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Details

Stereochemistry ACHIRAL
Molecular Formula C20H17F3N2O4
Molecular Weight 406.3552
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TASQUINIMOD

SMILES

COC1=C2C(=CC=C1)N(C)C(=O)C(C(=O)N(C)C3=CC=C(C=C3)C(F)(F)F)=C2O

InChI

InChIKey=ONDYALNGTUAJDX-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Molecular Formula C20H17F3N2O4
Molecular Weight 406.3552
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Tasquinimod is a drug, developed by Active Biotech Research and tested in phase III of clinical trials for the treatment of Castrate Resistant Prostate Cancer. The drug acts by targeting the tumor microenvironment with S100A9 being one of molecular targets.

Originator

Active Biotech
4
Sources: www.ncbi.nlm.nih.gov/pubmed/24600234

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Protein S100-A9
1
Target ID: P06702
Gene ID: 6280.0
Gene Symbol: S100A9
Target Organism: Homo sapiens (Human)
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase III
656
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.26 μM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19755981/
0.5 mg 1 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TASQUINIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
4.8 μM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19755981/
0.5 mg 1 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TASQUINIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
40 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/19755981/
0.5 mg 1 times / day steady-state, oral
dose: 0.5 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
TASQUINIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY107103
https://www.001chemical.com/chem/search?q=DY107103
1PlusChem LLC
1P00BFLJ
https://www.1pchem.com/search?query=1P00BFLJ
AChemBlock
O33808
http://www.achemblock.com/catalogsearch/result/?q=O33808
AK Scientific
2746AH
https://aksci.com/item_detail.php?cat=2746AH
AOBIOUS INC
AOB87360
http://aobious.com/aobious/search?search_query=AOB87360
Ambeed
A337216
http://www.ambeed.com/search/Search.html?keyword=A337216
Angene
AGN-PC-0WH9AP
http://www.angenechemical.com/productshow/AGN-PC-0WH9AP.html
ApexBio Technology
A3860
https://www.apexbt.com/catalogsearch/result/?q=A3860
AstaTech
42289
http://astatechinc.com/CPSResult.php?CRNO=42289
BLD Pharm
BD305716
http://www.bldpharm.com/search/Search.html?keyword=BD305716
Cayman Chemical
17692
http://www.caymanchem.com/app/template/Product.vm/catalog/17692
ChemShuttle
112778
https://www.chemshuttle.com/catalogsearch/result/?q=112778
Hairui
HR144074
http://www.hairuichem.com/en/product/search.do?q=HR144074
KeyOrganics
AS-35208
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-35208
Lab Seeker
SC-96760
http://www.labseeker.com/search.php?keywords=SC-96760&category=0
LabSeeker
SC-96760
http://www.labseeker.com/search.php?keywords=SC-96760&category=0
Matrix Scientific
132691
http://www.matrixscientific.com/132691.html
MedChem Express
HY-10528
https://www.medchemexpress.com/search.html?q=HY-10528&ft=&fa=&fp=
MolPort
MolPort-035-789-708
https://www.molport.com/shop/molecule-link/MolPort-035-789-708
Molcore
MC107103
http://www.molcore.com/CatMC107103.html
Molnova
M13764
https://www.molnova.com/en/serch-list.html?keywords=M13764
Selleck Chemicals
S7617
http://www.selleckchem.com/search.html?searchDTO.searchParam=S7617
ShangHai Biochempartner
BCP10352
http://www.biochempartner.com/search_BCP10352
TargetMol
T6695
https://www.targetmol.com/search?keyword=T6695
eMolecules
44811557
https://orderbb.emolecules.com/search/#?query=44811557
mcule
MCULE-2997375322
https://mcule.com/MCULE-2997375322/
PubMed

PubMed

TitleDatePubMed
Identification of ABR-215050 as lead second generation quinoline-3-carboxamide anti-angiogenic agent for the treatment of prostate cancer.
2006 Dec 1
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.
2007 May 15
Open-label, clinical phase I studies of tasquinimod in patients with castration-resistant prostate cancer.
2009 Oct 20
Angiogenesis inhibitors in the treatment of prostate cancer.
2010 Aug 2
Tasquinimod (ABR-215050), a quinoline-3-carboxamide anti-angiogenic agent, modulates the expression of thrombospondin-1 in human prostate tumors.
2010 May 17
The long and winding road for the development of tasquinimod as an oral second-generation quinoline-3-carboxamide antiangiogenic drug for the treatment of prostate cancer.
2010 Oct
Tasquinimod Is an Allosteric Modulator of HDAC4 survival signaling within the compromised cancer microenvironment.
2013 Feb 15
Patents

Patents

06133285
1
06605616
3

Sample Use Guides

In Vivo Use Guide
Tasquinimod is given orally at a dose of 1 mg once daily.
Route of Administration: Oral
In Vitro Use Guide
Sources: www.ncbi.nlm.nih.gov/pubmed/20470445
LNCaP prostate tumor cells were cultured with 50 uM of tasquinimod for 24 h to test its effect on gene expression. At 10 uM tasquinimod the TSP1 mRNA expression was elevated at 6 h and peaked after 72 h. Moreover, after 72 h exposure the TSP1 mRNA levels was already elevated at a dose of 1 uM tasquinimod.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:14:11 GMT 2023
Edited
by admin
on Fri Dec 15 16:14:11 GMT 2023
Record UNII
756U07KN1R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TASQUINIMOD
INN   MI   WHO-DD  
INN  
Official Name English
Tasquinimod [WHO-DD]
Common Name English
tasquinimod [INN]
Common Name English
TASQUINIMOD [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1742
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
FDA ORPHAN DRUG 561916
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
NCI_THESAURUS C129820
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
FDA ORPHAN DRUG 877022
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
Code System Code Type Description
SMS_ID
100000139620
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
NCI_THESAURUS
C74080
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
FDA UNII
756U07KN1R
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
CAS
254964-60-8
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
INN
8538
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
WIKIPEDIA
TASQUINIMOD
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID90180183
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
PUBCHEM
54682876
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
DRUG BANK
DB05861
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
EVMPD
SUB88412
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
MESH
C516109
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107784
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY
MERCK INDEX
m10480
Created by admin on Fri Dec 15 16:14:11 GMT 2023 , Edited by admin on Fri Dec 15 16:14:11 GMT 2023
PRIMARY Merck Index
Related Record Type Details
Structure of TASQUINIMOD
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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