Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C14H18N4O3 |
| Molecular Weight | 290.3177 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(CC2=C(N)N=C(N)N=C2)=CC(OC)=C1OC
InChI
InChIKey=IEDVJHCEMCRBQM-UHFFFAOYSA-N
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)
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 |
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 Date3.96748784E11 |
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] | ||||
Page: 2,4 |
yes [Inhibition 250 uM] | |||
Page: 2,4 |
yes [Inhibition 250 uM] | |||
Page: 2,4 |
yes [Inhibition 250 uM] | |||
Page: 2,4 |
yes [Inhibition 250 uM] | |||
Page: 2,4 |
yes [Inhibition <250 uM] | |||
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 |
|---|---|---|
| The pro-apoptotic Bcl-2 family member tBid localizes to mitochondrial contact sites. | 2001 |
|
| Antimicrobial resistance of Shigella spp isolated from diarrheal patients between 1989 and 1998 in Vietnam. | 2001 Dec |
|
| Rapid detection of Haemophilus influenzae type b in Bangladeshi children with pneumonia and meningitis by PCR and analysis of antimicrobial resistance. | 2001 Dec |
|
| Pneumocystis carinii pneumonitis in haemophagocytic lymphohistiocytosis. | 2001 Dec |
|
| 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 |
|
| Neonatal brucellosis and blood transfusion: case report and review of the literature. | 2001 Dec |
|
| Prevalence of antimicrobial resistance in Streptococcus pneumoniae circulating in Italy: results of the Italian Epidemiological Observatory Survey (1997-1999). | 2001 Fall |
|
| Epidemic of Vibrio cholerae serogroup O139 in Berhampur, Orissa. | 2001 Jul |
|
| Infectious complications in chronic lymphoid malignancy. | 2001 Jun |
|
| Changing pattern of biotypes, phage types & drug resistance of Salmonella typhi in Ludhiana during 1980-1999. | 2001 May |
|
| Epidemiology of major respiratory pathogens. | 2001 Nov |
|
| A common-source water-borne outbreak of multidrug-resistant typhoid fever in a rural Thai community. | 2001 Nov |
|
| Susceptibility patterns of enteroaggregative Escherichia coli associated with traveller's diarrhoea: emergence of quinolone resistance. | 2001 Nov |
|
| 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 |
|
| Occurrence of enteric redmouth disease in rainbow trout (Oncorhynchus mykiss) on farms in Croatia. | 2002 |
|
| [Antibiotic resistance of staphylococci isolated from outpatients]. | 2002 |
|
| Staphylococcus aureus and Wegener's granulomatosis. | 2002 |
|
| Incidence and molecular analysis of Vibrio cholerae associated with cholera outbreak subsequent to the super cyclone in Orissa, India. | 2002 Apr |
|
| [General antibiotic therapy in acne]. | 2002 Apr 15 |
|
| Burkholderia pseudomallei: abscess in an unusual site. | 2002 Apr-Jun |
|
| Trimethoprim-induced aseptic meningitis in an adolescent male. | 2002 Aug |
|
| Shigellosis linked to sex venues, Australia. | 2002 Aug |
|
| Clinical efficacy of co-trimoxazole versus amoxicillin twice daily for treatment of pneumonia: a randomised controlled clinical trial in Pakistan. | 2002 Feb |
|
| Prophylactic antibiotic use in transurethral prostatic resection: a meta-analysis. | 2002 Feb |
|
| Clinical and biological evolution of HIV-1 seroconverters in Abidjan, Côte d'Ivoire, 1997-2000. | 2002 Feb 1 |
|
| Allergic adverse reactions to sulfonamides. | 2002 Jan |
|
| Inhibition of Pneumocystis carinii, Toxoplasma gondii, and Mycobacterium avium dihydrofolate reductases by 2,4-diamino-5-[2-methoxy-5-(omega-carboxyalkyloxy)benzyl]pyrimidines: marked improvement in potency relative to trimethoprim and species selectivity relative to piritrexim. | 2002 Jan 3 |
|
| A double-hand transplant can be worth the effort! | 2002 Jul 15 |
|
| Facilitating changes in perinatal smoking. The impact of a stage-based workshop for care-providers in British Columbia. | 2002 Jul-Aug |
|
| Prevalence of and resistance to anti-microbial drugs in selected microbial species isolated from bulk milk samples. | 2002 Jun |
|
| In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species. | 2002 Jun |
|
| HIV-1/AIDS and maternal and child health in Africa. | 2002 Jun 15 |
|
| A disseminated multidrug-resistant clonal group of uropathogenic Escherichia coli in pyelonephritis. | 2002 Jun 29 |
|
| Modified antimicrobial disc susceptibility testing for nutritionally-variant streptococci. | 2002 Mar |
|
| The relation between sale of antimicrobial drugs and antibiotic resistance in uropathogens in general practice. | 2002 Mar |
|
| Q fever during pregnancy: diagnosis, treatment, and follow-up. | 2002 Mar 25 |
|
| 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 |
|
| Urinary tract-derived Escherichia coli resistant to co-trimoxazole in Japan, where the drug is seldom used for treating acute urinary tract infections. | 2002 May |
|
| 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
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).
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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WHO-ATC |
J01EE07
Created by
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CFR |
21 CFR 520.2611
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WHO-VATC |
QJ01EW09
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WHO-VATC |
QJ01EW18
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WHO-VATC |
QJ01EW13
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WHO-ATC |
J04AM08
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NDF-RT |
N0000175489
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LIVERTOX |
NBK547937
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WHO-VATC |
QJ01EW30
Created by
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WHO-ESSENTIAL MEDICINES LIST |
6.2.2 (SUL/TRI)
Created by
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WHO-VATC |
QJ01EW12
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WHO-ESSENTIAL MEDICINES LIST |
6.2.2
Created by
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WHO-VATC |
QJ01EW11
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WHO-VATC |
QJ01EW17
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WHO-VATC |
QJ01EW16
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WHO-ATC |
J01EE03
Created by
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CFR |
21 CFR 520.2610
Created by
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WHO-ESSENTIAL MEDICINES LIST |
6.5.4 (SUL/TRI)
Created by
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WHO-VATC |
QJ01EW10
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WHO-ATC |
J01EE05
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NCI_THESAURUS |
C255
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WHO-ATC |
J01EE02
Created by
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WHO-ATC |
J01EE01
Created by
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NDF-RT |
N0000000191
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WHO-VATC |
QJ01EW15
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WHO-VATC |
QJ01EA01
Created by
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CFR |
21 CFR 522.2610
Created by
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WHO-VATC |
QJ01EW03
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WHO-ATC |
J01EA01
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WHO-VATC |
QJ01EW14
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WHO-VATC |
QJ51RE01
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WHO-VATC |
QJ51EA01
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WHO-ATC |
J01EE04
Created by
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CFR |
21 CFR 520.2613
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NDF-RT |
N0000000191
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CFR |
21 CFR 520.2612
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| Code System | Code | Type | Description | ||
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1692505
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PRIMARY | |||
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Trimethoprim
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N0000187061
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PRIMARY | Organic Cation Transporter 2 Inhibitors [MoA] | ||
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1047
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TRIMETHOPRIM
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PRIMARY | Description: A white, crystalline powder; odourless or almost odourless. Solubility: Sparingly soluble in water; soluble in methanol R; practically insoluble in ether R. Category: Antibacterial. Storage: Trimethoprim should be kept in a well-closed container. Definition: Trimethoprim contains not less than 98.5% and not more than 101.0% of C14H18N4O3, calculated with reference to the dried substance. | ||
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AN164J8Y0X
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D014295
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M11148
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PRIMARY | Merck Index | ||
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TRIMETHOPRIM
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N0000187062
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PRIMARY | Cytochrome P450 2C8 Inhibitors [MoA] | ||
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2755
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10829
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PRIMARY | RxNorm | ||
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C908
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5578
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AN164J8Y0X
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738-70-5
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DTXSID3023712
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106568
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Trimethoprim-Sulfamethoxazole
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PRIMARY | |||
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212-006-2
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SUB11310MIG
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DB00440
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admin on Sat Dec 17 18:01:40 UTC 2022 , Edited by admin on Sat Dec 17 18:01:40 UTC 2022
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CHEMBL22
Created by
admin on Sat Dec 17 18:01:40 UTC 2022 , Edited by admin on Sat Dec 17 18:01:40 UTC 2022
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6781
Created by
admin on Sat Dec 17 18:01:40 UTC 2022 , Edited by admin on Sat Dec 17 18:01:40 UTC 2022
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45924
Created by
admin on Sat Dec 17 18:01:40 UTC 2022 , Edited by admin on Sat Dec 17 18:01:40 UTC 2022
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ACTIVE MOIETY
METABOLITE (PARENT)
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METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
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SALT/SOLVATE (PARENT)
