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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

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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:
51101500
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

Related Categories

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

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Repr. 2

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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