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Merck
CN

T7883

Trimethoprim

≥98.5%

Synonym(s):

2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine, NSC 106568

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About This Item

Empirical Formula (Hill Notation):
C14H18N4O3
CAS Number:
738-70-5
Molecular Weight:
290.32
UNSPSC Code:
51285203
NACRES:
NA.85
PubChem Substance ID:
24278201
EC Number:
212-006-2
Beilstein/REAXYS Number:
625127
MDL number:
MFCD00036761

Key Documents

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Quality Level

200

assay

≥98.5%

form

powder

storage condition

(Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.)

color

white to light yellow

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycobacteria

mode of action

DNA synthesis | interferes, enzyme | inhibits

storage temp.

2-8°C

SMILES string

COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC

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

Gene Information

human ... DHFRP1(573971), KCNH1(3756)
rat ... Dhfr(24312)

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Related Categories

General description

Chemical structure: pyrimidine

Application

Primarily used as an antibacterial agent. Dihydrofolate reductase inhibitor with selectivity for the prokaryote enzyme.
Trimethoprim is primarily used as an antibacterial agent. It has dihydrofolate reductase inhibitor activity with selectivity for the prokaryote enzyme. It is used to treat urinary tract infections, mild acute prostatitis, recurrent cystitis, asymptomatic bacteriuria during pregnancy and respiratory tract infections.

Biochem/physiol Actions

The combination of trimethoprim and sulfamethoxazole interferes with the cellular metabolism of folic acid in the bacterial cell by blocking the biosynthesis of nucleotides. Trimethoprim binds to dihydrofolate reductase and inhibits the reduction of dihydrofolic acid (DHF) to tetrahydrofolic acid (THF). THF is an essential precursor in the thymidine synthesis pathway and interference with this pathway inhibits bacterial DNA synthesis.

Packaging

5G,25G,100G

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000527337
0000527337
0000503486
0000503486
0000491347

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Ariel Gilad et al.
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PLoS pathogens, 5(4), e1000392-e1000392 (2009-04-22)
The role of CD8 T cells in anti-tuberculosis immunity in humans remains unknown, and studies of CD8 T cell-mediated protection against tuberculosis in mice have yielded controversial results. Unlike mice, humans and nonhuman primates share a number of important features
Mira Rakic-Martinez et al.
Applied and environmental microbiology, 77(24), 8714-8721 (2011-10-18)
Listeria monocytogenes is a leading agent for severe food-borne illness and death in the United States and other nations. Even though drug resistance has not yet threatened therapeutic interventions for listeriosis, selective pressure associated with exposure to antibiotics and disinfectants
Kate S Baker et al.
The Lancet. Infectious diseases, 15(8), 913-921 (2015-05-06)
Shigellosis is an acute, severe bacterial colitis that, in high-income countries, is typically associated with travel to high-risk regions (Africa, Asia, and Latin America). Since the 1970s, shigellosis has also been reported as a sexually transmitted infection in men who
Kyuho Han et al.
Nature methods, 11(1), 86-93 (2013-11-12)
Protein concentrations are often regulated by dynamic changes in translation rates. Nevertheless, it has been challenging to directly monitor changes in translation in living cells. We have developed a reporter system to measure real-time changes of translation rates in human
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Global Trade Item Number

SKUGTIN
T7883-100G04061837378706
T7883-25G04061835514304
T7883-5G04061835550319

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