Array ( [0] => {{Short description|Antibiotic}} [1] => {{Distinguish|Thymidine monophosphate}} [2] => {{Use dmy dates|date=March 2024}} [3] => {{cs1 config|name-list-style=vanc|display-authors=6}} [4] => {{infobox drug [5] => | Watchedfields = changed [6] => | verifiedrevid = 470615131 [7] => | image = Trimethoprim.svg [8] => | width = 240 [9] => | alt = Structural formula of trimethoprim [10] => | image2 = Trimethoprim-from-hydrochloride-xtal-1984-3D-balls.png [11] => | width2 = 250 [12] => | alt2 = Ball-and-stick model of the trimethoprim molecule [13] => [14] => [15] => | pronounce = {{IPAc-en|t|r|aɪ|ˈ|m|ɛ|θ|ə|p|r|ɪ|m}} [16] => | tradename = Proloprim, Monotrim, Triprim, others [17] => | Drugs.com = {{drugs.com|monograph|trimethoprim}} [18] => | MedlinePlus = a684025 [19] => | DailyMedID = Trimethoprim [20] => | pregnancy_AU = B3 [21] => | routes_of_administration = [[By mouth]] [22] => | class = [[Diaminopyrimidine]]s [23] => | ATC_prefix = J01 [24] => | ATC_suffix = EA01 [25] => | ATC_supplemental = {{ATCvet|J51|EA01}} [26] => [27] => | legal_AU = S4 [28] => | legal_CA = Rx-only [29] => | legal_UK = POM [30] => | legal_US = Rx-only [31] => [32] => [33] => | bioavailability = 90–100% [34] => | protein_bound = 44% [35] => | metabolism = [[Liver]] [36] => | elimination_half-life = 8–12 hours [37] => | excretion = [[Kidney]] (50–60%), faeces (4%) [38] => [39] => [40] => | CAS_number_Ref = {{cascite|correct|??}} [41] => | CAS_number = 738-70-5 [42] => | PubChem = 5578 [43] => | DrugBank_Ref = {{drugbankcite|correct|drugbank}} [44] => | DrugBank = DB00440 [45] => | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} [46] => | ChemSpiderID = 5376 [47] => | UNII_Ref = {{fdacite|correct|FDA}} [48] => | UNII = AN164J8Y0X [49] => | KEGG_Ref = {{keggcite|correct|kegg}} [50] => | KEGG = D00145 [51] => | ChEBI_Ref = {{ebicite|correct|EBI}} [52] => | ChEBI = 45924 [53] => | ChEMBL_Ref = {{ebicite|correct|EBI}} [54] => | ChEMBL = 22 [55] => | PDB_ligand = TOP [56] => [57] => [58] => | IUPAC_name = 5-(3,4,5-Trimethoxybenzyl)pyrimidine-2,4-diamine [59] => | C=14 | H=18 | N=4 | O=3 [60] => | smiles = Nc1nc(N)ncc1Cc(cc2OC)cc(OC)c2OC [61] => | StdInChI_Ref = {{stdinchicite|correct|chemspider}} [62] => | StdInChI = 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) [63] => | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} [64] => | StdInChIKey = IEDVJHCEMCRBQM-UHFFFAOYSA-N [65] => }} [66] => [67] => '''Trimethoprim''' ('''TMP''') is an [[antibiotic]] used mainly in the treatment of [[urinary tract infection|bladder infections]].{{cite web|title=Trimethoprim|url=https://www.drugs.com/monograph/trimethoprim.html|publisher=The American Society of Health-System Pharmacists|access-date=1 August 2015|url-status=live|archive-url=https://web.archive.org/web/20150924014936/http://www.drugs.com/monograph/trimethoprim.html|archive-date=24 September 2015}} Other uses include for [[acute otitis media|middle ear infections]] and [[travelers' diarrhea]]. With [[Trimethoprim/sulfamethoxazole|sulfamethoxazole]] or [[dapsone]] it may be used for [[Pneumocystis pneumonia|''Pneumocystis'' pneumonia]] in people with [[HIV/AIDS]].{{cite journal | vauthors = Masur H, Brooks JT, Benson CA, Holmes KK, Pau AK, Kaplan JE | title = 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 | journal = Clinical Infectious Diseases | volume = 58 | issue = 9 | pages = 1308–1311 | date = May 2014 | pmid = 24585567 | pmc = 3982842 | doi = 10.1093/cid/ciu094 }} It is taken [[oral administration|orally]] (swallowed by mouth). [68] => [69] => [70] => 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.{{cite web|title=Prescribing medicines in pregnancy database|url=http://www.tga.gov.au/hp/medicines-pregnancy.htm#.U1Yw8Bc3tqw|work=Australian Government|access-date=22 April 2014|date=3 March 2014|url-status=live|archive-url=https://web.archive.org/web/20140408040902/http://www.tga.gov.au/hp/medicines-pregnancy.htm#.U1Yw8Bc3tqw|archive-date=8 April 2014}} 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. [71] => [72] => [73] => Trimethoprim was first used in 1962.{{cite journal | vauthors = Huovinen P | title = Resistance to trimethoprim-sulfamethoxazole | journal = Clinical Infectious Diseases | volume = 32 | issue = 11 | pages = 1608–1614 | date = June 2001 | pmid = 11340533 | doi = 10.1086/320532 | doi-access = free }} It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 22nd list (2021) | year = 2021 | hdl = 10665/345533 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2021.02 | hdl-access=free }} It is available as a generic medication.{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=978-1-284-05756-0|page=113}} [74] => [75] => ==Medical uses== [76] => It is primarily used in the treatment of [[urinary tract infections]], although it may be used against any susceptible [[Aerobic organism|aerobic bacterial species]].{{cite book | veditors = Rossi S | isbn = 978-0-9805790-9-3 | title = Australian Medicines Handbook | place = Adelaide | publisher = The Australian Medicines Handbook Unit Trust | year = 2013 | edition = 2013 }} It may also be used to treat and prevent ''[[Pneumocystis jirovecii]]'' pneumonia. It is generally not recommended for the treatment of [[Anaerobic organism|anaerobic infections]] such as [[Clostridium difficile colitis|''Clostridium difficile'' colitis]] (the leading cause of antibiotic-induced diarrhea). Trimethoprim has been used in trials to treat [[toxoplasmic chorioretinitis|retinitis]].{{cite journal | vauthors = Pradhan E, Bhandari S, Gilbert RE, Stanford M | title = Antibiotics versus no treatment for toxoplasma retinochoroiditis | journal = The Cochrane Database of Systematic Reviews | volume = 2016 | issue = 5 | pages = CD002218 | date = May 2016 | pmid = 27198629 | pmc = 7100541 | doi = 10.1002/14651858.CD002218.pub2 }} [77] => [78] => Resistance to trimethoprim is increasing, but it is still a first line antibiotic in many countries.{{cite web |url=https://www.nice.org.uk/advice/ktt10/chapter/evidence-context |title=Three-day courses of antibiotics for uncomplicated urinary tract infection | Guidance and guidelines | NICE |date=15 January 2015 |access-date=30 December 2015 |url-status=live |archive-url=https://web.archive.org/web/20151208004951/http://www.nice.org.uk/advice/ktt10/chapter/Evidence-context |archive-date=8 December 2015 }} [79] => [80] => ===Spectrum of susceptibility=== [81] => Cultures and susceptibility tests should be done to make sure bacteria are treated by trimethoprim.{{Cite web| work = DailyMed | title = TRIMETHOPRIM- trimethoprim tablet|url = http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a4e9183f-d0eb-4ba7-9204-760b1fd62010| publisher = U.S. National Library of Medicine |access-date = 4 November 2015|url-status = live|archive-url = https://web.archive.org/web/20150930162821/http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a4e9183f-d0eb-4ba7-9204-760b1fd62010|archive-date = 30 September 2015}}{{Cite web| work = DailyMed | title = PRIMSOL- trimethoprim hydrochloride solution|url = http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a06ea7d8-a884-4b62-a87f-c36d824f2aa4| publisher = U.S. National Library of Medicine |access-date = 4 November 2015|url-status = live|archive-url = https://web.archive.org/web/20151117024132/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a06ea7d8-a884-4b62-a87f-c36d824f2aa4|archive-date = 17 November 2015}} [82] => * ''[[Escherichia coli]]'' [83] => * ''[[Proteus mirabilis]]'' [84] => * ''[[Klebsiella pneumoniae]]'' [85] => * ''[[Enterobacter]]'' species [86] => * [[Coagulase|Coagulase-negative]] ''[[Staphylococcus]]'' species, including [[Staphylococcus saprophyticus|''S. saprophyticus'']] [87] => * ''[[Streptococcus pneumoniae]]'' [88] => * ''[[Haemophilus influenzae]]'' [89] => [90] => ==Side effects== [91] => [92] => === Common === [93] => * Nauseas [94] => * Change in taste [95] => * Vomiting [96] => * Diarrhea [97] => * Rashes [98] => * Sun sensitivity [99] => * Itchiness{{Cite web| work = DailyMed | title = PROLOPRIM® (trimethoprim)100-mg and 200-mg Scored Tablets|url = http://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=3220| publisher = U.S. National Library of Medicine |access-date = 4 November 2015|url-status = live|archive-url = https://web.archive.org/web/20151117015344/http://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=3220|archive-date = 17 November 2015}}{{Cite book|title = American Hospital Formulary Service- Drug Information 2002.| vauthors = Ellenhorn MJ, Schonwald S, Ordog G, Wasserberger J |publisher = Williams and Wilkins|location = Baltimore, MD|pages = 236}} [100] => [101] => === Rare === [102] => * Can cause [[thrombocytopenia]] (low levels of [[platelets]]) by lowering [[folic acid]] levels; this may also cause [[megaloblastic anemia]].{{Cite book|title = Drug Information for the Health Care Professional | edition = 22nd | volume = 1 |last = MICROMEDEX Thomson Health Care. USPDI | publisher = Thomson Health Care |location = Greenwood Village, CO. | date = 2002 | page = 2849 }} [103] => * Trimethoprim antagonizes the [[epithelial sodium channel]] in the [[distal tubule]], thus acting like [[amiloride]]. This can cause increased potassium levels in the body ([[hyperkalemia]]).{{cite journal | vauthors = Choi MJ, Fernandez PC, Patnaik A, Coupaye-Gerard B, D'Andrea D, Szerlip H, Kleyman TR | title = Brief report: trimethoprim-induced hyperkalemia in a patient with AIDS | journal = The New England Journal of Medicine | volume = 328 | issue = 10 | pages = 703–706 | date = March 1993 | pmid = 8433730 | doi = 10.1056/NEJM199303113281006 | doi-access = free }} [104] => * Can compete with [[creatinine]] for secretion into the renal tubule. This can cause an artificial rise in the serum creatinine.{{cite journal | vauthors = Naderer O, Nafziger AN, Bertino JS | title = Effects of moderate-dose versus high-dose trimethoprim on serum creatinine and creatinine clearance and adverse reactions | journal = Antimicrobial Agents and Chemotherapy | volume = 41 | issue = 11 | pages = 2466–2470 | date = November 1997 | pmid = 9371351 | pmc = 164146 | doi = 10.1128/AAC.41.11.2466 }} [105] => * Use in [[Enterohemorrhagic Escherichia coli|EHEC]] infections may lead to an increase in expression of [[Shiga toxin]].{{cite journal | vauthors = Kimmitt PT, Harwood CR, Barer MR | title = Toxin gene expression by shiga toxin-producing Escherichia coli: the role of antibiotics and the bacterial SOS response | journal = Emerging Infectious Diseases | volume = 6 | issue = 5 | pages = 458–465 | year = 2000 | pmid = 10998375 | pmc = 2627954 | doi = 10.3201/eid0605.000503 }} [106] => [107] => === Contraindications === [108] => * Known [[hypersensitivity]] to trimethoprim [109] => * History of [[megaloblastic anemia]] due to folate deficiency{{Cite web| work = DailyMed | title = PRIMSOL- trimethoprim hydrochloride solution|url = https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a06ea7d8-a884-4b62-a87f-c36d824f2aa4| publisher = U.S. National Library of Medicine |access-date = 4 November 2015|url-status = live|archive-url = https://web.archive.org/web/20151117024132/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=a06ea7d8-a884-4b62-a87f-c36d824f2aa4|archive-date = 17 November 2015}} [110] => [111] => It may be involved in a reaction similar to [[disulfiram]] when alcohol is consumed after it is used, in particular when used in combination with [[sulfamethoxazole]].{{cite journal | vauthors = Edwards DL, Fink PC, Van Dyke PO | title = Disulfiram-like reaction associated with intravenous trimethoprim-sulfamethoxazole and metronidazole | journal = Clinical Pharmacy | volume = 5 | issue = 12 | pages = 999–1000 | date = December 1986 | pmid = 3492326 | url = http://cat.inist.fr/?aModele=afficheN&cpsidt=8287529 | url-status = live | archive-url = https://web.archive.org/web/20090124113327/http://cat.inist.fr/?aModele=afficheN&cpsidt=8287529 | archive-date = 24 January 2009 }}{{cite journal | vauthors = Heelon MW, White M | title = Disulfiram-cotrimoxazole reaction | journal = Pharmacotherapy | volume = 18 | issue = 4 | pages = 869–870 | year = 1998 | pmid = 9692665 | doi = 10.1002/j.1875-9114.1998.tb03913.x | url = http://cat.inist.fr/?aModele=afficheN&cpsidt=2340043 | url-status = live | s2cid = 23968977 | archive-url = https://web.archive.org/web/20090124113456/http://cat.inist.fr/?aModele=afficheN&cpsidt=2340043 | archive-date = 24 January 2009 }} [112] => [113] => === Pregnancy === [114] => Based on the studies that show that trimethoprim crosses the [[placenta]] and can affect folate metabolism, there has been growing evidence of the risk of structural birth defects associated with trimethoprim, especially during the first [[Pregnancy|trimester]] of pregnancy.{{cite journal | vauthors = Sivojelezova A, Einarson A, Shuhaiber S, Koren G | title = Trimethoprim-sulfonamide combination therapy in early pregnancy | journal = Canadian Family Physician | volume = 49 | pages = 1085–1086 | date = September 2003 | pmid = 14526858 | pmc = 2214286 }} [115] => [116] => The trophoblasts in the early fetus are sensitive to changes in the folate cycle. A 2013 study found a doubling in the risk of miscarriage in women exposed to trimethoprim in the early pregnancy.{{cite journal | vauthors = Andersen JT, Petersen M, Jimenez-Solem E, Broedbaek K, Andersen EW, Andersen NL, Afzal S, Torp-Pedersen C, Keiding N, Poulsen HE | title = Trimethoprim use in early pregnancy and the risk of miscarriage: a register-based nationwide cohort study | journal = Epidemiology and Infection | volume = 141 | issue = 8 | pages = 1749–1755 | date = August 2013 | pmid = 23010291 | pmc = 9151599 | doi = 10.1017/S0950268812002178 | s2cid = 19917493 }} [117] => [118] => ==Mechanism of action== [119] => [[File:Wild-type staphylococcus aureus DHFR in complex with NADPH and trimethoprim.gif|thumb|upright=1.25|''Staphylococcus aureus'' DHFR in complex with NADPH and trimethoprim PDB entry {{PDBe|2W9G}} {{cite journal | vauthors = Heaslet H, Harris M, Fahnoe K, Sarver R, Putz H, Chang J, Subramanyam C, Barreiro G, Miller JR | title = Structural comparison of chromosomal and exogenous dihydrofolate reductase from Staphylococcus aureus in complex with the potent inhibitor trimethoprim | journal = Proteins | volume = 76 | issue = 3 | pages = 706–717 | date = August 2009 | pmid = 19280600 | doi = 10.1002/prot.22383 | s2cid = 1373618 }}]] [120] => 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 inhibitory activity for bacterial dihydrofolate reductase is sixty thousand times greater than for human dihydrofolate reductase.{{cite journal | vauthors = Burchall JJ | title = Mechanism of action of trimethoprim-sulfamethoxazole. II | journal = The Journal of Infectious Diseases | volume = 128 | pages = Suppl: 437-Suppl: 441 | date = November 1973 | pmid = 4585969 | doi = 10.1093/infdis/128.Supplement_3.S437 | ref = TMP1 | jstor = 30105875 }} [[Sulfamethoxazole]] inhibits [[dihydropteroate synthase]], an enzyme involved further upstream in the same pathway. [[Trimethoprim/sulfamethoxazole|Trimethoprim and sulfamethoxazole]] are commonly used in combination due to possible synergistic effects, and reduced development of resistance.{{cite journal | vauthors = Brogden RN, Carmine AA, Heel RC, Speight TM, Avery GS | title = Trimethoprim: a review of its antibacterial activity, pharmacokinetics and therapeutic use in urinary tract infections | journal = Drugs | volume = 23 | issue = 6 | pages = 405–430 | date = June 1982 | pmid = 7049657 | doi = 10.2165/00003495-198223060-00001 | s2cid = 21806926 }} This benefit has been questioned.{{cite journal | vauthors = Brumfitt W, Hamilton-Miller JM | title = Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines | journal = Journal of Chemotherapy | volume = 5 | issue = 6 | pages = 465–469 | date = December 1993 | pmid = 8195839 | doi = 10.1080/1120009X.1993.11741097 }} [121] => [[Image:THFsynthesispathway.png|[[Tetrahydrofolate]] synthesis pathway|thumb|none|upright=1.25]] [122] => [123] => ==History== [124] => Trimethoprim was first used in 1962. In 1972, it was used as a prophylactic treatment for urinary tract infections in Finland. [125] => [126] => Its name is derived from ''trimeth''yl''o''xy-[[pyrimidine|''p''y''rim''idine]]. [127] => [128] => {{Clear right}} [129] => [130] => == References == [131] => {{reflist}} [132] => [133] => {{Sulfonamides and trimethoprim}} [134] => {{Portal bar | Medicine}} [135] => [136] => [[Category:Antibiotics]] [137] => [[Category:Antimetabolites]] [138] => [[Category:Aromatic amines]] [139] => [[Category:Bacterial dihydrofolate reductase inhibitors]] [140] => [[Category:Phenol ethers]] [141] => [[Category:Protozoal dihydrofolate reductase inhibitors]] [142] => [[Category:Pyrimidines]] [143] => [[Category:World Health Organization essential medicines]] [144] => [[Category:Wikipedia medicine articles ready to translate]] [145] => [[Category:CYP2C8 inhibitors]] [] => )
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Trimethoprim

Trimethoprim is an antibiotic medication primarily used to treat urinary tract infections, respiratory tract infections, and traveler's diarrhea caused by certain bacteria. It belongs to a class of drugs known as dihydrofolate reductase inhibitors, which work by preventing the synthesis of folic acid necessary for bacterial growth and replication.

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It belongs to a class of drugs known as dihydrofolate reductase inhibitors, which work by preventing the synthesis of folic acid necessary for bacterial growth and replication. The Wikipedia page on Trimethoprim provides a comprehensive overview of the medication, including its mechanism of action, indications, dosage, and adverse effects. It explains how Trimethoprim is often used in combination with sulfamethoxazole, another antibiotic, to create a synergistic effect and enhance its effectiveness against a wider range of bacteria. The page also covers the history of Trimethoprim's development, including its initial discovery in the 1950s and subsequent introduction into clinical practice. It discusses the patent issues surrounding the medication and the availability of generic versions, which have contributed to its widespread use and affordability. In addition, the Wikipedia page highlights the importance of appropriate antibiotic use and the potential for antibiotic resistance to develop. It emphasizes the need for healthcare professionals to prescribe Trimethoprim judiciously, only for bacterial infections, and to educate patients on the importance of completing the full course of treatment to prevent the emergence of resistant strains. Furthermore, the page provides information on the pharmacokinetics and pharmacodynamics of Trimethoprim, as well as its drug interactions and contraindications. It also mentions the availability of Trimethoprim in different formulations, such as tablets, oral suspension, and intravenous injection, to cater to varying patient needs. Overall, the Wikipedia page on Trimethoprim offers a comprehensive overview of the medication, covering its uses, history, pharmacology, and potential risks. It serves as a valuable resource for healthcare professionals, patients, and individuals seeking information about this antibiotic.

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