5,6-Dimethylxanthenone-4-acetic acid
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5,6-Dimethylxanthenone-4-acetic acid
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CAS No:
117570-53-3
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Formula:
C17H14O4
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Chemical Name:
5,6-Dimethylxanthenone-4-acetic acid
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Synonyms:
9H-Xanthene-4-acetic acid,5,6-dimethyl-9-oxo-;5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic acid;5,6-Dimethylxanthenone-4-acetic acid;NSC 640488;DMXAA;AS 1404;5,6-Dimethyl-9-oxo-9H-xanthen-4-ylacetic acid;Vadimezan;ASA 404;2-(5,6-Dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid;D5817;2-(5,6-Dimethyl-9-oxoxanthen-4-yl)acetic acid
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CAS No:
Description
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.
Vadimezan is 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. It has a role as an antineoplastic agent. It is a member of xanthones and a monocarboxylic acid.|Vadimezan is a fused tricyclic analogue of flavone acetic acid with potential antineoplastic activity. Vadimezan induces the cytokines tumor necrosis alpha (TNF-alpha), serotonin and nitric oxide, resulting in hemorrhagic necrosis and a decrease in angiogenesis. This agent also stimulates the anti-tumor activity of tumor-associated macrophages.
5,6-Dimethylxanthenone-4-acetic acid Basic Attributes
282.29
282.29
700-141-4
0829J8133H
DTXSID2040949
C2504
2932999099
Characteristics
63.6
3.2
light brown solid
1.321±0.06 g/cm3(Predicted)
259-261 °C
520.9±50.0 °C(Predicted)
197.1±23.6 °C
1.633
DMSO: 17 mg/mL, soluble
2-8°C
1.12E-11mmHg at 25°C
Safety Information
UN 3077 9/PG 3
3
22-50/53
60-61
ZD5536200
Xn,N
P273
H302-H400
|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P301+P312, P330, P391, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Investigated for use/treatment in solid tumors, lung cancer, ovarian cancer, and prostate cancer.
Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)
DMXAA has known human metabolites that include (2S,3S,4S,5R)-6-[2-(5,6-dimethyl-9-oxoxanthen-4-yl)acetyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid and 6-hydroxy-MXAA.
ASA404 (DMXAA) is a small-molecule vascular disrupting agent which targets the blood vessels that nourish tumours. The proposed mechanism of action for ASA404 is directly increasing permeability of the tumor's endothelial cells. Vasoactive mediators such as tumor necrosis factor (TNF) may also be implicated. Increased permeability of tumor cell vasculature may allow increased permeation of anticancer treatments such as cytotoxic drugs, antibodies, drug conjugates and gene therapy.
5,6-dimethyl xanthenone acetic acid
5,6-Dimethylxanthenone-4-acetic acid Use and Manufacturing
Vadimezan is a drug that displayed vascular-disrupting activity and induced haemorrhagic necrosis and tumour regression in pre-clinical animal models.
Computed Properties
Molecular Weight:282.29
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:282.08920892
Monoisotopic Mass:282.08920892
Topological Polar Surface Area:63.6
Heavy Atom Count:21
Complexity:433
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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5,6-Dimethylxanthenone-4-acetic acid
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