Trimethoprim

Trimethoprim
Clinical data
Pronunciation	/traɪˈmɛθəprɪm/
Trade names	Proloprim, Monotrim, Triprim, others
AHFS/Drugs.com	Monograph
MedlinePlus	a684025
License data	US DailyMed: Trimethoprim;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth
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	Liver
Elimination half-life	8–12 hours
Excretion	Kidney (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.^[1] Other uses include for middle ear infections and travelers' diarrhea.^[1] With sulfamethoxazole or dapsone it may be used for Pneumocystis pneumonia in people with HIV/AIDS.^[1]^[2] It is taken orally (swallowed by mouth).^[1]

Common side effects include nausea, changes in taste, and rash.^[1] Rarely it may result in blood problems such as not enough platelets or white blood cells.^[1] Trimethoprim may cause sun sensitivity.^[1] There is evidence of potential harm during pregnancy in some animals but not humans.^[3] 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.^[1]

Trimethoprim was first used in 1962.^[4] It is on the World Health Organization's List of Essential Medicines.^[5] It is available as a generic medication.^[6]

^ ^a ^b ^c ^d ^e ^f ^g ^h "Trimethoprim". The American Society of Health-System Pharmacists. Archived from the original on 24 September 2015. Retrieved 1 August 2015.
^ Masur H, Brooks JT, Benson CA, Holmes KK, Pau AK, Kaplan JE (May 2014). "Prevention and treatment of opportunistic infections in HIV-infected adults and adolescents: Updated Guidelines from the Centers for Disease Control and Prevention, National Institutes of Health, and HIV Medicine Association of the Infectious Diseases Society of America". Clinical Infectious Diseases. 58 (9): 1308–1311. doi:10.1093/cid/ciu094. PMC 3982842. PMID 24585567.
^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
^ Huovinen P (June 2001). "Resistance to trimethoprim-sulfamethoxazole". Clinical Infectious Diseases. 32 (11): 1608–1614. doi:10.1086/320532. PMID 11340533.
^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 113. ISBN 978-1-284-05756-0.

[AHFS2015-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h "Trimethoprim". The American Society of Health-System Pharmacists. Archived from the original on 24 September 2015. Retrieved 1 August 2015.

[2] Masur H, Brooks JT, Benson CA, Holmes KK, Pau AK, Kaplan JE (May 2014). "Prevention and treatment of opportunistic infections in HIV-infected adults and adolescents: Updated Guidelines from the Centers for Disease Control and Prevention, National Institutes of Health, and HIV Medicine Association of the Infectious Diseases Society of America". Clinical Infectious Diseases. 58 (9): 1308–1311. doi:10.1093/cid/ciu094. PMC 3982842. PMID 24585567.

[TGA2014-3] "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.

[Huo2001-4] Huovinen P (June 2001). "Resistance to trimethoprim-sulfamethoxazole". Clinical Infectious Diseases. 32 (11): 1608–1614. doi:10.1086/320532. PMID 11340533.

[WHO22nd-5] World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.

[Ric2015-6] Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 113. ISBN 978-1-284-05756-0.

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