738-70-5 Trimethoprim AKSci J10046
 
 
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  J10046    AKSci Reference Standard
Trimethoprim, 99% (HPLC)
 
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine
IDENTITY
CAS Number:738-70-5
MDL Number:MFCD00036761
MF:C14H18N4O3
MW:290.32
EINECS:212-006-2
SPECIFICATIONS & PROPERTIES
Min. Purity Spec:99% (HPLC)
Physical Form (at 20°C):Solid
Melting Point:199-203°C
Long-Term Storage:Store long-term at 2-8°C
DOT/IATA TRANSPORT INFORMATION
Not hazardous material

BIOLOGICAL INFO
Solubility:DMSO
Application(s):Pyrimidine inhibitor of dihydrofolate reductase

REVIEW
 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 dihydrofolate synthetase (aka 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.

REFERENCES
[1]Brumfitt W, Hamilton-Miller JM: Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines. J Chemother. 1993 Dec;5(6):465-9.
[2] Brumfitt W, Hamilton-Miller JM: Limitations of and indications for the use of co-trimoxazole. J Chemother. 1994 Feb;6(1):3-11.
[3] Bean DC, Livermore DM, Papa I, Hall LM: Resistance among Escherichia coli to sulphonamides and other antimicrobials now little used in man. J Antimicrob Chemother. 2005 Nov;56(5):962-4. Epub 2005 Sep 8.
[4] Felmingham D, Reinert RR, Hirakata Y, Rodloff A: Increasing prevalence of antimicrobial resistance among isolates of Streptococcus pneumoniae from the PROTEKT surveillance study, and compatative in vitro activity of the ketolide, telithromycin. J Antimicrob Chemother. 2002 Sep;50 Suppl S1:25-37.

GLOBALLY HARMONIZED SYSTEM (GHS)

Pictograms

Signal Word
Warning

Hazard Statements
H315; H319; H335

Precautionary Statements
P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501

Current as of April 25, 2024

AKSci Reference Standards are high-purity, low-impurity compounds suitable for use as standards.


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CATEGORIES
 APIs and Bioactives > Antibacterials, Sulfonamides


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