Sunitinib

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

What is the Sunitinib?

The molecule Sunitinib presents a molecular formula of C22H27FN4O2 and its IUPAC name is N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide.

Sunitinib (SUTENT®, Pfizer) is a small molecule inhibitor of multiple receptor tyrosine kinases. Sunitinib was the first cancer drug in its class to be approved by the U.S. Food and Drug Administration (FDA). It is approved for the treatment of gastrointestinal stromal tumors (GIST), pancreatic neuroendocrine tumors (PNETs), and renal cell carcinoma (RCC)..

Sunitinib works by inhibiting the activity of multiple tyrosine kinases, proteins that are involved in cell signaling. Inhibition of these proteins leads to cell death..

Sunitinib has shown activity in several types of cancer, including GIST, PNETs, and RCC. In clinical trials, sunitinib has been shown to improve progression-free survival and overall survival in patients with GIST, PNETs, and RCC..

Sunitinib is generally well-tolerated, with the most common side effects being fatigue, diarrhea, nausea, and vomiting. Less common side effects include low blood counts, hypertension, and skin rash..

If you have been diagnosed with GIST, PNETs, or RCC and are considering treatment with sunitinib, talk to your doctor about the potential benefits and risks of this medication..

3D structure

Cartesian coordinates

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

2D drawing

 

Sunitinib WINHZLLDWRZWRT-ATVHPVEESA-N chemical compound 2D structure molecule svg
Sunitinib

 

Molecule descriptors

 
IUPAC nameN-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide
InChI codeInChI=1S/C22H27FN4O2/c1-5-27(6-2)10-9-24-22(29)20-13(3)19(25-14(20)4)12-17-16-11-15(23)7-8-18(16)26-21(17)28/h7-8,11-12,25H,5-6,9-10H2,1-4H3,(H,24,29)(H,26,28)/b17-12-
InChI KeyWINHZLLDWRZWRT-ATVHPVEESA-N
SMILESCCN(CC)CCNC(=O)c1c(C)[nH]c(/C=C2\C(=O)Nc3ccc(F)cc32)c1C

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.

  • (Z)-N-(2-(Diethylamino)ethyl)-5-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide
  • (Z)-Sunitinib
  • 1,2,4,5-tetramethylpyrrole-3-carboxamide
  • 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, 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,2-dihydro-2-oxo-3H-indol-3-ylidene)methyl]-2,4-dimethyl-
  • 342641-94-5
  • 5-(5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide
  • 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid (2-diethylamino-ethyl)-amide
  • 5-[5-fluoro-2-oxo-1,2-dihydro-indol-(3Z)-ylidenemethyl]-2,4-dimethyl-1H-pyrrole-3-carboxylic acid(2-diethylamino-ethyl)-amide
  • 557795-19-4
  • 95S194
  • A822143
  • A830806
  • AB01273976-01
  • AB01273976-02
  • AB01273976_04
  • AM20090630
  • BCPP000057
  • BD164426
  • BDBM4814
  • CCG-268638
  • CS-1670
  • D08552
  • DB01268
  • EX-A553
  • GTPL5713
  • HSDB 7932
  • HY-10255A
  • K00588a
  • KS-5022
  • MFCD09260778
  • 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-((5-fluoro-2-oxoindolin-3-ylidene)methyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide
  • N-[2-(Diethylamino)ethyl]-5-(2-oxo-5-fluoroindoline-3-ylidenemethyl)-2,4-dimethyl-1H-pyrrole-3-carboxamide
  • N-[2-(diethylamino)ethyl]-5-[(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide
  • N-[2-(diethylamino)ethyl]-5-[(5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide
  • N-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1,2-dihydro-3H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carbo
  • 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-{[(3Z)-5-fluoro-2-oxo-2,3-dihydro-1H-indol-3-ylidene]methyl}-2,4-dimethyl-1H-pyrrole-3-carboxamide
  • NCGC00164631-02
  • NCGC00164631-04
  • NSC 736511
  • NSC 750690
  • NSC-736511
  • NSC-750690
  • NSC-800937
  • NSC750690
  • NSC800937
  • Q27163278
  • Q417542
  • SR-00000000005
  • SR-00000000005-2
  • SU 11248
  • SU-11248
  • SU011248
  • SU11248
  • Su-011248
  • Sunitinib
  • Sunitinib (INN)
  • Sunitinib (free base)
  • Sunitinib Base
  • Sutent
  • Sutent (free base)
  • Sutent, Sunitinib, SU11248
  • V99T50803M
  • Z2568722545
  • 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
  • s7781
  • sunitinibum

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC3964325
  • UNII-V99T50803M
  • AKOS015908193
  • AKOS025312424
  • CHEMBL535
  • CHEBI:38940
  • CHEBI:91430
  • SCHEMBL8081

Physico-Chemical properties

IUPAC nameN-[2-(diethylamino)ethyl]-5-[(Z)-(5-fluoro-2-oxo-1H-indol-3-ylidene)methyl]-2,4-dimethyl-1H-pyrrole-3-carboxamide
Molecular formulaC22H27FN4O2
Molecular weight398.474
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity116.31
LogP3.9
Topological polar surface area77.2

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.