Tasquinimod | ABR-215050 | CAS#254964-60-8 | Antiangiogenic

MedKoo Cat#: 202852 | Name: Tasquinimod

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Tasquinimod

CAS#254964-60-8

Theoretical Analysis

MedKoo Cat#: 202852

Name: Tasquinimod

CAS#: 254964-60-8

Chemical Formula: C20H17F3N2O4

Exact Mass: 406.1140

Molecular Weight: 406.35

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 950.00
100mg	USD 1,450.00

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Related CAS #

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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.

Certificate of Analysis

View CoA: current batch, Lot#M9C02E05

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

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.

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

1: Li Z, Wu YH, Guo YQ, Min XJ, Lin Y. Tasquinimod promotes the sensitivity of ovarian cancer cells to cisplatin by down-regulating the HDAC4/p21 pathway. Korean J Physiol Pharmacol. 2024 Nov 14. doi: 10.4196/kjpp.24.132. Epub ahead of print. PMID: 39539173. 2: Wu D, Zheng K, Yin W, Hu B, Yu M, Yu Q, Wei X, Deng J, Zhang C. Enhanced osteochondral regeneration with a 3D-Printed biomimetic scaffold featuring a calcified interfacial layer. Bioact Mater. 2024 Mar 8;36:317-329. doi: 10.1016/j.bioactmat.2024.03.004. PMID: 38496032; PMCID: PMC10940945. 3: Wu S, Wang Y, Duan J, Teng Y, Wang D, Qi F. Identification of a shared gene signature and biological mechanism between diabetic foot ulcers and cutaneous lupus erythemnatosus by transcriptomic analysis. Front Physiol. 2024 Feb 16;15:1297810. doi: 10.3389/fphys.2024.1297810. PMID: 38434138; PMCID: PMC10907995. 4: Fan R, Satilmis H, Vandewalle N, Verheye E, De Bruyne E, Menu E, De Beule N, De Becker A, Ates G, Massie A, Kerre T, Törngren M, Eriksson H, Vanderkerken K, Breckpot K, Maes K, De Veirman K. Targeting S100A9 protein affects mTOR-ER stress signaling and increases venetoclax sensitivity in Acute Myeloid Leukemia. Blood Cancer J. 2023 Dec 18;13(1):188. doi: 10.1038/s41408-023-00962-z. PMID: 38110349; PMCID: PMC10728073. 5: Gao J, Li L. Enhancement of neural regeneration as a therapeutic strategy for Alzheimer's disease (Review). Exp Ther Med. 2023 Aug 1;26(3):444. doi: 10.3892/etm.2023.12143. PMID: 37614437; PMCID: PMC10443056. 6: Isaacs JT, Dalrymple SL, Antony L, Marc Rosen D, Coleman IM, Nelson PS, Kostova M, Murray IA, Perdew GH, Denmeade SR, Akinboye ES, Brennen WN. Third generation quinoline-3-carboxamide transcriptional disrupter of HDAC4, HIF-1α, and MEF-2 signaling for metastatic castration-resistant prostate cancer. Prostate. 2023 Nov;83(15):1470-1493. doi: 10.1002/pros.24606. Epub 2023 Aug 9. PMID: 37559436; PMCID: PMC10559933. 7: Lin Y, Liu YQ, Zhu KA, Hu MQ, Li Z, Min XJ. Tasquinimod enhances the sensitivity of ovarian cancer cells to cisplatin by regulating the Nur77-Bcl-2 apoptotic pathway. Adv Clin Exp Med. 2024 Feb;33(2):151-161. doi: 10.17219/acem/166044. PMID: 37501511. 8: Sun X, Zhang K, Peng X, Zhou P, Qu C, Yang L, Shen L. HDAC4 mediated LHPP deacetylation enhances its destabilization and promotes the proliferation and metastasis of nasopharyngeal carcinoma. Cancer Lett. 2023 May 28;562:216158. doi: 10.1016/j.canlet.2023.216158. Epub 2023 Apr 5. PMID: 37023940. 9: Bao X, Wang D, Dai X, Liu C, Zhang H, Jin Y, Tong Z, Li B, Tong C, Xin S, Li X, Wang Y, Liu L, Zhu X, Fu Q, Zheng Y, Deng J, Tian W, Guo T, Zhao P, Chen W, Fang W. An immunometabolism subtyping system identifies S100A9+ macrophage as an immune therapeutic target in colorectal cancer based on multiomics analysis. Cell Rep Med. 2023 Apr 18;4(4):100987. doi: 10.1016/j.xcrm.2023.100987. Epub 2023 Mar 28. PMID: 36990096; PMCID: PMC10140461. 10: Lin C, Garcia-Gerique L, Bonner EE, Mastio J, Rosenwasser M, Cruz Z, Lawler M, Bernabei L, Muthumani K, Liu Q, Poncz M, Vogl T, Törngren M, Eriksson H, Vogl DT, Gabrilovich DI, Nefedova Y. S100A8/S100A9 Promote Progression of Multiple Myeloma via Expansion of Megakaryocytes. Cancer Res Commun. 2023 Mar 13;3(3):420-430. doi: 10.1158/2767-9764.CRC-22-0368. PMID: 36923707; PMCID: PMC10010194. 11: Fan R, Satilmis H, Vandewalle N, Verheye E, Vlummens P, Maes A, Muylaert C, De Bruyne E, Menu E, Evans H, Chantry A, De Beule N, Hose D, Törngren M, Eriksson H, Vanderkerken K, Maes K, Breckpot K, De Veirman K. Tasquinimod suppresses tumor cell growth and bone resorption by targeting immunosuppressive myeloid cells and inhibiting c-MYC expression in multiple myeloma. J Immunother Cancer. 2023 Jan;11(1):e005319. doi: 10.1136/jitc-2022-005319. PMID: 36650020; PMCID: PMC9853259. 12: Du Y, Cai Y, Lv Y, Zhang L, Yang H, Liu Q, Hong M, Teng Y, Tang W, Ma R, Wu J, Wu J, Wang Q, Chen H, Li K, Feng J. Single-cell RNA sequencing unveils the communications between malignant T and myeloid cells contributing to tumor growth and immunosuppression in cutaneous T-cell lymphoma. Cancer Lett. 2022 Dec 28;551:215972. doi: 10.1016/j.canlet.2022.215972. Epub 2022 Oct 17. PMID: 36265653. 13: Undi RB, Larabee JL, Filiberti A, Ulahannan S, Aravindan S, Stroberg E, Barton LM, Duval EJ, Mukhopadhyay S, Henthorn JC, Akins D, Houchen CW, Huycke MM, Ali N. Targeting Doublecortin-Like Kinase 1 (DCLK1)-Regulated SARS-CoV-2 Pathogenesis in COVID-19. J Virol. 2022 Sep 14;96(17):e0096722. doi: 10.1128/jvi.00967-22. Epub 2022 Aug 9. PMID: 35943255; PMCID: PMC9472619. 14: Shen F, Hou X, Li T, Yu J, Chen H, Liu N, Qiu A, Zhuang S. Pharmacological and Genetic Inhibition of HDAC4 Alleviates Renal Injury and Fibrosis in Mice. Front Pharmacol. 2022 Jun 28;13:929334. doi: 10.3389/fphar.2022.929334. PMID: 35847036; PMCID: PMC9277565. 15: Schmidt S, Wolf D. Entwicklungen im Verständnis und der Behandlung myeloproliferativer Neoplasien [What's new in myeloproliferative neoplasia?]. Dtsch Med Wochenschr. 2022 Mar;147(6):306-311. German. doi: 10.1055/a-1643-4357. Epub 2022 Mar 15. PMID: 35291035. 16: Rikken G, van den Brink NJM, van Vlijmen-Willems IMJJ, van Erp PEJ, Pettersson L, Smits JPH, van den Bogaard EH. Carboxamide Derivatives Are Potential Therapeutic AHR Ligands for Restoring IL-4 Mediated Repression of Epidermal Differentiation Proteins. Int J Mol Sci. 2022 Feb 4;23(3):1773. doi: 10.3390/ijms23031773. PMID: 35163694; PMCID: PMC8836151. 17: Xu J, Zhang C, Cheng C, Yang J, Li C, Liu X, Sang Y. A Tasquinomod-loaded dopamine-modified pH sensitive hydrogel is effective at inhibiting the proliferation of KRAS mutant lung cancer cells. J Appl Biomater Funct Mater. 2022 Jan-Dec;20:22808000211073729. doi: 10.1177/22808000211073729. PMID: 35088614. 18: Paramonova II, Vilchinskaya NA, Shenkman BS. HDAC4 Is Indispensable for Reduced Slow Myosin Expression at the Early Stage of Hindlimb Unloading in Rat Soleus Muscle. Pharmaceuticals (Basel). 2021 Nov 16;14(11):1167. doi: 10.3390/ph14111167. PMID: 34832949; PMCID: PMC8617770. 19: Jin J, Zhang J, Bu S. Tasquinimod efficacy and S100A9 expression in glucose- treated HREC cells. Int Ophthalmol. 2022 Feb;42(2):661-676. doi: 10.1007/s10792-021-02038-y. Epub 2021 Nov 18. PMID: 34796432. 20: Li Z, Zhang X, Liu C, Peng Q, Wu Y, Wen Y, Zheng R, Yan Q, Ma J. Macrophage- Biomimetic Nanoparticles Ameliorate Ulcerative Colitis through Reducing Inflammatory Factors Expression. J Innate Immun. 2022;14(4):380-392. doi: 10.1159/000519363. Epub 2021 Nov 1. PMID: 34724662; PMCID: PMC9274947.