Zomepirac

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

What is the Zomepirac?

The molecule Zomepirac presents a molecular formula of C15H14ClNO3 and its IUPAC name is 2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetic acid.

Zomepirac is a non-steroidal anti-inflammatory drug (NSAID) of the pyrazolone class. It was patented in 1966 and approved for medical use in 1978. It is typically used for the relief of pain and inflammation in conditions such as arthritis and musculoskeletal pain. It is also used to reduce fever..

Zomepirac exists as a generic drug. In the United States the brand names Zomax and Zomaxx are no longer available..

Zomepirac works by inhibiting the cyclooxygenase enzymes (COX-1 and COX-2) which are involved in the production of prostaglandins. Prostaglandins are mediators of pain and inflammation. By inhibiting their production, Zomepirac reduces pain and inflammation..

Zomepirac is typically well tolerated. The most common side effects are gastrointestinal, such as nausea, vomiting, diarrhea, and abdominal pain. Other common side effects include headache, dizziness, and rashes..

Zomepirac should not be used in people with a history of hypersensitivity to pyrazolone drugs, such as phenylbutazone. It should also be used with caution in people with liver or kidney impairment, as well as in people with a history of ulcers or gastrointestinal bleeding..

Zomepirac is a valuable medication for the relief of pain and inflammation. However, it should be used with caution in certain populations and it is important to be aware of the potential side effects..

3D structure

Cartesian coordinates

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

2D drawing

 

Zomepirac ZXVNMYWKKDOREA-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Zomepirac

 

Molecule descriptors

 
IUPAC name2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetic acid
InChI codeInChI=1S/C15H14ClNO3/c1-9-7-12(8-13(18)19)17(2)14(9)15(20)10-3-5-11(16)6-4-10/h3-7H,8H2,1-2H3,(H,18,19)
InChI KeyZXVNMYWKKDOREA-UHFFFAOYSA-N
SMILESCc1cc(CC(=O)O)n(C)c1C(=O)c1ccc(Cl)cc1

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.

  • 1,4-Dimethyl-5-p-chlorobenzoylpyrrole-2-acetic acid
  • 1H-Pyrrole-2-acetic acid, 5-(4-chlorobenzoyl)-1,4-dimethyl-
  • 1H-Pyrrole-2-aceticacid, 5-(4-chlorobenzoyl)-1,4-dimethyl-
  • 2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetic acid
  • 33369-31-2
  • 5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrole-2-acetic acid
  • 5-(p-chlorobenzoyl)-1,4-dimethyl-pyrrole-2-acetic acid
  • 5-(p-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetic acid
  • 5-(rho-chlorobenzoyl)-1,4-dimethylpyrrole-2-acetic acid
  • 822G987U9J
  • AB00052126_03
  • BDBM50027952
  • BPBio1_000944
  • BSPBio_000858
  • BSPBio_002038
  • CCG-39056
  • DA-06775
  • DB04828
  • DivK1c_000953
  • FT-0708860
  • HMS1921K11
  • HMS2092E04
  • HMS502P15
  • IDI1_000953
  • KBio1_000953
  • KBio2_000786
  • KBio2_003354
  • KBio2_005922
  • KBio3_001538
  • KBioGR_000905
  • KBioSS_000786
  • NCGC00094811-01
  • NCGC00094811-02
  • NCGC00094811-03
  • NCGC00094811-04
  • NINDS_000953
  • NSC757379
  • Pharmakon1600-01500615
  • Prestwick0_000779
  • Prestwick1_000779
  • Prestwick2_000779
  • Prestwick3_000779
  • Q4024685
  • SBI-0051557.P002
  • SPECTRUM1500615
  • SR-05000001739
  • SR-05000001739-1
  • ZOM
  • Zomepirac
  • Zomepirac; AIF; CE0; CorrDec
  • Zomepiracum
  • [5-(4-Chlorobenzoyl)-1,4-dimethyl-1H-pyrrol-2-yl]acetic acid
  • zomepirac
  • {5-[(4-chlorophenyl)carbonyl]-1,4-dimethyl-1H-pyrrol-2-yl}acetic acid

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC57537
  • UNII-822G987U9J
  • BRD-K81326768-001-02-4
  • BRD-K81326768-236-03-4
  • DTXSID9023754
  • CHEMBL19490
  • CHEBI:35859
  • EINECS 251-474-2
  • SPBio_000950
  • SPBio_002797
  • SCHEMBL25735
  • Spectrum_000306
  • Spectrum2_000955
  • Spectrum3_000589
  • Spectrum4_000383
  • Spectrum5_001427

Physico-Chemical properties

IUPAC name2-[5-(4-chlorobenzoyl)-1,4-dimethylpyrrol-2-yl]acetic acid
Molecular formulaC15H14ClNO3
Molecular weight291.73
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity77.09
LogP2.8
Topological polar surface area59.3

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.