Sunitinib

ChemicalBook > CAS DataBase List > Sunitinib

Binding Mode

Product Name: Sunitinib
CAS No.: 557795-19-4
Chemical Name: Sunitinib
Synonyms: SUNITINIB BASE;SUNITINIB MALEATE;SNTI;Suniti;Sutini;SU-11248;Sutent-d4;sunitinib;SU-11248-d4;SUNITINIB-D4
CBNumber: CB9728174
Molecular Formula: C22H27FN4O2
Formula Weight: 398.47
MOL File: 557795-19-4.mol

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Sunitinib Property

Melting point:: 189-191°C
Boiling point:: 572.1±50.0 °C(Predicted)
Density: 1.2
Flash point:: 299.8℃
storage temp.: 2-8°C
solubility: Chloroform (Slightly), Methanol (Slightly)
pka: 8.5(at 25℃)
form: Solid
color: Yellow to Dark Orange
CAS DataBase Reference: 557795-19-4(CAS DataBase Reference)

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Safety

Safety Statements: 24/25
HS Code: 29337900
Hazardous Substances Data: 557795-19-4(Hazardous Substances Data)

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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

H332Harmful if inhaled

H335May cause respiratory irritation

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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

P310Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Usbiological

Product number: S8032
Product name: Sunitinib Maleate
Packaging: 100mg
Price: $127
Updated: 2021/12/16

Usbiological

Product number: 170080
Product name: Sunitinib, Free base
Packaging: 25mg
Price: $240
Updated: 2021/12/16

ApexBio Technology

Product number: B1045
Product name: Sunitinib
Packaging: 100mg
Price: $50
Updated: 2021/12/16

Biosynth Carbosynth

Product number: BD164426
Product name: Sunitinib base
Packaging: 100mg
Price: $50
Updated: 2021/12/16

ApexBio Technology

Product number: B1045
Product name: Sunitinib
Packaging: 10mM(in 1mL DMSO)
Price: $55
Updated: 2021/12/16

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Sunitinib Chemical Properties,Usage,Production

Binding Mode

Sunitinib binds the DFG-out conformation of VEGFR2 at the front cleft and gate area (type II). It occupies the ATP-binding site, forming three hydrogen bonds: (1) between the oxindole NH and the amide carbonyl of Glu-917 of the hinge, (2) the oxindole carbonyl and the amide NH of Cys919, and (3) the pyrrole NH and the amide carbonyl of Cys919. Several hydrophobic interactions with VEGFR also contribute to the potency.

Description

Sunitinib is an inhibitor of multiple receptor tyrosine kinases (RTKs) involved in tumor proliferation and angiogenesis, including platelet-derived growth factor receptors (PDGFR), vascular endothelial growth factor receptors (VEGFR), and stem cell factor receptor (KIT). It was launched as an oral treatment for gastrointestinal stromal tumors (GIST) and advanced renal-cell carcinoma (RCC). In vitro, sunitib inhibits VEGFR2, PDGFRα, PDGFRβ, KIT, and FLT3 receptors with IC₅₀ values in the 4–14nM range, and the ligand-dependent autophosphorylation of VEGFR2 and PDGFRb with IC₅₀s of approximately 10 nM. In addition, it inhibits the growth of tumor cells expressing dysregulated target RTKs in vitro and inhibits PDGFRb- and VEGFR2-dependent tumor angiogenesis in vivo. Sunitinib exhibits broad and potent antitumor activity, causing regression in murine models of human epidermal (A431), colon (Colo205 and HT-29), lung (NCI-H226 and H460), breast (MDA-MB-435), prostate (PC3-3M-luc), and renal (786-O) cancers, and suppressing or delaying the growth of many others, including the C6 rat and SF763 T human glioma xenografts and B16 melanoma lung cancer.

Chemical Properties

Yellow Solid

Originator

Sugen (US)

Uses

Sunitinib Malate (Sutent, SU11248) is a multi-targeted RTK inhibitor targeting VEGFR2 (Flk-1) and PDGFRβ with IC50 of 80 nM and 2 nM, and also inhibits c-Kit.

Uses

Labelled Sunitinib (S820000), a multi-kinase inhibitor targeting several receptor tyrosine kinases (RTK).

Definition

ChEBI: Sunitinib is a member of pyrroles and a monocarboxylic acid amide. It has a role as an angiogenesis inhibitor, an antineoplastic agent, an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor, a vascular endothelial growth factor receptor antagonist, an immunomodulator and a neuroprotective agent. It is functionally related to a 3-methyleneoxindole.

brand name

(Pfizer).

Characteristics

Class: receptor tyrosine kinase
Treatment: RCC, GIST
Elimination half-life = 70 h
Protein binding = 95%

Clinical Use

Tyrosine kinase inhibitor:
Treatment of metastatic renal cell carcinoma (MRCC), gastrointestinal stromal tumours (GIST) and pancreatic neuroendocrine tumours (pNET)

target

VEGFR-1

Drug interactions

Potentially hazardous interactions with other drugs
Antipsychotics: avoid with clozapine (increased risk of agranulocytosis).
Antivirals: avoid concomitant use with boceprevir.
Avoid concomitant use with other inhibitors or inducers of CYP3A4. Dose alterations may be required.

Metabolism

Metabolised mainly via the cytochrome P450 isoenzyme CYP3A4 to its primary active metabolite, which itself is then further metabolised via CYP3A4.
Elimination is primarily via faeces. In a human mass balance study of [14C]sunitinib, 61% of the dose was eliminated in faeces and 16% by the renal route.

References

[1]hui ep1, lui vw, wong cs, ma bb, lau cp, cheung cs, ho k, cheng sh, ng mh, chan at. preclinical evaluation of sunitinib as single agent or in combination with chemotherapy in nasopharyngeal carcinoma. invest new drugs. 2011 dec;29(6):1123-31.

Sunitinib Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Sunitinib manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD

Product: Sunitinib 557795-19-4
Price: US $0.00/g
Min. Order: 1g
Purity: 99%min
Supply Ability: 1000G
Release date: 2021-06-24

Sinoway Industrial co., ltd.

Product: Sunitinib 557795-19-4
Price: US $0.00-0.00/G/Bag
Min. Order: 1G/Bag
Purity: 0.99
Supply Ability: 100kg
Release date: 2024-06-27

Nanjing Fred Technology Co., Ltd

Product: Sunitinib 557795-19-4
Price: US $0.00-0.00/kg
Min. Order: 1kg
Purity: 99%, Single impurity＜0.1
Supply Ability: 1 ton
Release date: 2023-12-20

557795-19-4, SunitinibRelated Search:

Dasatinib monohydrate Methyl 2-hydroxyethyl cellulose Ethylparaben Gefitinib Lapatinib Ethyl cyanoacetate Ethyl acrylate Teniposide Erlotinib Ethanol N,N-Dimethyl-1,4-phenylenediamine Tris(hydroxymethyl)aminomethane Ethyl acetate Imatinib ISOXADIFEN-ETHYL Dihydromyrcenol Imatinib mesylate Sunitinib Malate

Sunitinib--- free base

Sunitinib，Sutent

5-(5-Fluoro-2-oxo-1,2-dihydroindol-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxylic acid N-(2-diethylaminoethyl)amide

Suniti

N-[2-(diethylaMino)ethyl]-5-{[(3Z)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]Methyl}-2,4-diMethyl-1H-pyrrole-3-carboxaMide

SUTENT SUNITINIB

N-(2-diethylaminoethyl)-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)meth yl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

Sunitinib malate(TINIBS)

Sunitinib malate for research

N-[2-(Diethylamino)ethyl]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide Maleate

SU-11248

N-[2-(Diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1,2- dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide

N-[2-(Diethylamino)ethyl]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide Malate

SUNITINIB (SU 11248)

SU-11248;SU11248

Sunitinib (Sutent, SU11248)

SNTI

N-[2-DiethylaMino(ethyl-d4)]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)Methyl]-2,4-diMethyl-1H-pyrrole-3-carboxaMide

SU-11248-d4

Sutent-d4

(Z)-N-(2-(DiethylaMino)ethyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)Methyl)-2,4-diMethyl-1H-pyrrole-3-carboxaMide

Sunitinib (Mixture of E and Z IsoMer)

Sunitinib N-(2-(Diethylamino)ethyl)-5-((Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide

Sunitinib, >=99%

sunitinib

SUNITINIB-D4

SUNITINIB MALEATE

n-(2-(diethylamino)ethyl)-5-((z)-(5-fluoro-1,2-dihydro-2-oxo-3h-indol-3-ylidene)methyl)-2,4-dimethyl-1h-pyrrole-3-carboxamide

SUNITINIB BASE

1H-Pyrrole-3-carboxamide, N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-1,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-

SUNITINIBMALEATE(FORR&DONLY)

(Z)-N-[2-(Diethylamino)ethyl]-5-[(5-fluoro-2-oxo-3-indolinylidene)methyl]-2,4-dimethylpyrrole-3-carboxamide

(Z)-Sunitinib

Sunitinib USP/EP/BP

Sunitinib DISCONTINUED

Sunitinib free base (SU-11248)

SunitinibQ: What is Sunitinib Q: What is the CAS Number of Sunitinib Q: What is the storage condition of Sunitinib Q: What are the applications of Sunitinib

Sutent, Sunitinib, SU11248

Sutini

557795-19-4

41031-54-7

C22H27FN4O2C4H6O5

C26H33FN4O7

C26H31FN4O6

C22H27N4O2C4H6O5

26H31FN4O6

SU-11248

Inhibitors

anti-neoplastic

Heterocycles

Intermediates & Fine Chemicals

Pharmaceuticals

Sunitinib

Molecular Targeted Antineoplastic

Heterocyclic Compounds

Pharmaceutical intermediate

API

Tyrosine Kinase Inhibitors