MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 318596 | Name: Pyrimethamine
Featured New

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Pyrimethamine
Pyrimethamine
CAS#58-14-0 (free base)

Theoretical Analysis

MedKoo Cat#: 318596

Name: Pyrimethamine

CAS#: 58-14-0 (free base)

Chemical Formula: C12H13ClN4

Exact Mass: 248.0829

Molecular Weight: 248.71

Elemental Analysis: C, 57.95; H, 5.27; Cl, 14.25; N, 22.53

Price and Availability

Size Price Availability Quantity
500mg USD 110.00 Ready to ship
1g USD 150.00 Ready to ship
2g USD 200.00 Ready to ship
5g USD 450.00 2 weeks
10g USD 750.00 2 weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
7681-25-6 (phosphate) 58-14-0 (free base) 14720-95-7 (isethionate) 19085-09-7 (HCl) 53640-38-3 (sulfate)
Synonym
Pyrimethamine; BW 50-63; BW-50-63; BW50-63; Khloridin; Malocid; Malocide; NCI-C01683; NSC 3061; Pirimecidan; Pirimetamin; RP 4753; Tindurin; WR 297
IUPAC/Chemical Name
5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine
InChi Key
WKSAUQYGYAYLPV-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
CCC1=C(C(=NC(=N1)N)N)C2=CC=C(C=C2)Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#T21C02I23
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
Pyrimethamine interferes with tetrahydrofolic acid synthesis from folic acid by inhibiting the enzyme dihydrofolate reductase with an IC50 value of 15.4 nM.
In vitro activity:
Pyrimethamine may be a promising candidate agent for colorectal cancer treatment. Pyrimethamine could inhibit cell growth by inducing S phase arrest followed by cellular senescence in CRC cells, and the p38MAPK-p53 axis was probably involved in that effect. Reference: Mol Biol Rep. 2022 Jun;49(6):4281-4292. https://pubmed.ncbi.nlm.nih.gov/35262820/
In vivo activity:
This study demonstrated that pyrimethamine can be repurposed as a BAF complex inhibitor to reverse HIV-1 latency in vivo in people living with HIV-1. There was a rapid, modest, and significant increase in cell-associated unspliced HIV-1 RNA in response to pyrimethamine exposure, which persisted throughout treatment and follow-up. Reference: Sci Adv. 2023 Mar 17;9(11):eade6675. https://pubmed.ncbi.nlm.nih.gov/36921041/
Solvent mg/mL mM
Solubility
DMSO 10.0 40.20
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 248.71 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Dong H, Hu L, Li W, Shi M, He L, Wang C, Hu Y, Wang H, Wen C, Liu H, Yang X. Pyrimethamine inhibits cell growth by inducing cell senescence and boosting CD8+ T-cell mediated cytotoxicity in colorectal cancer. Mol Biol Rep. 2022 Jun;49(6):4281-4292. doi: 10.1007/s11033-022-07262-y. Epub 2022 Mar 9. PMID: 35262820; PMCID: PMC9262800. 2. Zhou X, Zhang J, Hu X, He P, Guo J, Li J, Lan T, Liu J, Peng L, Li H. Pyrimethamine Elicits Antitumor Effects on Prostate Cancer by Inhibiting the p38-NF-κB Pathway. Front Pharmacol. 2020 May 25;11:758. doi: 10.3389/fphar.2020.00758. PMID: 32523533; PMCID: PMC7261869. 3. Prins HAB, Crespo R, Lungu C, Rao S, Li L, Overmars RJ, Papageorgiou G, Mueller YM, Stoszko M, Hossain T, Kan TW, Rijnders BJA, Bax HI, van Gorp ECM, Nouwen JL, de Vries-Sluijs TEMS, Schurink CAM, de Mendonça Melo M, van Nood E, Colbers A, Burger D, Palstra RJ, van Kampen JJA, van de Vijver DAMC, Mesplède T, Katsikis PD, Gruters RA, Koch BCP, Verbon A, Mahmoudi T, Rokx C. The BAF complex inhibitor pyrimethamine reverses HIV-1 latency in people with HIV-1 on antiretroviral therapy. Sci Adv. 2023 Mar 17;9(11):eade6675. doi: 10.1126/sciadv.ade6675. Epub 2023 Mar 15. PMID: 36921041; PMCID: PMC10017042. 4. Sina S, Mohammad JM, Reza S, Anita M, Soudabeh E, Hadi M. Determination of parasitic burden in the brain tissue of infected mice in acute toxoplasmosis after treatment by fluconazole combined with sulfadiazine and pyrimethamine. Eur J Med Res. 2021 Jun 30;26(1):65. doi: 10.1186/s40001-021-00537-3. PMID: 34193287; PMCID: PMC8243906.
In vitro protocol:
1. Dong H, Hu L, Li W, Shi M, He L, Wang C, Hu Y, Wang H, Wen C, Liu H, Yang X. Pyrimethamine inhibits cell growth by inducing cell senescence and boosting CD8+ T-cell mediated cytotoxicity in colorectal cancer. Mol Biol Rep. 2022 Jun;49(6):4281-4292. doi: 10.1007/s11033-022-07262-y. Epub 2022 Mar 9. PMID: 35262820; PMCID: PMC9262800. 2. Zhou X, Zhang J, Hu X, He P, Guo J, Li J, Lan T, Liu J, Peng L, Li H. Pyrimethamine Elicits Antitumor Effects on Prostate Cancer by Inhibiting the p38-NF-κB Pathway. Front Pharmacol. 2020 May 25;11:758. doi: 10.3389/fphar.2020.00758. PMID: 32523533; PMCID: PMC7261869.
In vivo protocol:
1. Prins HAB, Crespo R, Lungu C, Rao S, Li L, Overmars RJ, Papageorgiou G, Mueller YM, Stoszko M, Hossain T, Kan TW, Rijnders BJA, Bax HI, van Gorp ECM, Nouwen JL, de Vries-Sluijs TEMS, Schurink CAM, de Mendonça Melo M, van Nood E, Colbers A, Burger D, Palstra RJ, van Kampen JJA, van de Vijver DAMC, Mesplède T, Katsikis PD, Gruters RA, Koch BCP, Verbon A, Mahmoudi T, Rokx C. The BAF complex inhibitor pyrimethamine reverses HIV-1 latency in people with HIV-1 on antiretroviral therapy. Sci Adv. 2023 Mar 17;9(11):eade6675. doi: 10.1126/sciadv.ade6675. Epub 2023 Mar 15. PMID: 36921041; PMCID: PMC10017042. 2. Sina S, Mohammad JM, Reza S, Anita M, Soudabeh E, Hadi M. Determination of parasitic burden in the brain tissue of infected mice in acute toxoplasmosis after treatment by fluconazole combined with sulfadiazine and pyrimethamine. Eur J Med Res. 2021 Jun 30;26(1):65. doi: 10.1186/s40001-021-00537-3. PMID: 34193287; PMCID: PMC8243906.
1: Asem L, Abdulia AG, Assuming PO, Abeka-Nkrumah G. The demand for intermittent preventive treatment of malaria in pregnancy using sulfadoxine-pyrimethamine in the Volta Region of Ghana. PLoS One. 2024 Sep 5;19(9):e0308321. doi: 10.1371/journal.pone.0308321. PMID: 39236029; PMCID: PMC11376531. 2: Adjei-Gyamfi S, Asirifi A, Peprah W, Abbey DA, Hamenoo KW, Zakaria MS, Mohammed O, Aryee PA. Anaemia at 36 weeks of pregnancy: Prevalence and determinants among antenatal women attending peri-urban facilities in a developing country, Ghana. PLOS Glob Public Health. 2024 Sep 5;4(9):e0003631. doi: 10.1371/journal.pgph.0003631. PMID: 39236023; PMCID: PMC11376517. 3: Li J, Wu K, Liu X, Yang D, Xie J, Wang Y, Liu K, Wang Z, Liu W, Jiang L. Anti-Toxoplasma gondii effects of XYP1-derived peptides and regulatory mechanisms of XYP1. Parasit Vectors. 2024 Sep 4;17(1):376. doi: 10.1186/s13071-024-06455-7. PMID: 39232817; PMCID: PMC11373213. 4: Azmi WA, Rizki AFM, Shidiq A, Djuardi Y, Artika IM, Siregar JE. Antimalarial drug sulfadoxine induces gametocytogenesis in Plasmodium berghei. Malar J. 2024 Sep 2;23(1):267. doi: 10.1186/s12936-024-05071-1. PMID: 39223522; PMCID: PMC11367840. 5: Mukala J, Mogere D, Kirira P, Kanoi B, Akisa V, Kobia F, Waweru H, Gitaka J. Knowledge, attitude and practices on intermittent preventive treatment in pregnant women with malaria: a mixed method facility-based study in Western Kenya. Pan Afr Med J. 2024 May 28;48:22. doi: 10.11604/pamj.2024.48.22.42196. PMID: 39220560; PMCID: PMC11364888. 6: Yi X, Liang JL, Wen P, Jia P, Feng SW, Liu SY, Zhuang YY, Guo YQ, Lu JL, Zhong SJ, Liao B, Wang Z, Shu WS, Li JT. Giant viruses as reservoirs of antibiotic resistance genes. Nat Commun. 2024 Aug 30;15(1):7536. doi: 10.1038/s41467-024-51936-z. PMID: 39214976; PMCID: PMC11364636. 7: Norouzi M, Javadi Mamaghani A, Seyyed Tabaei SJ, Niyyati M, Ghorbani- Bidkorpeh F. Evaluation of the Efficacy of Chitosan Nanoparticles based on Rosuvastatin in the Treatment of acute Toxoplasmosis : An In vitro and In vivo study. Microb Pathog. 2024 Aug 27:106897. doi: 10.1016/j.micpath.2024.106897. Epub ahead of print. PMID: 39208959. 8: Teixeira G, Brandão P, Lobo Ferreira AIMC, Abranches DO, Santos LMNBF, Ferreira O, Coutinho JAP. Designing type V deep eutectic solvents with antimalarial pharmaceutical ingredients. Eur J Pharm Biopharm. 2024 Aug 26:114463. doi: 10.1016/j.ejpb.2024.114463. Epub ahead of print. PMID: 39197540. 9: Ñacata I, Early AM, Boboy J, Neafsey DE, Sáenz FE. Effects of drug pressure and human migration on antimalarial resistance in circulating Plasmodium falciparum malaria parasites in Ecuador. Res Sq [Preprint]. 2024 Aug 16:rs.3.rs-4638168. doi: 10.21203/rs.3.rs-4638168/v1. PMID: 39184096; PMCID: PMC11343295. 10: Donovan L, Shafique M, Wharton-Smith A, Richardson S, Viganò E, Traore A, Compaoré C, Tounaikok N, Honoré B, Dingamtel N, Awokou F, Sewu E, Tougri G, Diar MSI, Atcha-Oubou T, Ward C, Baker K. Using the role model approach to optimise caregiver administration of sulfadoxine-pyrimethamine amodiaquine to children aged 3-59 months in Burkina Faso, Chad and Togo: findings from an evaluation. Malar J. 2024 Aug 24;23(1):255. doi: 10.1186/s12936-024-05067-x. PMID: 39180068; PMCID: PMC11344284. 11: Juliano JJ, Giesbrecht DJ, Simkin A, Fola AA, Lyimo BM, Pereus D, Bakari C, Madebe RA, Seth MD, Mandara CI, Popkin-Hall ZR, Moshi R, Mbwambo RB, Niaré K, MacInnis B, Francis F, Mbwambo D, Garimo I, Chacky F, Aaron S, Lusasi A, Molteni F, Njau RJA, Nhiga SL, Mohamed A, Bailey JA, Ishengoma DS. Prevalence of mutations associated with artemisinin partial resistance and sulfadoxine- pyrimethamine resistance in 13 regions in Tanzania in 2021: a cross-sectional survey. Lancet Microbe. 2024 Aug 14:100920. doi: 10.1016/S2666-5247(24)00160-5. Epub ahead of print. PMID: 39159629. 12: Adeojo OS, Fayehun O. Determinants of the optimal uptake of sulfadoxine- pyrimethamine doses for intermittent treatment of malaria in pregnancy in urban Nigeria. Sci Rep. 2024 Aug 17;14(1):19097. doi: 10.1038/s41598-024-52927-2. PMID: 39154035; PMCID: PMC11330452. 13: Diawara H, Healy SA, Mwakingwe-Omari A, Issiaka D, Diallo A, Traore S, Soumbounou IH, Gaoussou S, Zaidi I, Mahamar A, Attaher O, Fried M, Wylie BJ, Mohan R, Doan V, Doritchamou JYA, Dolo A, Morrison RD, Wang J, Hu Z, Rausch KM, Zeguime A, Murshedkar T, Kc N, Sim BKL, Billingsley PF, Richie TL, Hoffman SL, Dicko A, Duffy PE; PfSPZ Vaccine Study Team. Safety and efficacy of PfSPZ Vaccine against malaria in healthy adults and women anticipating pregnancy in Mali: two randomised, double-blind, placebo-controlled, phase 1 and 2 trials. Lancet Infect Dis. 2024 Aug 14:S1473-3099(24)00360-8. doi: 10.1016/S1473-3099(24)00360-8. Epub ahead of print. PMID: 39153490. 14: Koita K, Kayentao K, Worrall E, Van Eijk AM, Hill J. Community-based strategies to increase coverage of intermittent preventive treatment of malaria in pregnancy with sulfadoxine-pyrimethamine in sub-Saharan Africa: a systematic review, meta-analysis, meta-ethnography, and economic assessment. Lancet Glob Health. 2024 Sep;12(9):e1456-e1469. doi: 10.1016/S2214-109X(24)00228-6. PMID: 39151981. 15: Fola AA, Ciubotariu II, Dorman J, Mwenda MC, Mambwe B, Mulube C, Kasaro R, Hawela MB, Hamainza B, Miller JM, Bailey JA, Moss WJ, Bridges DJ, Carpi G. National genomic profiling of Plasmodium falciparum antimalarial resistance in Zambian children participating in the 2018 Malaria Indicator Survey. medRxiv [Preprint]. 2024 Aug 6:2024.08.05.24311512. doi: 10.1101/2024.08.05.24311512. PMID: 39148823; PMCID: PMC11326323. 16: Suwanakitti N, Talawanich Y, Vanichtanankul J, Taweechai S, Yuthavong Y, Kamchonwongpaisan S, Kongkasuriyachai D. folA thyA knockout E. coli as a suitable surrogate model for evaluation of antifolate sensitivity against PfDHFR-TS. Acta Trop. 2024 Oct;258:107360. doi: 10.1016/j.actatropica.2024.107360. Epub 2024 Aug 12. PMID: 39142549. 17: Jacques Z, Catherine T, Yacouba S, Kongnimissom SA, Ibrahim S, Blaise SL. Hyperimmune malarial splenomegaly in a malaria-endemic area of southwest Burkina Faso: case of Bobo-Dioulasso. BMC Infect Dis. 2024 Aug 13;24(1):823. doi: 10.1186/s12879-024-09671-9. PMID: 39138395; PMCID: PMC11323575. 18: Vydyam P, Chand M, Gihaz S, Renard I, Heffernan GD, Jacobus LR, Jacobus DP, Saionz KW, Shah R, Shieh H-M, Terpinski J, Zhao W, Cornillot E, Ben Mamoun C. In vitro efficacy of next-generation dihydrotriazines and biguanides against babesiosis and malaria parasites. Antimicrob Agents Chemother. 2024 Sep 4;68(9):e0042324. doi: 10.1128/aac.00423-24. Epub 2024 Aug 13. PMID: 39136469; PMCID: PMC11373198. 19: Thaloengsok S, Chaisatit C, Saingam P, Lertsethtakarn P, Spring M, Sriwichai S, Pholwat S, Guler JL, Houpt ER, Vesely BA. Prevalence and dynamics of antimalarial drug resistance mutations among the Plasmodium falciparum isolates in TAK Province, Thailand, during the period of 1998-2001. Antimicrob Agents Chemother. 2024 Sep 4;68(9):e0077924. doi: 10.1128/aac.00779-24. Epub 2024 Aug 13. PMID: 39136466; PMCID: PMC11373219. 20: Ogwang R, Osoti V, Wamae K, Ndwiga L, Muteru K, Ningwa A, Tuju J, Kinyanjui S, Osier F, Marsh K, Bejon P, Idro R, Ochola-Oyier LI. A retrospective analysis of P. falciparum drug resistance markers detects an early (2016/17) high prevalence of the k13 C469Y mutation in asymptomatic infections in Northern Uganda. Antimicrob Agents Chemother. 2024 Sep 4;68(9):e0157623. doi: 10.1128/aac.01576-23. Epub 2024 Aug 13. PMID: 39136465.