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Fruquintinib

Product Name
Fruquintinib
CAS No.
1194506-26-7
Chemical Name
Fruquintinib
Synonyms
CS-1643;HMPL-013;R-228060;EOS-61054;BMS-986472;Fruquintinib;Fruquintinib|HMPL-013;Fruquintinib Impurity;Fruquintinib, 10 mM in DMSO;Fruquintinib|HMPL-013 USP/EP/BP
CBNumber
CB23037638
Molecular Formula
C21H19N3O5
Formula Weight
393.39
MOL File
1194506-26-7.mol
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Fruquintinib Property

Boiling point:
600.5±55.0 °C(Predicted)
Density 
1.302±0.06 g/cm3(Predicted)
storage temp. 
Sealed in dry,Store in freezer, under -20°C
solubility 
Soluble in DMSO (up to 5 mg/ml).
pka
14.35±0.46(Predicted)
form 
solid
color 
White
Stability:
Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
InChI
InChI=1S/C21H19N3O5/c1-11-19(20(25)22-2)13-6-5-12(7-16(13)28-11)29-21-14-8-17(26-3)18(27-4)9-15(14)23-10-24-21/h5-10H,1-4H3,(H,22,25)
InChIKey
BALLNEJQLSTPIO-UHFFFAOYSA-N
SMILES
O1C2=CC(OC3=C4C(=NC=N3)C=C(OC)C(OC)=C4)=CC=C2C(C(NC)=O)=C1C
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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

Cayman Chemical
Product number
29425
Product name
Fruquintinib
Packaging
10mg
Price
$50
Updated
2024/03/01
Cayman Chemical
Product number
29425
Product name
Fruquintinib
Packaging
250mg
Price
$849
Updated
2024/03/01
Cayman Chemical
Product number
29425
Product name
Fruquintinib
Packaging
50mg
Price
$220
Updated
2024/03/01
Cayman Chemical
Product number
29425
Product name
Fruquintinib
Packaging
100mg
Price
$389
Updated
2024/03/01
American Custom Chemicals Corporation
Product number
API0026222
Product name
FRUQUINTINIB
Purity
95.00%
Packaging
5MG
Price
$501.66
Updated
2021/12/16
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Fruquintinib Chemical Properties,Usage,Production

Description

Fruquintinib is a VEGFR inhibitor (IC50s = 33, 35, and 0.5 nM for VEGFR1, -2, and -3, respectively). It also inhibits RET, FGFR1, and c-Kit (IC50s = 128, 181, and 458 nM, respectively) in a panel of 253 kinases. Fruquintinib inhibits VEGF-A-induced proliferation of human umbilical vein endothelial cells (HUVECs) and VEGF-C-induced proliferation of human lymphatic endothelial cells (HLECs; IC50s = 1.7 and 4.2 nM, respectively). It decreases tube formation by HUVECs by 74 and 94% when used at concentrations of 30 and 300 nM, respectively. Fruquintinib (0.5-20 mg/kg per day for 21 days) reduces tumor growth in BGC-823, HT-29, Caki-1, and NCI H460 mouse xenograft models.

Uses

Fruquintinib (HMPL-013) is a highly selective VEGFR-1/2/3 tyrosine kinase inhibitor. It was approved by the FDA on 8 November 2023 for the treatment of adult patients with metastatic colorectal cancer. and these patients had previously received fluoropyrimidine, oxaliplatin and irinotecan chemotherapy, anti-vascular endothelial growth factor therapy, and anti-epidermal growth factor receptor (EGFR) therapy. Fruquintinib has also been shown to improve cognitive deficits and pathological changes in a mouse model of cerebral amyloid angiopathy (CAA).

Uses

Fruquintinib is a multi-targeted tyrosine kinase inhibitor, a third-line regimen involved in the treatment of advanced non-small cell lung cancer in humans. Fruquintinib is a potent, highly selective and orally active inhibitor of VEGFR1, 2, 3 tyrosine kinases.

brand name

Fruzaqla

Mechanism of action

By blocking the vascular endothelial growth factor signalling pathway, Fruquintinib inhibits the formation of new blood vessels in tumours, thereby reducing blood supply and inhibiting tumour growth.

Side effects

The most common side effects of Fruquintinib|HMPL-013 include hypertension, palmar-plantar erythrodysesthesia, proteinuria, dysphonia, abdominal pain, diarrhea, and asthenia.

Synthesis

638217-08-0

13790-39-1

1194506-26-7

Example 1 Synthesis of 6-((6,7-dimethoxyquinazolin-4-yl)oxy)-N,2-dimethylbenzofuran-3-carboxamide: 4-Chloro-6,7-dimethoxyquinazoline (1 eq.) was dissolved in 2 mL of acetonitrile, followed by addition of 6-hydroxy-N,2-dimethylbenzofuran-3-carboxamide (1 eq.) and potassium carbonate (1.5 eq.). The reaction mixture was refluxed under stirring conditions for 10 hours. After completion of the reaction, the solvent was removed by evaporation, the residue was washed with water, dried over anhydrous magnesium sulfate, filtered, concentrated and finally purified by column chromatography to afford the target compound 6-((6,7-dimethoxyquinazolin-4-yl)oxy)-N,2-dimethylbenzofuran-3-carboxamide in 85% yield. The product was characterized by 1H NMR (DMSO-d6, 400 MHz) and mass spectrometry (MS): 1H NMR δ 2.49 (s, 3H), 2.81 (d, J = 8.4 Hz, 3H), 3.97 (s, 3H), 3.98 (s, 3H), 7.24 (dd, J = 2.0, 8.4 Hz, 1H), 7.38 (s, 1H), 7.58 (s, 1H), 7.61 (d, J = 2.0 Hz, 1H), 7.79 (d, J = 8.4 Hz, 1H), 7.96 (m, 1H), 8.52 (s, 1H); MS (m/e): 394.1 (M + 1).

in vitro

fruquintinib was found to inhibit vegfr2 with an ic50 of 25 nmol/l. the kinase selectivity of fruquintinib was evaluated against a panel of 253 kinases. the results showed that fruquintinib inhibited vegfr family members with weak inhibition of ret, fgfr-1 and c-kit kinases [1].

in vivo

anti-tumor activity of fruquintinib was evaluated in a variety of tumor xenografts. the results from gastric cancer bgc-823 model seemed to indicate that the drug concentration needs to be at least maintained above ec85 for around 8 hours in order to achieve >80% tumor growth inhibition. bgc-823 was found to be most sensitive to fruquintinib [1].

IC 50

33 nmol/l, 35 nmol/l and 0.5 nmol/l for vegfr1, 2, 3

References

[1] QIAOLING SUN. Discovery of fruquintinib, a potent and highly selective small molecule inhibitor of VEGFR 1, 2, 3 tyrosine kinases for cancer therapy.[J]. Cancer Biology & Therapy, 2014, 15 12: 1635-1645. DOI:10.4161/15384047.2014.964087
[2] JIN LI. Effect of Fruquintinib vs Placebo on Overall Survival in Patients With Previously Treated Metastatic Colorectal Cancer: The FRESCO Randomized Clinical Trial.[J]. Jama-Journal of the American Medical Association, 2018, 319 24: 2486-2496. DOI:10.1001/jama.2018.7855
[3] SHUN LU. Randomized, Double-Blind, Placebo-Controlled, Multicenter Phase II Study of Fruquintinib After Two Prior Chemotherapy Regimens in Chinese Patients With Advanced Nonsquamous Non‒Small-Cell Lung Cancer.[J]. Journal of Clinical Oncology, 2018: 1207-1217. DOI:10.1200/jco.2017.76.7145

Fruquintinib Preparation Products And Raw materials

Raw materials

Preparation Products

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Fruquintinib Suppliers

Canada 1 China 185 India 2 United Kingdom 1 United States 13 Global 202
Shandong utilizing biological technology co., LTD
Tel
15966937598
Fax
3407640895 3071519937
Email
3407650895@qq.com
Country
China
ProdList
2274
Advantage
58
Qingdao Fansen Biotechnology Co., Ltd
Tel
18661607483
Email
qddxhn@163.com
Country
China
ProdList
210
Advantage
58
Jinan Demai Medical Technology Co., LTD
Tel
15209235325 18669728830
Email
865681093@qq.com
Country
China
ProdList
501
Advantage
58
Sichuan Qingmu Pharmaceutical Co., Ltd.
Tel
028-87827187 18681376319
Email
sales@eastonpharma.cn
Country
China
ProdList
66
Advantage
60
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6003
Advantage
61
Beijing HwrkChemical Technology Co., Ltd
Tel
18515581800 18501085097
Fax
010-89508210
Email
sales.bj@hwrkchemical.com
Country
China
ProdList
9400
Advantage
55
NanTong Chemistar Chemical Co.,Ltd
Tel
025-52643182 13914798241
Fax
025-52643184
Email
doria@chemipioneer.com.cn
Country
China
ProdList
56
Advantage
62
Nanjing Chemipioneer Pharma& Tech Co., LTD
Tel
025-52643182 13914798241
Fax
025-52643182
Email
zhoulq@chemipioneer.com.cn
Country
China
ProdList
90
Advantage
62
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
sales@meilune.com
Country
China
ProdList
4747
Advantage
58
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View Lastest Price from Fruquintinib manufacturers

Sinoway Industrial co., ltd.
Product
Fruquintinib|HMPL-013 1194506-26-7
Price
US $0.00-0.00/kg
Min. Order
1kg
Purity
98%
Supply Ability
20tons
Release date
2025-04-14
Jinan Jianfeng Chemical Co., Ltd
Product
Fruquintinib|HMPL-013 1194506-26-7
Price
US $0.00-0.00/g
Min. Order
2g
Purity
99%
Supply Ability
1000kg
Release date
2024-08-07
Moxin Chemicals
Product
Fruquintinib Impurity 1194506-26-7
Price
US $0.00-0.00/mg
Min. Order
10mg
Purity
95%+
Supply Ability
10000
Release date
2025-01-20

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  • CS-1643
  • Fruquintinib|HMPL-013
  • Fruquintinib
  • 6-(6,7-dimethoxyquinazolin-4-yloxy)-N,2-dimethylbenzofuran-3-carboxamide
  • HMPL-013
  • 3-Benzofurancarboxamide, 6-[(6,7-dimethoxy-4-quinazolinyl)oxy]-N,2-dimethyl-
  • 6-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-N,2-dimethyl-3-benzofurancarboxamide
  • R-228060
  • 6-[(6,7-Dimethoxy-4-quinazolinyl)oxy]-N,2-dimethyl-1-benzofuran-3-carboxamide
  • EOS-61054
  • Fruquintinib|HMPL-013 USP/EP/BP
  • BMS-986472
  • Fruquintinib, 10 mM in DMSO
  • Fruquintinib Impurity
  • 1194506-26-7
  • Inhibitors
  • API