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

Modify Date: 2024-01-05 21:07:25

5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine hydrochloride structure	Common Name	5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine hydrochloride
	CAS Number	60834-30-2	Molecular Weight	326.77900
	Density	N/A	Boiling Point	526ºC at 760 mmHg
	Molecular Formula	C₁₄H₁₉ClN₄O₃	Melting Point	N/A
	MSDS	N/A	Flash Point	271.9ºC

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

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].

Name	5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidine-2,4-diamine,hydrochloride
Synonym	More Synonyms

Description	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].
Related Catalog	Signaling Pathways >> Anti-infection >> Influenza Virus Research Areas >> Infection Signaling Pathways >> Cell Cycle/DNA Damage >> Antifolate Signaling Pathways >> Anti-infection >> Bacterial
Target	Dihydrofolate reductase, Bacteria[1] Influenza A virus[4]
In Vitro	Trimethoprim interrupts folate metabolism by inhibition of the activity of dihydrofolase reductase (DHFR), which reduces dihydrofolate to tetrahydrofolate (THF)[1]. 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[1]. 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[1].
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. [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. [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.\ [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.

Boiling Point	526ºC at 760 mmHg
Molecular Formula	C₁₄H₁₉ClN₄O₃
Molecular Weight	326.77900
Flash Point	271.9ºC
Exact Mass	326.11500
PSA	106.97000
LogP	1.91980

Trimplex

UNII-9XE000OU9B

Trimethoprim HCl

9XE000OU9B

5-((3,4,5-Trimethoxyphenyl)methyl)pyrimidine-2,4-diamine hydrochloride

Trimplex 200

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

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

Names

Biological Activity

Chemical & Physical Properties

Synonyms