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Namespace Prefixes

PrefixIRI
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n7http://linked.opendata.cz/ontology/sukl/drug/

Statements

Subject Item
n2:DB00440
rdf:type
n3:Drug
n3: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. [PubChem]
n3:dosage
n14:271B4F96-363D-11E5-9242-09173F13E4C5 n14:271B4F95-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# Brumfitt W, Hamilton-Miller JM: Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines. J Chemother. 1993 Dec;5(6):465-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8195839 # Brumfitt W, Hamilton-Miller JM: Limitations of and indications for the use of co-trimoxazole. J Chemother. 1994 Feb;6(1):3-11. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/8071675 # Bean DC, Livermore DM, Papa I, Hall LM: Resistance among Escherichia coli to sulphonamides and other antimicrobials now little used in man. J Antimicrob Chemother. 2005 Nov;56(5):962-4. Epub 2005 Sep 8. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/16150859 # Felmingham D, Reinert RR, Hirakata Y, Rodloff A: Increasing prevalence of antimicrobial resistance among isolates of Streptococcus pneumoniae from the PROTEKT surveillance study, and compatative in vitro activity of the ketolide, telithromycin. J Antimicrob Chemother. 2002 Sep;50 Suppl S1:25-37. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12239226 # Johnson JR, Manges AR, O'Bryan TT, Riley LW: A disseminated multidrug-resistant clonal group of uropathogenic Escherichia coli in pyelonephritis. Lancet. 2002 Jun 29;359(9325):2249-51. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/12103291
n3:group
approved
n3:halfLife
8-11 hours in adults with normal renal function
n3: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.
n3:manufacturer
n11:271B4F83-363D-11E5-9242-09173F13E4C5 n11:271B4F81-363D-11E5-9242-09173F13E4C5 n11:271B4F82-363D-11E5-9242-09173F13E4C5 n11:271B4F7F-363D-11E5-9242-09173F13E4C5 n11:271B4F80-363D-11E5-9242-09173F13E4C5 n11:271B4F7E-363D-11E5-9242-09173F13E4C5
owl:sameAs
n10:DB00440 n31:DB00440
dcterms:title
Trimethoprim
adms:identifier
n20:46507125 n21:PA451788 n22:5578 n23:D00145 n24:61570-057-01 n25:C01965 n26:5376 n27:DB00440 n28:18069 n29:9731 n30:Trimethoprim
n3:mechanismOfAction
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 times greater than its affinity for human dihydrofolate reductase. Sulfamethoxazole inhibits dihydrofolate synthetase (aka dihydropteroate synthetase), an enzyme involved further upstream in the same pathway. Trimethoprim and sulfamethoxazole are commonly used in combination due to their synergistic effects. This drug combination also reduces the development of resistance that is seen when either drug is used alone.
n3:packager
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n3:patent
n13:5763449
n3:routeOfElimination
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.
n3:synonym
2,4-Diamino-5-(3,4,5-trimethoxybenzyl)pyrimidine Triméthoprime Trimethoprimum Trimethoprim Proloprim Trimetoprima 5-[(3,4,5-Trimethoxyphenyl)methyl]-2,4-pyrimidinediamine Trimpex
n3:toxicity
LD<sub>50</sub>=4850 (orally in mice)
n7:hasAHFSCode
n16:08-36-00
n3:foodInteraction
Take on empty stomach: 1 hour before or 2 hours after meals. Take with a full glass of water. Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.
n3:mixture
n17:271B4F0F-363D-11E5-9242-09173F13E4C5 n17:271B4F10-363D-11E5-9242-09173F13E4C5 n17:271B4F17-363D-11E5-9242-09173F13E4C5 n17:271B4F15-363D-11E5-9242-09173F13E4C5 n17:271B4F16-363D-11E5-9242-09173F13E4C5 n17:271B4F13-363D-11E5-9242-09173F13E4C5 n17:271B4F14-363D-11E5-9242-09173F13E4C5 n17:271B4F11-363D-11E5-9242-09173F13E4C5 n17:271B4F12-363D-11E5-9242-09173F13E4C5
n3:proteinBinding
42-46% bound to plasma proteins
n3:synthesisReference
Yasushi Takagishi, Kiichiro Ohsuga, Sadao Ohama, "Suppository containing sulfamethoxazole/trimethoprim complex and process for preparing the same." U.S. Patent US4461765, issued December, 1975.
foaf:page
n5:trimethoprim.html n12:trimeth.htm
n3:IUPAC-Name
n6:271B4F9B-363D-11E5-9242-09173F13E4C5
n3:InChI
n6:271B4FA1-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n6:271B4FA0-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n6:271B4F9D-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n6:271B4F9E-363D-11E5-9242-09173F13E4C5
n3:SMILES
n6:271B4F9F-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n6:271B4F99-363D-11E5-9242-09173F13E4C5 n6:271B4FB1-363D-11E5-9242-09173F13E4C5
n3:logP
n6:271B4F97-363D-11E5-9242-09173F13E4C5 n6:271B4F9A-363D-11E5-9242-09173F13E4C5 n6:271B4FB3-363D-11E5-9242-09173F13E4C5
n3:logS
n6:271B4F98-363D-11E5-9242-09173F13E4C5 n6:271B4FB4-363D-11E5-9242-09173F13E4C5
n3:pKa
n6:271B4FB5-363D-11E5-9242-09173F13E4C5
n7:hasATCCode
n8:J01EA01
n3:H-Bond-Acceptor-Count
n6:271B4FA7-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n6:271B4FA8-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n6:271B4FA2-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n6:271B4FA3-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n6:271B4FA5-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n6:271B4FA4-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n6:271B4FA6-363D-11E5-9242-09173F13E4C5
n3: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.
n3:affectedOrganism
Gram negative and gram positive bacteria Escherichia coli Listeria monocytogenes
n3:casRegistryNumber
738-70-5
n3:category
n3:containedIn
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n3:Bioavailability
n6:271B4FAD-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n6:271B4FAF-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n6:271B4FB0-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n6:271B4FB2-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n6:271B4FAC-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n6:271B4FAB-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n6:271B4FAE-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n6:271B4F9C-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n6:271B4FA9-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n6:271B4FAA-363D-11E5-9242-09173F13E4C5