Tasquinimod

CAT: 0804-HY-10528-02Size: 10 mM - 1 mLDry Ice: NoHazardous: No

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CAT#:0804-HY-10528-02Size:10 mM - 1 mL

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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 Number	254964-60-8
PubChem CID	54682876
IUPAC Name	4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]quinoline-3-carboxamide
Molecular Formula	C20H17F3N2O4
Molecular Weight	406.4
XLogP	3.5
Topological Polar Surface Area	70.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Heavy Atom Count	29
Formal Charge	0
Complexity	686

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

CAS: 254964-60-8

CID: 54682876

Formula: C20H17F3N2O4

MW: 406.4

Interactive 3D Structure

Loading 3D structure...

View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	406.4
XLogP3	3.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	3
Exact Mass	406.11404151
Monoisotopic Mass	406.11404151
Topological Polar Surface Area	70.1 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	686
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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