Trimethoprim

Category	Influenza Virus
CAS	738-70-5
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).

Quotation Now

Product Information

Synonyms	Trimpex; Proloprim
IUPAC Name	5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine
Molecular Weight	290.32
Molecular Formula	C14H18N4O3
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)
InChIKey	IEDVJHCEMCRBQM-UHFFFAOYSA-N
Boiling Point	526°C at 760 mmHg
Melting Point	199-203°C
Flash Point	271.9°C
Purity	>98%
Density	1.252 g/cm3
Solubility	Soluble in DMSO
Appearance	White to Light Yellow Solid
Application	Anti-infective agents, Urinary; antimalarials; antimetabolites; folic acid antagonists
Storage	Store at 2-8°C
Complexity	307
Exact Mass	290.13789045
Index Of Refraction	1.600
In Vitro	Trimethoprim interrupts folate metabolism by inhibition of the activity of dihydrofolase reductase (DHFR), which reduces dihydrofolate to tetrahydrofolate (THF). Trimethoprim (3 μg/mL; 1 h) induces protein aggregation and main heat shock proteins (Hsps) in E. coli cells, which indicates that Trimethoprim sulfate presence leads to protein misfolding. Trimethoprim (1.5-3 μg/mL; 1 h) causes induction of DnaK, DnaJ, GroEL, ClpB, and IbpA/B Hsps in E. coli cells exposed to folate and heat stress.
In Vivo	Trimethoprim (10 mg/kg; i.v.; once every 12 h; 3 d) shows antibacterial activity against H. influenzae, S. pneumoniae, E. coli and N. meningitidis in infected mice. Trimethoprim can be connected with the thiomaltose (TM-TMP) and shows stability with a half-life of about 1 hour in complete serum, and has an MIC value around 1 μM against E. coli. Trimethoprim (10 mg/mL; 0.5 mL; inject with Trimethoprim-Zn combined suspension) decreases the virus titer and increases the survival rate of chicken embryo.
PSA	15.51
Target	Antifolate; Bacterial; Antibiotic; Influenza Virus
Vapor Pressure	0.0±0.9 mmHg at 25°C
XLogP3-AA	0.9