MedKoo Cat#: 407300 | Name: SAR131675

Description:

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

SAR131675 is a potent and selective VEGFR-3 inhibitor. It inhibited VEGFR-3 tyrosine kinase activity and VEGFR-3 autophosphorylation in HEK cells with IC(50) values of 20 and 45 nmol/L, respectively. SAR131675 was found to be highly selective for VEGFR-3 versus 107 receptors, enzymes, ion channels, and 65 kinases. SAR131675 is the first highly specific VEGFR-3-TK inhibitor described to date, displaying significant antitumoral and antimetastatic activities in vivo through inhibition of lymphangiogenesis and TAM invasion.

Chemical Structure

SAR131675
SAR131675
CAS#1092539-44-0

Theoretical Analysis

MedKoo Cat#: 407300

Name: SAR131675

CAS#: 1092539-44-0

Chemical Formula: C18H22N4O4

Exact Mass: 358.1641

Molecular Weight: 358.40

Elemental Analysis: C, 60.32; H, 6.19; N, 15.63; O, 17.86

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Related CAS #
1433953-83-3 1092538-80-1
Synonym
SAR131675; SAR 131675; SAR-131675.
IUPAC/Chemical Name
2-amino-1-ethyl-7-(3-hydroxy-4-methoxy-3-methylbut-1-yn-1-yl)-N-methyl-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxamide
InChi Key
PFMPOBVAYMTUOX-UHFFFAOYSA-N
InChi Code
InChI=1S/C18H22N4O4/c1-5-22-15(19)13(17(24)20-3)14(23)12-7-6-11(21-16(12)22)8-9-18(2,25)10-26-4/h6-7,25H,5,10,19H2,1-4H3,(H,20,24)
SMILES Code
O=C(C(C(NC)=O)=C(N)N1CC)C2=C1N=C(C#CC(O)(COC)C)C=C2
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
>2 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

Preparing Stock Solutions

The following data is based on the product molecular weight 358.40 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
1: Babaei Z, Panjehpour M, Parsian H, Aghaei M. SAR131675 Receptor Tyrosine Kinase Inhibitor Induces Apoptosis through Bcl- 2/Bax/Cyto c Mitochondrial Pathway in Human Umbilical Vein Endothelial Cells. Anticancer Agents Med Chem. 2022;22(5):943-950. doi: 10.2174/1871520621666210708102619. PMID: 34238175. 2: Bei Y, Huang Z, Feng X, Li L, Wei M, Zhu Y, Liu S, Chen C, Yin M, Jiang H, Xiao J. Lymphangiogenesis contributes to exercise-induced physiological cardiac growth. J Sport Health Sci. 2022 Jul;11(4):466-478. doi: 10.1016/j.jshs.2022.02.005. Epub 2022 Feb 23. PMID: 35218948; PMCID: PMC9338339. 3: Babaei Z, Panjehpour M, Parsian H, Aghaei M. SAR131675 exhibits anticancer activity on human ovarian cancer cells through inhibition of VEGFR-3/ERK1/2/AKT signaling pathway. Cell Signal. 2023 Nov;111:110856. doi: 10.1016/j.cellsig.2023.110856. Epub 2023 Aug 19. PMID: 37598918. 4: Walsh KA, Kastrappis G, Fifis T, Paolini R, Christophi C, Perini MV. SAR131675, a VEGRF3 Inhibitor, Modulates the Immune Response and Reduces the Growth of Colorectal Cancer Liver Metastasis. Cancers (Basel). 2022 May 31;14(11):2715. doi: 10.3390/cancers14112715. PMID: 35681695; PMCID: PMC9179346. 5: Alam A, Blanc I, Gueguen-Dorbes G, Duclos O, Bonnin J, Barron P, Laplace MC, Morin G, Gaujarengues F, Dol F, Hérault JP, Schaeffer P, Savi P, Bono F. SAR131675, a potent and selective VEGFR-3-TK inhibitor with antilymphangiogenic, antitumoral, and antimetastatic activities. Mol Cancer Ther. 2012 Aug;11(8):1637-49. doi: 10.1158/1535-7163.MCT-11-0866-T. Epub 2012 May 14. PMID: 22584122. 6: Wang Z, Shi X, Zhao Y, Zhou J, Zhang S, Wang J, Yu W, Zhang X, Ren X, Zhao H. DC101, an anti-VEGFR2 agent, promotes high-endothelial venule formation and immune infiltration versus SAR131675 and fruquintinib. Biochem Biophys Res Commun. 2023 Jun 18;661:10-20. doi: 10.1016/j.bbrc.2023.04.018. Epub 2023 Apr 10. PMID: 37084488. 7: Hwang SD, Song JH, Kim Y, Lim JH, Kim MY, Kim EN, Hong YA, Chung S, Choi BS, Kim YS, Park CW. Inhibition of lymphatic proliferation by the selective VEGFR-3 inhibitor SAR131675 ameliorates diabetic nephropathy in db/db mice. Cell Death Dis. 2019 Mar 4;10(3):219. doi: 10.1038/s41419-019-1436-1. PMID: 30833548; PMCID: PMC6399322. 8: Peng M, Li H, Cao H, Huang Y, Yu W, Shen C, Gu J. Dual FGFR and VEGFR inhibition synergistically restrain hexokinase 2-dependent lymphangiogenesis and immune escape in intrahepatic cholangiocarcinoma. J Gastroenterol. 2023 Sep;58(9):908-924. doi: 10.1007/s00535-023-02012-8. Epub 2023 Jul 11. PMID: 37433897; PMCID: PMC10423168. 9: Zheng H, Chen C, Luo Y, Yu M, He W, An M, Gao B, Kong Y, Ya Y, Lin Y, Li Y, Xie K, Huang J, Lin T. Tumor-derived exosomal BCYRN1 activates WNT5A/VEGF-C/VEGFR3 feedforward loop to drive lymphatic metastasis of bladder cancer. Clin Transl Med. 2021 Jul;11(7):e497. doi: 10.1002/ctm2.497. PMID: 34323412; PMCID: PMC8288020. 10: Espagnolle N, Barron P, Mandron M, Blanc I, Bonnin J, Agnel M, Kerbelec E, Herault JP, Savi P, Bono F, Alam A. Specific Inhibition of the VEGFR-3 Tyrosine Kinase by SAR131675 Reduces Peripheral and Tumor Associated Immunosuppressive Myeloid Cells. Cancers (Basel). 2014 Feb 28;6(1):472-90. doi: 10.3390/cancers6010472. PMID: 24589997; PMCID: PMC3980599. 11: Wang C, Xu J, Cheng X, Sun G, Li F, Nie G, Zhang Y. Anti-lymphangiogenesis for boosting drug accumulation in tumors. Signal Transduct Target Ther. 2024 Apr 15;9(1):89. doi: 10.1038/s41392-024-01794-4. Erratum in: Signal Transduct Target Ther. 2024 Jun 8;9(1):157. doi: 10.1038/s41392-024-01883-4. PMID: 38616190; PMCID: PMC11016544. 12: Tong X, Zhang T, Li S, Chen Y, Xu Y, Deng C, Hu J, Lu H. Rotator cuff healing is regulated by the lymphatic vasculature. J Orthop Translat. 2022 Oct 21;38:65-75. doi: 10.1016/j.jot.2022.09.014. PMID: 36313978; PMCID: PMC9593253. 13: Gloger M, Menzel L, Grau M, Vion AC, Anagnostopoulos I, Zapukhlyak M, Gerlach K, Kammertöns T, Hehlgans T, Zschummel M, Lenz G, Gerhardt H, Höpken UE, Rehm A. Lymphoma Angiogenesis Is Orchestrated by Noncanonical Signaling Pathways. Cancer Res. 2020 Mar 15;80(6):1316-1329. doi: 10.1158/0008-5472.CAN-19-1493. Epub 2020 Jan 13. PMID: 31932457. 14: Bhuiyan MI, Kim JC, Hwang SN, Lee MY, Kim SY. Ischemic tolerance is associated with VEGF-C and VEGFR-3 signaling in the mouse hippocampus. Neuroscience. 2015 Apr 2;290:90-102. doi: 10.1016/j.neuroscience.2015.01.025. Epub 2015 Jan 28. PMID: 25637798. 15: Tempfer H, Spitzer G, Lehner C, Wagner A, Gehwolf R, Fierlbeck J, Weissenbacher N, Jessen M, Heindl LM, Traweger A. VEGF-D-mediated signaling in tendon cells is involved in degenerative processes. FASEB J. 2022 Feb;36(2):e22126. doi: 10.1096/fj.202100773RRR. PMID: 35044682. 16: Chen SM, Zhao CK, Yao LC, Wang LX, Ma YN, Meng L, Cai SQ, Liu CY, Qu LK, Jia YX, Shou CC. Aiphanol, a multi-targeting stilbenolignan, potently suppresses mouse lymphangiogenesis and lymphatic metastasis. Acta Pharmacol Sin. 2023 Jan;44(1):189-200. doi: 10.1038/s41401-022-00940-4. Epub 2022 Jul 1. PMID: 35778489; PMCID: PMC9813257. 17: Han Y, Sengupta S, Lee BJ, Cho H, Kim J, Choi HG, Dash U, Kim JH, Kim ND, Kim JH, Sim T. Identification of a Unique Resorcylic Acid Lactone Derivative That Targets Both Lymphangiogenesis and Angiogenesis. J Med Chem. 2019 Oct 24;62(20):9141-9160. doi: 10.1021/acs.jmedchem.9b01025. Epub 2019 Oct 7. PMID: 31513411. 18: Fang K, Xu Z, Jiang S, Yan C, Tang D, Huang Y. Integrated profiling uncovers prognostic, immunological, and pharmacogenomic features of ferroptosis in triple-negative breast cancer. Front Immunol. 2022 Nov 25;13:985861. doi: 10.3389/fimmu.2022.985861. PMID: 36505498; PMCID: PMC9732280. 19: Dong X, Yin J, Yun B, Lü B, Yin G. [Research on influence mechanism of G protein coupled receptor kinase interacting protein 1 on differentiation of bone marrow mesenchymal stem cells into endothelial cells]. Zhongguo Xiu Fu Chong Jian Wai Ke Za Zhi. 2018 Mar 15;32(3):257-263. Chinese. doi: 10.7507/1002-1892.201709090. PMID: 29806272; PMCID: PMC8414267. 20: Zuo HY, Wu SB, Wu X, Cui S, Wang K, Zhu C, Wang L, Zhou MQ. [Electroacupuncture ameliorates inflammatory response of mice with acute myocardial ischemia by regulating vascular endothelial growth factor C/vascular endothelial growth factor receptor 3 pathway]. Zhen Ci Yan Jiu. 2022 Oct 25;47(10):851-8. Chinese. doi: 10.13702/j.1000-0607.20210984. PMID: 36301160.