SML1549
Ombrabulin hydrochloride
≥98% (HPLC)
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
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About This Item
Empirical Formula (Hill Notation):
C21H26N2O6 · HCl
CAS Number:
Molecular Weight:
438.90
UNSPSC Code:
12352200
NACRES:
NA.77
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
SMILES string
Cl.NC(CO)C(=O)Nc1c(ccc(c1)C=Cc2cc(c(c(c2)OC)OC)OC)OC
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 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.
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 is an antitubulin vascular disrupting agent.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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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)
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)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| SML1549-25MG | 04061833226339 |
| SML1549-5MG | 04061833226346 |