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QuickView for trimethoprim (compound)


PubChem
Name: Trimethoprim
PubChem Compound ID: 173769
Description: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. The interference with folic acid metabolism may cause a depression of hematopoiesis. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM-SULFAMETHOXAZOLE COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.
Molecular formula: C14H19ClN4O3
Molecular weight: 326.779 g/mol
Synonyms:
60834-30-2; 5-((3,4,5-Trimethoxyphenyl)methyl)pyrimidine-2,4-diamine hydrochloride; EINECS 262-450-6
DrugBank
Identification
Name: Trimethoprim
Name (isomeric): DB00440
Drug Type: small molecule
Description: A pyrimidine inhibitor of dihydrofolate reductase, it is an antibacterial related to PYRIMETHAMINE. The interference with folic acid metabolism may cause a depression of hematopoiesis. It is potentiated by SULFONAMIDES and the TRIMETHOPRIM-SULFAMETHOXAZOLE COMBINATION is the form most often used. It is sometimes used alone as an antimalarial. TRIMETHOPRIM RESISTANCE has been reported.
Brand: Abaprim, Sigaprim, Kepinol, Trimethopriom, Trimexazole, Trimethioprim, Uretrim, Teleprim, Fectrim, Uroplus SS, Sulfatrim-SS, Thiocuran, Sulmeprim Pediatric, Bactrim Pediatric, Septra DS, Instalac, Lidaprim, Primosept, Sulprim, Proloprim, Unitrim, Trimeth/Sulfa, Sulfamethoprim-DS, Sulfamethoxazole & Trimethoprim, Uroplus DS, Trimopan, Suprim, Abacin, Supracombin, Microtrim, Trimpex, Trimesulf, Drylin, Primsol, Bactin, Uroplus, Monoprim, Apo-Sulfatrim, Oraprim, Trimetoprim, Alprim, Methoprim, Sulfatrim Pediatric, Co-Trimoxazole, Priloprim, Sulfotrim, Sulmeprim, Trimanyl, Trigonyl, Cotrim, Bactrim DS, Monotrim, Sulfatrim, Trimpex 200, Baktar, Cotrim D.S., Laratrim, Sumetrolim, Chemotrim, Gantrim, Comox, Imexim, Sulfatrim-DS, Trimogal, Gantaprim, Monotrimin, Syraprim, Ipral, Septra, Sulfamethoprim, Bactrim, Septrin, Septra Grape, Eusaprim, Wellcoprim, Uro-Septra, Idotrim, Nopil, Triprim, Tmp-Ratiopharm, Tiempe, Bactramin
Category: Antimalarials, Anti-Infective Agents, Urinary, Folic Acid Antagonists, Anti-Infectives
CAS number: 738-70-5
Pharmacology
Indication: For the treatment of urinary tract infections, uncomplicated pyelonephritis (with sulfamethoxazole) and mild acute prostatitis. May be used as pericoital (with sulfamethoxazole) or continuous prophylaxis in females with recurrent cystitis. May be used as an alternative to treat asymptomatic bacteriuria during pregnancy (only before the last 6 weeks of pregnancy). Other uses include: alternative agent in respiratory tract infections (otitis, sinusitus, bronchitis and pneumonia), treatment of Pneumocystis jirovecii pneumonia (acute or prophylaxis), Nocardia infections, and traveller's diarrhea.
Pharmacology: Trimethoprim is a pyrimidine analogue that disrupts folate synthesis, an essential part of the thymidine synthesis pathway. Inhibition of the enzyme starves the bacteria of nucleotides necessary for DNA replication.The drug, therefore, exhibits bactericidal activity.
Mechanism of Action:
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. Trimethoprim's affinity for bacterial dihydrofolate reductase is several thousand tim...
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Absorption: Readily and almost completely absorbed in the GI tract with peak serum concentrations attained 1-4 hours after oral administration. Widely distributed to tissues and fluids including kidney, lung, seminal fluid, aqueous humour, middle ear fluid, sputum, vaginal secretions, bile, bone and CSF.
Protein binding: 42-46% bound to plasma proteins
Biotransformation: Hepatic metabolism to oxide and hydroxylated metabolites.
Route of elimination: Ten to twenty percent of trimethoprim is metabolized, primarily in the liver; the remainder is excreted unchanged in the urine. After oral administration, 50% to 60% of trimethoprim is excreted in the urine within 24 hours, approximately 80% of this being unmetabolized trimethoprim. Trimethoprim also passes the placental barrier and is excreted in human milk.
Half Life: 8-11 hours in adults with normal renal function
Toxicity: LD50=4850 (orally in mice)
Affected organisms: Gram negative and gram positive bacteria
Interactions
Food interaction:
Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.
Take on empty stomach: 1 hour before or 2 hours after meals.
Take with a full glass of water.
Drug interaction:
DofetilideTrimethoprim may significantly reduced the clearance of Dofetilide. Trimethoprim is a cation transport inhibitor and may interfere with renal excretion of Dofetilide. Concomitant use is contraindicated.
FluorouracilThe strong CYP2C9 inhibitor, Fluorouracil, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Fluorouracil is initiated, discontinued or dose changed.
FosphenytoinTrimethoprim increases the effect of hydantoin
MiconazoleThe strong CYP2C9 inhibitor, Miconazole, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Miconazole is initiated, discontinued or dose changed.
PiroxicamThe strong CYP2C9 inhibitor, Piroxicam, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Piroxicam is initiated, discontinued or dose changed.
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