U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of SULFAMETHOXAZOLE

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)

HIDE SMILES / InChI
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

Description

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

1961
132
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
 0.71 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8360
BACTRIM

Approved Use

To 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 Date

1.12752001E11
Curative
Approved
8360
BACTRIM

Approved Use

To 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 Date

1.12752001E11
Curative
Approved
8360
BACTRIM

Approved Use

To 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 Date

1.12752001E11
Curative
Approved
8360
BACTRIM

Approved Use

To 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 Date

1.12752001E11
Curative
Approved
8360
BACTRIM

Approved Use

To 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 Date

1.12752001E11
Curative
Approved
8360
BACTRIM

Approved Use

To 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 Date

1.12752001E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018374s025lbl.pdf
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TRIMETHOPRIM
TRIMETHOPRIM
 SULFAMETHOXAZOLE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
12.8 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018374s025lbl.pdf
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TRIMETHOPRIM
TRIMETHOPRIM
 SULFAMETHOXAZOLE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
30%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/018374s025lbl.pdf
800 mg single, oral
dose: 800 mg
route of administration: Oral
experiment type: SINGLE
co-administered: TRIMETHOPRIM
TRIMETHOPRIM
 SULFAMETHOXAZOLE plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse 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
Co-administed with::
TRIMETHOPRIM(160 mg; 2/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
n = 1
Health Status: unhealthy
Condition: lower urinary infection
Age Group: 86 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
Disc. AE: Insomnia...
Other AEs: Fear, Behaviour abnormal...
AEs leading to
discontinuation/dose reduction:
Insomnia
Other AEs:
Fear
Behaviour abnormal
Visual hallucinations
Disorientation
Auditory hallucinations
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
1600 mg multiple, oral
Recommended
Dose: 1600 mg
Route: oral
Route: multiple
Dose: 1600 mg
Co-administed with::
TRIMETHOPRIM(320 mg; daily)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4936539/
unhealthy, adult
n = 14
Health Status: unhealthy
Condition: renal transplantation
Age Group: adult
Population Size: 14
Sources:
https://pubmed.ncbi.nlm.nih.gov/4936539/
Other AEs: Leucopenia...
Other AEs:
Leucopenia
Sources:
https://pubmed.ncbi.nlm.nih.gov/4936539/
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
Co-administed with::
TRIMETHOPRIM(480 mg; single)
Sources:
https://pubmed.ncbi.nlm.nih.gov/6724874/
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-105_Zotrim_medr.pdf
unhealthy, mean age 20 years
n = 31
Health Status: unhealthy
Condition: urinary tract infection
Age Group: mean age 20 years
Sex: F
Population Size: 31
Sources:
https://pubmed.ncbi.nlm.nih.gov/6724874/
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-105_Zotrim_medr.pdf
Sources:
https://pubmed.ncbi.nlm.nih.gov/6724874/
https://www.accessdata.fda.gov/drugsatfda_docs/nda/2001/21-105_Zotrim_medr.pdf
1200 mg 2 times / day multiple, oral
Recommended
Dose: 1200 mg, 2 times / day
Route: oral
Route: multiple
Dose: 1200 mg, 2 times / day
Co-administed with::
TRIMETHOPRIM(240 mg; 2/day)
amphotericin B(800 mg; day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/6794406/
unhealthy, mean age 47 years
n = 26
Health Status: unhealthy
Condition: acute nonlymphocytic leukaemia
Age Group: mean age 47 years
Population Size: 26
Sources:
https://pubmed.ncbi.nlm.nih.gov/6794406/
Disc. AE: Allergic reaction...
Other AEs: Granulocytopenia...
AEs leading to
discontinuation/dose reduction:
Allergic reaction (3.8%)
Other AEs:
Granulocytopenia
Sources:
https://pubmed.ncbi.nlm.nih.gov/6794406/
800 mg 2 times / day multiple, oral
Recommended
Dose: 800 mg, 2 times / day
Route: oral
Route: multiple
Dose: 800 mg, 2 times / day
Co-administed with::
TRIMETHOPRIM(160 mg; 2/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4885025/
unhealthy, mean age 58 years
n = 41
Health Status: unhealthy
Condition: urinary infection
Age Group: mean age 58 years
Sex: M+F
Population Size: 41
Sources:
https://pubmed.ncbi.nlm.nih.gov/4885025/
Disc. AE: Skin rash...
AEs leading to
discontinuation/dose reduction:
Skin rash (4.9%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4885025/
1200 mg multiple, oral (mean)
Studied dose
Dose: 1200 mg
Route: oral
Route: multiple
Dose: 1200 mg
Co-administed with::
TRIMETHOPRIM(240 mg; day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12963573/
unhealthy, median age 69 years
n = 91
Health Status: unhealthy
Condition: septicemia
Age Group: median age 69 years
Sex: M+F
Population Size: 91
Sources:
https://pubmed.ncbi.nlm.nih.gov/12963573/
Other AEs: Agranulocytosis...
Other AEs:
Agranulocytosis (9.9%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12963573/
AEs

AEs

AESignificanceDosePopulation
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
Co-administed with::
TRIMETHOPRIM(160 mg; 2/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
n = 1
Health Status: unhealthy
Condition: lower urinary infection
Age Group: 86 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
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
Co-administed with::
TRIMETHOPRIM(160 mg; 2/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
n = 1
Health Status: unhealthy
Condition: lower urinary infection
Age Group: 86 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
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
Co-administed with::
TRIMETHOPRIM(160 mg; 2/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
n = 1
Health Status: unhealthy
Condition: lower urinary infection
Age Group: 86 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
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
Co-administed with::
TRIMETHOPRIM(160 mg; 2/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
n = 1
Health Status: unhealthy
Condition: lower urinary infection
Age Group: 86 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
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
Co-administed with::
TRIMETHOPRIM(160 mg; 2/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
n = 1
Health Status: unhealthy
Condition: lower urinary infection
Age Group: 86 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
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
Co-administed with::
TRIMETHOPRIM(160 mg; 2/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
n = 1
Health Status: unhealthy
Condition: lower urinary infection
Age Group: 86 years
Sex: F
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
Leucopenia
1600 mg multiple, oral
Recommended
Dose: 1600 mg
Route: oral
Route: multiple
Dose: 1600 mg
Co-administed with::
TRIMETHOPRIM(320 mg; daily)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4936539/
unhealthy, adult
n = 14
Health Status: unhealthy
Condition: renal transplantation
Age Group: adult
Population Size: 14
Sources:
https://pubmed.ncbi.nlm.nih.gov/4936539/
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
Co-administed with::
TRIMETHOPRIM(240 mg; 2/day)
amphotericin B(800 mg; day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/6794406/
unhealthy, mean age 47 years
n = 26
Health Status: unhealthy
Condition: acute nonlymphocytic leukaemia
Age Group: mean age 47 years
Population Size: 26
Sources:
https://pubmed.ncbi.nlm.nih.gov/6794406/
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
Co-administed with::
TRIMETHOPRIM(240 mg; 2/day)
amphotericin B(800 mg; day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/6794406/
unhealthy, mean age 47 years
n = 26
Health Status: unhealthy
Condition: acute nonlymphocytic leukaemia
Age Group: mean age 47 years
Population Size: 26
Sources:
https://pubmed.ncbi.nlm.nih.gov/6794406/
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
Co-administed with::
TRIMETHOPRIM(160 mg; 2/day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/4885025/
unhealthy, mean age 58 years
n = 41
Health Status: unhealthy
Condition: urinary infection
Age Group: mean age 58 years
Sex: M+F
Population Size: 41
Sources:
https://pubmed.ncbi.nlm.nih.gov/4885025/
Agranulocytosis 9.9%
1200 mg multiple, oral (mean)
Studied dose
Dose: 1200 mg
Route: oral
Route: multiple
Dose: 1200 mg
Co-administed with::
TRIMETHOPRIM(240 mg; day)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12963573/
unhealthy, median age 69 years
n = 91
Health Status: unhealthy
Condition: septicemia
Age Group: median age 69 years
Sex: M+F
Population Size: 91
Sources:
https://pubmed.ncbi.nlm.nih.gov/12963573/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1579

substrate
1709
inhibitor
1752

substrate
1010
inhibitor
1837

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
1509

CYP2A6
704

CYP2C8
901

CYP2C19
1463

CYP2E1
876
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
1803
 moderate [Ki 271 uM]
CYP1A2
1673
 unlikely
CYP2A6
736
 unlikely
CYP2C19
1537
 unlikely
CYP2C8
955
 unlikely
CYP2D6
1875
 unlikely
CYP2E1
964
 unlikely
CYP3A4
1909
 unlikely
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1709
 yes
CYP2C9
1010
 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%
Page: 3.0
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:9332
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:9332
ChemicalBook
CB6473303
https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6473303
MolPort
MolPort-000-145-787
https://www.molport.com/shop/molecule-link/MolPort-000-145-787
Selleck Chemicals
Sulfamethoxazole
http://www.selleckchem.com/products/Sulfamethoxazole.html
ZINC
ZINC000000089763
http://zinc15.docking.org/substances/ZINC000000089763
eMolecules
511895
https://www.emolecules.com/cgi-bin/more?vid=511895
PubMed

PubMed

TitleDatePubMed
Neonatal mouse model: review of methods and results.
2001
Phenotyping of Campylobacter jejuni and Campylobacter coli by a quantitative antibiogram [MIC] typing scheme using Euclidean distances [QATED].
2001
Molecular characterization of Salmonella weltevreden isolated from poultry: evidence of conjugal transfer of plasmid and antibiotic resistance.
2001
Pharmacokinetics of sulfadimethoxine and sulfamethoxazole in combination with trimethoprim after oral single- and multiple-dose administration to healthy pigs.
2001 Aug
Hydrogen bonding in sulfonamides.
2001 Dec
Resistance to trimethoprim-sulfamethoxazole and modifications in genes coding for dihydrofolate reductase and dihydropteroate synthase in European Streptococcus pneumoniae isolates.
2001 Dec
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
Natural antimicrobial susceptibilities of Plesiomonas shigelloides strains.
2001 Dec
Molecular epidemiology of multiple drug resistant type 6B Streptococcus pneumoniae in the Northern Territory and Queensland, Australia.
2001 Feb
Treatment of cat-scratch disease.
2001 Feb
Primary prevention with cotrimoxazole for HIV-1-infected adults: results of the pilot study in Dakar, Senegal.
2001 Feb 1
In vitro quantitative analysis of (3)H-uracil incorporation by Sarcocytis neurona to determine efficacy of anti-protozoal agents.
2001 Feb 26
Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones.
2001 Jul
Abnormal ACTH-stimulation test in a patient with AIDS: adrenal insufficiency or toxoplasmosis?
2001 Jun
Drug interactions as a cause of overanticoagulation on phenprocoumon or acenocoumarol predominantly concern antibacterial drugs.
2001 Jun
Transition of drug susceptibilities of Vibrio cholerae O1 in Lao People's Democratic Republic.
2001 Mar
Topical bactrim versus trimethoprim and sulfonamide against nocardia keratitis.
2001 Mar
Multiple actinomyces brain abscesses: case report.
2001 Mar
Randomized intervention study comparing several regimens for the treatment of moderate anemia among refugee children in Kigoma Region, Tanzania.
2001 Mar-Apr
A suspected case of primary cutaneous actinomycosis on the buttock.
2001 May
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
Plasmid mediated antibiotic resistance in Klebsiella pneumoniae.
2001 Oct
Antimicrobial susceptibility and plasmids from Escherichia coli isolated from rats.
2001 Oct
Possible interaction between gliclazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia.
2001 Oct
CMY-2-producing Salmonella enterica, Klebsiella pneumoniae, Klebsiella oxytoca, Proteus mirabilis and Escherichia coli strains isolated in Spain (October 1999-December 2000).
2001 Sep
Transfer and distribution profiles of dietary sulphonamides in the tissues of the laying hen.
2002 Apr
Inhibition by atovaquone of CYP2C9-mediated sulphamethoxazole hydroxylamine formation.
2002 Apr
Prevalence and predictors of trimethoprim-sulfamethoxazole resistance among uropathogenic Escherichia coli isolates in Michigan.
2002 Apr 15
Determination of anti-microbial susceptibilities of Haemophilus influenzae, Streptococcus pneumoniae and Moraxella catarrhalis.
2002 Feb
Folic acid antagonism of sulfa drug treatments.
2002 Feb
Bacterial infections in cirrhosis: epidemiological changes with invasive procedures and norfloxacin prophylaxis.
2002 Jan
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
Pharmacokinetics of sulfamethoxazole and trimethoprim in donkeys, mules, and horses.
2002 Mar
Patents

Patents

06794372
28
20010014670
2
JP2002511777A
412
JPH10295777A
2
JPS572218A
2
JPS6023318A
2

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
Bacterias were treated with 23.75 ug sulfamethoxazole to test the susceptibility of microorganisms. MIC values were 38 mcg/ml (Enterobacteriaceae), 9.5 mcg/ml (Haemophilus influenzae), 9.5 mcg/ml (Streptococcus pneumoniae).
Substance Class Chemical
Created
by admin
on Wed Jul 05 23:04:28 UTC 2023
Edited
by admin
on Wed Jul 05 23:04:28 UTC 2023
Record UNII
JE42381TNV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SULFAMETHOXAZOLE
EP   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
USAN   INN  
Official Name English
RO 4-2130
Code English
SULFAMETHOXAZOLE COMPONENT OF UROPLUS
Common Name English
sulfamethoxazole [INN]
Common Name English
SULFAMETHOPRIM COMPONENT SULFAMETHOXAZOLE
Common Name English
UROPLUS COMPONENT SULFAMETHOXAZOLE
Common Name English
NSC-147832
Code English
COTRIM COMPONENT SULFAMETHOXAZOLE
Common Name English
COTRIM D.S. COMPONENT SULFAMETHOXAZOLE
Common Name English
SULFAMETHOXAZOLE COMPONENT OF COTRIM D.S.
Common Name English
SULFAMETHOXAZOLE COMPONENT OF BACTRIM PEDIATRIC
Common Name English
GANTANOL
Brand Name English
SULFAMETHOXAZOLE [USP-RS]
Common Name English
AZO GANTANOL COMPONENT SULFAMETHOXAZOLE
Common Name English
SULFAMETHOXAZOLE [MART.]
Common Name English
BACTRIM PEDIATRIC COMPONENT SULFAMETHOXAZOLE
Common Name English
SULFAMETHOXAZOLE COMPONENT OF COTRIM
Common Name English
SULFAMETHOXAZOLE COMPONENT OF SULFAMETHOPRIM
Common Name English
SEPTRA COMPONENT SULFAMETHOXAZOLE
Common Name English
STX-608
Code English
SULFAMETHOXAZOLE [ORANGE BOOK]
Common Name English
SULFAMETHOXAZOLUM [WHO-IP LATIN]
Common Name English
SULFAMETHOXAZOLE COMPONENT OF BACTRIM DS
Common Name English
BACTRIM DS COMPONENT SULFAMETHOXAZOLE
Common Name English
SULFAMETHOXAZOLE [JAN]
Common Name English
SULFAMETHOXAZOLE COMPONENT OF BACTRIM
Common Name English
SULFAMETHOXAZOLE COMPONENT OF SEPTRA
Common Name English
SULFATRIM COMPONENT SULFAMETHOXAZOLE
Common Name English
SULFAMETHOXAZOLE [VANDF]
Common Name English
BACTRIM COMPONENT SULFAMETHOXAZOLE
Common Name English
SULFAMETHOXAZOLE [IARC]
Common Name English
BENZENESULFONAMIDE, 4-AMINO-N-(5-METHYL-3-ISOXAZOLYL)-
Systematic Name English
SULFAMETHOXAZOLE [USP MONOGRAPH]
Common Name English
SULFAMETHOXAZOLE COMPONENT OF SULMEPRIM
Common Name English
SULPHAMETHOXAZOLE
Common Name English
SULFAMETHOXAZOLE COMPONENT OF SULFATRIM
Common Name English
SULFAMETHOXAZOLE [USAN]
Common Name English
RO-4-2130
Code English
SULFAMETHOXAZOLE [MI]
Common Name English
SULMEPRIM COMPONENT SULFAMETHOXAZOLE
Common Name English
N(SUP 1)-(5-METHYL-3-ISOXAZOLYL)SULFANILAMIDE
Systematic Name English
Sulfamethoxazole [WHO-DD]
Common Name English
SULFAMETHOXAZOLE COMPONENT OF AZO GANTANOL
Common Name English
SULFAMETHOXAZOLE [HSDB]
Common Name English
SMX
Common Name English
Co-trimethoxazole component sulfamethoxazole
Common Name English
SULFAMETHOXAZOLE [EP MONOGRAPH]
Common Name English
SULFAMETHOXAZOLE [WHO-IP]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 6.5.4 (SUL/TRI)
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.2.2 (SUL/TRI)
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
NDF-RT N0000008048
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
WHO-ATC J01EE01
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
WHO-VATC QJ01EQ11
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
WHO-VATC QJ01EW11
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
NCI_THESAURUS C29739
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
NDF-RT N0000008048
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
LIVERTOX NBK547937
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
NDF-RT N0000175504
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
WHO-ATC J04AM08
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
WHO-ATC J01EC01
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
NDF-RT N0000008048
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
Code System Code Type Description
LACTMED
Sulfamethoxazole
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
CHEBI
9332
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
EPA CompTox
DTXSID8026064
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
FDA UNII
JE42381TNV
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
WIKIPEDIA
SULFAMETHOXAZOLE
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
DRUG CENTRAL
2514
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
EVMPD
SUB10711MIG
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
NCI_THESAURUS
C47737
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
RXCUI
10180
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
SULFAMETHOXAZOLE
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
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.
NDF-RT
N0000185504
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY Cytochrome P450 2C9 Inhibitors [MoA]
ECHA (EC/EINECS)
211-963-3
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
MESH
D013420
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
HSDB
3186
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
ChEMBL
CHEMBL443
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
NSC
147832
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
PUBCHEM
5329
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
RS_ITEM_NUM
1631001
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
INN
1386
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
SMS_ID
100000092618
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
DAILYMED
JE42381TNV
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
DRUG BANK
DB01015
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
CAS
723-46-6
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
LACTMED
Trimethoprim-Sulfamethoxazole
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY
MERCK INDEX
M10320
Created by admin on Wed Jul 05 23:04:28 UTC 2023 , Edited by admin on Wed Jul 05 23:04:28 UTC 2023
PRIMARY Merck Index
Related Record Type Details
Structure of SULFAMETHOXAZOLE SODIUM
SALT/SOLVATE -> PARENT
METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS
TARGET ORGANISM->INHIBITOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
ARYLAMINE N-ACETYLTRANSFERASE 2
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
Structure of ACETYLSULFAMETHOXAZOLE
METABOLITE -> PARENT
Structure of SULFAMETHOXAZOLE HYDROXYLAMINE
METABOLITE -> PARENT
Structure of 4-NITROSOSULFAMETHOXAZOLE
METABOLITE REACTIVE TYPE->PARENT
Structure of 4-NITRO-SULFAMETHOXAZOLE
METABOLITE REACTIVE TYPE->PARENT
Related Record Type Details
Structure of ISOSULFAMETHOXAZOLE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 4-AMINO-N-(4-(N-(5-METHYLISOXAZOL-3-YL)SULFAMOYL)PHENYL)BENZENESULFONAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of SULFANILIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of SULFANILAMIDE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of ACETYLSULFAMETHOXAZOLE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 5-METHYL-3-ISOXAZOLAMINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of SULFAMETHOXAZOLE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
NIH
NCATS
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ACCESSIBILITY
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