Pyrimethamine

• CAT Number: A000474
• CAS Number: 58-14-0
• Molecular Formula: C12H13ClN4
• Molecular Weight: 248.7
• Purity: ≥95%
• Target: DHFR
• Solubility: Soluble in DMSO > 10 mM
• Storage: -20°C
• InChI: 1S/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)
• InChIKey: WKSAUQYGYAYLPV-UHFFFAOYSA-N
• SMILES: CCC1=C(C(=NC(=N1)N)N)C2=CC=C(C=C2)Cl

Pyrimethamine is an antiprotozoal agent that inhibits the protozoal enzyme dihydrofolate reductase. Pyrimethamine prevents the production of tetrahydrofolic acid, an essential coenzyme involved in DNA and RNA synthesis. Pyrimethamine is a dihydrofolate reductase inhibitor antimalarial. The mechanism of action of pyrimethamine is as a Dihydrofolate Reductase Inhibitor. Pyrimethamine has also been found to limit the expression of the superoxide dismutase 1 gene, a protein involved in amyotrophic lateral sclerosis.

Reference

1: Salman S, Davis TME. Regarding /Lactation Status and Studies of Pyrimethamine
Pharmacokinetics in Pregnancy/. CPT Pharmacometrics Syst Pharmacol. 2017 Oct 24.
doi: 10.1002/psp4.12257. [Epub ahead of print] PubMed PMID: 29064165.

2: de Kock M, Tarning J, Barnes KI, Denti P. Response to /Lactation Status and
Studies of Pyrimethamine Pharmacokinetics in Pregnancy/. CPT Pharmacometrics Syst
Pharmacol. 2017 Oct 20. doi: 10.1002/psp4.12256. [Epub ahead of print] PubMed
PMID: 29052341.

3: Elsby R, Chidlaw S, Outteridge S, Pickering S, Radcliffe A, Sullivan R, Jones
H, Butler P. Mechanistic in vitro studies confirm that inhibition of the renal
apical efflux transporter multidrug and toxin extrusion (MATE) 1, and not altered
absorption, underlies the increased metformin exposure observed in clinical
interactions with cimetidine, trimethoprim or pyrimethamine. Pharmacol Res
Perspect. 2017 Oct;5(5). doi: 10.1002/prp2.357. PubMed PMID: 28971610; PubMed
Central PMCID: PMC5625161.

4: Ben-Harari RR, Goodwin E, Casoy J. Adverse Event Profile of
Pyrimethamine-Based Therapy in Toxoplasmosis: A Systematic Review. Drugs R D.
2017 Sep 6. doi: 10.1007/s40268-017-0206-8. [Epub ahead of print] Review. PubMed
PMID: 28879584.

5: Khan MW, Saadalla A, Ewida AH, Al-Katranji K, Al-Saoudi G, Giaccone ZT,
Gounari F, Zhang M, Frank DA, Khazaie K. The STAT3 inhibitor pyrimethamine
displays anti-cancer and immune stimulatory effects in murine models of breast
cancer. Cancer Immunol Immunother. 2017 Sep 5. doi: 10.1007/s00262-017-2057-0.
[Epub ahead of print] PubMed PMID: 28875329.

6: Owusu-Boateng I, Anto F. Intermittent preventive treatment of malaria in
pregnancy: a cross-sectional survey to assess uptake of the new
sulfadoxine-pyrimethamine five dose policy in Ghana. Malar J. 2017 Aug
10;16(1):323. doi: 10.1186/s12936-017-1969-7. PubMed PMID: 28797296; PubMed
Central PMCID: PMC5553599.

7: Okell LC, Griffin JT, Roper C. Mapping sulphadoxine-pyrimethamine-resistant
Plasmodium falciparum malaria in infected humans and in parasite populations in
Africa. Sci Rep. 2017 Aug 7;7(1):7389. doi: 10.1038/s41598-017-06708-9. PubMed
PMID: 28785011; PubMed Central PMCID: PMC5547055.

8: Abugri DA, Witola WH, Russell AE, Troy RM. In vitro activity of the
interaction between taxifolin (dihydroquercetin) and pyrimethamine against
Toxoplasma gondii. Chem Biol Drug Des. 2017 Jul 11. doi: 10.1111/cbdd.13070.
[Epub ahead of print] PubMed PMID: 28696589.

9: Sharma A, Jaiswal S, Shukla M, Lal J. Effect of arteether and pyrimethamine
coadministration on the pharmacokinetic and pharmacodynamic profile of
ormeloxifene. Naunyn Schmiedebergs Arch Pharmacol. 2017 Jul 8. doi:
10.1007/s00210-017-1401-4. [Epub ahead of print] PubMed PMID: 28689253.

10: Chhonker YS, Bhosale VV, Sonkar SK, Chandasana H, Kumar D, Vaish S, Choudhary
SC, Bhadhuria S, Sharma S, Singh RK, Jain GK, Vaish AK, Gaur SPS, Bhatta RS.
Assessment of Clinical Pharmacokinetic Drug-Drug Interaction of Antimalarial
Drugs α/β-Arteether and Sulfadoxine-Pyrimethamine. Antimicrob Agents Chemother.
2017 Aug 24;61(9). pii: e02177-16. doi: 10.1128/AAC.02177-16. Print 2017 Sep.
PubMed PMID: 28674061; PubMed Central PMCID: PMC5571326.