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Merck

1692505

USP

Trimethoprim

United States Pharmacopeia (USP) Reference Standard

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
UNSPSC Code:
41116107
NACRES:
NA.24
PubChem Substance ID:
329751414
MDL number:
MFCD00036761
Beilstein/REAXYS Number:
625127

Product Name

Trimethoprim, United States Pharmacopeia (USP) Reference Standard

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)

SMILES string

COc1cc(Cc2cnc(N)nc2N)cc(OC)c1OC

InChI key

IEDVJHCEMCRBQM-UHFFFAOYSA-N

grade

pharmaceutical primary standard

API family

trimethoprim

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

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Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Application

Primarily used as an antibacterial agent. Dihydrofolate reductase inhibitor with selectivity for the prokaryote enzyme.
Trimethoprim USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia.
Also, for use with USP monographs such as:
  • Trimethoprim Tablets
  • Trimethoprim Sulfate
  • Sulfamethoxazole and Trimethoprim Tablets
  • Sulfamethoxazole and Trimethoprim Injection
  • Sulfamethoxazole and Trimethoprim Oral Suspension
  • Polymyxin B Sulfate and Trimethoprim Ophthalmic Solution

General description

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Other Notes

Sales restrictions may apply.

pictograms

Health hazardExclamation mark
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

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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?

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  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.

  6. My question is not addressed here, how can I contact Technical Service for assistance?

    Ask a Scientist here.

Karin Tegmark Wisell et al.
The Journal of antimicrobial chemotherapy, 62(1), 35-40 (2008-04-15)
The lack of oral treatment alternatives for enterococcal urinary tract infections (UTIs) has led to a renewed interest in trimethoprim. Enterococci can incorporate exogenously produced folates and thereby reverse the effect of trimethoprim. Although a large proportion of enterococci appear
Christine Manyando et al.
PloS one, 9(5), e96017-e96017 (2014-05-17)
Antibiotic therapy during pregnancy may be beneficial and impacts positively on the reduction of adverse pregnancy outcomes. No studies have been done so far on the effects of daily Co-trimoxazole (CTX) prophylaxis on birth outcomes. A phase 3b randomized trial
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
Dolores Camacho-Muñoz et al.
Chemosphere, 111, 70-79 (2014-07-07)
The distribution of pharmaceutically active compounds in the environment has been reported in several works in which wastewater treatment plants have been identified as the main source of these compounds to the environment. The concentrations of these compounds in influent
Sarah L Svensson et al.
PloS one, 9(8), e106063-e106063 (2014-08-29)
Campylobacter jejuni is a leading cause of foodbourne gastroenteritis, despite fragile behaviour under standard laboratory conditions. In the environment, C. jejuni may survive within biofilms, which can impart resident bacteria with enhanced stress tolerance compared to their planktonic counterparts. While
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