ChemicalBook Product Catalog API Synthetic Anti-infective Drugs Sulfonamides and synergist 5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine hydrochloride

5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine hydrochloride

Product Name5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine hydrochloride
CAS60834-30-2
MFC14H19ClN4O3
MW326.77866
EINECS262-450-6
MOL File60834-30-2.mol

Chemical Properties

Melting point

280-285 °C

Usage And Synthesis

Uses

Trimethoprim hydrochloride is a bacteriostatic antibiotic and an orally active dihydrofolate reductase inhibitor. Trimethoprim hydrochloride is active against a wide range of Gram-positive and Gram-negative aerobic bacteria. Trimethoprim hydrochloride has the potential for the research of urinary tract infections, Shigellosis and Pneumocystis pneumonia. Trimethoprim hydrochloride can inhibit infection of Influenza A virus in chick embryo when combinated with zinc[1][2][3][4].

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^[2].
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^[2].
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^[4].

Animal Model:	Female C3H/HeOuJ mice (transurethrally infected with a 50 μL suspension containing 1-2×10⁷ CFU of E. coli under 3% isoflurane)^[2]
Dosage:	10 mg/kg
Administration:	i.v.; once every 12 h; for 3 d
Result:	Showed antibacterial activity against H. influenzae, S. pneumoniae, E. coli and N. meningitidis with CD₅₀s of 150 mg/kg, 335 mg/kg, 27.5 mg/kg and 8.4 mg/kg, respectively in infected mice.

Animal Model:	Fertilized eggs (injected H3N2 virus into amniotic and allantoic space at day 8)^[4]
Dosage:	10 mg/mL; 0.5 mL
Administration:	The Trimethoprim-Zn combined suspension was injected into the air sac; single dosage
Result:	Decreased the virus titer and increased the survival rate of chicken embryo. The survival rate peaked at ratio about 0.18 (Zn/Trimethoprim).

References

[1] Laskowska, E., et al., Trimethoprim induces heat shock proteins and protein aggregation in E. coli cells. Curr Microbiol, 2003. 47(4): p. 286-9. DOI:10.1007/s00284-002-4007-z
[2] Brogden, R.N., et al., Trimethoprim: a review of its antibacterial activity, pharmacokinetics and therapeutic use in urinary tract infections. Drugs, 1982. 23(6): p. 405-30. DOI:10.2165/00003495-198223060-00001
[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.\ DOI:10.1021/acs.bioconjchem.8b00177
[4] El Habbal MH. Combination therapy of zinc and trimethoprim inhibits infection of influenza A virus in chick embryo. Virol J. 2021 Jun 3;18(1):113. DOI:10.1186/s12985-021-01585-1

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