An antibiotic
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Isomer(s)
34634Benomyl
Labeled Version(s)
26119Trimethoprim-d3
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Trimethoprim

Item No. 16473

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-pyrimidinediamine
CAS Number
738-70-5
Synonyms
  • NIH 204
  • NSC 106568
Molecular Formula
C14H18N4O3
Formula Weight
290.3
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 13 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:1): 0.5 mg/ml
λmax
287 nm
SMILES
COC1=C(OC)C(OC)=CC(CC2=CN=C(N)N=C2N)=C1
InChi Code
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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Trimethoprim is a synthetic antibiotic that inhibits dihydrofolate reductase (DHFR), which is necessary for the synthesis of purines, amino acids, and thymidylic acid.1,2 Trimethoprim shows prominent selectivity for bacterial DHFR over mammalian DHFR (IC50s = 5 and 30,000 nM, respectively).2 Formulations containing trimethoprim, commonly used in combination with sulfamethoxazole to minimize acquired resistance, have been used in the treatment of urinary tract infections.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lam, T., Hilgers, M.T., Cunningham, M.L., et al. Structure-based design of new dihydrofolate reductase antibacterial agents: 7-(Benzimidazol-1-yl)-2,4-diaminoquinazolines. J. Med. Chem. 57(3), 651-668 (2014).

    2. Schweitzer, B.I., Dicker, A.P., and Bertino, J.R. Dihydrofolate reductase as a therapeutic target. The FASEB Journal 4(8), 2441-2452 (1990).