Trimethoprim

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Trimethoprim
Category Antibiotics
Catalog number BBF-04040
CAS 738-70-5
Molecular Weight 290.32
Molecular Formula C14H18N4O3
Purity >98%

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Description

Trimethoprim is a bacteriostatic antibiotic used mainly in the prophylaxis and treatment of urinary tract infections. It caused induction of DnaK, DnaJ, GroEL, ClpB, and IbpA/B Hsps. It binds to dihydrofolate reductase and inhibits the reduction of dihydrofolic acid (DHF) to tetrahydrofolic acid (THF).

Specification

Synonyms Trimpex; Proloprim
Storage Store at 2-8°C
IUPAC Name 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Canonical SMILES COC1=CC(=CC(=C1OC)OC)CC2=CN=C(N=C2N)N
InChI 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

Properties

Appearance White to Light Yellow Solid
Application Anti-infective agents, Urinary; antimalarials; antimetabolites; folic acid antagonists
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 526°C at 760 mmHg
Melting Point 199-203°C
Flash Point 271.9°C
Density 1.252 g/cm3
Solubility Soluble in DMSO
LogP 2.42000

Reference Reading

1.Frequency, Antimicrobial Resistance and Genetic Diversity of Klebsiella pneumoniae in Food Samples.
Guo Y1, Zhou H2,3, Qin L1, Pang Z1, Qin T2,3, Ren H2, Pan Z1, Zhou J1. PLoS One. 2016 Apr 14;11(4):e0153561. doi: 10.1371/journal.pone.0153561. eCollection 2016.
This study aimed to assess the frequency of Klebsiella pneumoniae in food samples and to detect antibiotic resistance phenotypes, antimicrobial resistance genes and the molecular subtypes of the recovered isolates. A total of 998 food samples were collected, and 99 (9.9%) K. pneumoniae strains were isolated; the frequencies were 8.2% (4/49) in fresh raw seafood, 13.8% (26/188) in fresh raw chicken, 11.4% (34/297) in frozen raw food and 7.5% (35/464) in cooked food samples. Antimicrobial resistance was observed against 16 antimicrobials. The highest resistance rate was observed for ampicillin (92.3%), followed by tetracycline (31.3%), trimethoprim-sulfamethoxazole (18.2%), and chloramphenicol (10.1%). Two K. pneumoniae strains were identified as extended-spectrum β-lactamase (ESBL)-one strain had three beta-lactamases genes (blaSHV, blaCTX-M-1, and blaCTX-M-10) and one had only the blaSHV gene. Nineteen multidrug-resistant (MDR) strains were detected; the percentage of MDR strains in fresh raw chicken samples was significantly higher than in other sample types (P<0.
2.Human oropharynx as natural reservoir of Streptobacillus hongkongensis.
Lau SK1,2,3,4,5, Chan JF1,2,3,4, Tsang CC2, Chan SM6, Ho ML1,7, Que TL7, Lau YL6, Woo PC1,2,3,4,5. Sci Rep. 2016 Apr 14;6:24419. doi: 10.1038/srep24419.
Recently, we reported the isolation of Streptobacillus hongkongensis sp. nov. from patients with quinsy or septic arthritis. In this study, we developed a PCR sequencing test after sulfamethoxazole/trimethoprim and nalidixic acid enrichment for detection of S. hongkongensis. During a three-month study period, among the throat swabs from 132 patients with acute pharyngitis and 264 controls, PCR and DNA sequencing confirmed that S. hongkongensis and S. hongkongensis-like bacteria were detected in 16 patients and 29 control samples, respectively. Among these 45 positive samples, five different sequence variants were detected. Phylogenetic analysis based on the 16S rRNA gene showed that sequence variant 1 was clustered with S. hongkongensis HKU33(T)/HKU34 with high bootstrap support; while the other four sequence variants formed another distinct cluster. When compared with the 16S rRNA gene of S. hongkongensis HKU33(T), the five sequence variants possessed 97.
3.Empirical therapy in Methicillin-resistant Staphylococcus Aureus infections: An Up-To-Date approach.
VanEperen AS1, Segreti J2. J Infect Chemother. 2016 Apr 8. pii: S1341-321X(16)30009-5. doi: 10.1016/j.jiac.2016.02.012. [Epub ahead of print]
Methicillin-resistant Staphylococcus aureus (MRSA) continues to be an important pathogen worldwide, with high prevalence of infection in both community and hospital settings. Timely and appropriate choice of empirical therapy in the setting of MRSA infection is imperative due to the high rate of associated morbidity and mortality with MRSA infections. Initial choices should be made based on the site and severity of the infection, most notably moderate skin and soft tissue infections which may be treated with oral antibiotics (trimethoprim-sulfamethoxazole, clindamycin, doxycycline/minocycline, linezolid) in the outpatient setting, versus choice of parenteral therapy in the inpatient setting of more invasive or severe disease. Though the current recommendations continue to strongly rely on vancomycin as a standard empiric choice in the setting of severe/invasive infections, alternative therapies exist with studies supporting their non-inferiority.
4.Malaria illness mediated by anaemia lessens cognitive development in younger Ugandan children.
Boivin MJ1, Sikorskii A2, Familiar-Lopez I3, Ruiseñor-Escudero H3, Muhindo M4, Kapisi J4, Bigira V4, Bass JK5, Opoka RO6, Nakasujja N7, Kamya M8, Dorsey G9. Malar J. 2016 Apr 14;15(1):210. doi: 10.1186/s12936-016-1266-x.
BACKGROUND: Asymptomatic falciparum malaria is associated with poorer cognitive performance in African schoolchildren and intermittent preventive treatment of malaria improves cognitive outcomes. However, the developmental benefits of chemoprevention in early childhood are unknown. Early child development was evaluated as a major outcome in an open-label, randomized, clinical trial of anti-malarial chemoprevention in an area of intense, year-round transmission in Uganda.

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