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)
| Molecular Formula | C14H18N4O3 |
| Molecular Weight | 290.3177 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 VISA/GISA problem: therapeutic implications. | 2001 |
|
| A report case of Cyclospora and Cryptosporidium mixed infection in a HIV-negative child in Thailand. | 2001 Apr |
|
| Prevalence of resistance to antimicrobials of Escherichia coli isolates from clinical sources at a private hospital in Trinidad. | 2001 Apr |
|
| [High sensitivity of Escherichia coli to antimicrobial agents used for first-line treatment of urinary tract infections; results of an examination of feces of healthy subjects in Friesland]. | 2001 Apr 7 |
|
| 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 |
|
| Predominance of a methicillin-resistant Staphylococcus aureus clone susceptible to erythromycin and several other non-beta-lactam antibiotics in a Greek hospital. | 2001 Aug |
|
| Effects of trimethoprim and co-trimoxazole on the morphology of Listeria monocytogenes in culture medium and after phagocytosis. | 2001 Aug |
|
| Effect of mutations in Pneumocystis carinii dihydropteroate synthase gene on outcome of P carinii pneumonia in patients with HIV-1: a prospective study. | 2001 Aug 18 |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Brucellosis in children of Dhofar Region, Oman. | 2001 Jul |
|
| Etiologies of the urinary tract infections in a Yemeni City. | 2001 Jul |
|
| Consensus on use of co-trimoxazole. | 2001 Jul |
|
| Pneumocystis carinii pneumonia in patients being registered for smear-negative pulmonary tuberculosis in Malawi. | 2001 Jul-Aug |
|
| Successful therapy combined with surgery for severe post-transplant nocardiosis. | 2001 Jul-Aug |
|
| Bacteriuria in the elderly population in a developing country. | 2001 Jul-Aug |
|
| 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 |
|
| Susceptibility patterns of enteroaggregative Escherichia coli associated with traveller's diarrhoea: emergence of quinolone resistance. | 2001 Nov |
|
| Synthesis of 2,4-diamino-6-(thioarylmethyl)pyrido[2,3-d]pyrimidines as dihydrofolate reductase inhibitors. | 2001 Nov |
|
| Epidemiological analysis of Salmonella enteritidis isolates in Singapore. | 2001 Oct |
|
| Bacterial aetiology and anti-microbial resistance of childhood diarrhoea in Yemen. | 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 |
|
| Isolation of rat dihydrofolate reductase gene and characterization of recombinant enzyme. | 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 |
|
| 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 |
|
| 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 |
|
| In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species. | 2002 Jun |
|
| Modified antimicrobial disc susceptibility testing for nutritionally-variant streptococci. | 2002 Mar |
|
| 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).
| Substance Class |
Chemical
Created
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| Record UNII |
AN164J8Y0X
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| Record Status |
Validated (UNII)
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| Record Version |
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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
Created by
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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
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|
WHO-ESSENTIAL MEDICINES LIST |
6.2.2 (SUL/TRI)
Created by
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WHO-VATC |
QJ01EW12
Created by
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WHO-ESSENTIAL MEDICINES LIST |
6.2.2
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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WHO-VATC |
QJ01EW11
Created by
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WHO-VATC |
QJ01EW17
Created by
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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
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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|
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
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WHO-ATC |
J01EE01
Created by
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NDF-RT |
N0000000191
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WHO-VATC |
QJ01EW15
Created by
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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
Created by
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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
Created by
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PRIMARY | |||
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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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PRIMARY | |||
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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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PRIMARY | |||
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10829
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PRIMARY | RxNorm | ||
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C908
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PRIMARY | |||
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5578
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PRIMARY | |||
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AN164J8Y0X
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PRIMARY | |||
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738-70-5
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PRIMARY | |||
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DTXSID3023712
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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106568
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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Trimethoprim-Sulfamethoxazole
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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212-006-2
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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SUB11310MIG
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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DB00440
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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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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| Related Record | Type | Details | ||
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METABOLIC ENZYME -> SUBSTRATE | |||
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SALT/SOLVATE -> PARENT | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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BINDER->LIGAND |
BINDING
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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METABOLIC ENZYME -> INHIBITOR |
MAJOR
Ki
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TARGET ORGANISM->INHIBITOR |
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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METABOLIC ENZYME -> SUBSTRATE |
MAJOR
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TARGET -> INHIBITOR | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
Several heterologously expressed P450 enzymes, including CYP1A1, CYP1B1, CYP2C19, CYP3A4, CYP3A5, and CYP3A7, were capable of catalyzing 1-NO-TMP formation
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT | |||
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METABOLITE -> PARENT |
CYP1A1 and CYP1B1 were the heterologously expressed enzymes that catalyzed the highest rates of 3-NO-TMP formation.
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| Related Record | Type | Details | ||
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
|---|---|---|---|---|---|---|
| Biological Half-life | PHARMACOKINETIC |
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