Trimethoprim lactate

Names

[ Name ]:
Trimethoprim lactate

[Synonym ]:
2-Hydroxypropanoic acid - 5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diamine (1:1)
EINECS 245-533-1
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine lactate salt
Trimethoprim lactate
2-hydroxypropanoic acid,5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Propanoic acid, 2-hydroxy-, compd. with 5-[(3,4,5-trimethoxyphenyl)methyl]-2,4-pyrimidinediamine (1:1)
MFCD00171722
2-Hydroxypropanoic acid - 5-(3,4,5-trimethoxybenzyl)-2,4-pyrimidinediamine (1:1)
UNII:P3K8GP9FDQ

Biological Activity

[Description]:

Trimethoprim lactic is a bacteriostatic antibiotic and an orally active dihydrofolate reductase inhibitor. Trimethoprim lactic is active against a wide range of Gram-positive and Gram-negative aerobic bacteria. Trimethoprim lactic has the potential for urinary tract infections, Shigellosis and Pneumocystis pneumonia treatment[1][2][3].

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Cell Cycle/DNA Damage >> Antifolate

Signaling Pathways >> Anti-infection >> Bacterial

[Target]

Dihydrofolate reductase[1] Bacteria[1]

[In Vitro]

Trimethoprim interrupts folate metabolism by inhibition of the activity of dihydrofolase reductase (DHFR), which reduces dihydrofolate to tetrahydrofolate (THF)[1]. Trimethoprim causes protein aggregation and induction of main heat shock proteins (Hsps) in E. coli cells, which indicates that Trimethoprim presence leads to protein misfolding. Trimethoprim causes induction of DnaK, DnaJ, GroEL, ClpB, and IbpA/B Hsps. Among these Hsps, IbpA/B are most efficiently induced by Trimethoprim and coaggregates with the insoluble proteins. Upon folate stress, deletion of the delta ibpA/B operon resulted in increased protein aggregation but does not influence cell viability[1].

[In Vivo]

In intraperitoneal infections in mice, the CD50 values for Trimethoprim alone against H. influenzae, S. pneumoniae, E. coli and N. meningitidis, is 150 mg/kg, 335 mg/kg, 27.5 mg/kg and 8.4 mg/kg, respectively[2].

[References]

[1]. Ewa Laskowska, et al. Trimethoprim Induces Heat Shock Proteins and Protein Aggregation in E. Coli Cells. Curr Microbiol. 2003 Oct;47(4):286-9.

[2]. R N Brogden, et al. Trimethoprim: A Review of Its Antibacterial Activity, Pharmacokinetics and Therapeutic Use in Urinary Tract Infections. Drugs. 1982 Jun;23(6):405-30.

[3]. Xiaojian Wang, et al. A Trimethoprim Conjugate of Thiomaltose Has Enhanced Antibacterial Efficacy In Vivo. Bioconjug Chem. 2018 May 16;29(5):1729-1735.

Chemical & Physical Properties

[ Boiling Point ]:
526ºC at 760mmHg

[ Molecular Formula ]:
C₁₇H₂₄N₄O₆

[ Molecular Weight ]:
380.396

[ Flash Point ]:
271.9ºC

[ Exact Mass ]:
380.169586

[ PSA ]:
163.04000

[ LogP ]:
1.87180

[ Vapour Pressure ]:
3.74E-11mmHg at 25°C

[ Storage condition ]:
2-8°C

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
T:Toxic;

[ Risk Phrases ]:
R23/24/25;R43;R61

[ Safety Phrases ]:
S22-S36/37/39-S45-S53

[ RIDADR ]:
UN 2811

[ WGK Germany ]:
3

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2942000000

Customs

[ HS Code ]: 2942000000

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