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
3D model (JSmol)
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
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).
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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]

References
  1. "Ombrabulin (AVE8062)". Sanofi-Aventis Oncology.
  2. Hori, K; Saito, S; Nihei, Y; Suzuki, M; Sato, Y (1999). "Antitumor effects due to irreversible stoppage of tumor tissue blood flow: evaluation of a novel combretastatin A-4 derivative, AC7700". Japanese Journal of Cancer Research. 90 (9): 1026–38. doi:10.1111/j.1349-7006.1999.tb00851.x. PMC 5926172. PMID 10551334.
  3. Hori, K; Saito, S; Kubota, K (2002). "A novel combretastatin A-4 derivative, AC7700, strongly stanches tumour blood flow and inhibits growth of tumours developing in various tissues and organs". British Journal of Cancer. 86 (10): 1604–14. doi:10.1038/sj.bjc.6600296. PMC 2746587. PMID 12085211.
  4. "Orphan Designation EU/3/11/853". European Medicines Agency. 15 April 2011.
  5. "Sanofi has 65 new compounds in development, says R&D chief".
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