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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Contraindications & Blackbox Warnings
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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
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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
  1. 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]
  2. 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]
PubChem Compound
54682876
PubChem Substance
175427045
ChemSpider
11444963
ChEMBL
CHEMBL2107784
ZINC
ZINC000000602397
Wikipedia
Tasquinimod

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentProstate Cancer1
3TerminatedTreatmentCastration Resistant Prostatic Neoplasms1
2CompletedTreatmentAdvanced or Metastatic Gastric Carcinoma / Advanced or Metastatic Hepatocellular Cancer / Advanced or Metastatic Ovarian Cancer / Renal Cell Cancer Metastatic1
2CompletedTreatmentHormone Resistant Prostate Cancer / Recurrent Prostate Carcinoma / Refractory, metastatic hormone-refractory Prostate cancer / Stage IV Prostate Cancer1
2CompletedTreatmentProstate Cancer1
2TerminatedTreatmentMetastatic Castration Resistant Prostate Cancer (CRPC)1
1CompletedNot AvailableHealthy Subjects (HS)1
1CompletedTreatmentProstate Cancer1
1RecruitingTreatmentMultiple Myeloma (MM)1
1WithdrawnTreatmentBone-only Metastatic Castration-Resistant Prostate Cancer (CRPC) / Prostate Cancer1

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
PropertyValueSource
Water Solubility0.00911 mg/mLALOGPS
logP3.26ALOGPS
logP2.31ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)4.73ChemAxon
pKa (Strongest Basic)-2.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area70.08 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity100.19 m3·mol-1ChemAxon
Polarizability36.89 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9941
Blood Brain Barrier+0.991
Caco-2 permeable+0.7063
P-glycoprotein substrateNon-substrate0.8073
P-glycoprotein inhibitor INon-inhibitor0.9345
P-glycoprotein inhibitor IINon-inhibitor0.9519
Renal organic cation transporterNon-inhibitor0.8279
CYP450 2C9 substrateNon-substrate0.8523
CYP450 2D6 substrateNon-substrate0.841
CYP450 3A4 substrateNon-substrate0.6779
CYP450 1A2 substrateInhibitor0.7691
CYP450 2C9 inhibitorNon-inhibitor0.8229
CYP450 2D6 inhibitorNon-inhibitor0.8356
CYP450 2C19 inhibitorNon-inhibitor0.6266
CYP450 3A4 inhibitorNon-inhibitor0.7228
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5971
Ames testNon AMES toxic0.7829
CarcinogenicityNon-carcinogens0.921
BiodegradationNot ready biodegradable0.9434
Rat acute toxicity1.7663 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9942
hERG inhibition (predictor II)Non-inhibitor0.8624
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at November 18, 2007 18:28 / Updated at February 21, 2021 18:51