Trimethoprim An antibacterial agent which selectively inhibits dihydrofolate reductase

Trimethoprim (CAS 738-70-5)

Trimethoprim | CAS 738-70-5 is rated 5.0 out of 5 by 1.
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Synonym: Trimpex
Application: An antibacterial agent which selectively inhibits dihydrofolate reductase
CAS Number: 738-70-5
Purity: ≥99%
Molecular Weight: 290.32
Molecular Formula: C14H18N4O3
* Refer to Certificate of Analysis for lot specific data (including water content).
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Trimethoprim is an antibacterial agent which selectively inhibits DHFR(dihydrofolate reductase) in prokaryotic microorganisms. in addition, trimethoprim is often combined with sulfamethoxazole (sc-208405) to inhibit the growth of Staphylococcus aureus. Studies suggest that electro-oxidation of trimethoprim is pH dependent and irreversible. Alternate studies show that trimethoprim can synergize with oxygen causing an increase in oxygen tensions in vitro, which decreases the minimal inhibitory concentrations of trimethoprim resulting in bactericidal effects.


References

1. Keck, P.E., et al. 1980. Undersea Biomed Res. 7: 95-106. PMID: 7404854
2. Rajith, L. and Kumar, K.G. 2010. Drug Test Anal. 2: 436-441. PMID: 20845390
3. Zander, J., et al. 2010. Int. J. Antimicrob. Agents. 36: 562-565. PMID: 20947313

Appearance :
Powder
Physical State :
Solid
Solubility :
Soluble in water (0.4 mg/ml), ethanol (2.6 mg/ml at 20° C), methanol (12.1 mg/ml), chloroform (22.2 mg/ml at 20° C), and DMSO (50 mg/ml).
Storage :
Store at 4° C
Melting Point :
234-236° C
Boiling Point :
~405.2° C at 760 mmHg (Predicted)
Density :
~1.3 g/cm3 (Predicted)
Refractive Index :
n20D 1.61 (Predicted)
IC50 :
Pneumocystis carini: IC50 = 0 nM; Toxoplasma gondii: IC50 = 0 nM; Dihydrofolate reductase: IC50 = 0.01 nM (rat); Dihydrofolate reductase: IC50 = 2.2 nM (Candida albicans); DHFR: IC50 = 54 nM (human)
Ki Data :
Dihydrofolate reductase: Ki= 1.24 nM (Staphylococcus aureus); DHFR: Ki= 1.3 nM (human); Dihydrofolate reductase: Ki= 1.3 nM (Escherichia coli K-12); Dihydrofolate reductase: Ki= 4.4 nM (Staphylococcus aureus); Dihydrofolate reductase: Ki= 10.3 nM (Plasmodium falciparum K1)
pK Values :
pKa: 6.6
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
UV8225000
PubChem CID :
5578
Merck Index :
14: 9709
MDL Number :
MFCD00036761
EC Number :
212-006-2
Beilstein Registry :
625127
SMILES :
COC1=CC(CC2=C(N)N=C(N)N=C2)=CC(OC)=C1OC

Download SDS (MSDS)

Certificate of Analysis

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Rated 5 out of 5 by from Keck et al Keck et al. (PubMed ID 7404854) used trimethoprim as a sulfonamide potentiator that prevented an increase in oxygen levels and proved to be beneficial bactericidal and bacteriostatic in pathogenic bacteria. -SCBT Publication Review
Date published: 2015-06-21
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