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Trimethoprim (Synonyms: NIH 204, NSC 106568)

Catalog No.GC10137

bacteriostatic antibiotic

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Trimethoprim Chemical Structure

Cas No.: 738-70-5

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10mM (in 1mL DMSO)
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500mg
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5g
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10g
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Sample solution is provided at 25 µL, 10mM.

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Quality Control & SDS

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Background

Trimethoprim is a bacteriostatic antibiotic used mainly in the prophylaxis and treatment of urinary tract infections.Target: DHFRTrimethoprim (TMP), an inhibitor of dihydrofolate reductase, decreases the level of tetrahydrofolate supplying one-carbon units for biosynthesis of nucleotides, proteins, and panthotenate. TMP caused induction of DnaK, DnaJ, GroEL, ClpB, and IbpA/B Hsps. Among these Hsps, IbpA/B were most efficiently induced by TMP and coaggregated with the insoluble proteins [1]. Trimethoprim binds to dihydrofolate reductase and inhibits the reduction of dihydrofolic acid (DHF) to tetrahydrofolic acid (THF). THF is an essential precursor in the thymidine synthesis pathway and interference with this pathway inhibits bacterial DNA synthesis. Trimethoprim's affinity for bacterial dihydrofolate reductase is several thousand times greater than its affinity for human dihydrofolate reductase. Sulfamethoxazole inhibits dihydropteroate synthetase, an enzyme involved further upstream in the same pathway. Trimethoprim and sulfamethoxazole are commonly used in combination due to their synergistic effects. This drug combination also reduces the development of resistance that is seen when either drug is used alone [2].

References:
[1]. Laskowska, E., et al., Trimethoprim induces heat shock proteins and protein aggregation in E. coli cells. Curr Microbiol, 2003. 47(4): p. 286-9.
[2]. Brogden, R.N., et al., Trimethoprim: a review of its antibacterial activity, pharmacokinetics and therapeutic use in urinary tract infections. Drugs, 1982. 23(6): p. 405-30.

Chemical Properties

Cas No. 738-70-5 SDF
Synonyms NIH 204, NSC 106568
Chemical Name 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Canonical SMILES COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N
Formula C14H18N4O3 M.Wt 290.32
Solubility ≥ 12.25mg/mL in DMSO Storage Store at 2-8°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 3.4445 mL 17.2224 mL 34.4448 mL
5 mM 0.6889 mL 3.4445 mL 6.889 mL
10 mM 0.3444 mL 1.7222 mL 3.4445 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 30 reference(s) in Google Scholar.)

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