Sunitinib Malate (HCID 6456015)

Überblick

Sunitinib malate is an organic molecular entity. It has a role as an antineoplastic agent and an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor. It contains a sunitinib.

Namen und Bezeichner

Bevorzugter Name: Sunitinib Malate
IUPAC: N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide;(2S)-2-hydroxybutanedioic acid
Englischer Name: Sunitinib Malate
Summenformel: C26H33FN4O7
Molmasse: 532.56

Namen und Synonyme

Sunitinib malate341031-54-7SU011248 L-malate saltPHA-290940ADsunitinib L-malateSU010398SU-011248 L-malate saltDTXSID4046492LVX8N1UT73SU-010398DTXCID801476195NSC736511

Weitere Namen anzeigen

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 (2S)-hydroxybutanedioate(Z)-N-(2-(Diethylamino)ethyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrCS-308NSC2677SU112248NSC 2677NSC-2677SU 011248Sunitinib MaL

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-, (2S)-hydroxybutanedioate (1:1)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-, (2S)-hydroxybutanedioate (1:1)RefChem:56081SutentSunitinib malate [USAN]MFCD08282795Sunitinib (Malate)N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide;(2S)-2-hydroxybutanedioic acid

Datenbank-Bezeichner

CAS: 341031-54-7
PubChem CID: 6456015
DTXSID: DTXSID4046492
ChEMBL: CHEMBL1567
ChEBI: CHEBI:232546
UNII: LVX8N1UT73
EC Number: 638-825-9

Eigenschaften

Berechnete Struktureigenschaften

Polarare Oberfläche (TPSA): 172 Å²
H-Brücken-Donoren: 6
H-Brücken-Akzeptoren: 9
Frei drehbare Bindungen: 10
Schwere Atome: 38
Formalladung: 0
Komplexität: 765

Experimentelle und physikochemische Eigenschaften

Human Drugs · 2 Einträge

FDA approved drugs -> Active ingredient

Physikochemische Eigenschaften

Schmelzpunkt: 189 · 189-191°C
storage temp.: room temp
Löslichkeit: 10 mg/mL · DMSO: >10mg/mL
Aggregatzustand: powder
pka: 8.95 · 8.95
Farbe: Orange
Stabilität: 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
InChIKey: XGQXULJHBWKUJY-LYIKAWCPSA-N
SMILES: [C@@H](O)(C(=O)O)CC(=O)O.C(/C1NC(C)=C(C(=O)NCCN(CC)CC)C=1C)=C1/C(NC2=CC=C(F)C=C/12)=O |&1:0,r|
CAS Datenbank: 341031 · 341031-54-7(CAS DataBase Reference)

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H360 (93.8%): May damage fertility or the unborn child [Danger Reproductive toxicity]

P203, P260, P264, P270, P273, P280, P318, P319, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 48 reports by companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Hazard Classes and CategoriesRepr. 1B (93.8%)

Toxikologische Informationen

Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Sunitinib malate

vMost-DILI-concern

8

Box warning

DOI:10.1016/j.drudis.2016.02.015

Sicherheitsdaten

wgk: 2
ridadr: UN3077
hs_code: 29337900
risk_code: 61-2-48/25-36/37-22-53
hazard_code: T
safety_code: 53-22-36/37-24/25
hazard_class: 9
Speicherklasse: 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects
Hazard Classifications: Repr. 1BSTOT RE 1 Oral

Chemie und Industrie

Pharmakologische Informationen

FDA Pharmacological Classification · 2 Einträge

SUNITINIB MALATE

Protein Kinase Inhibitors [MoA]; Kinase Inhibitor [EPC]

MeSH Pharmacological Classification · 3 Einträge

Substances that inhibit or prevent the proliferation of NEOPLASMS.

Agents and endogenous substances that antagonize or inhibit the development of new blood vessels.

Agents that inhibit PROTEIN KINASES.

Anwendungen · 2 Einträge

BeschreibungSunitinib is a small molecule inhibitor of receptor tyrosine kinases, including FLK1 (Ki = 9 nM), PDGFRβ (Ki = 8 nM), and FLT3. It is at least 10-fold selective for FLK1 and PDGFRβ over a variety of tyrosine kinases in a panel, including EGFR, Cdk2, Met, IGFR-1, Abl, and Src. Sunitinib inhibits VEGF-dependent FLK1 and PDGF-dependent PDGFRβ phosphorylation (IC50s = 10 and 10 nM, respectively) as well as phosphorylation of FLT3 and FLT3 carrying the activating internal tandem duplication mutation (FLT3-ITD; IC50s = 250 and 50 nM, respectively). It decreases VEGF- and FGF-induced proliferation of human umbilical vein endothelial cells (HUVECs; IC50s = 30 and 700 nM, respectively) and reduces tumor growth in a variety of mouse xenograft models when administered at doses ranging from 20 to 80 mg/kg per day. Formulations containing sunitinib have been used in the treatment of gastrointestinal stromal tumors and metastatic renal cell carcinoma.

VerwendenSunitinib 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.