(R)-Pemetrexed

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

What is the (R)-Pemetrexed?

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

Pemetrexed (INN) /ˈpɛmətrɛksɛd/ is a chemotherapy drug used in the treatment of cancer. It is a multitargeted antifolate that inhibits thymidylate synthase, dihydrofolate reductase, and glycinamide ribonucleotide formyltransferase. It is marketed by Eli Lilly and Company under the brand name Alimta..

Pemetrexed is a multitargeted antifolate. It inhibits thymidylate synthase, dihydrofolate reductase, and glycinamide ribonucleotide formyltransferase..

Pemetrexed has shown activity against a number of malignancies, including non-small cell lung cancer, mesothelioma, and head and neck cancer..

Pemetrexed is typically given as a single agent, but has also been studied in combination with other drugs, such as cisplatin..

The most common side effects of pemetrexed include fatigue, nausea, vomiting, diarrhea, and decreased appetite. More serious side effects can include low white blood cell counts, which can increase the risk of infection, and kidney damage..

Pemetrexed is an important treatment option for patients with cancer. It is generally well tolerated, with manageable side effects..

3D structure

Cartesian coordinates

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

2D drawing

 

(R)-Pemetrexed WBXPDJSOTKVWSJ-CYBMUJFWSA-N chemical compound 2D structure molecule svg
(R)-Pemetrexed

 

Molecule descriptors

 
IUPAC name(2R)-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-/m1/s1
InChI KeyWBXPDJSOTKVWSJ-CYBMUJFWSA-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.

  • (2R)-2-((4-(2-(2-Amino-4-oxo-3H,4H,7H-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)phenyl)formamido)pentanedioic acid
  • (2R)-2-((4-(2-(2-Amino-4-oxo-4,7-dihydro-1H-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)amino)pentanedioic acid
  • (2R)-2-[[4-[2-(2-amino-4-oxo-1,7-dihydropyrrolo[4,5-e]pyrimidin-5-yl)ethyl]benzoyl]amino]pentanedioic acid
  • (2R)-2-{[4-(2-{2-amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioic acid
  • (2R)-2-{[4-(2-{2-amino-4-oxo-3H,4H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}ethyl)phenyl]formamido}pentanedioicacid
  • (4-(2-(2-Amino-4-oxo-4,7-dihydro-3H-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)-D-glutamic acid
  • (D)-Pemetrexed; Pemetrexed R-Isomer; Pemetrexed BP Impurity E; (2R)-2-[[[4-[2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl]phenyl]carbonyl]amino]pentanedioic acid
  • (R)-2-(4-(2-(2-amino-4-oxo-4,7-dihydro-1H-pyrrolo[2,3-d]pyrimidin-5-yl)ethyl)benzamido)pentanedioic acid? (Pemetrexed Impurity pound(c)
  • (R)-2-[[4-[2-[(2-Amino-3,7-dihydro-4-oxo-4H-pyrrolo[2,3-d]pyrimidin)-5-yl]ethyl]benzoyl]amino]pentanedioic acid
  • (R)-Pemetrexed
  • 182009-04-7
  • AM84464
  • CS-0164029
  • D-Glutamic acid, N-(4-(2-(2-amino-4,7-dihydro-4-oxo-3H-pyrrolo(2,3-d)pyrimidin-5-yl)ethyl)benzoyl)-
  • FG8Q47888S
  • GTPL6837
  • MLS006011486
  • Pemetrexed (R) enantiomer
  • Pemetrexed EP Impurity E
  • Pemetrexed, (R)-
  • SMR004703269
  • Z1691545275

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1851132
  • UNII-FG8Q47888S
  • AKOS015895961
  • BRD-K55395145-001-01-7
  • DTXSID70861342
  • CHEBI:95021
  • SCHEMBL7969

Physico-Chemical properties

IUPAC name(2R)-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.