Skip to Content
Merck
All Photos(2)

Documents

T0667

Sigma-Aldrich

Trimethoprim lactate salt

≥98%

Synonym(s):

5-(3,4,5-Trimethoxybenzyl)pyrimidine-2,4-diamine 2-hydroxypropanoate, 2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine lactate salt

Sign Into View Organizational & Contract Pricing
All Photos(2)

About This Item

Empirical Formula (Hill Notation):
C14H18N4O3 · C3H6O3
CAS Number:
23256-42-0
Molecular Weight:
380.40
EC Number:
245-533-1
MDL number:
MFCD00171722
UNSPSC Code:
51285203
PubChem Substance ID:
329826610
NACRES:
NA.85

Quality Level

200

Assay

≥98%

form

powder

storage condition

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

color

white

solubility

H2O: soluble 20 mg/mL

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

CC(O)C(O)=O.COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC

InChI

1S/C14H18N4O3.C3H6O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15;1-2(4)3(5)6/h5-7H,4H2,1-3H3,(H4,15,16,17,18);2,4H,1H3,(H,5,6)

InChI key

IIZVTUWSIKTFKO-UHFFFAOYSA-N

General description

Chemical structure: pyrimidine

Application

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

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 prokaryote-specific dihydrofolate reductase (DHFR) 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.

Other Notes

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

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H301,H361d

Hazard Classifications

Acute Tox. 3 Oral - Repr. 2

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Andrea Navas-Olive et al.
Nature communications, 11(1), 2217-2217 (2020-05-07)
Theta oscillations play a major role in temporarily defining the hippocampal rate code by translating behavioral sequences into neuronal representations. However, mechanisms constraining phase timing and cell-type-specific phase preference are unknown. Here, we employ computational models tuned with evolutionary algorithms
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
Sarah De Smet et al.
Applied and environmental microbiology, 77(5), 1732-1738 (2011-01-11)
Healthy pigs are an important reservoir for the emerging human pathogen Arcobacter which can result in contamination of porcine carcasses and pork and the spread of arcobacters into the environment. Up to now, the excretion of arcobacters by pigs has
Yongchuan Zhu et al.
Nature communications, 10(1), 3469-3469 (2019-08-04)
The formation of new memories requires transcription. However, the mechanisms that limit signaling of relevant gene programs in space and time for precision of information coding remain poorly understood. We found that, during learning, the cellular patterns of expression of
Craig Knox et al.
Nucleic acids research, 39(Database issue), D1035-D1041 (2010-11-10)
DrugBank (http://www.drugbank.ca) is a richly annotated database of drug and drug target information. It contains extensive data on the nomenclature, ontology, chemistry, structure, function, action, pharmacology, pharmacokinetics, metabolism and pharmaceutical properties of both small molecule and large molecule (biotech) drugs.
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service