Semaxanib

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

What is the Semaxanib?

The molecule Semaxanib presents a molecular formula of C15H14N2O and its IUPAC name is (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one.

Semaxanib (SU11248) is a small molecule inhibitor of the vascular endothelial growth factor receptor (VEGFR). Semaxanib was originally developed by Sugen and then acquired by Pfizer as part of its acquisition of Sugen in 1999..

Semaxanib was studied in a Phase I clinical trial as a treatment for solid tumors. The trial found that semaxanib was well tolerated and had anti-tumor activity in some patients. Semaxanib was then studied in a Phase II clinical trial in patients with metastatic renal cell carcinoma. This trial found that semaxanib had activity in this patient population and led to the drug being studied in a Phase III clinical trial..

The Phase III clinical trial of semaxanib was terminated early due to lack of efficacy. Pfizer then decided to discontinue development of the drug..

Semaxanib is a small molecule inhibitor of the VEGFR. VEGFR is a protein that is important for the growth and development of blood vessels. Semaxanib works by inhibiting the activity of VEGFR, which leads to the inhibition of the growth of new blood vessels. This action of semaxanib makes it an anti-angiogenic agent..

Semaxanib was originally developed by Sugen and then acquired by Pfizer as part of its acquisition of Sugen in 1999..

Semaxanib was studied in a Phase I clinical trial as a treatment for solid tumors. The trial found that semaxanib was well tolerated and had anti-tumor activity in some patients. Semaxanib was then studied in a Phase II clinical trial in patients with metastatic renal cell carcinoma. This trial found that semaxanib had activity in this patient population and led to the drug being studied in a Phase III clinical trial..

The Phase III clinical trial of semaxanib was terminated early due to lack of efficacy. Pfizer then decided to discontinue development of the drug..

3D structure

Cartesian coordinates

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

2D drawing

 

Semaxanib WUWDLXZGHZSWQZ-WQLSENKSSA-N chemical compound 2D structure molecule svg
Semaxanib

 

Molecule descriptors

 
IUPAC name(3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one
InChI codeInChI=1S/C15H14N2O/c1-9-7-10(2)16-14(9)8-12-11-5-3-4-6-13(11)17-15(12)18/h3-8,16H,1-2H3,(H,17,18)/b12-8-
InChI KeyWUWDLXZGHZSWQZ-WQLSENKSSA-N
SMILESCc1cc(C)c(/C=C2\C(=O)Nc3ccccc32)[nH]1

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.

  • (3Z)-3-((3,5-DIMETHYL-1H-PYRROL-2-YL)METHYLIDENE)-1,3-DIHYDRO-2H-INDOL-2-ONE
  • (3Z)-3-[(3,5-DIMETHYL-1H-PYRROL-2-YL)METHYLIDENE]-2,3-DIHYDRO-1H-INDOL-2-ONE
  • (3Z)-3-[(3,5-Dimethyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-2H-indol-2-one
  • (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylene]indolin-2-one
  • (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-1,3-dihydro-2H-indol-2-one
  • (3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one
  • (Z)-3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)indolin-2-one
  • (Z)-SU 5416
  • (Z)-Semaxanib
  • (Z)-Semaxinib
  • 1,3-Dihydro-3-[(3,5-dimethyl-1H-pyrrol-2-yl)
  • 194413-58-6
  • 204005-46-9
  • 2H-INDOL-2-ONE, 3-(3,5-DIMETHYL-1H-PYRROL-2-YL)METHYLENE)- 1,3-DIHYDRO-,(Z)-
  • 2H-Indol-2-one, 3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-1,3-dihydro-, (3Z)-
  • 2H-Indol-2-one, 3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-1,3-dihydro-, (Z)-
  • 2H-Indol-2-one, 3-(3,5-dimethyl-1H-pyrrol-2-yl)methylene)- 1,3-dihydro-, (Z)-
  • 2H-Indol-2-one,3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-, (3Z)-
  • 2H-Indol-2-one,5-dimethyl-2-pyrrolyl)methylene]-
  • 2x2m
  • 3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)indolin-2-one
  • 3-((Z)-(3,5-Dimethylpyrrol-2-yl)methylene)-2-indolinone
  • 3-(1-(3,5-Dimethyl-1H-pyrrol-2-yl)meth-(Z)-ylidene)-2-oxo-2,3-dihydroindole
  • 3-(2,4-dimethylpyrrol-5-yl)methylidene-indolin-2-one
  • 3-[(2,4-Dimethylpyrrol-5-yl)methylidenyl]-2-indolinon
  • 3-[(2,4-dimethylpyrrol-5-yl)methylidenyl]-2-indolinone
  • 3-[(2,4-dimethylpyrrol-5-yl)methylidenyl]-indolin-2-one
  • 3-[(2,4-dimethylpyrrol-5-yl)methylidenyl]indolin-2-one
  • 3-[(3,5-Dimethyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro- 2H-indol-2-one
  • 3-[(3,5-Dimethyl-2H-pyrrol-2-ylidene)methyl]-1H-indol-2-ol
  • 3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-1,3-dihydro-2H-indol-2-one
  • 3-[(3,5-dimethyl-1h-pyrrol-2-yl)methylene]-1,3-dihydro-2h-indol-2-one
  • 3-[1-(3,5-dimethyl-1h-pyrrol-2-yl)-meth-(z)-ylidene]-2-oxo-2,3-dihydro-indole
  • 71IA9S35AJ
  • A857052
  • A899499
  • AC-35250
  • AMY10847
  • BCP06068
  • BDBM4810
  • BDBM497339
  • CCG-205186
  • CS-1225
  • D05819
  • DB06436
  • ES-0010
  • EU-0101110
  • EX-A2158
  • GTPL5056
  • H-Indol-2-one, 3-((3,5-dimethyl-1H-pyrrol-2-yl)methylene)-1,3-dihydro-
  • HMS2234L12
  • HMS3229O13
  • HMS3263M22
  • HMS3268J13
  • HMS3413H10
  • HMS3648O12
  • HMS3677H10
  • HSCI1_000303
  • HY-10374
  • J-013281
  • LP01110
  • Lopac0_001110
  • MFCD09763655
  • MLS001074896
  • MLS001332519
  • MLS001332520
  • N11132
  • NCGC00094381-01
  • NCGC00094381-02
  • NCGC00094381-03
  • NCGC00094381-04
  • NCGC00094381-05
  • NCGC00094381-19
  • NCGC00261795-01
  • NSC 696819
  • NSC-696819
  • NSC696819
  • Q7449140
  • S 8442
  • SDCCGSBI-0051079.P003
  • SMR000568416
  • SR-01000076044
  • SR-01000076044-2
  • SR-01000076044-8
  • SU 5416
  • SU-5416
  • SU005416
  • SU5146
  • SU5416
  • SW219791-1
  • Semaxanib
  • Semaxanib (SU5416)
  • Semaxanib (USAN/INN)
  • Semaxanib(SU5416)
  • Semaxanib, Semoxind, TSU-16, NSC-696819, SU-5416
  • Semaxanib; SU5416
  • Semaxinib
  • Semaxnib
  • Semoxind
  • Sugen 5416
  • TSU 16
  • TSU-16
  • Tox21 111271
  • US11001595, Compound SU5416
  • VEGF Receptor 2 Kinase Inhibitor III
  • VEGFR2 Kinase Inhibitor III
  • Z-Semaxanib
  • cid_5329098
  • methylene]-2H-indol-2-one
  • s2845

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC12410091
  • UNII-71IA9S35AJ
  • AKOS015994557
  • BRD-K63504947-001-05-5
  • DTXSID801025708
  • CHEMBL276711
  • CHEBI:91083
  • Tox21_501110
  • SCHEMBL8190
  • SCHEMBL19571

Physico-Chemical properties

IUPAC name(3Z)-3-[(3,5-dimethyl-1H-pyrrol-2-yl)methylidene]-1H-indol-2-one
Molecular formulaC15H14N2O
Molecular weight238.284
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity76.42
LogP3.3
Topological polar surface area44.9

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.