydroxy-N-{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
CAS Number	181816-48-8 Y 253426-24-3 (HCl) Y
3D model (JSmol)	Interactive image
ChemSpider	5293602 N
PubChem CID	6918405 6918404 (HCl)
UNII	82JB1524Q6 Y KXZ9NDO6H0 (HCl) Y
CompTox Dashboard (EPA)	DTXSID50939477
InChI 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
SMILES COC1=C(C=C(C=C1)/C=C\C2=CC(=C(C(=C2)OC)OC)OC)NC(=O)[C@H](CO)N
Properties
Chemical formula	C21H26N2O6
Molar mass	402.447 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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]