Tasquinimod

Identification

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Name
Tasquinimod
Accession Number
DB05861
Type
Small Molecule
Groups
Investigational
Description

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

Structure
Thumb
Synonyms
  • TASQ
External IDs
ABR-215050
Categories
Not Available
UNII
756U07KN1R
CAS number
254964-60-8
Weight
Average: 406.361
Monoisotopic: 406.114041524
Chemical Formula
C20H17F3N2O4
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

Pharmacology

Indication

Investigated for use/treatment in prostate cancer.

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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

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. [PubMed:17373719]
  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. [PubMed:16955399]
External Links
PubChem Compound
54682876
PubChem Substance
175427045
ChemSpider
11444963
ChEMBL
CHEMBL2107784
Wikipedia
Tasquinimod

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers1
1CompletedTreatmentProstate Cancer1
1WithdrawnTreatmentBone-only Metastatic Castration-Resistant Prostate Cancer (CRPC) / Prostate Cancer1
2CompletedTreatmentAdvanced or Metastatic Gastric Carcinoma / Advanced or Metastatic Hepatocellular Cancer / Advanced or Metastatic Ovarian Cancer / Metastatic Renal Cell Cancer1
2CompletedTreatmentHormone-Resistant Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer1
2CompletedTreatmentProstate Cancer1
2TerminatedTreatmentMetastatic Castrate Resistant Prostate Cancer1
3CompletedTreatmentProstate Cancer1
3TerminatedTreatmentAsian Chemo-naïve Patients With Metastatic Castrate-resistant 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

Taxonomy

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
Aromatic anilide / Quinoline-3-carboxamide / Dihydroquinolone / Dihydroquinoline / Trifluoromethylbenzene / Quinoline / Pyridine carboxylic acid or derivatives / Anisole / Alkyl aryl ether / Pyridinone
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on November 18, 2007 11:28 / Updated on June 04, 2019 06:20