Gimeracil

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

What is the Gimeracil?

The molecule Gimeracil presents a molecular formula of C5H4ClNO2 and its IUPAC name is 5-chloro-4-hydroxy-1H-pyridin-2-one.

Gimeracil (also known as 5-fluorouracil or 5-FU) is a molecule used in cancer chemotherapy. It belongs to a class of drugs called antimetabolites, which interfere with DNA synthesis and cell proliferation. 5-FU is one of the most commonly used chemotherapy drugs, and is approved for the treatment of several types of cancer, including breast, colorectal, and gastric cancer..

5-FU works by inhibiting the enzyme thymidylate synthase (TS), which participes in the synthesis of DNA. This results in the death of cells that are actively dividing, since they are unable to produce new DNA. 5-FU is typically given as a continuous infusion over a period of several days, or as a part of a combination chemotherapy regimen..

Common side effects of 5-FU include nausea, vomiting, diarrhea, mouth sores, hair loss, and fatigue. More serious side effects can include low blood counts, inflammation of the liver or pancreas, and kidney damage. 5-FU can also increase the risk of developing secondary cancers, such as leukemia..

5-FU is an effective chemotherapy drug for many types of cancer, but it can also cause serious side effects. Patients should discuss the risks and benefits of 5-FU with their doctor before starting treatment..

3D structure

Cartesian coordinates

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

2D drawing

 

Gimeracil ZPLQIPFOCGIIHV-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Gimeracil

 

Molecule descriptors

 
IUPAC name5-chloro-4-hydroxy-1H-pyridin-2-one
InChI codeInChI=1S/C5H4ClNO2/c6-3-2-7-5(9)1-4(3)8/h1-2H,(H2,7,8,9)
InChI KeyZPLQIPFOCGIIHV-UHFFFAOYSA-N
SMILESO=c1cc(O)c(Cl)c[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.

  • 103766-25-2
  • 1349387-07-0
  • 2(1H)-Pyridinone, 5-chloro-4-hydroxy-
  • 5-CHLORO-4-HYDROXY-2-PYRIDONE
  • 5-CHLORO-4-HYDROXYPYRIDIN-2(1H)-ONE
  • 5-Chloro-2,4-dihydroxypyridine
  • 5-Chloro-2,4-pyridinediol
  • 5-Chloro-4-hydroxy-1H-pyridin-2-one
  • 5-Chloro-4-hydroxy-2(1H)-pyridinone
  • 5-Chloro-4-hydroxy-2(1H)-pyridone
  • 5-chloro-2-hydroxypyridin-4(1H)-one
  • 5-chloropyridine-2,4-diol
  • 766G252
  • A800802
  • A935098
  • AB01566858_01
  • AC-475
  • ACT04735
  • AMY2406
  • BCP05824
  • BCP9000727
  • CCG-266172
  • CS-1822
  • Cdhp compound
  • D01846
  • DB09257
  • DSSTox_CID_26799
  • DSSTox_GSID_46799
  • DSSTox_RID_81914
  • FT-0645353
  • GIMERACIL COMPONENT OF TEYSUNO
  • GIMERACIL IMPURITY 1
  • Gimeracil
  • Gimeracil (CDHP)
  • Gimeracil (JAN/INN)
  • HMS3655B15
  • HY-17469
  • KS-5133
  • MFCD08458352
  • NCGC00181011-01
  • NCGC00181011-02
  • Q-100034
  • Q22075887
  • S2055
  • SR-01000945072
  • SR-01000945072-1
  • STL452964
  • SW219483-1
  • SY029154
  • TEYSUNO COMPONENT GIMERACIL
  • UA8SE1325T
  • gimestat

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC13831809
  • CAS-103766-25-2
  • UNII-UA8SE1325T
  • AKOS006346735
  • AKOS015891515
  • AKOS026749993
  • DTXSID8046799
  • CHEMBL1730601
  • CHEBI:31652
  • Tox21_112661
  • Tox21_112661_1
  • SCHEMBL124438

Physico-Chemical properties

IUPAC name5-chloro-4-hydroxy-1H-pyridin-2-one
Molecular formulaC5H4ClNO2
Molecular weight145.544
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity34.10
LogP0.7
Topological polar surface area53.1

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.