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T7883

Sigma-Aldrich

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
Beilstein:
625127
EC Number:
212-006-2
MDL number:
MFCD00036761
UNSPSC Code:
51285203
PubChem Substance ID:
24278201
NACRES:
NA.85
Pricing and availability is not currently available.

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

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[1].

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[1].

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

Signal Word

Warning

Hazard Statements

H302,H361d

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000424096
0000424096
0000409199
0000363195
0000360822

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Ariel Gilad et al.
Nature communications, 11(1), 1744-1744 (2020-04-10)
Association areas in neocortex encode novel stimulus-outcome relationships, but the principles of their engagement during task learning remain elusive. Using chronic wide-field calcium imaging, we reveal two phases of spatiotemporal refinement of layer 2/3 cortical activity in mice learning whisker-based
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
E Van Duijkeren et al.
Journal of veterinary pharmacology and therapeutics, 17(1), 64-73 (1994-02-01)
The indications for use, side-effects, and pharmacokinetic parameters of trimethoprim, sulfonamides and their combinations in the horse are reviewed. Trimethoprim/sulfonamide (TMPS) combinations are used for the treatment of various diseases caused by gram-positive and gram-negative bacteria, including infections of the
Crystal Y Chen et al.
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
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Questions

1–5 of 5 Questions  

  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  3. Is it soluable in water or dmso and at what concentration should I use it?

    1 answer

    1. This material is practically insoluble in water at 0.4 mg/mL Additional solvents include the following:
      DMSO at 50 mg/mL
      methanol at 12 mg/mL
      chloroform at 18 mg/mL
      propyleneglycol at 25 mg/mL
      benzyl alcohol at 72 mg/mL
      dimethylacetamide at 138 mg/mL

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  4. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  5. Is Trimethoprim stable in solution?

    1 answer

    1. Triemethoprim in a solution of 52% N,N dimethylacetamide:48% propylene glycol at 50 mg/ml is stable when stored at 25° C. There is only a 10% degradation of trimethoprim under these conditions after 885 days.

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