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
146
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 0.71 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
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

1973
Curative
Approved
8583
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

1973
Curative
Approved
8583
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

1973
Curative
Approved
8583
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

1973
Curative
Approved
8583
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

1973
Curative
Approved
8583
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

1973
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
Health Status: unhealthy
Age Group: 86 years
Sex: F
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/4936539/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
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
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
Health Status: unhealthy
Age Group: mean age 20 years
Sex: F
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/6794406/
unhealthy, mean age 47 years
Health Status: unhealthy
Age Group: mean age 47 years
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/4885025/
unhealthy, mean age 58 years
Health Status: unhealthy
Age Group: mean age 58 years
Sex: M+F
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
Studied dose
Dose: 1200 mg
Route: oral
Route: multiple
Dose: 1200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/12963573/
unhealthy, median age 69 years
Health Status: unhealthy
Age Group: median age 69 years
Sex: M+F
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
Health Status: unhealthy
Age Group: 86 years
Sex: F
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
Health Status: unhealthy
Age Group: 86 years
Sex: F
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
Health Status: unhealthy
Age Group: 86 years
Sex: F
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
Health Status: unhealthy
Age Group: 86 years
Sex: F
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
Health Status: unhealthy
Age Group: 86 years
Sex: F
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
unhealthy, 86 years
Health Status: unhealthy
Age Group: 86 years
Sex: F
Sources:
https://pubmed.ncbi.nlm.nih.gov/24268951/
Leucopenia
1600 mg multiple, oral
Recommended
Dose: 1600 mg
Route: oral
Route: multiple
Dose: 1600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/4936539/
unhealthy, adult
Health Status: unhealthy
Age Group: adult
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/6794406/
unhealthy, mean age 47 years
Health Status: unhealthy
Age Group: mean age 47 years
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/6794406/
unhealthy, mean age 47 years
Health Status: unhealthy
Age Group: mean age 47 years
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
Sources:
https://pubmed.ncbi.nlm.nih.gov/4885025/
unhealthy, mean age 58 years
Health Status: unhealthy
Age Group: mean age 58 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/4885025/
Agranulocytosis 9.9%
1200 mg multiple, oral
Studied dose
Dose: 1200 mg
Route: oral
Route: multiple
Dose: 1200 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/12963573/
unhealthy, median age 69 years
Health Status: unhealthy
Age Group: median age 69 years
Sex: M+F
Sources:
https://pubmed.ncbi.nlm.nih.gov/12963573/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
2252

substrate
1946
inhibitor
2438

substrate
1193
inhibitor
2507

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP1A2
2153

CYP2A6
879

CYP2C8
1057

CYP2C19
2057

CYP2E1
1060
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
2497
 moderate [Ki 271 uM]
CYP1A2
2333
 unlikely
CYP2A6
911
 unlikely
CYP2C19
2141
 unlikely
CYP2C8
1117
 unlikely
CYP2D6
2546
 unlikely
CYP2E1
1146
 unlikely
CYP3A4
2633
 unlikely
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
CYP3A4
1946
 yes
CYP2C9
1193
 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
eMolecules
511895
https://www.emolecules.com/cgi-bin/more?vid=511895
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
PubMed

PubMed

TitleDatePubMed
Current treatment options for chronic granulomatous disease.
2002-07
Study of different off-line sample processing procedures and the measurement of antibiotic and antiviral levels in human serum by high-performance liquid chromatography.
2002-06-25
Second derivative spectrophotometric determination of trimethoprime and sulfamethoxazole in the presence of hydroxypropyl-beta-cyclodextrin (HP-beta-CD).
2002-06-20
Sensitivity and resistance of antibiotics in common infection of male and female.
2002-06-05
[Characterization of Vibrio cholerae eltor in the city of Kazan in 2001].
2002-06-05
Ofuji's disease: a report on 20 patients with clinical and histopathologic analysis.
2002-06
Trimethoprim and sulfamethoxazole are selective inhibitors of CYP2C8 and CYP2C9, respectively.
2002-06
In vitro activities of pentamidine, pyrimethamine, trimethoprim, and sulfonamides against Aspergillus species.
2002-06
Prevalence and predictors of trimethoprim-sulfamethoxazole resistance among uropathogenic Escherichia coli isolates in Michigan.
2002-04-15
Quantification of veterinary antibiotics (sulfonamides and trimethoprim) in animal manure by liquid chromatography-mass spectrometry.
2002-04-05
Can the enhanced renal clearance of antibiotics in cystic fibrosis patients be explained by P-glycoprotein transport?
2002-04
Salmonella enterica serotype Typhimurium DT104 isolated from humans, United States, 1985, 1990, and 1995.
2002-04
Transfer and distribution profiles of dietary sulphonamides in the tissues of the laying hen.
2002-04
Inhibition by atovaquone of CYP2C9-mediated sulphamethoxazole hydroxylamine formation.
2002-04
Pneumocystis carinii infection in bilateral aural polyps in a human immunodeficiency virus-positive patient.
2002-04
Drug specific cytotoxic T-cells in the skin lesions of a patient with toxic epidermal necrolysis.
2002-04
Liquid chromatographic determination of multiple sulfonamides, nitrofurans, and chloramphenicol residues in pasteurized milk.
2002-03-07
Simultaneous dissolution profiles of two drugs in pharmaceutical formulations by an FIA manifold.
2002-03-01
Septicaemic pasteurellosis in ostriches (Struthio camelus) in central Saudi Arabia.
2002-03
Pharmacokinetics of sulfamethoxazole and trimethoprim in donkeys, mules, and horses.
2002-03
Iminodibenzyl as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives.
2002-03
Determination of anti-microbial susceptibilities of Haemophilus influenzae, Streptococcus pneumoniae and Moraxella catarrhalis.
2002-02
Role of endotoxin in 6-sulfanilamidoindazole(6SAI)-induced arthritis in rats.
2002-02
Brucellosis in the etiology of febrile neutropenia: case report.
2002-02
Occurrence of Salmonella enterica serotype typhimurium DT104A in retail ground beef.
2002-02
Folic acid antagonism of sulfa drug treatments.
2002-02
Amniotic membrane in the surgical management of acute toxic epidermal necrolysis.
2002-02
Allergic adverse reactions to sulfonamides.
2002-01
Linkage between toxin production and purine biosynthesis in Clostridium difficile.
2002-01
Bacterial infections in cirrhosis: epidemiological changes with invasive procedures and norfloxacin prophylaxis.
2002-01
Antimicrobial susceptibility of Haemophilus influenzae among children in Beijing, China, 1999-2000.
2002
Determination of selected sulfonamide antibiotics and trimethoprim in manure by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry.
2002
Matrix solid-phase dispersion extraction and high-performance liquid chromatographic determination of residual sulfonamides in chicken.
2001-12-07
Bilirubin-albumin binding and free bilirubin.
2001-12
High-performance liquid chromatographic procedure for routine residue monitoring of seven sulfonamides in milk.
2001-12
Hydrogen bonding in sulfonamides.
2001-12
Resistance to trimethoprim-sulfamethoxazole and modifications in genes coding for dihydrofolate reductase and dihydropteroate synthase in European Streptococcus pneumoniae isolates.
2001-12
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.
2001-12
Natural antimicrobial susceptibilities of Plesiomonas shigelloides strains.
2001-12
Folic acid utilisation related to sulfa drug resistance in Saccharomyces cerevisiae.
2001-11-13
Paraplegia secondary to Burkholderia pseudomallei myelitis: a case report.
2001-11
Plasmid mediated antibiotic resistance in Klebsiella pneumoniae.
2001-10
Antimicrobial susceptibility and plasmids from Escherichia coli isolated from rats.
2001-10
Possible interaction between gliclazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia.
2001-10
Cotrimoxazole treatment for rheumatoid arthritis.
2001-10
Estimating the relative stability of polymorphs and hydrates from heats of solution and solubility data.
2001-09
The occurrence of sinusitis in HIV-infected patients with fever.
2001-09
Practice guidelines for the treatment of uncomplicated cystitis.
2001-08
Tg.AC genetically altered mouse: assay working group overview of available data.
2001
Neonatal mouse model: review of methods and results.
2001
Patents

Patents

06794372
28
20010014670
2
JP2002511777A
420
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 Mon Mar 31 18:02:01 GMT 2025
Edited
by admin
on Mon Mar 31 18:02:01 GMT 2025
Record UNII
JE42381TNV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AZO GANTANOL COMPONENT SULFAMETHOXAZOLE
Preferred Name English
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 [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
GANTANOL
Brand Name English
SULFAMETHOXAZOLE [USP-RS]
Common Name English
SULFAMETHOXAZOLE [MART.]
Common Name English
BACTRIM PEDIATRIC COMPONENT SULFAMETHOXAZOLE
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
BACTRIM DS COMPONENT SULFAMETHOXAZOLE
Common Name English
SULFAMETHOXAZOLE [JAN]
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
SULPHAMETHOXAZOLE
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 [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 Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
WHO-ESSENTIAL MEDICINES LIST 6.2.2 (SUL/TRI)
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
NDF-RT N0000008048
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
WHO-ATC J01EE01
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
WHO-VATC QJ01EQ11
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
WHO-VATC QJ01EW11
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
NCI_THESAURUS C29739
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
NDF-RT N0000008048
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
LIVERTOX NBK547937
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
NDF-RT N0000175504
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
WHO-ATC J04AM08
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
WHO-ATC J01EC01
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
NDF-RT N0000008048
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
Code System Code Type Description
LACTMED
Sulfamethoxazole
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
CHEBI
9332
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
EPA CompTox
DTXSID8026064
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
FDA UNII
JE42381TNV
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
WIKIPEDIA
SULFAMETHOXAZOLE
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
DRUG CENTRAL
2514
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
EVMPD
SUB10711MIG
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
NCI_THESAURUS
C47737
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
RXCUI
10180
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY RxNorm
WHO INTERNATIONAL PHARMACOPEIA
SULFAMETHOXAZOLE
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
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 Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY Cytochrome P450 2C9 Inhibitors [MoA]
ECHA (EC/EINECS)
211-963-3
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
MESH
D013420
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
HSDB
3186
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
ChEMBL
CHEMBL443
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
NSC
147832
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
PUBCHEM
5329
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
RS_ITEM_NUM
1631001
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
INN
1386
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
SMS_ID
100000092618
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
DAILYMED
JE42381TNV
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
DRUG BANK
DB01015
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
CAS
723-46-6
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
LACTMED
Trimethoprim-Sulfamethoxazole
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
PRIMARY
MERCK INDEX
m10320
Created by admin on Mon Mar 31 18:02:01 GMT 2025 , Edited by admin on Mon Mar 31 18:02:01 GMT 2025
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 4-AMINO-N-(4-(N-(5-METHYLISOXAZOL-3-YL)SULFAMOYL)PHENYL)BENZENESULFONAMIDE
IMPURITY -> PARENT
Structure of ISOSULFAMETHOXAZOLE
IMPURITY -> PARENT
Structure of ACETYLSULFAMETHOXAZOLE
IMPURITY -> PARENT
Structure of 5-METHYL-3-ISOXAZOLAMINE
IMPURITY -> PARENT
Structure of SULFANILIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of SULFANILAMIDE
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
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
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