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SBR00024

Sigma-Aldrich

Trimethoprim Ready Made Solution

25 mg/mL in DMSO

Synonym(s):

Trimethoprim Ready Made Solution

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About This Item

Empirical Formula (Hill Notation):
C14H18N4O3
Molecular Weight:
290.32
UNSPSC Code:
51285203
NACRES:
NA.76

biological source

synthetic

Assay

≥98% (HPLC)

form

liquid

concentration

25 mg/mL in DMSO

color

colorless to faint yellow

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria

Mode of action

DNA synthesis | interferes
enzyme | inhibits

storage temp.

−20°C

InChI

1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18

InChI key

IEDVJHCEMCRBQM-UHFFFAOYSA-N

General description

Trimethoprim, an aminopyrimidine antibiotic belonging to the methoxybenzenes group, exhibits activity against a broad spectrum of both gram-negative and gram-positive aerobic bacteria. As a synthetic derivative of pyrimidine, it plays a multifaceted role as an inhibitor, xenobiotic, and allergen, featuring antibacterial, diuretic, and antiprotozoal properties. Trimethoprim selectively targets dihydrofolate reductase (DHFR), diminishing the levels of tetrahydrofolate that supply one-carbon units crucial for biosynthesis processes, including nucleotides, proteins, and panthotenate, especially in prokaryotic microorganisms.

Additionally, it is frequently employed in combination with sulfamethoxazole (sc-208405) to effectively inhibit the growth of Staphylococcus aureus, functioning as a dihydrofolate reductase inhibitor. This versatile compound finds applications in metabolomics, cell biology, and biochemical research.

Application

Trimethoprim is used at a final concentration of ~4μg/mL for antibacterial activty.

Biochem/physiol Actions

Mode of Action: Trimethoprim is an inhibitor of bacterial dihydrofolate reductase (DHFR), interfering with the conversion of dihydrofolate (DHF) to tetrahydrofolate (THF). THF is an essential precursor in the thymidine synthesis pathway, interference with this pathway inhibits bacterial DNA synthesis. Trimethoprim′s affinity for bacterial DHFR is several thousand times greater than its affinity for human DHFR.

Activity Spectrum: Effective against Gram-negative bacteria, Gram-positive bacteria, and mycobacteria

Some of the pathogens that trimethoprim can be effective against include:
  • Escherichia coli (E. coli)
  • Staphylococcus aureus (including methicillin-resistant Staphylococcus aureus or MRSA)
  • Streptococcus pneumoniae
  • Haemophilus influenzae
  • Enterococcus faecalis
  • Klebsiella species
  • Proteus species

Features and Benefits

  • High-quality antibiotic suitable for multiple research applications
  • Ideal for Cell Biology, Metabolomics, and Biochemical research.

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Storage Class Code

10 - Combustible liquids

WGK

WGK 2

Flash Point(F)

188.6 °F

Flash Point(C)

87 °C


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Stephen Hawser et al.
Biochemical pharmacology, 71(7), 941-948 (2005-12-20)
Although only a few DHFR inhibitors have progressed as antibiotics to the market there is much renewed interest in the discovery and development of new generation DHFR inhibitors as antibacterial agents. This article describes the success in exploiting DHFR as
The binding of trimethoprim to bacterial dihydrofolate reductase.
D J Baker et al.
FEBS letters, 126(1), 49-52 (1981-04-06)
R N Brogden et al.
Drugs, 23(6), 405-430 (1982-06-01)
Trimethoprim, which has been widely available for several years in combination with sulphamethoxazole as co-trimoxazole, is now available for use alone in the treatment of acute uncomplicated urinary tract infections. Trimethoprim, which is active against a wide range of Gram-positive
Mahamadou A Thera et al.
The Journal of infectious diseases, 192(10), 1823-1829 (2005-10-20)
Trimethoprim-sulfamethoxazole (TS) prophylaxis is recommended for persons living with human immunodeficiency virus infection and acquired immunodeficiency syndrome in Africa. TS and the antimalarial combination sulfadoxine-pyrimethamine (SP) share mechanisms of action and resistance patterns, and concerns about the impact of TS
A Binelli et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 150(3), 329-336 (2009-06-02)
A battery of eight biomarkers was applied in the freshwater mussel Dreissena polymorpha to evaluate potential sub-lethal effects of the antimicrobial trimethoprim (TMP, 5-[3,4,5-trimethoxybenzyl]pyrimidine-2,4-diamine). Mussels were exposed for 96 h to increasing concentrations (1, 3, 10 nM) of TMP in

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