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T7883

Sigma-Aldrich

Trimetoprim

≥98.5%

Sinónimos:

2,4-Diamino-5-(3,4,5-trimetoxibencil)pirimidina, NSC 106568

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About This Item

Fórmula empírica (notación de Hill):
C14H18N4O3
Número de CAS:
738-70-5
Peso molecular:
290.32
Beilstein/REAXYS Number:
625127
EC Number:
212-006-2
MDL number:
MFCD00036761
UNSPSC Code:
51285203
PubChem Substance ID:
24278201
NACRES:
NA.85

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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General description

Estructura química: pirimidina

Application

El trimetoprim se utiliza principalmente como agente antibacteriano. Tiene actividad inhibidora de la dihidrofolato reductasa con selectividad por la enzima procariota. Se utiliza para tratar infecciones de las vías urinarias, prostatitis aguda leve, cistitis recurrente, bacteriuria asintomática durante el embarazo e infecciones del sistema respiratorio.
Se utiliza principalmente como un antibacteriano. Inhibidor de la dihidrofolato reductasa con selectividad por la enzima procariota.

Biochem/physiol Actions

La combinación de trimetoprim y sulfametoxazol interfiere en el metabolismo celular del ácido fólico en la célula bacteriana al bloquear la biosíntesis de los nucleótidos. El trimetoprim se une a la dihidrofolato reductasa e inhibe la reducción del ácido dihidrofólico (DHF) a ácido tetrahidrofólico (THF). El THF es un precursor esencial en la vía de síntesis de timidina y la interferencia con esta vía inhibe la síntesis bacteriana de ADN.

Packaging

5G, 25G, 100G

Other Notes

Mantenga el recipiente herméticamente cerrado y en un lugar bien ventilado. Consérvese en un lugar seco.

pictograms

Health hazardExclamation mark
GHS08,GHS07

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)

Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Sulfamethoxazole European Pharmacopoeia (EP) Reference Standard

S2100000

Sulfamethoxazole

Sulfamethoxazole certified reference material, TraceCERT®, Manufactured by: Sigma-Aldrich Production GmbH, Switzerland

Supelco

76177

Sulfamethoxazole

Trimetoprim British Pharmacopoeia (BP) Reference Standard

BP344

Trimetoprim

Trimetoprim European Pharmacopoeia (EP) Reference Standard

Y0000684

Trimetoprim

Sulfamethoxazole Pharmaceutical Secondary Standard; Certified Reference Material

Supelco

PHR1126

Sulfamethoxazole

Sulfamethoxazole VETRANAL®, analytical standard

Supelco

31737

Sulfamethoxazole

Sulfamethoxazole British Pharmacopoeia (BP) Reference Standard

BP314

Sulfamethoxazole

Sulfamethoxazole United States Pharmacopeia (USP) Reference Standard

USP

1631001

Sulfamethoxazole

Sulfadiazine 99.0-101.0%

Sigma-Aldrich

S8626

Sulfadiazine

Ariel Gilad et al.
Nature communications, 11(1), 1744-1744 (2020-04-10)
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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
O Sköld
Veterinary research, 32(3-4), 261-273 (2001-07-04)
Sulfonamides and trimethoprim have been used for many decades as efficient and inexpensive antibacterial agents for animals and man. Resistance to both has, however, spread extensively and rapidly. This is mainly due to the horizontal spread of resistance genes, expressing
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