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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

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.

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.

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
0000409199
0000363195
0000360822
0000348062
0000348061

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

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

    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. 

  5. Is Trimethoprim stable in solution?

    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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