ChemicalBook > CAS DataBase List > Sitravatinib

Sitravatinib

Product Name: Sitravatinib
CAS No.: 1123837-84-2
Chemical Name: Sitravatinib
Synonyms: MG516;CS-2638;MGCD-516;Sitravatinib;MGCD516 (SITRAVATINIB);Sitravatinib (MGCD516);Sitravatinib, 10 mM in DMSO;N-(3-fluoro-4-((2-(5-(((2-methoxyethyl)amino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yl)oxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide;1,1-Cyclopropanedicarboxamide, N-[3-fluoro-4-[[2-[5-[[(2-methoxyethyl)amino]methyl]-2-pyridinyl]thieno[3,2-b]pyridin-7-yl]oxy]phenyl]-N'-(4-fluorophenyl)-;RTK,MG-516,PD-1,SCFR,DDR1,inhibit,VEGFR2,MG 516,MGCD 516,MER,immune,TRKA,Cluster of differentiation antigen 135,Cancer,Discoidin Domain Receptor,VEGFR3,Inhibitor,Vascular endothelial growth factor receptor,Trk Receptor,Tropomyosin related kinase receptor,CD135,VEGFR,immunotherapy,Macrophages,c-Kit,DDR2,VEGFR1,Tyrosine,Fms like tyrosine kinase 3,FLT3,Axl,TRKB,Sitravatinib,MGCD-516,KIT,kinase,CD117
CBNumber: CB03128970
Molecular Formula: C33H29F2N5O4S
Formula Weight: 629.68
MOL File: 1123837-84-2.mol

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Sitravatinib Property

Boiling point:: 833.5±65.0 °C(Predicted)
Density: 1.417±0.06 g/cm3(Predicted)
storage temp.: -20°C
solubility: Soluble in DMSO (up to at least 25 mg/ml), or in Ethanol (up to at least 25 mg/ml)
form: solid
pka: 13.17±0.70(Predicted)
color: Off-white
Stability:: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.
InChIKey: WLAVZAAODLTUSW-UHFFFAOYSA-N
SMILES: C1(C(NC2=CC=C(F)C=C2)=O)(C(NC2=CC=C(OC3C=CN=C4C=C(C5=NC=C(CNCCOC)C=C5)SC4=3)C(F)=C2)=O)CC1

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Cayman Chemical

Product number: 27338
Product name: Sitravatinib
Packaging: 5mg
Price: $57
Updated: 2024/03/01

Cayman Chemical

Product number: 27338
Product name: Sitravatinib
Packaging: 10mg
Price: $107
Updated: 2024/03/01

Cayman Chemical

Product number: 27338
Product name: Sitravatinib
Packaging: 25mg
Price: $233
Updated: 2024/03/01

Cayman Chemical

Product number: 27338
Product name: Sitravatinib
Packaging: 50mg
Price: $437
Updated: 2024/03/01

Usbiological

Product number: 456189
Product name: MGCD 516
Packaging: 10mg
Price: $425
Updated: 2021/12/16

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Sitravatinib Chemical Properties,Usage,Production

Description

Sitravatinib is a multi-kinase inhibitor. It inhibits 35 kinases (IC₅₀s = 0.5-5,550 nM) in a panel of 55 receptor tyrosine kinases (RTKs). Sitravatinib reduces proliferation of A-673, LPS141, MPNST, DDLS, and Saos-2 cancer cells (IC₅₀s = 1,750, 340.1, 705.7, 266, and 1,830 nM, respectively) and decreases phosphorylation of insulin-like growth factor 1 receptor (IGF1-R), PDGFRβ, and Akt in these same cells when used at concentrations ranging from 62.5 to 4,000 nM. It decreases tumor growth in LPS141 and MPNST mouse xenograft models when administered at a dose of 15 mg/kg per day.

Description

Sitravatinib, known as MGCD516, is a multikinase (MET, RET, AXL, NTRK1, or NTRK3 genes) inhibitor used in a phase 1/1b clinical trial (NCT02219711) for patients with advanced cancers (NCT02219711).

Uses

MGCD 516 is an intermediate used to prepare substituted thienopyridines as inhibitors of protein tyrosine kinase activity.

Synthesis

1123837-39-7

1123837-84-2

Step 2. Synthesis of N-(3-fluoro-4-((2-(5-(((2-methoxyethyl)amino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7- yl)oxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1 -dicarboxamide (147): Compound 146 (0.59 g, 0.81 mmol) was dissolved in dichloromethane (50 mL) in dichloromethane (50 mL) and trifluoroacetic acid (TFA, 3 mL) was added. The reaction mixture was stirred at room temperature for 18 hours. Upon completion of the reaction, the solution was concentrated to remove the solvent. The residue was partitioned between dichloromethane and 1 M sodium hydroxide solution and filtered to remove insoluble impurities. The organic phase was separated, washed sequentially with 1 M sodium hydroxide solution and saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated to afford the target compound 147 (0.35 g, 69% yield).1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.40 (s, 1H), 10.01 (s, 1H), 8.55 (d, J = 1.6 Hz 1H), 8.51 (d, J = 5.3 Hz, 1H), 8.31 (s, 1H), 8.22 (d, J = 8.0 Hz, 1H), 7.92-7.87 (m, 2H), 7.65-7.61 (m, 2H), 7.52-7.43 (m, 2H), 7.17-7.12 (m, 2H), 6.64 (d, J = 5.5 Hz, 1H), 3.77 (s, 2H), 3.40 (t, J = 5.7 Hz, 2H), 3.23 (s, 3H), 2.64 (t, J = 5.7 Hz, 2H), 1.46 (br s, 4H). Mass spectrum (m/z): 630.1 (M + H).

in vivo

Sitravatinib (20 mg/kg; p.o.; once per day for 6 days) significantly inhibits tumor progression and induces tumor regression in C57BL/6 mice bearing CT1B-A5 cells model^[2].

Animal Model:	6-week-old C57BL/6 mice (bearing CT1B-A5 cells) ^[2]
Dosage:	20 mg/kg
Administration:	Oral administration; once per day for 6 days
Result:	Significantly inhibited tumor progression and induced tumor regression.

IC 50

Axl: 1.5 nM (IC₅₀); MER: 2 nM (IC₅₀); VEGFR3: 2 nM (IC₅₀); VEGFR2: 5 nM (IC₅₀); VEGFR1: 6 nM (IC₅₀); TrkA: 5 nM (IC₅₀); TrkB: 9 nM (IC₅₀); KIT: 6 nM (IC₅₀); FLT3: 8 nM (IC₅₀); DDR2: 0.5 nM (IC₅₀); DDR1: 29 nM (IC₅₀)

References

[1] PARAG P. PATWARDHAN. Significant blockade of multiple receptor tyrosine kinases by MGCD516 (Sitravatinib), a novel small molecule inhibitor, shows potent anti-tumor activity in preclinical models of sarcoma[J]. Oncotarget, 2015, 7 1: 4093-4109. DOI:10.18632/oncotarget.6547
[2] T. LEAL. MA 02.01 Evidence of Clinical Activity of Sitravatinib in Combination with Nivolumab in NSCLC Patients Progressing on Prior Checkpoint Inhibitors[J]. Journal of Thoracic Oncology, 2017. DOI:10.1016/j.jtho.2017.09.451
[3] WENTING DU. Sitravatinib potentiates immune checkpoint blockade in refractory cancer models.[J]. JCI insight, 2018. DOI:10.1172/jci.insight.124184

Sitravatinib Preparation Products And Raw materials

Raw materials

Preparation Products

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1123837-84-2, SitravatinibRelated Search:

Sivelestat sodium Adapalene SU 4312 Geldanamycin Troglitazone Skepinone-L Sitaxentan sodium

CS-2638

Sitravatinib

N-(3-fluoro-4-((2-(5-(((2-methoxyethyl)amino)methyl)pyridin-2-yl)thieno[3,2-b]pyridin-7-yl)oxy)phenyl)-N-(4-fluorophenyl)cyclopropane-1,1-dicarboxamide

MGCD-516

MG516

Sitravatinib (MGCD516)

1,1-Cyclopropanedicarboxamide, N-[3-fluoro-4-[[2-[5-[[(2-methoxyethyl)amino]methyl]-2-pyridinyl]thieno[3,2-b]pyridin-7-yl]oxy]phenyl]-N'-(4-fluorophenyl)-

RTK,MG-516,PD-1,SCFR,DDR1,inhibit,VEGFR2,MG 516,MGCD 516,MER,immune,TRKA,Cluster of differentiation antigen 135,Cancer,Discoidin Domain Receptor,VEGFR3,Inhibitor,Vascular endothelial growth factor receptor,Trk Receptor,Tropomyosin related kinase receptor,CD135,VEGFR,immunotherapy,Macrophages,c-Kit,DDR2,VEGFR1,Tyrosine,Fms like tyrosine kinase 3,FLT3,Axl,TRKB,Sitravatinib,MGCD-516,KIT,kinase,CD117

MGCD516 (SITRAVATINIB)

Sitravatinib, 10 mM in DMSO

1123837-84-2

C33H29F2N5O4S