Trimethoprim

Not to be confused with Thymidine monophosphate.

Trimethoprim
Structural formula of trimethoprim
Ball-and-stick model of the trimethoprim molecule
Clinical data
Pronunciation/traɪˈmɛθəprɪm/
Trade namesProloprim, Monotrim, Triprim, others
AHFS/Drugs.comMonograph
MedlinePlusa684025
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
Drug classDiaminopyrimidines
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability90–100%
Protein binding44%
MetabolismLiver
Elimination half-life8–12 hours
ExcretionKidney (50–60%), faeces (4%)
Identifiers
  • 5-(3,4,5-Trimethoxybenzyl)pyrimidine-2,4-diamine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.010.915 Edit this at Wikidata
Chemical and physical data
FormulaC14H18N4O3
Molar mass290.323 g·mol−1
3D model (JSmol)
  • Nc1nc(N)ncc1Cc(cc2OC)cc(OC)c2OC
  • 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) checkY
  • Key:IEDVJHCEMCRBQM-UHFFFAOYSA-N checkY
  (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]

  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.
  3. ^ "Prescribing medicines in pregnancy database". Australian Government. 3 March 2014. Archived from the original on 8 April 2014. Retrieved 22 April 2014.
  4. ^ Huovinen P (June 2001). "Resistance to trimethoprim-sulfamethoxazole". Clinical Infectious Diseases. 32 (11): 1608–1614. doi:10.1086/320532. PMID 11340533.
  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.
  6. ^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 113. ISBN 978-1-284-05756-0.