Structure via PubChem · Public domain (PubChem)
pyrimethamine
Sign in to saveAlso known as Daraprim®, GNF-Pf-5586, TCMDC-125860, Primethamine, Chloridyn, Chloridine, CD, Ethylpyrimidine
Pyrimethamine, sold under the brand name Daraprim among others, is a medication used with leucovorin (leucovorin is used to decrease side effects of pyrimethamine; it does not have intrinsic anti-parasitic activity) to treat the parasitic diseases toxoplasmosis and cystoisosporiasis. It is also used with dapsone as a second-line option to prevent Pneumocystis jiroveci pneumonia in people with HIV/AIDS. It was previously used for malaria but is no longer recommended due to resistance. Pyrimethamine is taken by mouth.
Key facts
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 464377204
- Drug.image
- Pyrimethamine2DACS.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 150px
- Drug.image2
- Pyrimethamine 3D.png
- Drug.image_class2
- bg-transparent
- Drug.caption
- Above: molecular structure of pyrimethamine Below: 3D representation of a pyrimethamine molecule
- Drug.tradename
- Daraprim, others
- Drug.MedlinePlus
- a601050
- Drug.DailyMedID
- Pyrimethamine
- Drug.licence_US
- Pyrimethamine
- Drug.pregnancy_AU
- B3
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- P01
- Drug.ATC_suffix
- BD01
- Drug.ATC_supplemental
- (combinations)
- Drug.legal_AU
- S4
via Wikipedia infobox
Chemical data
- Formula
- C12H13ClN4
- Molecular weight
- 248.71 g/mol
- IUPAC name
- 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
- SMILES
- CCC1=C(C(=NC(=N1)N)N)C2=CC=C(C=C2)Cl
- InChIKey
- WKSAUQYGYAYLPV-UHFFFAOYSA-N
- XLogP
- 2.7
- Polar surface area
- 77.8 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
7,680 papers- The multifaceted antineoplastic role of pyrimethamine against human malignancies.IUBMB life · 2022
- Pyrimethamine poisoning.British medical journal · 1973
- Dihydroartemisinin-piperaquine plus sulfadoxine-pyrimethamine versus either drug alone for intermittent preventive treatment of malaria in pregnancy: A double-blind, randomized, controlled phase 3 trial from Uganda.PLoS medicine · 2025
- PYRIMETHAMINE.Journal of the American Medical Association · 1956
- Safety and toxicity of sulfadoxine/pyrimethamine: implications for malaria prevention in pregnancy using intermittent preventive treatment.Drug safety · 2007
via PubMed
~11 min read
Encyclopedic overview
19 sectionsContents
- Medical uses
- Toxoplasmosis
- Pregnancy consideration
- Malaria
- Contraindications
- Side effects
- Interactions
- Mechanism of action
- Other medications
- Mechanism of resistance
- History
- Society and culture
- Economics
- United States
- Other countries
- Research
- See also
- References
- External links
Pyrimethamine, sold under the brand name Daraprim among others, is a medication used with leucovorin (leucovorin is used to decrease side effects of pyrimethamine; it does not have intrinsic anti-parasitic activity) to treat the parasitic diseases toxoplasmosis and cystoisosporiasis. It is also used with dapsone as a second-line option to prevent Pneumocystis jiroveci pneumonia in people with HIV/AIDS. It was previously used for malaria but is no longer recommended due to resistance. Pyrimethamine is taken by mouth.
Common side effects include gastrointestinal upset, severe allergic reactions, and bone marrow suppression. It should not be used by people with folate deficiency that has resulted in anemia. There is concern that it may increase the risk of cancer. While occasionally used in pregnancy it is unclear if pyrimethamine is safe for the baby. Pyrimethamine is classified as a folic acid antagonist. It works by inhibiting folic acid metabolism and therefore the making of DNA.
Excerpted from Wikipedia’s “pyrimethamine” article, available under the CC BY-SA 4.0 licence.