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 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 |
---|---|---|
Clinical significance and impact on mortality of extended-spectrum beta lactamase-producing Enterobacteriaceae isolates in nosocomial bacteremia. | 2001 |
|
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 |
|
Antimicrobial resistance of Shigella spp isolated from diarrheal patients between 1989 and 1998 in Vietnam. | 2001 Dec |
|
Antibiotic failure in the treatment of urinary tract infections in young women. | 2001 Dec |
|
Travel-associated Burkholderia pseudomallei infection (Melioidosis) in a patient with cystic fibrosis: a case report. | 2001 Jan |
|
[Antimicrobial therapy of urinary tract infections]. | 2001 Jan-Feb |
|
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 |
|
Infectious complications in chronic lymphoid malignancy. | 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 |
|
Co-trimoxazole and genital ulceration. | 2001 Mar |
|
Effect of early chemoprophylaxis with co-trimoxazole on nutritional status evolution in HIV-1-infected adults in Abidjan, Côte d'Ivoire. | 2001 May 4 |
|
Epidemiology of major respiratory pathogens. | 2001 Nov |
|
Susceptibility patterns of enteroaggregative Escherichia coli associated with traveller's diarrhoea: emergence of quinolone resistance. | 2001 Nov |
|
Susceptibility patterns and serotypes of non-typhoidal salmonella in Trinidad. | 2001 Oct |
|
Antibiotic use and resistance of Streptococcus pneumoniae in The Netherlands during the period 1994-1999. | 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 |
|
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 |
|
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 |
|
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species. | 2002 Jun |
|
A European study on the relationship between antimicrobial use and antimicrobial resistance. | 2002 Mar |
|
Q fever during pregnancy: diagnosis, treatment, and follow-up. | 2002 Mar 25 |
|
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 |
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).
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 05:13:50 GMT 2023
by
admin
on
Sat Dec 16 05:13:50 GMT 2023
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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
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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
admin on Sat Dec 16 05:13:50 GMT 2023 , Edited by admin on Sat Dec 16 05:13:50 GMT 2023
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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 16 05:13:50 GMT 2023 , Edited by admin on Sat Dec 16 05:13:50 GMT 2023
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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
Created by
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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
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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
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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
Created by
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WHO-VATC |
QJ51EA01
Created by
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WHO-ATC |
J01EE04
Created by
admin on Sat Dec 16 05:13:50 GMT 2023 , Edited by admin on Sat Dec 16 05:13:50 GMT 2023
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CFR |
21 CFR 520.2613
Created by
admin on Sat Dec 16 05:13:50 GMT 2023 , Edited by admin on Sat Dec 16 05:13:50 GMT 2023
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NDF-RT |
N0000000191
Created by
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CFR |
21 CFR 520.2612
Created by
admin on Sat Dec 16 05:13:50 GMT 2023 , Edited by admin on Sat Dec 16 05:13:50 GMT 2023
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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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PRIMARY | |||
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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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AN164J8Y0X
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738-70-5
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DTXSID3023712
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106568
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PRIMARY | |||
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Trimethoprim-Sulfamethoxazole
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PRIMARY | |||
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212-006-2
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PRIMARY | |||
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100000092388
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PRIMARY | |||
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SUB11310MIG
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PRIMARY | |||
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DB00440
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CHEMBL22
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6781
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45924
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PRIMARY |
Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
|
METABOLIC ENZYME -> SUBSTRATE | |||
|
SALT/SOLVATE -> PARENT | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
|
||
|
BINDER->LIGAND |
BINDING
|
||
|
SALT/SOLVATE -> PARENT | |||
|
SALT/SOLVATE -> PARENT | |||
|
TARGET ORGANISM->INHIBITOR |
|
||
|
SALT/SOLVATE -> PARENT | |||
|
METABOLIC ENZYME -> INHIBITOR |
MAJOR
Ki
|
||
|
METABOLIC ENZYME -> SUBSTRATE |
MAJOR
|
||
|
TARGET -> INHIBITOR | |||
|
BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT | |||
|
METABOLITE -> PARENT |
Several heterologously expressed P450 enzymes, including CYP1A1, CYP1B1, CYP2C19, CYP3A4, CYP3A5, and CYP3A7, were capable of catalyzing 1-NO-TMP formation
|
||
|
METABOLITE -> PARENT | |||
|
METABOLITE -> PARENT | |||
|
METABOLITE -> PARENT |
CYP1A1 and CYP1B1 were the heterologously expressed enzymes that catalyzed the highest rates of 3-NO-TMP formation.
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
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 |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (GC)
EP
|
||
|
IMPURITY -> PARENT |
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
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
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |
|
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
---|---|---|---|---|---|---|
Biological Half-life | PHARMACOKINETIC |
|
|
|||