Vadimezan Chemical Properties

Melting point:

259-261 °C

Boiling point:

520.9±50.0 °C(Predicted)

Density 

1.321±0.06 g/cm3(Predicted)

vapor pressure 

0Pa at 20℃

storage temp. 

2-8°C

solubility 

DMSO: 17 mg/mL, soluble

form 

solid

pka

4.21±0.10(Predicted)

color 

light brown

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or DMF may be stored at -20°C for up to 3 months.

Safety Information

Hazard Codes 

Xn,N

Risk Statements 

22-50/53

Safety Statements 

60-61

RIDADR 

UN 3077 9/PG 3

WGK Germany 

3

RTECS 

ZD5536200

HS Code 

2932.99.7000

Vadimezan Usage And Synthesis

Description

DMXAA (117570-53-3) is a STING (Stimulator of Interferon Genes) agonist selective for mouse STING.1,2 Intratumoral administration of DMXAA resulted in tumor regression and complete rejection in mouse xenografts.3 Tumor regression induced by DMXAA results from a cascade of cellular events which include disruption of tumor vasculature followed by the release of chemokines which trigger the recruitment of immune cells.4 DMXAA induced expression of IFN-β resulting in a striking expansion of leukemia-specific T cells extending survival in two acute myeloid leukemia models.5

Uses

Vadimezan is a drug that displayed vascular-disrupting activity and induced haemorrhagic necrosis and tumour regression in pre-clinical animal models. It is a substrate for the immune adaptor protein STING in mice.

Definition

ChEBI: A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is replaced by a 5,6-dimethyl-9-oxoxanthen-4-yl group.

General Description

5,6-dimethylxanthenone-4-acetic acid (DMXAA) is a flavone acetic acid derivative. It acts as a vascular disrupting agent (VDA), which damages tumor vasculature and stimulates an anti-tumor immune response. It stimulates hemorrhagic necrosis.

Biochem/physiol Actions

DMXAA is an apoptosis inducer; anti-vascular.

storage

Store at +4°C

References

1) Prantner et al. (2012), 5,6-Dimethylzanthenone-4-acetic acid (DMXAA) activates stimulator of interferon gene (STING)-dependent innate immune pathways and is regulated by mitochondrial membrane potential; J. Biol. Chem., 287 39776 2) Conlon et al. (2013), Mouse, but not human STING, binds and signals in response to the vascular disrupting agent 5,6-dimethylxanthenone-4-acetic acid; J. Immunol., 190 5216 3) Corrales et al. (2015), Direct Activation of STING in the Tumor Microenvironment Leads to Potent and Systemic Tumor Regression and immunity; Cell Rep., 11 1018 4) Weiss et al. (2017), The STING agonist DMXAA triggers a cooperation between T lymphocytes and myeloid cells that leads to tumor regression; Oncoimmunology, 6 e1346765 5) Curran et al. (2016), STING Pathway Activation Stimulates Potent Immunity Against Acute Myeloid Leukemia; Cell Rep., 15 2357

Vadimezan(117570-53-3)Related Product Information

• Pentoxifylline
• 2,6-Lutidine
• Acetone oxime
• Methyl 2,2-dimethylphenylacetate
• Ethyl 2-(Chlorosulfonyl)acetate
• Dimethyl sulfoxide
• Poly(dimethylsiloxane)
• N,N-Dimethylformamide
• N,N-Dimethylacetamide
• Theobromine
• Dimethylbenzylcarbinyl acetate
• Acetic anhydride
• Phenylacetic acid
• 2-Propylpiperidine
• 3-BENZOYLPHENYLACETIC ACID
• Xanthene
• 2-PHENOXYPHENYLACETIC ACID
• xanthenone-4-acetic acid