All Photos(1)
Synonym(s):
(2S)-2-Amino-3-hydroxy-N-[2-methoxy-5-[(1Z)-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl]-propanamide hydrochloride, AC 7700, AVE 8062A, AVE8062, Ombrabulin HCl
Empirical Formula (Hill Notation):
C21H26N2O6 · HCl
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Quality Level
Assay
≥98% (HPLC)
form
powder
storage condition
desiccated
color
white to beige
solubility
H2O: 20 mg/mL, clear
storage temp.
2-8°C
InChI
1S/C21H26N2O6.ClH/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);1H
InChI key
UQNRTPFLTRZEIM-UHFFFAOYSA-N
General description
Ombrabulin is a member of the combretastatin A-4 compound class and is a tubulin-depolymerising tumour vascular-disrupting compound.
Biochem/physiol Actions
Ombrabulin is a synthetic water-soluble combretastatin analog vascular disrupting agent. Ombrabulin is a tubulin polymerization inhibitor. Ombrabulin binds to the colchicine binding site of endothelial cell tubulin, inhibiting tubulin polymerization and inducing mitotic arrest and apoptosis in endothelial cells.
Ombrabulin leads to the constriction of the arteries, inhibits cell proliferation and causes detachment of endothelial cells, thereby leading to cytotoxicity. In pre-clinical studies, this compound, along with cisplatin, has shown anti-tumor activity. In tumors, it is responsible for the destruction of the vasculature.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Regulatory Information
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Certificates of Analysis (COA)
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Ombrabulin plus cisplatin versus placebo plus cisplatin in patients with advanced soft-tissue sarcomas after failure of anthracycline and ifosfamide chemotherapy: a randomised, double-blind, placebo-controlled, phase 3 trial.
Blay JY et al
Lancet Oncology, 16(5), 531-540 (2015)
Phase I safety, pharmacokinetic and pharmacodynamic evaluation of the vascular disrupting agent ombrabulin (AVE8062) in patients with advanced solid tumors.
Sessa C et al
Clinical Cancer Research, 19(17), 4832-4842 (2013)
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