Trimethoprim

Trimethoprim
Clinical data
Pronunciation	/traɪˈmɛθəprɪm/
Trade names	Proloprim, Monotrim, Triprim, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684025
License data	US FDA: Trimethoprim;
Pregnancy; category	AU: B3;
Routes of; administration	Oral
Drug class	Diaminopyrimidines
ATC code	J01EA01 (WHO) QJ51EA01 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	90–100%
Protein binding	44%
Metabolism	hepatic
Elimination half-life	8–12 hours
Excretion	Urine (50–60%), faeces (4%)
Identifiers
	IUPAC name 5-(3,4,5-Trimethoxybenzyl)pyrimidine-2,4-diamine;
CAS Number	738-70-5 ;
PubChem CID	5578;
DrugBank	DB00440 ;
ChemSpider	5376 ;
UNII	AN164J8Y0X;
KEGG	D00145 ;
ChEBI	CHEBI:45924 ;
ChEMBL	ChEMBL22 ;
PDB ligand	TOP (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID3023712 ;
ECHA InfoCard	100.010.915
Chemical and physical data
Formula	C14H18N4O3
Molar mass	290.323 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Nc1nc(N)ncc1Cc(cc2OC)cc(OC)c2OC;
	InChI 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) ; Key:IEDVJHCEMCRBQM-UHFFFAOYSA-N ;
	(verify)

Trimethoprim (TMP) is an antibiotic used mainly in the treatment of bladder infections. Other uses include for middle ear infections and travelers' diarrhea. With sulfamethoxazole or dapsone it may be used for Pneumocystis pneumonia in people with HIV/AIDS. It is taken orally (swallowed by mouth).

Common side effects include nausea, changes in taste, and rash. Rarely it may result in blood problems such as not enough platelets or white blood cells. Trimethoprim may cause sun sensitivity. There is evidence of potential harm during pregnancy in some animals but not humans. It works by blocking folate metabolism via dihydrofolate reductase in some bacteria, preventing creation of bacterial DNA and RNA and leading to bacterial cell death.

Trimethoprim was first used in 1962. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication.

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