tasquinimod

Product Name: tasquinimod
CAS No.: 254964-60-8
Chemical Name: tasquinimod
Synonyms: TASQ);ABR-215050;tasquinimod;Tasquinimod, >98%;Tasquinimod(ABR-215050);Tasquinimod, 10 mM in DMSO;7-diMethoxy-4-quinolinyl)oxy]-;ABR-215050; ABR215050; ABR 215050;7-Dimethoxy-quinolin-4-yloxy)-phenylamine;4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]quinoline-3-carboxamide
CBNumber: CB61508619
Molecular Formula: C20H17F3N2O4
Formula Weight: 406.36
MOL File: 254964-60-8.mol

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tasquinimod Property

Boiling point:: 501.5±50.0 °C(Predicted)
Density: 1.427±0.06 g/cm3(Predicted)
storage temp.: 2-8°C
solubility: insoluble in H2O; ≥20.32 mg/mL in DMSO; ≥4.75 mg/mL in EtOH with gentle warming and ultrasonic
form: solid
pka: 4.50±1.00(Predicted)
color: White to light yellow

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: SML2489
Product name: Tasquinimod
Purity: ≥98% (HPLC)
Packaging: 5 mg
Price: $125.4
Updated: 2025/07/31

Sigma-Aldrich

Product number: SML2489
Product name: Tasquinimod
Purity: ≥98% (HPLC)
Packaging: 25 mg
Price: $423
Updated: 2025/07/31

Cayman Chemical

Product number: 17692
Product name: Tasquinimod
Purity: ≥98%
Packaging: 1mg
Price: $49
Updated: 2024/03/01

Cayman Chemical

Product number: 17692
Product name: Tasquinimod
Purity: ≥98%
Packaging: 5mg
Price: $202
Updated: 2024/03/01

Cayman Chemical

Product number: 17692
Product name: Tasquinimod
Purity: ≥98%
Packaging: 10mg
Price: $356
Updated: 2024/03/01

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tasquinimod Chemical Properties,Usage,Production

Description

Tasquinimod is an orally-active quinoline-3-carboxamide derived from roquinimex, an immunomodulatory quinolone with applications in some cancers and autoimmune diseases. Tasquinimod inhibits tumor angiogenesis and supplements radiation or chemotherapy in animal models of prostate cancer. While its precise mechanism of action remains unclear, tasquinimod has been reported to alter signaling through S100A9, thrombospondin-1, HIF-1α, androgen receptor, VEGF, and HDAC3/4.

Uses

Tasquinimod is an orally active antiangiogenic agent which may inhibit HDAC4 signalling. This affects cancer cell survival thus making this compound and anti-cancer agent.

Synthesis

22864-65-9

248282-18-0

254964-60-8

General procedure for Example 8 N-methyl-N-(4-trifluoromethylphenyl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxoquinoline-3-carboxamide (Method B): 1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxoquinoline-3-carboxylic acid (8 g, 0.032 mol) and triethylamine ( 15.5 ml, 0.11 mol) were dissolved in 10 ml of dichloromethane and cooled to 0°C. Within 0.5 h, 150 ml of a dichloromethane solution of thionyl chloride (3.0 ml, 0.042 mol) was added dropwise to this solution while maintaining the temperature at 4°C. After the dropwise addition, stirring was continued at 4°C for 4 hours. After completion of the reaction, the reaction mixture was diluted with 10 ml of dichloromethane and washed sequentially with cold 1 M sulfuric acid and 1 M sodium hydroxide solution. The pH of the aqueous phase was adjusted to 8-8.5, clarified by filtration and acidified with hydrochloric acid to pH 4. Upon standing, a crystalline precipitate was formed, the precipitate was collected by filtration, washed with water and dried to afford the target product 4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-(4-(trifluoromethyl)phenyl)-1,2-dihydroquinoline-3-carboxamide (8.5 g, 65% yield). The product was structurally confirmed by 1H NMR and 13C NMR and analyzed by ESI MS/MS.

in vivo

The bioavailability and oral absorption of Tasquinimod is excellent when adult male mice (i.e., C57Bl/6J, or athymic nude mice) are given 0.1-30 mg/kg (i.e., 0.2-74 μmoles/kg) via gavage or the drinking water. The potency of Tasquinimod expressed as the daily oral dose of Tasquinimod which inhibits cancer growth by 50% ranges from 0.1-1.0 mg/kg/d (i.e., 0.24-2.40 μmoles/kg/day) against a series (n>5) of human prostate cancer xenografts in immune-deficient mice. Tasquinimod at a chronic dose of 5 mg/kg/day via the drinking water produces > 80% inhibition (p<0.05) of TRAMP-C2 mouse prostate cancer growth in immune-competent syngeneic mice^[2]. Nude mice carrying subcutaneous LNCaP tumors are treated with Tasquinimod for 3 weeks. Exposure to Tasquinimod at 1 mg/kg/day and 10 mg/kg/day started on day 7 after inoculation. There is a statistically significant dose dependent reduction in tumor weight both at 1 mg/kg/day and 10 mg/kg/day compare to the untreated control group 28 days after inoculation (p<0.001), illustrating the anti-tumor effect of Tasquinimod^[3].

target

tumor microenvironment

IC 50

HDAC4: 10-30 nM (Kd)

storage

Store at -20°C

References

[1] Patent: US6133285, 2000, A
[2] Patent: EP1095021, 2003, B1. Location in patent: Page/Page column 9

tasquinimod Preparation Products And Raw materials

Raw materials

Preparation Products

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tasquinimod Suppliers

China 112 India 2 United States 13 Global 127

Hangzhou Zyter Biological & Chemical Technology Co., Ltd.

Tel: 18858184290; 18858184290
Fax: 0086-571-28313105
Email: sales@zyterpharm.com
Country: China
ProdList: 48
Advantage: 49

Dalian Meilun Biotech Co., Ltd.

Tel: 0411-62910999 13889544652
Email: sales@meilune.com
Country: China
ProdList: 4747
Advantage: 58

Hangzhou Sage Chemical Co., Ltd.

Tel: +86057186818502 13588463833
Fax: Pls mail us for more information!
Email: info@sagechem.com
Country: China
ProdList: 10266
Advantage: 58

NCE Biomedical Co.,Ltd.

Tel: 4000-027-021 |24 +86-13986109188 | +86-15623472865 | +81-08033611988
Fax: +86-27-87599188
Country: China
ProdList: 1493
Advantage: 55

Jiangsu Aikon Biopharmaceutical R&D co.,Ltd.

Tel: 025-66113011 17798518460
Fax: (1)02557626880
Email: cfzhang@aikonchem.com
Country: China
ProdList: 19913
Advantage: 55

Haoyuan Chemexpress Co., Ltd.

Tel: 021-58950125
Fax: (86) 21-58955996
Email: info@chemexpress.com
Country: China
ProdList: 7552
Advantage: 61

Shanghai Aladdin Bio-Chem Technology Co.,LTD

Tel: 400-6206333 13167063860
Fax: 021-50323701
Email: anhua.mao@aladdin-e.com
Country: China
ProdList: 25003
Advantage: 65

Bide Pharmatech Ltd.

Tel: 400-164-7117 13681763483
Fax: +86-21-61629029
Email: product02@bidepharm.com
Country: China
ProdList: 42446
Advantage: 60

Hangzhou J&H Chemical Co., Ltd.

Tel: 0571-87396432
Fax: 0571-87396431
Email: sales@jhechem.com
Country: China
ProdList: 14912
Advantage: 59

AdooQ Bioscience CHINA

Tel: 025-58849295 18951903616;
Fax: 025-68650336
Email: info@adooq.cn
Country: China
ProdList: 2990
Advantage: 60

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View Lastest Price from tasquinimod manufacturers

Career Henan Chemical Co

Product: tasquinimod 254964-60-8
Price: US $1.00/KG
Min. Order: 1KG
Purity: 98-100%
Supply Ability: 1000kg
Release date: 2018-08-20

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4-Hydroxy-5-methoxy-N-methyl-1-methyl-2-oxo-N-(4-trifluoromethylphenyl)-1,2-dihydroquinoline-3-carboxamide

N-Methyl-N-(4-trifluoromethylphenyl)-1,2-dihydro-4-hydroxy-5-methoxy-1-methyl-2-oxoquinoline-3-carboxamide

tasquinimod

ABR-215050

3-QuinolinecarboxaMide, 1,2-dihydro-4-hydroxy-5-Methoxy-N,1-diMethyl-2-oxo-N-[4-(trifluoroMethyl)phenyl]-

4-Hydroxy-5-Methoxy-1-Methyl-2-oxo-1,2- dihydro-quinoline-3-carboxylic acid Methyl- (4-trifluoroMethyl-phenyl)-aMide

1,2-dihydro-4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-trifluoromethyl)phenyl]-3-quinolinecarboxamide

4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-(4-(trifluoromethyl)-phenyl)-1,2-dihydroquinoline-3-c

4-Hydroxy-N-[4-(trifluoromethyl)phenyl]-5-methoxy-N,1-dimethyl-2-oxo-1,2-dihydroquinoline-3-carboxamide

ABR-215050; ABR215050; ABR 215050

Tasquinimod, >98%

Tasquinimod(ABR-215050)

TASQ)

7-diMethoxy-4-quinolinyl)oxy]-

7-Dimethoxy-quinolin-4-yloxy)-phenylamine

4-Hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-(4-(trifluoromethyl)phenyl)-1,2-dihydroquinoline-3-carboxamide

4-hydroxy-5-methoxy-N,1-dimethyl-2-oxo-N-[4-(trifluoromethyl)phenyl]quinoline-3-carboxamide

Tasquinimod, 10 mM in DMSO

254964-60-8

Angiogenesis inhibitor

S100 calcium binding protein A9 modulator

Inhibitors