Trimethoprim

Structural formula
General
Non-proprietary name	Trimethoprim
other names	5- (3,4,5-trimethoxybenzyl) pyrimidine-2,4-diamine ( IUPAC ) ; 2,4-diamino-5- (3,4,5-trimethoxybenzyl) pyrimidine;
Molecular formula	C 14 H 18 N 4 O 3
External identifiers / databases
EC number	212-006-2
ECHA InfoCard	100.010.915
PubChem	5578
ChemSpider	5376
DrugBank	DB00440
Wikidata	Q422665
Drug information
ATC code	J01 EA01
Drug class	antibiotic
Mechanism of action	Dihydrofolate reductase inhibitor
properties
Molar mass	290.32 g mol −1
Physical state	firmly
Melting point	199-203 ° C
pK s value	7.12 (at 20 ° C)
solubility	slightly soluble in water (0.4 g l −1 at 25 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
Toxicological data	2764 mg kg −1 ( LD 50 , mouse , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Trimethoprim is a drug from the group of antibiotics .

Mechanism and spectrum of action

Trimethoprim is bacteriostatic by the dihydrofolate reductase is blocked, whereby the folic acid - metabolism of gram-positive and gram-negative inhibit germs. The affinity for bacterial dihydrofolate reductase is over a thousand times higher than that for human dihydrofolate reductase. As a single substance, it is mainly used to treat uncomplicated urinary tract infections, but also against infections of the upper respiratory tract . The combination with active ingredients such as sulfamethoxazole from the group of sulfonamides (results in cotrimoxazole ) extends the spectrum of activity to include protozoa such as Toxoplasma gondii or the fungus Pneumocystis jirovecii , but also increases the spectrum of side effects. The fixed combination of trimethoprim and sulfamethoxazole is known as cotrimoxazole (Cotrim for short). The combination of trimethoprim and sulfamethoxazole is also used to treat the autoimmune disease granulomatosis with polyangiitis in the localized stage.

Side effects

In addition to gastrointestinal complaints, which are often observed with antibiotics, rashes with itchy spots can occasionally occur. In individual cases, severe skin symptoms up to Lyell's syndrome have been described. The following are rare: aseptic meningitis , an increase in transaminases , the yellow blood pigment bilirubin or the urinary substances creatinine and urea , minor changes in the blood count and fever. There are individual descriptions of skin reactions caused by light damage ( phototoxic reactions ) and inflammation of the pancreas. After prolonged use, the formation of sperm ( spermatogenesis ) and superinfection by fungi or resistant bacteria can also occur.

Forms of trade

Trimethoprim is available as a tablet with 50, 100, 150 or 200 mg active ingredient and as a juice with 50 mg in 5 ml.

Trade names

Monopreparations

Infectotrimet (D, A), Motrim (A), Triprim (A)

Combination preparations

Bactrim (A), Cotribene (A), Cotrim (D), Drylin (D), Eusaprim (D, A), Kepinol (D), Lidaprim (A), TMS forte (D)

Individual evidence

↑ ^a ^b ^c ^d Entry on trimethoprim in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b Data sheet Trimethoprim, crystallized, ≥99.0% (HPLC) from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).
↑ RN Brogden, AA Carmine, RC Heel, TM Speight, GS Avery: Trimethoprim . In: Drugs . tape 23 , no. 6 June 1982, pp. 405-430 , doi : 10.2165 / 00003495-198223060-00001 ( springer.com [accessed July 21, 2018]).
↑ AllEx, The Compendium for the 2nd ÄP, Volume A: Immunsysthem und Rheumatologischeillen, Thieme (2012), p. 470.
↑ CA Stegeman, JW Tervaert, PE de Jong, CG Kallenberg: Trimethoprim-sulfamethoxazole (co-trimoxazole) for the prevention of relapses of Wegener's granulomatosis. Dutch Co-Trimoxazole Wegener Study Group. In: The New England Journal of Medicine . Volume 335, Number 1, July 1996, pp. 16-20, doi : 10.1056 / NEJM199607043350103 (free full text), PMID 8637536 .

[ChemIDplus-1] Entry on trimethoprim in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Sigma-2] Data sheet Trimethoprim, crystallized, ≥99.0% (HPLC) from Sigma-Aldrich , accessed on December 1, 2019 ( PDF ).

[3] RN Brogden, AA Carmine, RC Heel, TM Speight, GS Avery: Trimethoprim . In: Drugs . tape 23 , no. 6 June 1982, pp. 405-430 , doi : 10.2165 / 00003495-198223060-00001 ( springer.com [accessed July 21, 2018]).

[4] AllEx, The Compendium for the 2nd ÄP, Volume A: Immunsysthem und Rheumatologischeillen, Thieme (2012), p. 470.

[5] CA Stegeman, JW Tervaert, PE de Jong, CG Kallenberg: Trimethoprim-sulfamethoxazole (co-trimoxazole) for the prevention of relapses of Wegener's granulomatosis. Dutch Co-Trimoxazole Wegener Study Group. In: The New England Journal of Medicine . Volume 335, Number 1, July 1996, pp. 16-20, doi : 10.1056 / NEJM199607043350103 (free full text), PMID 8637536 .