Synonym: 5-(3,4,5-Trimethoxybenzyl)pyrimidine-2,4-diamine 2-hydroxypropanoate; 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine lactate salt
CAS Number: 23256-42-0
Empirical Formula (Hill Notation): C14H18N4O3 · C3H6O3
Molecular Weight: 380.40
EC Number: 245-533-1
MDL Number: MFCD00171722
Linear Formula: C14H18N4O3 · C3H6O3
Product Type: Chemical
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antibiotic activity spectrum |
Gram-negative bacteria |
|
Gram-positive bacteria |
|
mycobacteria |
assay |
≥98% |
color |
white |
form |
powder |
InChI |
1S/C14H18N4O3.C3H6O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15;1-2(4)3(5)6/h5-7H,4H2,1-3H3,(H4,15,16,17,18);2,4H,1H3,(H,5,6) |
InChI key |
IIZVTUWSIKTFKO-UHFFFAOYSA-N |
mode of action |
DNA synthesis | interferes |
|
enzyme | inhibits |
Quality Level |
200 ![External link](https://krackeler.com/images/sigma/ext-link.gif) |
SMILES string |
CC(O)C(O)=O.COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC |
solubility |
H2O: soluble 20 mg/mL |
storage condition |
(Keep container tightly closed in a dry and well-ventilated place.) |
storage temp. |
2-8°C |
Application: |
Trimethoprim is primarily used as an antibacterial agent. It has dihydrofolate reductase inhibitor activity with selectivity for the prokaryote enzyme. It is used clinically to treat urinary tract infections, mild acute prostatitis, recurrent cystitis, asymptomatic bacteriuria during pregnancy and respiratory tract infections. Trimethoprim lactate salt is used as a selection agent. |
Biochem/physiol Actions: |
The combination of trimethoprim and sulfamethoxazole interferes with the cellular metabolism of folic acid in the bacterial cell by blocking the biosynthesis of nucleotides. Trimethoprim binds to prokaryote-specific dihydrofolate reductase (DHFR) 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. |
General description: |
Chemical structure: pyrimidine |
Other Notes: |
Keep container tightly closed in a dry and well-ventilated place. |
Packaging: |
250 mg in glass bottle |
Purity |
≥98% |
Storage Temp. |
2-8°C |
UNSPSC |
51101500 |