sorafenib

Also known as BAY 43-9006, Nexavar®, N-(4-Chloro-3-(trifluoromethyl)phenyl)-N'-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea, 4-(4-((((4-Chloro-3-(trifluoromethyl)phenyl)amino)carbonyl)amino)phenoxy)-N-methyl-2-pyridinecarboxamide, sorafenibum, Sorafenibum, N-(4-Chloro-3-(trifluoromethyl)phenyl)-n'-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea

Sorafenib, sold under the brand name Nexavar, is a kinase inhibitor drug approved for the treatment of primary kidney cancer (advanced renal cell carcinoma), advanced primary liver cancer (hepatocellular carcinoma), FLT3-ITD positive AML and radioactive iodine resistant advanced thyroid carcinoma.

In the Vinony graph

Within Vinony's link graph, sorafenib is referenced by 725 other articles, and connects out to VEGF receptors, pharmacokinetics and interferon gamma.

Vinony files it under 1-Chloro-2-(trifluoromethyl)benzene derivatives, 4-Aminophenyl compounds and 4-Hydroxyphenyl compounds.

Its subject is documented across 22 Wikipedia language editions.

Key facts

Drug.ChEMBL: 1336
Drug.PDB_ligand: BAX
Drug.verifiedrevid: 464405524
Drug.image: Sorafenib2DACS.svg
Drug.image_class: skin-invert-image
Drug.width: 300
Drug.image2: Sorafenib 3D 3gcs.png
Drug.image_class2: bg-transparent
Drug.width2: 250
Drug.tradename: Nexavar, others
Drug.MedlinePlus: a607051
Drug.DailyMedID: Sorafenib
Drug.licence_EU: yes
Drug.licence_US: Sorafenib
Drug.pregnancy_AU: D
Drug.routes_of_administration: By mouth
Drug.ATC_prefix: L01
Drug.ATC_suffix: EX02

via Wikipedia infobox

Chemical data

Formula: C21H16ClF3N4O3
Molecular weight: 464.8 g/mol
IUPAC name: 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methylpyridine-2-carboxamide
SMILES: CNC(=O)C1=NC=CC(=C1)OC2=CC=C(C=C2)NC(=O)NC3=CC(=C(C=C3)Cl)C(F)(F)F
InChIKey: MLDQJTXFUGDVEO-UHFFFAOYSA-N
XLogP: 4.1
Polar surface area: 92.4 Å²
H-bond donors: 3
H-bond acceptors: 7
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2005
Admin. routes: oral
Indications: neoplasm, hepatocellular carcinoma, acute myeloid leukemia, lymphoma

via ChEMBL · EBI

Research

14,346 papers

Current status of sorafenib nanoparticle delivery systems in the treatment of hepatocellular carcinoma.Theranostics · 2021
Sorafenib attenuates liver fibrosis by triggering hepatic stellate cell ferroptosis via HIF-1α/SLC7A11 pathway.Cell proliferation · 2022
Sorafenib.Current opinion in oncology · 2006
SLC27A5 promotes sorafenib-induced ferroptosis in hepatocellular carcinoma by downregulating glutathione reductase.Cell death & disease · 2023
Adjuvant Transarterial Chemoembolization With Sorafenib for Portal Vein Tumor Thrombus: A Randomized Clinical Trial.JAMA surgery · 2024

via PubMed

Wikidata facts

Subclass of: chemical compound
Has part: chlorine
Mass: 464.086
Has use: medication

Show 9 more facts

chemical formula: C₂₁H₁₆ClF₃N₄O₃
subject has role: protein kinase inhibitors
canonical SMILES: CNC(=O)C1=NC=CC(=C1)OC2=CC=C(C=C2)NC(=O)NC3=CC(=C(C=C3)Cl)C(F)(F)F
medical condition treated: hepatocellular carcinoma
physically interacts with: ret proto-oncogene
significant drug interaction: clarithromycin
stylized name: NexAVAR
Commons category: Sorafenib
found in taxon: Phoma

Sources (7)

via Wikidata · CC0

~7 min read

Encyclopedic overview

21 sections

Contents

Mechanism of action
Medical uses
Kidney cancer
Liver cancer
Thyroid cancer
Acute Myeloid Leukaemia
Adverse effects
History
Renal cancer
Liver cancer
Society and culture
Nexavar controversy
Research
Lung
Ovarian cancer
Brain (recurrent glioblastoma)
Desmoid tumor (aggressive fibromatosis)
See also
Notes
References
External links

==Mechanism of action== Sorafenib is a protein kinase inhibitor with activity against many protein kinases, including VEGFR, PDGFR and RAF kinases. Of the RAF kinases, sorafenib is more selective for c-Raf than B-RAF. (See BRAF (gene)#Sorafenib for details the drug's interaction with B-Raf.)

Excerpted from Wikipedia’s “sorafenib” article, available under the CC BY-SA 4.0 licence.