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Key Documents

92131

Sigma-Aldrich

Trimethoprim

≥99.0% (HPLC)

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:
Molecular Weight:
290.32
Beilstein/REAXYS Number:
625127
EC Number:
MDL number:
UNSPSC Code:
51285203
PubChem Substance ID:
NACRES:
NA.85

biological source

synthetic

Quality Level

assay

≥99.0% (HPLC)

form

powder

color

white to light yellow

mp

≥199.0 °C

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

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General description

Chemical structure: pyrimidine

Application

Trimethoprim is primarily used as an antibacterial agent. It is used in susceptibility studies of Mycobacterium tuberculosis and mechanism of resistance studies in Haemophilus influenzae .
Primarily used as an antibacterial agent. Dihydrofolate reductase inhibitor with selectivity for the prokaryote enzyme.

Biochem/physiol Actions

Inhibits the synthesis of tetrahydrofolate by procaryote specific dihydrofolate reductase (DHFR).
Trimethoprim is a dihydrofolate reductase inhibitor with selectivity for the prokaryote enzyme.

Packaging

1g,5g,25g

Other Notes

Keep container tightly closed in a dry and well-ventilated place.Light sensitive. Store under inert gas. Moisture sensitive. Product is sensitive to light and moisture.

pictograms

Health hazardExclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Susceptibility of Mycobacterium tuberculosis to sulfamethoxazole, trimethoprim and their combination over a 12 year period in Taiwan.
Tsi-Shu Huang1,2,3, Calvin M. Kunin, et al.
The Journal of Antimicrobial Chemotherapy, 10, 633-637 (2011)
R de Groot et al.
Antimicrobial agents and chemotherapy, 32(4), 477-484 (1988-04-01)
We studied 10 trimethoprim-resistant (Tmpr) Haemophilus influenzae isolates for which agar dilution MICs were 10 to greater than 200 micrograms/ml. Trimethoprim resistance was transferred from two Tmpr H. influenzae isolates to a Tmps strain by conjugation or transformation. Wild-type Tmpr
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
Karin Tegmark Wisell et al.
The Journal of antimicrobial chemotherapy, 62(1), 35-40 (2008-04-15)
The lack of oral treatment alternatives for enterococcal urinary tract infections (UTIs) has led to a renewed interest in trimethoprim. Enterococci can incorporate exogenously produced folates and thereby reverse the effect of trimethoprim. Although a large proportion of enterococci appear
Christine Manyando et al.
PloS one, 9(5), e96017-e96017 (2014-05-17)
Antibiotic therapy during pregnancy may be beneficial and impacts positively on the reduction of adverse pregnancy outcomes. No studies have been done so far on the effects of daily Co-trimoxazole (CTX) prophylaxis on birth outcomes. A phase 3b randomized trial

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