Identification
- Generic Name
- Vadimezan
- DrugBank Accession Number
- DB06235
- Background
Not Available
- Type
- Small Molecule
- Groups
- Investigational
- Structure
Structure for Vadimezan (DB06235)
- Weight
- Average: 282.2907
Monoisotopic: 282.089208936 - Chemical Formula
- C17H14O4
- Synonyms
- (5,6-dimethyl-9-oxoxanthen-4-yl)acetic acid
- 5,6-Dimethyl-9-oxo-9H-xanthene-4-acetic acid
- 5,6-Dimethylxanthenone-4-acetic acid
- 5,6-Dimethylxanthenoneacetic acid
- 5,6-MeXAA
- Dimethyloxoxanthene acetic acid
- DMXAA
- Vadimezan
- Vadimézan
- Vadimezanum
- External IDs
- AS-1404
- AS1404
- ASA-404
- ASA404
- NSC-640488
Pharmacology
- Indication
Investigated for use/treatment in solid tumors, lung cancer, ovarian cancer, and prostate cancer.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
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.
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Vadimezan can be increased when it is combined with Abametapir. Abatacept The metabolism of Vadimezan can be increased when combined with Abatacept. Abiraterone The serum concentration of Vadimezan can be increased when it is combined with Abiraterone. Acenocoumarol The metabolism of Vadimezan can be decreased when combined with Acenocoumarol. Acetaminophen The metabolism of Vadimezan can be decreased when combined with Acetaminophen. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Vadimezan sodium C35T92HIZM 129095-08-5 CUHSZPRXKQDLCJ-UHFFFAOYSA-M
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as xanthones. These are polycyclic aromatic compounds containing a xanthene moiety conjugated to a ketone group at carbon 9. Xanthene is a tricyclic compound made up of two benzene rings linearly fused to each other through a pyran ring.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Benzopyrans
- Sub Class
- 1-benzopyrans
- Direct Parent
- Xanthones
- Alternative Parents
- Chromones / Pyranones and derivatives / Benzenoids / Heteroaromatic compounds / Oxacyclic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
- Substituents
- Aromatic heteropolycyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Chromone / Heteroaromatic compound / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxide
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- monocarboxylic acid, xanthones (CHEBI:75934)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 0829J8133H
- CAS number
- 117570-53-3
- InChI Key
- XGOYIMQSIKSOBS-UHFFFAOYSA-N
- InChI
- InChI=1S/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)
- IUPAC Name
- 2-(5,6-dimethyl-9-oxo-9H-xanthen-4-yl)acetic acid
- SMILES
- CC1=C(C)C2=C(C=C1)C(=O)C1=CC=CC(CC(O)=O)=C1O2
References
- General References
- Zhao L, Ching LM, Kestell P, Kelland LR, Baguley BC: Mechanisms of tumor vascular shutdown induced by 5,6-dimethylxanthenone-4-acetic acid (DMXAA): Increased tumor vascular permeability. Int J Cancer. 2005 Aug 20;116(2):322-6. [Article]
- McKeage MJ: The potential of DMXAA (ASA404) in combination with docetaxel in advanced prostate cancer. Expert Opin Investig Drugs. 2008 Jan;17(1):23-9. [Article]
- Link [Link]
- External Links
- PubChem Compound
- 123964
- PubChem Substance
- 347827766
- ChemSpider
- 110486
- ChEBI
- 75934
- ChEMBL
- CHEMBL71263
- ZINC
- ZINC000003777432
- PDBe Ligand
- 1YE
- Wikipedia
- Vadimezan
- PDB Entries
- 4lol / 4qxo / 4qxp / 4qxq / 4qxr
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Terminated Treatment Non-Small Cell Lung Cancer (NSCLC) 2 2 Completed Treatment Lung Cancer 1 2 Completed Treatment Prostate Cancer 1 2 Withdrawn Treatment Urothelial Carcinoma 1 1 Completed Treatment Advanced or Recurrent Solid Tumors 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0225 mg/mL ALOGPS logP 3.06 ALOGPS logP 3.62 Chemaxon logS -4.1 ALOGPS pKa (Strongest Acidic) 3.6 Chemaxon pKa (Strongest Basic) -3.8 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 3 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 63.6 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 78.21 m3·mol-1 Chemaxon Polarizability 29.37 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-000i-1590000000-d4efa2ba1592bc477025 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0159-0090000000-3f2cbd38862dc4b21e04 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0090000000-3915b41c549986e6fcf0 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0090000000-bc797e8197a70b393abf Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0090000000-46995de19af5e0b36e28 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0kmi-0790000000-390555dc1e8b0a9f10cb Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0r6v-2970000000-32f9119ca9721ff47346 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 172.4767059 predictedDarkChem Lite v0.1.0 [M-H]- 164.38644 predictedDeepCCS 1.0 (2019) [M+H]+ 172.8669059 predictedDarkChem Lite v0.1.0 [M+H]+ 166.74443 predictedDeepCCS 1.0 (2019) [M+Na]+ 172.4084059 predictedDarkChem Lite v0.1.0 [M+Na]+ 172.8376 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Retinoic acid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform has specificity for phenols. Isoform 2 lacks trans...
- Gene Name
- UGT1A9
- Uniprot ID
- O60656
- Uniprot Name
- UDP-glucuronosyltransferase 1-9
- Molecular Weight
- 59940.495 Da
References
- Zhou S, Kestell P, Baguley BC, Paxton JW: 5,6-dimethylxanthenone-4-acetic acid (DMXAA): a new biological response modifier for cancer therapy. Invest New Drugs. 2002 Aug;20(3):281-95. [Article]
- Zhou S, Kestell P, Paxton JW: Predicting pharmacokinetics and drug interactions in patients from in vitro and in vivo models: the experience with 5,6-dimethylxanthenone-4-acetic acid (DMXAA), an anti-cancer drug eliminated mainly by conjugation. Drug Metab Rev. 2002 Nov;34(4):751-90. [Article]
- Miners JO, Valente L, Lillywhite KJ, Mackenzie PI, Burchell B, Baguley BC, Kestell P: Preclinical prediction of factors influencing the elimination of 5,6-dimethylxanthenone-4-acetic acid, a new anticancer drug. Cancer Res. 1997 Jan 15;57(2):284-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Glucuronosyltransferase activity
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds.Its unique specificity for 3,4-catechol estrogens and estriol su...
- Gene Name
- UGT2B7
- Uniprot ID
- P16662
- Uniprot Name
- UDP-glucuronosyltransferase 2B7
- Molecular Weight
- 60694.12 Da
References
- Zhou S, Paxton JW, Tingle MD, Kestell P: Identification of the human liver cytochrome P450 isoenzyme responsible for the 6-methylhydroxylation of the novel anticancer drug 5,6-dimethylxanthenone-4-acetic acid. Drug Metab Dispos. 2000 Dec;28(12):1449-56. [Article]
- Zhou S, Kestell P, Baguley BC, Paxton JW: Preclinical factors affecting the interindividual variability in the clearance of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid. Biochem Pharmacol. 2003 Jun 1;65(11):1853-65. [Article]
- Zhou S, Kestell P, Baguley BC, Paxton JW: 5,6-dimethylxanthenone-4-acetic acid (DMXAA): a new biological response modifier for cancer therapy. Invest New Drugs. 2002 Aug;20(3):281-95. [Article]
- Zhou S, Kestell P, Paxton JW: Predicting pharmacokinetics and drug interactions in patients from in vitro and in vivo models: the experience with 5,6-dimethylxanthenone-4-acetic acid (DMXAA), an anti-cancer drug eliminated mainly by conjugation. Drug Metab Rev. 2002 Nov;34(4):751-90. [Article]
- Miners JO, Valente L, Lillywhite KJ, Mackenzie PI, Burchell B, Baguley BC, Kestell P: Preclinical prediction of factors influencing the elimination of 5,6-dimethylxanthenone-4-acetic acid, a new anticancer drug. Cancer Res. 1997 Jan 15;57(2):284-9. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- Curator comments
- Data supporting this enzyme action are limited to in vitro studies.
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Zhou S, Paxton JW, Tingle MD, Kestell P: Identification of the human liver cytochrome P450 isoenzyme responsible for the 6-methylhydroxylation of the novel anticancer drug 5,6-dimethylxanthenone-4-acetic acid. Drug Metab Dispos. 2000 Dec;28(12):1449-56. [Article]
- Zhou S, Kestell P, Baguley BC, Paxton JW: Preclinical factors affecting the interindividual variability in the clearance of the investigational anti-cancer drug 5,6-dimethylxanthenone-4-acetic acid. Biochem Pharmacol. 2003 Jun 1;65(11):1853-65. [Article]
- Zhou S, Kestell P, Baguley BC, Paxton JW: 5,6-dimethylxanthenone-4-acetic acid (DMXAA): a new biological response modifier for cancer therapy. Invest New Drugs. 2002 Aug;20(3):281-95. [Article]
- Zhou S, Kestell P, Paxton JW: Predicting pharmacokinetics and drug interactions in patients from in vitro and in vivo models: the experience with 5,6-dimethylxanthenone-4-acetic acid (DMXAA), an anti-cancer drug eliminated mainly by conjugation. Drug Metab Rev. 2002 Nov;34(4):751-90. [Article]
Drug created at March 19, 2008 16:18 / Updated at June 12, 2020 16:52