Details
Stereochemistry | ACHIRAL |
Molecular Formula | C10H11N3O3S |
Molecular Weight | 253.278 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC(NS(=O)(=O)C2=CC=C(N)C=C2)=NO1
InChI
InChIKey=JLKIGFTWXXRPMT-UHFFFAOYSA-N
InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)
Molecular Formula | C10H11N3O3S |
Molecular Weight | 253.278 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Sulfamethoxazole is a synthetic antibacterial drug,which is used in combination with trimethoprim (Bactrim, Septra) for the treatment or prevention of infections that are proven or strongly suspected to be caused by bacteria. Sulfamethoxazole acts by inhibiting folic acid synthesis via enzyme called dihydropteroate synthase.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2364668 |
0.71 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | BACTRIM Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of Bactrim (sulfamethoxazole and trimethoprim) tablets and other antibacterial drugs, Bactrim (sulfamethoxazole and trimethoprim) tablets 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 empiric selection of therapy. Launch Date1973 |
|||
Curative | BACTRIM Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of Bactrim (sulfamethoxazole and trimethoprim) tablets and other antibacterial drugs, Bactrim (sulfamethoxazole and trimethoprim) tablets 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 empiric selection of therapy. Launch Date1973 |
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Curative | BACTRIM Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of Bactrim (sulfamethoxazole and trimethoprim) tablets and other antibacterial drugs, Bactrim (sulfamethoxazole and trimethoprim) tablets 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 empiric selection of therapy. Launch Date1973 |
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Curative | BACTRIM Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of Bactrim (sulfamethoxazole and trimethoprim) tablets and other antibacterial drugs, Bactrim (sulfamethoxazole and trimethoprim) tablets 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 empiric selection of therapy. Launch Date1973 |
|||
Curative | BACTRIM Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of Bactrim (sulfamethoxazole and trimethoprim) tablets and other antibacterial drugs, Bactrim (sulfamethoxazole and trimethoprim) tablets 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 empiric selection of therapy. Launch Date1973 |
|||
Curative | BACTRIM Approved UseTo reduce the development of drug-resistant bacteria and maintain the effectiveness of Bactrim (sulfamethoxazole and trimethoprim) tablets and other antibacterial drugs, Bactrim (sulfamethoxazole and trimethoprim) tablets 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 empiric selection of therapy. Launch Date1973 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
94.42 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20110016 |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFAMETHOXAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
46.3 μg/mL |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: TRIMETHOPRIM |
SULFAMETHOXAZOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1202.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/20110016 |
1200 mg single, oral dose: 1200 mg route of administration: Oral experiment type: SINGLE co-administered: |
SULFAMETHOXAZOLE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
12.8 h |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: TRIMETHOPRIM |
SULFAMETHOXAZOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30% |
800 mg single, oral dose: 800 mg route of administration: Oral experiment type: SINGLE co-administered: TRIMETHOPRIM |
SULFAMETHOXAZOLE plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
800 mg 2 times / day multiple, oral Recommended Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
unhealthy, 86 years |
Disc. AE: Insomnia... Other AEs: Fear, Behaviour abnormal... AEs leading to discontinuation/dose reduction: Insomnia Other AEs:Fear Sources: Behaviour abnormal Visual hallucinations Disorientation Auditory hallucinations |
1600 mg multiple, oral Recommended Dose: 1600 mg Route: oral Route: multiple Dose: 1600 mg Sources: |
unhealthy, adult |
Other AEs: Leucopenia... |
2400 mg 1 times / day single, oral Highest studied dose Dose: 2400 mg, 1 times / day Route: oral Route: single Dose: 2400 mg, 1 times / day Sources: |
unhealthy, mean age 20 years Health Status: unhealthy Age Group: mean age 20 years Sex: F Sources: |
|
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: |
unhealthy, mean age 47 years Health Status: unhealthy Age Group: mean age 47 years Sources: |
Disc. AE: Allergic reaction... Other AEs: Granulocytopenia... AEs leading to discontinuation/dose reduction: Allergic reaction (3.8%) Other AEs:Granulocytopenia Sources: |
800 mg 2 times / day multiple, oral Recommended Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
unhealthy, mean age 58 years Health Status: unhealthy Age Group: mean age 58 years Sex: M+F Sources: |
Disc. AE: Skin rash... AEs leading to discontinuation/dose reduction: Skin rash (4.9%) Sources: |
1200 mg multiple, oral Studied dose Dose: 1200 mg Route: oral Route: multiple Dose: 1200 mg Sources: |
unhealthy, median age 69 years Health Status: unhealthy Age Group: median age 69 years Sex: M+F Sources: |
Other AEs: Agranulocytosis... |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Auditory hallucinations | 800 mg 2 times / day multiple, oral Recommended Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
unhealthy, 86 years |
|
Behaviour abnormal | 800 mg 2 times / day multiple, oral Recommended Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
unhealthy, 86 years |
|
Disorientation | 800 mg 2 times / day multiple, oral Recommended Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
unhealthy, 86 years |
|
Fear | 800 mg 2 times / day multiple, oral Recommended Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
unhealthy, 86 years |
|
Visual hallucinations | 800 mg 2 times / day multiple, oral Recommended Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
unhealthy, 86 years |
|
Insomnia | Disc. AE | 800 mg 2 times / day multiple, oral Recommended Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
unhealthy, 86 years |
Leucopenia | 1600 mg multiple, oral Recommended Dose: 1600 mg Route: oral Route: multiple Dose: 1600 mg Sources: |
unhealthy, adult |
|
Granulocytopenia | 1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: |
unhealthy, mean age 47 years Health Status: unhealthy Age Group: mean age 47 years Sources: |
|
Allergic reaction | 3.8% Disc. AE |
1200 mg 2 times / day multiple, oral Recommended Dose: 1200 mg, 2 times / day Route: oral Route: multiple Dose: 1200 mg, 2 times / day Sources: |
unhealthy, mean age 47 years Health Status: unhealthy Age Group: mean age 47 years Sources: |
Skin rash | 4.9% Disc. AE |
800 mg 2 times / day multiple, oral Recommended Dose: 800 mg, 2 times / day Route: oral Route: multiple Dose: 800 mg, 2 times / day Sources: |
unhealthy, mean age 58 years Health Status: unhealthy Age Group: mean age 58 years Sex: M+F Sources: |
Agranulocytosis | 9.9% | 1200 mg multiple, oral Studied dose Dose: 1200 mg Route: oral Route: multiple Dose: 1200 mg Sources: |
unhealthy, median age 69 years Health Status: unhealthy Age Group: median age 69 years Sex: M+F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 5.0 |
moderate [Ki 271 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0 |
unlikely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0 |
unlikely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0 |
unlikely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0 |
unlikely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0 |
unlikely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0 |
unlikely | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0 |
unlikely |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/9602961/ Page: 4.0 |
yes | |||
Sources: https://bpspubs.onlinelibrary.wiley.com/doi/epdf/10.1046/j.1365-2125.1996.40110.x#page=3 Page: 3.0 |
yes | yes (co-administration study) Comment: ketoconazole did not inhibit hydroxylamine formation or any route of SMX metabolism; fluconazole decreased 5OH-SMX-acetate by64.0% Sources: https://bpspubs.onlinelibrary.wiley.com/doi/epdf/10.1046/j.1365-2125.1996.40110.x#page=3 Page: 3.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Recognition of sulfamethoxazole and its reactive metabolites by drug-specific CD4+ T cells from allergic individuals. | 2000 Jun 15 |
|
A common polymorphism associated with antibiotic-induced cardiac arrhythmia. | 2000 Sep 12 |
|
Tg.AC genetically altered mouse: assay working group overview of available data. | 2001 |
|
Molecular characterization of Salmonella weltevreden isolated from poultry: evidence of conjugal transfer of plasmid and antibiotic resistance. | 2001 |
|
Infrared studies on Co and Cd complexes of sulfamethoxazole. | 2001 Apr |
|
Practice guidelines for the treatment of uncomplicated cystitis. | 2001 Aug |
|
Vibrio cholerae O1 outbreak isolates in Mozambique and South Africa in 1998 are multiple-drug resistant, contain the SXT element and the aadA2 gene located on class 1 integrons. | 2001 Dec |
|
Molecular epidemiological analysis of Salmonella enterica serotype Derby infections in Hong Kong. | 2001 Feb |
|
Viable but nonculturable uropathogenic bacteria are present in the mouse urinary tract following urinary tract infection and antibiotic therapy. | 2001 Feb |
|
Resistance patterns of non-O157 Shiga toxin-producing Escherichia coli (STEC) strains isolated from animals, food and asymptomatic human carriers in Switzerland. | 2001 Feb |
|
In vitro quantitative analysis of (3)H-uracil incorporation by Sarcocytis neurona to determine efficacy of anti-protozoal agents. | 2001 Feb 26 |
|
Multifocal Staphylococcus aureus infection originating from the sacroiliac joint in a patient with rheumatoid arthritis. | 2001 Jan |
|
Drug interactions as a cause of overanticoagulation on phenprocoumon or acenocoumarol predominantly concern antibacterial drugs. | 2001 Jun |
|
Impact of prophylaxis for Mycobacterium avium complex on bacterial infections in patients with advanced human immunodeficiency virus disease. | 2001 Jun 1 |
|
Indirect potentiometric titration of sulphamethoxazole in the presence of trimethoprim in co-trimazole tablets using copper based mercury film electrode. | 2001 Mar |
|
Serogroups and antimicrobial susceptibility among Escherichia coli isolated from farmed mink (Mustela vison Schreiber) in Denmark. | 2001 Mar 20 |
|
Induction of delayed-type hypersensitivity to sulfamethoxazole in mice: role of metabolites. | 2001 Mar 8 |
|
Association between antibiotic resistance and the expression of Dr adhesin among uropathogenic Escherichia coli. | 2001 Mar-Apr |
|
Twenty-six-week carcinogenicity study of sulfamethoxazole in CB6F1-Tg-rasH2 mice. | 2001 May |
|
Antigenicity and immunogenicity of sulphamethoxazole: demonstration of metabolism-dependent haptenation and T-cell proliferation in vivo. | 2001 May |
|
Prevention of invasive aspergillosis in AIDS by sulfamethoxazole. | 2001 May 25 |
|
Design and evaluation of drug-loaded wound dressing having thermoresponsive, adhesive, absorptive and easy peeling properties. | 2001 Nov |
|
Antimicrobial susceptibility and plasmids from Escherichia coli isolated from rats. | 2001 Oct |
|
Estimating the relative stability of polymorphs and hydrates from heats of solution and solubility data. | 2001 Sep |
|
[Guidelines for Prevention of Pneumocystis carinii Pneumonitis in Children and Adolescents with Cancer]. | 2001 Sep |
|
Antimicrobial susceptibility of Haemophilus influenzae among children in Beijing, China, 1999-2000. | 2002 |
|
Determination of anti-microbial susceptibilities of Haemophilus influenzae, Streptococcus pneumoniae and Moraxella catarrhalis. | 2002 Feb |
|
Role of endotoxin in 6-sulfanilamidoindazole(6SAI)-induced arthritis in rats. | 2002 Feb |
|
Brucellosis in the etiology of febrile neutropenia: case report. | 2002 Feb |
|
Linkage between toxin production and purine biosynthesis in Clostridium difficile. | 2002 Jan |
|
Bacterial infections in cirrhosis: epidemiological changes with invasive procedures and norfloxacin prophylaxis. | 2002 Jan |
|
Current treatment options for chronic granulomatous disease. | 2002 Jul |
|
Trimethoprim and sulfamethoxazole are selective inhibitors of CYP2C8 and CYP2C9, respectively. | 2002 Jun |
|
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species. | 2002 Jun |
|
Study of different off-line sample processing procedures and the measurement of antibiotic and antiviral levels in human serum by high-performance liquid chromatography. | 2002 Jun 25 |
|
Septicaemic pasteurellosis in ostriches (Struthio camelus) in central Saudi Arabia. | 2002 Mar |
Sample Use Guides
The usual adult dosage in the treatment of urinary tract infections and otitis media is 1 DS (double strength) tablet (each DS tablets contains 800 mg sulfamethoxazole and 160 mg trimethoprim) every 12 hours for 10 to 14 days. An identical daily dosage is used for 5 days in the treatment of shigellosis. The recommended dose for children with urinary tract infections or acute otitis media is 40 mg/kg sulfamethoxazole and 8 mg/kg trimethoprim per 24 hours, given in two divided doses every 12 hours for 10 days. An identical daily dosage is used for 5 days in the treatment of shigellosis.The usual adult dosage in the treatment of acute exacerbations of chronic bronchitis is 1 DS tablet every 12 hours for 14 days. The recommended dosage for treatment of patients with documented Pneumocystis jiroveci pneumonia is 75 to 100 mg/kg sulfamethoxazole and 15 to 20 mg/kg trimethoprim per 24 hours given in equally divided doses every 6 hours for 14 to 21 days. The recommended dosage for prophylaxis in adults is 1 DS tablet daily. For the treatment of traveler’s diarrhea, the usual adult dosage is 1 DS tablet every 12 hours for 5 days.
Route of Administration:
Oral
Substance Class |
Chemical
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JE42381TNV
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WHO-ESSENTIAL MEDICINES LIST |
6.5.4 (SUL/TRI)
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WHO-ESSENTIAL MEDICINES LIST |
6.2.2 (SUL/TRI)
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NDF-RT |
N0000008048
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WHO-ATC |
J01EE01
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WHO-VATC |
QJ01EQ11
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WHO-VATC |
QJ01EW11
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NCI_THESAURUS |
C29739
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NDF-RT |
N0000008048
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LIVERTOX |
NBK547937
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N0000175504
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J04AM08
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J01EC01
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N0000008048
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Code System | Code | Type | Description | ||
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Sulfamethoxazole
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9332
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DTXSID8026064
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JE42381TNV
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SULFAMETHOXAZOLE
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2514
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SUB10711MIG
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C47737
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10180
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PRIMARY | RxNorm | ||
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SULFAMETHOXAZOLE
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PRIMARY | Description: A white or yellowish white, crystalline powder; odourless. Solubility: Very slightly soluble in water; soluble in 50 parts of ethanol (~750 g/l) TS and in 3 parts of acetone R. Category: Antibacterial. Storage: Sulfamethoxazole should be kept in a well-closed container, protected from light. Definition: Sulfamethoxazole contains not less than 99.0% and not more than 101.0% of C10H11N3O3S, calculated with reference to the dried substance. | ||
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N0000185504
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PRIMARY | Cytochrome P450 2C9 Inhibitors [MoA] | ||
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211-963-3
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D013420
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CHEMBL443
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1631001
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1386
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100000092618
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JE42381TNV
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DB01015
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723-46-6
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Trimethoprim-Sulfamethoxazole
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m10320
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PRIMARY | Merck Index |
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SALT/SOLVATE -> PARENT |
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TARGET ORGANISM->INHIBITOR |
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BINDER->LIGAND |
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METABOLIC ENZYME -> SUBSTRATE |
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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METABOLITE REACTIVE TYPE->PARENT |
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METABOLITE REACTIVE TYPE->PARENT |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
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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