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Tasquinimod

CAT: 0804-HY-10528-01Size: 5 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-10528-01Size:5 mg
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Description
Tasquinimod is an oral antiangiogenic agent, which has the potential for castration-resistant prostate cancer treatment. Tasquinimod binds to the regulatory Zn2+ binding domain of HDAC4 with Kd of 10-30 nM. Tasquinimod also is a S100A9 inhibitor[1][2][3].
CAS Number
254964-60-8
Product Name Alternative
ABR-215050
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
HDAC
Type
Reference compound
Related Pathways
Cell Cycle/DNA Damage; Epigenetics
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/Tasquinimod.html
Purity
99.94
Solubility
DMSO : ≥ 42 mg/mL|H2O : < 0.1 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=C(C1=C(O)C2=C(N(C)C1=O)C=CC=C2OC)N(C)C3=CC=C(C(F)(F)F)C=C3
Molecular Formula
C20H17F3N2O4
Molecular Weight
406.36
Precautions
H302, H315, H319, H335
References & Citations
[1]Isaacs JT, et al. Tasquinimod Is an Allosteric Modulator of HDAC4 survival signaling within the compromised cancer microenvironment. Cancer Res. 2013 Feb 15;73 (4) :1386-99.|[2]Isaacs JT, et al. Anti-cancer potency of tasquinimod is enhanced via albumin-binding facilitating increased uptake in the tumor microenvironment. Oncotarget. 2014 Sep 30;5 (18) :8093-106.|[3]Olsson A, et al. Tasquinimod (ABR-215050), a quinoline-3-carboxamide anti-angiogenic agent, modulates the expression of thrombospondin-1 in human prostate tumors. Mol Cancer. 2010 May 17;9:107.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
Phase 3
Isoform
HDAC4

Chemical Information

Tasquinimod

Tasquinimod is a quinoline-3-carboxamide linomide analogue with antiangiogenic and potential antineoplastic activities. Tasquinimod has been shown to decrease blood vessel density but the exact mechanism of action is not known. This agent has also been shown to augment the antineoplastic effects of docetaxel and androgen ablation in a murine model of prostate cancer involving human prostate cancer xenografts.

CAS Number254964-60-8
PubChem CID54682876
IUPAC Name4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]quinoline-3-carboxamide
Molecular FormulaC20H17F3N2O4
Molecular Weight406.4
XLogP3.5
Topological Polar Surface Area70.1
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Heavy Atom Count29
Formal Charge0
Complexity686
SMILES
CN1C2=C(C(=CC=C2)OC)C(=C(C1=O)C(=O)N(C)C3=CC=C(C=C3)C(F)(F)F)O
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
InChIKey
ONDYALNGTUAJDX-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of Tasquinimod
CAS: 254964-60-8
CID: 54682876
Formula: C20H17F3N2O4
MW: 406.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight406.4
XLogP33.5
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count3
Exact Mass406.11404151
Monoisotopic Mass406.11404151
Topological Polar Surface Area70.1 Ų
Heavy Atom Count29
Formal Charge0
Complexity686
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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