Sorafenib

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Sorafenib are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Sorafenib?

The molecule Sorafenib presents a molecular formula of C21H16ClF3N4O3 and its IUPAC name is 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methylpyridine-2-carboxamide.

Sorafenib (marketed under the brand name Nexavar) is a cancer medication that targets the kinase enzymes RAF1 and BRAF. These enzymes are involved in the growth and spread of cancer cells..

Sorafenib was first approved by the U.S. Food and Drug Administration (FDA) in 2005 to treat kidney cancer. It is now also approved to treat liver cancer and certain types of thyroid cancer..

Sorafenib is a pill that is taken twice a day. The most common side effects are fatigue, diarrhea, hand-foot syndrome (a condition that causes redness, swelling, and pain in the hands and feet), and loss of appetite..

Sorafenib is typically used as a last resort after other cancer treatments have failed. It is a very powerful drug with serious side effects, so it is important that you discuss the risks and benefits of sorafenib with your doctor before starting treatment..

3D structure

Cartesian coordinates

Geometry of Sorafenib in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Sorafenib MLDQJTXFUGDVEO-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Sorafenib

 

Molecule descriptors

 
IUPAC name4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methylpyridine-2-carboxamide
InChI codeInChI=1S/C21H16ClF3N4O3/c1-26-19(30)18-11-15(8-9-27-18)32-14-5-2-12(3-6-14)28-20(31)29-13-4-7-17(22)16(10-13)21(23,24)25/h2-11H,1H3,(H,26,30)(H2,28,29,31)
InChI KeyMLDQJTXFUGDVEO-UHFFFAOYSA-N
SMILESCNC(=O)c1cc(Oc2ccc(NC(=O)Nc3ccc(Cl)c(C(F)(F)F)c3)cc2)ccn1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • 100012-18-8
  • 1210608-86-8
  • 1uwh
  • 2-Pyridinecarboxamide, 4-(4-((((4-chloro-3-(trifluoromethyl)phenyl)amino)carbonyl)amino)phenoxy)-N-methyl-
  • 2-Pyridinecarboxamide, 4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-N-methyl-
  • 284461-73-0
  • 284461-73-0 (free base)
  • 3gcs
  • 3heg
  • 4(4-{3-[4-Chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)-N(sup 2)-methylpyridine-2-carboxamide
  • 4-(4-((((4-Chloro-3-(trifluoromethyl)phenyl)amino)carbonyl)amino)phenoxy)-N-methyl-2-pyridinecarboxamide
  • 4-(4-(3-(4-CHLORO-3-(TRIFLUOROMETHYL)PHENYL)UREIDO)PHENOXY)-N(SUP 2)-METHYLPYRIDINE-2-CARBOXAMIDE
  • 4-(4-(3-(4-CHLORO-3-(TRIFLUOROMETHYL)PHENYL)UREIDO)PHENOXY)-N-METHYLPICOLINAMIDE
  • 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl) ureido) phenoxy)-N-methylpicolinamide
  • 4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl) ureido)phenoxy)-N-methylpicolinamide
  • 4-(4-{3-(4-Chloro-3-(trifluoromethyl)phenyl)ureido}phenoxy)-N(sup 2)-methylpyridine-2-carboxamide
  • 4-(4-{3-[4-Chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)-N2-methylpyridine-2-carboxamide
  • 4-(4-{3-[4-chloro-3-(trifluoromethyl)phenyl]ureido}phenoxy)- N-methylpyridine-2-carboxamide
  • 4-[4-({[4-chloro-3-(trifluoromethyl)phenyl]carbamoyl}amino)phenoxy]-N-methylpyridine-2-carboxamide
  • 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methyl-picolinamide;tosylic acid
  • 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methyl-pyridine-2-carboxamide
  • 4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methylpyridine-2-carboxamide
  • 4-[4-[[[[4-chloro-3-(trifluoromethyl)phenyl]amino]carbonyl]amino]phenoxy]-N-methyl-2-pyridinecarboxamide
  • 4-{4-[({[4-CHLORO-3-(TRIFLUOROMETHYL)PHENYL]AMINO}CARBONYL)AMINO]PHENOXY}-N-METHYLPYRIDINE-2-CARBOXAMIDE
  • 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)-amino]phenoxy}-N-methylpyridine-2-carboxamide
  • 4-{4-[({[4-chloro-3-(trifluoromethyl)phenyl]amino}carbonyl)amino]phenoxy}-N-methyl-pyridine-2-carboxamide
  • 461S730
  • 4asd
  • 9ZOQ3TZI87
  • A819449
  • AB00933189-05
  • AB00933189-06
  • AB00933189_08
  • AC-1674
  • ACT06732
  • AM20090614
  • BAX
  • BAY 43-9006
  • BAY 43-9006; Sorafenib
  • BAY 439006
  • BAY 439006; BAY439006; BAY-439006
  • BAY-43-0006
  • BAY-43-9006
  • BAY-439006
  • BAY43-9006
  • BAY439006
  • BCP01767
  • BCP34023
  • BCPP000064
  • BDBM16673
  • BS164413
  • CCG-269400
  • CS-1590
  • D08524
  • DB00398
  • Donafenib (Sorafenib D3)
  • EC 608-209-4
  • EX-A2894
  • FT-0650736
  • FT-0674632
  • GTPL5711
  • HMS2043A18
  • HMS3244A15
  • HMS3244A16
  • HMS3244B15
  • HMS3656N20
  • HSDB 8173
  • HY-10201
  • Hit compound, 8
  • K00597a
  • Kinome_766
  • MFCD06411450
  • Manganese(4+), chloro[[4,4',4'',4'''-(21H,23H-porphine-5,10,15,20-tetrayl-kappaN21,kappaN22,kappaN23,kappaN24)tetrakis[1-methylpyridiniumato]](2-)]-, chloride (1:4), (SP-5-12)-
  • MnTMPyP pentachloride
  • N-(3-trifluoromethyl-4-chlorophenyl)-N'-(4-(2-methylcarbamoyl pyridin-4-yl)oxyphenyl)urea
  • N-(4-Chloro-3-(trifluoromethyl)phenyl)-N'-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl)urea
  • N-(4-chloro-3-(trifluoromethyl)phenyl)-N'-(4-(2-(N-methylcar bamoyl)-4-pyridyloxy)phenyl)urea
  • N-(4-chloro-3-(trifluoromethyl)phenyl)-N'-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl) urea
  • NCGC00167488-01
  • NCGC00167488-02
  • NCGC00167488-03
  • NCGC00167488-04
  • NCGC00167488-05
  • NCGC00167488-07
  • NCGC00167488-14
  • NSC-724772
  • NSC-747971
  • NSC-800934
  • NSC747971
  • NSC800934
  • Nexavar
  • PB14443
  • Q-201728
  • Q421136
  • SB19942
  • SF-0529
  • SORAFENIB BASE
  • SR-00000000529
  • SR-00000000529-1
  • STK627350
  • SW202562-4
  • SY009239
  • Sorafenib
  • Sorafenib (D3); CM-4307; CM 4307; CM4307;Bay 43-9006 (D3)
  • Sorafenib (Nexavar)
  • Sorafenib (USAN/INN)
  • Sorafenib free base
  • Sorafenib free base (BAY-43-9006)
  • Sorafenib, 4
  • Sorafenib-[13C,d3]
  • Z89277543
  • cid_216239
  • s7397
  • sorafenibum

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1493878
  • UNII-9ZOQ3TZI87
  • AKOS005560229
  • BRD-K23984367-001-01-8
  • DTXSID7041128
  • CHEMBL1336
  • CHEBI:50924
  • SCHEMBL8218

Physico-Chemical properties

IUPAC name4-[4-[[4-chloro-3-(trifluoromethyl)phenyl]carbamoylamino]phenoxy]-N-methylpyridine-2-carboxamide
Molecular formulaC21H16ClF3N4O3
Molecular weight464.825
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity112.48
LogP6.1
Topological polar surface area92.4

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.