Pemetrexed

from Wikipedia, the free encyclopedia
Structural formula
Structure of pemetrexed
General
Non-proprietary name Pemetrexed
other names

( S ) -2- {4- [2- (4-Amino-2-oxo-3,5,7-triazabicyclo- [4.3.0] nona-3,8,10-trien-9-yl) -ethyl ] benzoyl} aminopentanedioic acid

Molecular formula C 20 H 21 N 5 O 6
External identifiers / databases
CAS number 137281-23-3
EC number 680-625-9
ECHA InfoCard 100.205.735
PubChem 446556
DrugBank DB00642
Wikidata Q415220
Drug information
ATC code

L01 BA04

Drug class
Mechanism of action

Inhibition of the enzymes

  • Thymidylate Synthase (TS)
  • Dihydrofolate reductase (DHFR)
  • Glycinamide Ribonucleotide Formyl Transferase (GARFT)
properties
Molar mass 427.41 g mol −1 (pemetrexed)
safety instructions
Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances
07 - Warning 08 - Dangerous to health

danger

H and P phrases H: 302-351-360
P: ?
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pemetrexed (trade name: Alimta ® , manufacturer: Lilly ) is a drug that is used as a cytostatic ( antimetabolite ).

In finished medicinal products, pemetrexed is used as a monohydrate of the free acid as well as the disodium salt, the hemipentahydrate and the heptahydrate of the disodium salt.

Princeton chemist Edward C. Taylor played a key role in the development.

Mechanism of action

As an analogue of folic acid , the active ingredient intervenes at several points in the DNA and RNA nucleotide synthesis and unfolds its effect by inhibiting the enzymes:

Indications

Pemetrexed is used both in monotherapy and in combination with cisplatin for numerous indications. As a monotherapy, it is used to treat locally advanced or metastatic non-small cell lung cancer (NSCLC) (second-line therapy). Combination therapy with cisplatin is an option for the treatment of advanced non-small cell lung cancer (NSCLC) (first-line therapy) and inoperable malignant pleural mesothelioma (MPM) (first-line therapy).

Side effects

The following side effects include (selection) changes in the blood count, fever , hair loss , reddening and scaling of the skin, as well as nausea and vomiting .

Contraindications

Contraindications are the simultaneous vaccination against yellow fever and pregnancy and breastfeeding .

Individual evidence

  1. ↑ A. Russ, S. Endres: Arzneimittelpocket Plus 2008. 4th edition. Börm Bruckmeier Verlag, 2007, ISBN 978-3-89862-287-5 .
  2. ↑ a b c Company information from Lilly .
  3. ↑ Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of (2S) -2 - ({4- [2- (2-amino-4-oxo-4,7-dihydro-1Hpyrrolo [2,3-d] pyrimidine-5) is shown, which is derived from a self-classification by the distributor -yl) ethyl] benzoyl} amino) -pentanedioic acid in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on December 3, 2018.
  4. ↑ External identifiers or database links for disodium pemetrexed : CAS number: 150399-23-8, EC number: 604-733-2, ECHA InfoCard: 100.122.913 , PubChem : 6918197 , Wikidata : Q59389120 .
  5. ↑ External identifiers of or database links for disodium pemetrexed hemipentahydrate : CAS number: 357166-30-4, EC number: 814-356-7, ECHA InfoCard: 100.247.327 , PubChem : 53486390 , ChemSpider : 24582072 , Wikidata : Q27277627 .
  6. ↑ External identifiers or database links to disodium pemetrexed heptahydrate : CAS number: 357166-29-1, EC number: 639-569-0, ECHA InfoCard: 100.167.223 , PubChem : 23725084 , ChemSpider : 23089153 , DrugBank : DB00642 , Wikidata : Q27132757 .
  7. ↑ Entry on pemetrexed in the DrugBank of the University of Alberta , accessed on December 3, 2018.
  8. ↑ a b c ABDA database (as of August 14, 2008) of DIMDI .