Pyrimethamine

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Structural formula
Structural formula of pyrimethamine
General
Non-proprietary name Pyrimethamine
other names
  • 5- (4-chlorophenyl) -6-ethyl-2,4-pyrimidinediamine
  • 5- (4-chlorophenyl) -6-ethylpyrimidine-2,4-diamine ( IUPAC )
Molecular formula C 12 H 13 ClN 4
Brief description

Crystals

External identifiers / databases
CAS number 58-14-0
EC number 200-364-2
ECHA InfoCard 100,000,331
PubChem 4993
DrugBank DB00205
Wikidata Q421072
Drug information
ATC code

P01 BD01

Drug class

Antiprotozoal drugs

properties
Molar mass 248.71 g · mol -1
Physical state

firmly

Melting point

238-242 ° C

pK s value

7.0

solubility

almost insoluble in water, slightly soluble in cold, readily soluble in boiling ethanol

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

Caution

H and P phrases H: 302
P: no P-phrases
Toxicological data

440 mg kg −1 ( LD 50ratoral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pyrimethamine is a drug in the diaminopyrimidine group and is used to treat infections with protozoa . A typical indication is toxoplasmosis including congenital (congenital) infections caused by toxoplasma. It is contained in the preparation Daraprim (manufacturer: GlaxoSmithKline ) in Germany and Switzerland . Pyrimethamine should always be given in combination with a sulfonamide . Pyrimethamine inhibits dihydrofolate reductase , an enzyme that is necessary for the supply of the vital vitamin folic acid .

history

Daraprim was developed by Nobel Prize Winner Gertrude Belle Elion (1988) - together with George Herbert Hitchings . In 1952, Wellcome launched the malaria drug Daraprim .

In 2015, the US company Turing Pharmaceuticals, which was founded this year, bought the marketing rights for Daraprim for the US. It caused a scandal in the US because it increased the retail price 55 times.

Individual evidence

  1. a b c d e entry on pyrimethamine. In: Römpp Online . Georg Thieme Verlag, accessed on April 13, 2014.
  2. a b Datasheet Pyrimethamine from Sigma-Aldrich , accessed on May 14, 2017 ( PDF ).
  3. Instructions for use Daraprim ( Memento of the original dated February 5, 2016 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. from GSK's health website, accessed February 5, 2016. @1@ 2Template: Webachiv / IABot / gesundheit.gsk.com
  4. The history of GSK on the GSK website, accessed on February 5, 2016.
  5. Price for drug increased from 13.50 to 750 dollars Die Welt from September 22, 2015, accessed on February 5, 2016.
  6. Pharma manager Shkreli grins the congress at SPON on February 5, 2016, accessed on February 5, 2016.