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117570-53-3

5,6-Dimethylxantheonone-4-acetic acid

CAS: 117570-53-3

Molecular Formula: C17H14O4

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117570-53-3 - Names and Identifiers

Name 5,6-Dimethylxantheonone-4-acetic acid
Synonyms DMXAA
CS-1975
vadimezan
DMXAA (ASA404,Vadimezan)
5,6-dimethylxanthenoneacetic acid
5,6-Dimethylxanthenone-4-acetic acid
5,6-Dimethylxantheonone-4-acetic acid
(5,6-DIMETHYL-9-OXO-XANTHEN)-4-ACETIC ACID
5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic acid
(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid
CAS 117570-53-3
InChI InChI=1/C17H14O4/c1-9-6-7-13-15(20)12-5-3-4-11(8-14(18)19)17(12)21-16(13)10(9)2/h3-7H,8H2,1-2H3,(H,18,19)

117570-53-3 - Physico-chemical Properties

Molecular FormulaC17H14O4
Molar Mass282.29
Density1.321±0.06 g/cm3(Predicted)
Melting Point259-261 °C
Boling Point520.9±50.0 °C(Predicted)
Flash Point197.1°C
Solubility DMSO: 17 mg/mL, soluble
Vapor Presure0Pa at 20℃
Appearancelight brown (solid)
Colorlight brown
pKa4.21±0.10(Predicted)
Storage Condition2-8°C
StabilityStable 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.
Refractive Index1.633
MDLMFCD00870555
Physical and Chemical PropertiesSolubility: DMSO: 17 mg/mL, soluble
storage condition: 2-8℃
WGK Germany:3
RTECS:ZD5536200
In vitro studyIn Vitro, DMXAA(ASA404) inhibited purified DT-diaphorase with IC50 of 62.5 μm and K I of 20 μm. DMXAA(ASA404) acts on DLD-1 human colon cancer cells to inhibit DT-diaphorase activity with IC50 of 49.6 μm, but has no significant effect on cytochrome b5 reductase and cytochrome P450 reductase. DMXAA(ASA404) is an antiviral drug that acts on RAW 264.7 macrophages to inhibit VSV-induced cytotoxicity and also inhibits influenza virus replication. Recent studies have shown that DMXAA(ASA404) acts on several kinase members of VEGFR, such as VEGFR2 signals in human umbilical vein endothelial cells, and has a non-immunomodulatory inhibitory effect.
In vivo studyDMXAA(ASA404) significantly delays chemical carcinogen-induced cell growth, increases tumor doubling time, and increases the time from treatment to euthanasia. DMXAA(ASA404) treatment of tumor-bearing animals increased mean tumor doubling time, mean tumor tripling time, and mean time from treatment to euthanasia by 4.4-, 1.8- 2.7-Times. DMXAA(ASA404) treatment significantly protected C57BL/6J mice infected with H1N1 Influenza PR8 virus adapted to 200 p. F. u. Mice, resulting in a survival rate of 60%, while the survival rate of the control group was only 20%.

117570-53-3 - Risk and Safety

Risk CodesR22 - Harmful if swallowed
R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. 
Safety DescriptionS60 - This material and its container must be disposed of as hazardous waste.
S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. 
UN IDsUN 3077 9/PG 3
WGK Germany3
RTECSZD5536200

117570-53-3 - Reference Information

biological activity DMXAA (Vadimezan) is a vascular disrupting agent (VDA) and a DT-diaphorase competitive inhibitor. Ki is 20 μM and IC50 is 62.5 μM in cell-free test. DMXAA (Vadimezan) is also a STING agonist with potential antitumor activity. DMXAA (Vadimezan) can effectively induce the expression of IFN-β and TNF-α in vitro, but has relatively low effect on TNF-α. DMXAA (Vadimezan) has antiviral activity. Phase 3.
TargetValue
DT-diaphorase (Cell-free assay) 20 μM(Ki)
20 μM(Ki)
Last Update:2024-04-09 20:52:54
117570-53-3
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117570-53-3
2-formylhydrazinecarboxamide
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