Pemetrexed

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

What is the Pemetrexed?

The molecule Pemetrexed presents a molecular formula of C20H21N5O6 and its IUPAC name is (2S)-2-[[4-[2-(2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid.

Pemetrexed (brand names Alimta and Pemetrexed Disodium Hexahydrate) is a chemotherapy medication used to treat cancer. It is a member of the class of drugs known as antifolates. It works by inhibiting the production of folic acid, which is needed for cell growth..

Pemetrexed was approved by the U.S. Food and Drug Administration (FDA) in 2004 for the treatment of mesothelioma, a type of cancer that is almost always fatal. It is also approved for the treatment of non-small cell lung cancer (NSCLC)..

Pemetrexed is typically given as an intravenous (IV) infusion over the course of 10 minutes. The usual dose is 500 mg/m2 of body surface area. The infusion can be given every 21 days..

Common side effects of pemetrexed include fatigue, nausea, vomiting, diarrhea, hair loss, and low blood cell counts. Pemetrexed can also cause inflammation of the lungs (pneumonitis), which can be fatal..

Pemetrexed is a powerful chemotherapy drug that can be effective in treating certain types of cancer. However, it can also cause serious side effects. Patients should be sure to discuss the risks and benefits of pemetrexed with their doctor before starting treatment..

3D structure

Cartesian coordinates

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

2D drawing

 

Pemetrexed WBXPDJSOTKVWSJ-ZDUSSCGKSA-N chemical compound 2D structure molecule svg
Pemetrexed

 

Molecule descriptors

 
IUPAC name(2S)-2-[[4-[2-(2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid
InChI codeInChI=1S/C20H21N5O6/c21-20-24-16-15(18(29)25-20)12(9-22-16)6-3-10-1-4-11(5-2-10)17(28)23-13(19(30)31)7-8-14(26)27/h1-2,4-5,9,13H,3,6-8H2,(H,23,28)(H,26,27)(H,30,31)(H4,21,22,24,25,29)/t13-/m0/s1
InChI KeyWBXPDJSOTKVWSJ-ZDUSSCGKSA-N
SMILESNc1nc2[nH]cc(CCc3ccc(C(=O)N[C@@H](CCC(=O)O)C(=O)O)cc3)c2c(=O)[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.

  • (2S)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid
  • (2S)-2-[[4-[2-(2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid
  • (S)-2-(4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo-[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid
  • (S)-2-(4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid
  • (S)-2-(4-(2-(2-amino-4-oxo-4,7-dihydro-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid
  • 04Q9AIZ7NO
  • 1006872-74-7
  • 137281-23-3
  • 1juj
  • 2-{4-[2-(2-AMINO-4-OXO-4,7-DIHYDRO-3H-PYRROLO[2,3-D]PYRIMIDIN-5-YL)-ETHYL]-BENZOYLAMINO}-PENTANEDIOIC ACID
  • 281P233
  • A807228
  • AB01273937-01
  • AC-1701
  • AS-30680
  • Alimta
  • BDBM50027656
  • BP164240
  • CS-1297
  • D07472
  • DB-024764
  • DB00642
  • HSDB 7316
  • HY-10820
  • J-502393
  • L-Glutamic acid, N-(4-(2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)-
  • L-Glutamic acid,3-d]pyrimidin-5-yl]ethyl]benzoyl]-
  • LY 231514
  • LY-2315
  • LY-231514
  • LY231514
  • LYA
  • N-(4-(2-(2-AMINO-4,7-DIHYDRO-4-OXO-1H-PYRROLO(2,3-D)PYRIMIDIN-5-YL)ETHYL)BENZOYL)-L-GLUTAMIC ACID
  • N-(4-(2-(2-Amino-3,4-dihydro-4-oxo-7H-pyrrolo(2,3-d)pyrimdin-5-yl)ethyl)benzoyl)glutamic acid
  • N-(4-[2-(2-amino-4,7-Dihydro-4-Oxo-1H-Pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl)-L-Glutamic Acid
  • N-(P-(2-(2-AMINO-4,7-DIHYDRO-4-OXO-1H-PYRROLO(2,3-D)PYRIMIDIN-5-YL)ETHYL)BENZOYL)-L-GLUTAMATE
  • N-({4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]phenyl}carbonyl)-L-glutamic acid
  • N-[4-[2(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo [2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid
  • N-[4-[2(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid
  • N-[4-[2-(2-Amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid disodium salt;Pemetrexed
  • N-[4-[2-(2-amino-3,4-dihydro-4-oxo-7h-pyrrolo[2,3-d]pyrimi-din-5-yl)ethyl]benzoyl]l-glutamic acid
  • N-[4-[2-(2-amino-4,7-dihydro-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid
  • N-[4-[2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]-L-glutamic acid
  • N-[4-[2-[2-Amino-4,7-dihydro-4-oxo-3H-pyrrolo[2,3-d]pyrimidin-5-yl]ethyl]benzoyl]glutamic acid
  • N-{4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl}-L-glutamic acid
  • NCGC00166414-11
  • NCGC00167517-01
  • NCGC00242485-01
  • NSC-698037
  • NSC698037
  • P2288
  • PEMFEXY
  • Pemetrexed
  • Pemetrexed (INN)
  • Pemetrexed disodium
  • Pemetrexed- Bio-X
  • Q415220
  • US9422297, Pemetrexed
  • s5971

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1540998
  • UNII-04Q9AIZ7NO
  • AKOS015896253
  • AKOS016842348
  • DTXSID2048329
  • CHEMBL225072
  • CHEBI:63616
  • SCHEMBL7968

Physico-Chemical properties

IUPAC name(2S)-2-[[4-[2-(2-amino-4-oxo-3,7-dihydropyrrolo[2,3-d]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid
Molecular formulaC20H21N5O6
Molecular weight427.411
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity111.15
LogP1.6
Topological polar surface area191.3

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.