Details
Stereochemistry | RACEMIC |
Molecular Formula | C14H18N4O3.C3H6O3 |
Molecular Weight | 380.3957 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(O)C(O)=O.COC1=CC(CC2=C(N)N=C(N)N=C2)=CC(OC)=C1OC
InChI
InChIKey=IIZVTUWSIKTFKO-UHFFFAOYSA-N
InChI=1S/C14H18N4O3.C3H6O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15;1-2(4)3(5)6/h5-7H,4H2,1-3H3,(H4,15,16,17,18);2,4H,1H3,(H,5,6)
Trimethoprim (TMP) is an antibiotic is used for the treatment of initial episodes of uncomplicated urinary tract infections due to susceptible strains of the following organisms: Escherichia coli, Proteus mirabilis, Klebsiella pneumoniae, Enterobacter species, and coagulase-negative Staphylococcus species, including S. saprophyticus. Cultures and susceptibility tests should be performed to determine the susceptibility of the bacteria to trimethoprim. Therapy may be initiated prior to obtaining the results of these tests. Trimethoprim is rapidly absorbed following oral administration. It exists in the blood as unbound, protein-bound, and metabolized forms. Ten to twenty percent of trimethoprim is metabolized, primarily in the liver; the remainder is excreted unchanged in the urine. The principal metabolites of trimethoprim are the 1- and 3-oxides and the 3'- and 4'-hydroxy derivatives. The free form is considered to be the therapeutically active form. Approximately 44% of trimethoprim is bound to plasma proteins. Trimethoprim blocks the production of tetrahydrofolic acid from dihydrofolic acid by binding to and reversibly inhibiting the required enzyme, dihydrofolate reductase. This binding is very much stronger for the bacterial enzyme than for the corresponding mammalian enzyme
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364669 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19622858 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | TRIMETHOPRIM Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of trimethoprim tablets, USP and other antibacterial drugs, trimethoprim tablets, USP should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. For the treatment of initial episodes of uncomplicated urinary tract infections due to susceptible strains of the following organisms: Escherichia coli, Proteus mirabilis, Klebsiella pneumoniae, Enterobacter species, and coagulase-negative Staphylococcus species, including S. saprophyticus. Cultures and susceptibility tests should be performed to determine the susceptibility of the bacteria to trimethoprim. Therapy may be initiated prior to obtaining the results of these tests. Launch Date1982 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5416179/ |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
TRIMETHOPRIM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
|
1 μg/mL |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
TRIMETHOPRIM plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/5416179/ |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
TRIMETHOPRIM plasma | Homo sapiens population: UNKNOWN age: ADULT sex: FEMALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10 h |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
TRIMETHOPRIM plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
56% |
1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered: |
TRIMETHOPRIM plasma | Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
300 mg 2 times / day multiple, oral Highest studied dose Dose: 300 mg, 2 times / day Route: oral Route: multiple Dose: 300 mg, 2 times / day Sources: |
unhealthy Health Status: unhealthy Condition: severe shigellosis Sources: |
|
1 g 1 times / day multiple, oral Overdose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Other AEs: Nausea, Vomiting... Other AEs: Nausea Sources: Vomiting Dizziness Headaches Confusion Bone marrow depression |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Bone marrow depression | 1 g 1 times / day multiple, oral Overdose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Confusion | 1 g 1 times / day multiple, oral Overdose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Dizziness | 1 g 1 times / day multiple, oral Overdose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Headaches | 1 g 1 times / day multiple, oral Overdose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Nausea | 1 g 1 times / day multiple, oral Overdose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
|
Vomiting | 1 g 1 times / day multiple, oral Overdose Dose: 1 g, 1 times / day Route: oral Route: multiple Dose: 1 g, 1 times / day Sources: |
unhealthy Health Status: unhealthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
strong [IC50 32 uM] | yes (co-administration study) Comment: selective inhibition; Trimethoprim raised the AUC(0,∞) and Cmax of repaglinide by 61% (range, 30–117%; P = 0.0008) and 41% (P = 0.005), respectively; Although there was no detectable increase in the effect of repaglinide on blood glucose at the doses used, an enhanced risk of hypoglycaemia during concomitant use of trimethoprim and repaglinide is a possibility Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/|https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1884466/ Page: 4.0 |
|||
yes [IC50 1318 uM] | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 2,4 |
yes [Inhibition 250 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 2,4 |
yes [Inhibition 250 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 2,4 |
yes [Inhibition 250 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 2,4 |
yes [Inhibition 250 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 2,4 |
yes [Inhibition <250 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 2,4 |
yes [Inhibition <250 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Interleukin 6 may be an important mediator of trimethoprim-induced systemic adverse reaction resembling aseptic meningitis. | 2000 Jul 10 |
|
Prevalence of resistance to antimicrobials of Escherichia coli isolates from clinical sources at a private hospital in Trinidad. | 2001 Apr |
|
[Whipple disease and non-Hodgkin lymphoma]. | 2001 Apr |
|
HIV and drug allergy. | 2001 Aug |
|
To test or not to test--ethical dilemmas and practical realities in the use of co-trimoxazole and nevirapine in HIV-infected adults. | 2001 Aug |
|
Effects of trimethoprim and co-trimoxazole on the morphology of Listeria monocytogenes in culture medium and after phagocytosis. | 2001 Aug |
|
Empirical treatment of uncomplicated urinary tract infection by community pharmacist in the Eastern province of Saudi Arabia. | 2001 Dec |
|
Gradient diffusion antibiotic susceptibility testing of potentially probiotic lactobacilli. | 2001 Dec |
|
Antibiotic failure in the treatment of urinary tract infections in young women. | 2001 Dec |
|
Bsoft: image and molecular processing in electron microscopy. | 2001 Feb-Mar |
|
[Antimicrobial therapy of urinary tract infections]. | 2001 Jan-Feb |
|
Pulmonary nocardiosis in human immunodeficiency virus infection: a tuberculosis mimic. | 2001 Jan-Mar |
|
Public health lessons from a pilot programme to reduce mother-to-child transmission of HIV-1 in Khayelitsha. | 2001 Jul |
|
Etiologies of the urinary tract infections in a Yemeni City. | 2001 Jul |
|
Consensus on use of co-trimoxazole. | 2001 Jul |
|
Infectious complications in chronic lymphoid malignancy. | 2001 Jun |
|
Antimicrobial sensitivity of Haemophilus influenzae isolates from bacterial conjunctivitis. | 2001 Jun |
|
Successful treatment of late onset infection due to multi-drug resistant Acinetobacter Lwoffii in a low birth weight neonate using ciprofloxacin. | 2001 Jun |
|
Initiating co-trimoxazole prophylaxis in HIV-infected patients in Africa: an evaluation of the provisional WHO/UNAIDS recommendations. | 2001 Jun 15 |
|
Co-trimoxazole and genital ulceration. | 2001 Mar |
|
Patterns of antibiotic resistance, serotype distribution, and patient demographics of Streptococcus pneumoniae in Hong Kong. | 2001 Mar-Apr |
|
Changing pattern of biotypes, phage types & drug resistance of Salmonella typhi in Ludhiana during 1980-1999. | 2001 May |
|
Co-trimoxazole compared with sulfadoxine-pyrimethamine in the treatment of uncomplicated malaria in Kenyan children. | 2001 Nov-Dec |
|
Epidemiological analysis of Salmonella enteritidis isolates in Singapore. | 2001 Oct |
|
Susceptibility patterns and serotypes of non-typhoidal salmonella in Trinidad. | 2001 Oct |
|
Epidemiology of shigellosis in Lagos, Nigeria: trends in antimicrobial resistance. | 2001 Sep |
|
Use of systemic anti-infective agents in Iran during 1997-1998. | 2001 Sep |
|
Antibiotic use and resistance of Streptococcus pneumoniae in The Netherlands during the period 1994-1999. | 2001 Sep |
|
Incidence and risk factors for the development of indinavir-associated renal complications. | 2001 Sep |
|
In vitro activity of novel fluoroquinolones against Streptococcus pneumoniae isolated from children with acute otitis media. | 2001 Sep-Oct |
|
Developing and testing instruments to measure client outcomes at the Comox Valley Nursing Center. | 2001 Sep-Oct |
|
Occurrence of enteric redmouth disease in rainbow trout (Oncorhynchus mykiss) on farms in Croatia. | 2002 |
|
[Antibiotic resistance of staphylococci isolated from outpatients]. | 2002 |
|
Incidence and molecular analysis of Vibrio cholerae associated with cholera outbreak subsequent to the super cyclone in Orissa, India. | 2002 Apr |
|
Burkholderia pseudomallei: abscess in an unusual site. | 2002 Apr-Jun |
|
Trimethoprim-induced aseptic meningitis in an adolescent male. | 2002 Aug |
|
Pneumocystis carinii: where are we now? | 2002 Feb |
|
Clinical efficacy of co-trimoxazole versus amoxicillin twice daily for treatment of pneumonia: a randomised controlled clinical trial in Pakistan. | 2002 Feb |
|
Clinical and biological evolution of HIV-1 seroconverters in Abidjan, Côte d'Ivoire, 1997-2000. | 2002 Feb 1 |
|
A double-hand transplant can be worth the effort! | 2002 Jul 15 |
|
Prevalence of and resistance to anti-microbial drugs in selected microbial species isolated from bulk milk samples. | 2002 Jun |
|
HIV-1/AIDS and maternal and child health in Africa. | 2002 Jun 15 |
|
A European study on the relationship between antimicrobial use and antimicrobial resistance. | 2002 Mar |
|
Changes in Escherichia coli resistance to co-trimoxazole in tuberculosis patients and in relation to co-trimoxazole prophylaxis in Thyolo, Malawi. | 2002 Mar-Apr |
|
A simple clinical and paraclinical score predictive of CD4 cells counts below 400/mm3 in HIV-infected adults in Dakar University Hospital, Senegal. | 2002 Mar-Apr |
|
Clinical signs and symptoms in the assessment of immunodeficiency in men with subtype C HIV infection in Harare, Zimbabwe. | 2002 Mar-Apr |
|
Rapid increase in macrolide resistance among penicillin non-susceptible pneumococci in Finland, 1996-2000. | 2002 May |
|
Emergence of vancomycin-intermediate Staphylococcus aureus and S. sciuri, Greece. | 2002 May |
|
Neutropenic enterocolitis (typhlitis) after pediatric bone marrow transplant. | 2002 May |
|
First characterization of a cluster of VanA-type glycopeptide-resistant Enterococcus faecium, Colombia. | 2002 Sep |
Sample Use Guides
The usual oral adult dosage is 100 mg of trimethoprim every 12 hours or 200 mg of trimethoprim every 24 hours, each for 10 days. The use of trimethoprim in patients with a creatinine clearance of less than 15 mL/min is not recommended. For patients with a creatinine clearance of 15 to 30 mL/min, the dose should be 50 mg every 12 hours.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20488468
Curator's Comment: Trimethoprim can be used as an alternative to trimethoprim/sulfamethoxazole based on in vitro antibacterial susceptibility.
In vitro susceptibility of bacterial isolates to sulfamethoxazole, trimethoprim and trimethoprim/sulfamethoxazole was determined using disk diffusion. E. coli susceptibility to trimethoprim was 70%, comparable to the 70% of trimethoprim/sulfamethoxazole (p = 0.9)and higher than the 56.9% of sulfamethoxazole (p <0.05).
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Brand Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
100000084666
Created by
admin on Fri Dec 15 15:25:31 GMT 2023 , Edited by admin on Fri Dec 15 15:25:31 GMT 2023
|
PRIMARY | |||
|
SUB04972MIG
Created by
admin on Fri Dec 15 15:25:31 GMT 2023 , Edited by admin on Fri Dec 15 15:25:31 GMT 2023
|
PRIMARY | |||
|
245-533-1
Created by
admin on Fri Dec 15 15:25:31 GMT 2023 , Edited by admin on Fri Dec 15 15:25:31 GMT 2023
|
PRIMARY | |||
|
235855
Created by
admin on Fri Dec 15 15:25:31 GMT 2023 , Edited by admin on Fri Dec 15 15:25:31 GMT 2023
|
PRIMARY | RxNorm | ||
|
P3K8GP9FDQ
Created by
admin on Fri Dec 15 15:25:31 GMT 2023 , Edited by admin on Fri Dec 15 15:25:31 GMT 2023
|
PRIMARY | |||
|
23256-42-0
Created by
admin on Fri Dec 15 15:25:31 GMT 2023 , Edited by admin on Fri Dec 15 15:25:31 GMT 2023
|
PRIMARY | |||
|
DTXSID00945947
Created by
admin on Fri Dec 15 15:25:31 GMT 2023 , Edited by admin on Fri Dec 15 15:25:31 GMT 2023
|
PRIMARY | |||
|
3084396
Created by
admin on Fri Dec 15 15:25:31 GMT 2023 , Edited by admin on Fri Dec 15 15:25:31 GMT 2023
|
PRIMARY |
ACTIVE MOIETY
SUBSTANCE RECORD