Tasquinimod
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MedKoo CAT#: 202852

CAS#: 254964-60-8

Description: Tasquinimod, also known as ABR215050, 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.

Chemical Structure

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Tasquinimod
CAS# 254964-60-8
Instruction

Theoretical Analysis

MedKoo Cat#: 202852
Name: Tasquinimod
CAS#: 254964-60-8
Chemical Formula: C20H17F3N2O4
Exact Mass: 406.11
Molecular Weight: 406.350
Elemental Analysis: C, 59.11; H, 4.22; F, 14.03; N, 6.89; O, 15.75.

Price and Availability

Size Price Availability Quantity
50mg USD 950
100mg USD 1450
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Synonym: ABR215050, ABR-215050, ABR 215050, Tasquinimod

IUPAC/Chemical Name: 4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-((4-trifluoromethyl)phenyl)-1,2-dihydroquinoline-3-carboxamide

InChi Key: ONDYALNGTUAJDX-UHFFFAOYSA-N

InChi Code: 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

SMILES Code: 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

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >5 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info: The orally active quinoline-3-carboxamide tasquinimod [ABR-215050; CAS number 254964-60-8), which currently is in a phase II-clinical trial in patients against metastatic prostate cancer, exhibits anti-tumor activity via inhibition of tumor angiogenesis in human and rodent tumors. Tasquinimod-induced up-regulation of TSP1 is part of a mechanism involving down-regulation of HIF1alpha and VEGF, which in turn leads to reduced angiogenesis via inhibition of the "angiogenic switch", that could explain tasquinimods therapeutic potential. see: http://www.ncbi.nlm.nih.gov/pubmed/20470445.         

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 406.35 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Schweizer MT, Carducci MA. From bevacizumab to tasquinimod: angiogenesis as a therapeutic target in prostate cancer. Cancer J. 2013 Jan-Feb;19(1):99-106. doi: 10.1097/PPO.0b013e31827e0b86. PubMed PMID: 23337763.

2: George S, Pili R. Tasquinimod: a novel angiogenesis inhibitor-development in prostate cancer. Curr Oncol Rep. 2013 Apr;15(2):65-8. doi: 10.1007/s11912-013-0295-7. PubMed PMID: 23334511.

3: Isaacs JT, Antony L, Dalrymple SL, Brennen WN, Gerber S, Hammers H, Wissing M, Kachhap S, Luo J, Xing L, Björk P, Olsson A, Björk A, Leanderson T. Tasquinimod Is an Allosteric Modulator of HDAC4 Survival Signaling within the Compromised Cancer Microenvironment. Cancer Res. 2013 Feb 15;73(4):1386-99. doi: 10.1158/0008-5472.CAN-12-2730. Epub 2012 Nov 13. PubMed PMID: 23149916; PubMed Central PMCID: PMC3578133.

4: Jennbacken K, Welén K, Olsson A, Axelsson B, Törngren M, Damber JE, Leanderson T. Inhibition of metastasis in a castration resistant prostate cancer model by the quinoline-3-carboxamide tasquinimod (ABR-215050). Prostate. 2012 Jun 1;72(8):913-24. doi: 10.1002/pros.21495. Epub 2011 Oct 5. PubMed PMID: 22287276.

5: Hansson GP, Olin M, Svanström C, Svensson LD, Sennbro CJ. Bioanalysis in clinical development of tasquinimod using liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2011 Nov 15;879(30):3401-6. doi: 10.1016/j.jchromb.2011.09.013. Epub 2011 Sep 13. Erratum in: J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Jun 15;899:167. PubMed PMID: 21963277.

6: Pili R, Häggman M, Stadler WM, Gingrich JR, Assikis VJ, Björk A, Nordle O, Forsberg G, Carducci MA, Armstrong AJ. Phase II randomized, double-blind, placebo-controlled study of tasquinimod in men with minimally symptomatic metastatic castrate-resistant prostate cancer. J Clin Oncol. 2011 Oct 20;29(30):4022-8. doi: 10.1200/JCO.2011.35.6295. Epub 2011 Sep 19. PubMed PMID: 21931019.

7: Dalrymple SL, Becker RE, Zhou H, DeWeese TL, Isaacs JT. Tasquinimod prevents the angiogenic rebound induced by fractionated radiation resulting in an enhanced therapeutic response of prostate cancer xenografts. Prostate. 2012 May 1;72(6):638-48. doi: 10.1002/pros.21467. Epub 2011 Aug 11. PubMed PMID: 21837778.

8: Isaacs JT. 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. Expert Opin Investig Drugs. 2010 Oct;19(10):1235-43. doi: 10.1517/13543784.2010.514262. Review. PubMed PMID: 20836618.

9: Olsson A, Björk A, Vallon-Christersson J, Isaacs JT, Leanderson T. 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. doi: 10.1186/1476-4598-9-107. PubMed PMID: 20470445; PubMed Central PMCID: PMC2885345.

10: Bratt O, Häggman M, Ahlgren G, Nordle O, Björk A, Damber JE. Open-label, clinical phase I studies of tasquinimod in patients with castration-resistant prostate cancer. Br J Cancer. 2009 Oct 20;101(8):1233-40. doi: 10.1038/sj.bjc.6605322. Epub 2009 Sep 15. PubMed PMID: 19755981; PubMed Central PMCID: PMC2768463.

11: 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 PMID: 17373719.