Tasquinimod
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Identification
- Generic Name
- Tasquinimod
- DrugBank Accession Number
- DB05861
- Background
The quinoline-3-carboxamide anti-angiogenic agent, tasquinimod, enhances the anti-prostate cancer efficacy of androgen ablation and taxotere without effecting serum PSA directly in human xenografts
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 406.361
Monoisotopic: 406.114041524 - Chemical Formula
- C20H17F3N2O4
- Synonyms
- TASQ
- Tasquinimod
- External IDs
- ABR-215050
Pharmacology
- Indication
Investigated for use/treatment in prostate cancer.
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- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- 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
- Not Available
Interactions
- Drug Interactions
- 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aromatic anilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with an aromatic group. They have the general structure RNC(=O)R', where R= benzene, and R = aryl group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Anilides
- Direct Parent
- Aromatic anilides
- Alternative Parents
- Quinoline-3-carboxamides / Hydroquinolones / Trifluoromethylbenzenes / Hydroquinolines / Pyridinecarboxylic acids and derivatives / Anisoles / Pyridinones / Alkyl aryl ethers / Hydroxypyridines / Vinylogous amides show 11 more
- Substituents
- Alkyl aryl ether / Alkyl fluoride / Alkyl halide / Anisole / Aromatic anilide / Aromatic heteropolycyclic compound / Azacycle / Carboxamide group / Carboxylic acid derivative / Dihydroquinoline show 24 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 756U07KN1R
- CAS number
- 254964-60-8
- InChI Key
- ONDYALNGTUAJDX-UHFFFAOYSA-N
- InChI
- InChI=1S/C20H17F3N2O4/c1-24(12-9-7-11(8-10-12)20(21,22)23)18(27)16-17(26)15-13(25(2)19(16)28)5-4-6-14(15)29-3/h4-10,26H,1-3H3
- IUPAC Name
- 4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]-1,2-dihydroquinoline-3-carboxamide
- SMILES
- COC1=CC=CC2=C1C(O)=C(C(=O)N(C)C1=CC=C(C=C1)C(F)(F)F)C(=O)N2C
References
- General References
- Dalrymple SL, Becker RE, Isaacs JT: The quinoline-3-carboxamide anti-angiogenic agent, tasquinimod, enhances the anti-prostate cancer efficacy of androgen ablation and taxotere without effecting serum PSA directly in human xenografts. Prostate. 2007 May 15;67(7):790-7. [Article]
- Isaacs JT, Pili R, Qian DZ, Dalrymple SL, Garrison JB, Kyprianou N, Bjork A, Olsson A, Leanderson T: Identification of ABR-215050 as lead second generation quinoline-3-carboxamide anti-angiogenic agent for the treatment of prostate cancer. Prostate. 2006 Dec 1;66(16):1768-78. [Article]
- External Links
- PubChem Compound
- 54682876
- PubChem Substance
- 175427045
- ChemSpider
- 11444963
- ChEMBL
- CHEMBL2107784
- ZINC
- ZINC000000602397
- Wikipedia
- Tasquinimod
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Prostate Cancer 1 3 Terminated Treatment Castration Resistant Prostatic Neoplasms 1 2 Completed Treatment Advanced or Metastatic Gastric Carcinoma / Advanced or Metastatic Hepatocellular Cancer / Advanced or Metastatic Ovarian Cancer / Metastatic Renal Cell Carcinoma ( mRCC) 1 2 Completed Treatment Hormone Resistant Prostate Cancer / Metastatic Carcinoma of the Prostate / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer 1 2 Completed Treatment Prostate Cancer 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 0.00911 mg/mL ALOGPS logP 3.26 ALOGPS logP 2.31 Chemaxon logS -4.6 ALOGPS pKa (Strongest Acidic) 4.73 Chemaxon pKa (Strongest Basic) -2.4 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 70.08 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 100.19 m3·mol-1 Chemaxon Polarizability 36.89 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
Property Value Probability Human Intestinal Absorption + 0.9941 Blood Brain Barrier + 0.991 Caco-2 permeable + 0.7063 P-glycoprotein substrate Non-substrate 0.8073 P-glycoprotein inhibitor I Non-inhibitor 0.9345 P-glycoprotein inhibitor II Non-inhibitor 0.9519 Renal organic cation transporter Non-inhibitor 0.8279 CYP450 2C9 substrate Non-substrate 0.8523 CYP450 2D6 substrate Non-substrate 0.841 CYP450 3A4 substrate Non-substrate 0.6779 CYP450 1A2 substrate Inhibitor 0.7691 CYP450 2C9 inhibitor Non-inhibitor 0.8229 CYP450 2D6 inhibitor Non-inhibitor 0.8356 CYP450 2C19 inhibitor Non-inhibitor 0.6266 CYP450 3A4 inhibitor Non-inhibitor 0.7228 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5971 Ames test Non AMES toxic 0.7829 Carcinogenicity Non-carcinogens 0.921 Biodegradation Not ready biodegradable 0.9434 Rat acute toxicity 1.7663 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9942 hERG inhibition (predictor II) Non-inhibitor 0.8624
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-001i-0090200000-d3e540ca17e385149183 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0010900000-c7e2162a946d091f47d6 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0kai-0091300000-45527771c5abce71273c Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0kur-0190300000-cf806034353683050d30 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0019-0970000000-12fb936340488c26e615 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-05n1-7962100000-30675a099dc778290dd7 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]- 182.5376 predictedDeepCCS 1.0 (2019) [M+H]+ 184.8956 predictedDeepCCS 1.0 (2019) [M+Na]+ 191.09828 predictedDeepCCS 1.0 (2019)
Drug created at November 18, 2007 18:28 / Updated at February 21, 2021 18:51