SULFAMETHOXAZOLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H11N3O3S
Molecular Weight	253.2791
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cc1cc(no1)NS(=O)(=O)c2ccc(cc2)N

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

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017377s074lbl.pdf

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
Bacterial dihydropteroate synthase 42 Target ID: CHEMBL2364668 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017377s074lbl.pdf	Inhibitor 7701		0.71 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 197 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017377s074lbl.pdf	Curative	Approved 7997	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
Acute otitis media 21 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017377s074lbl.pdf	Curative	Approved 7997	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
Acute exacerbations of chronic bronchitis in adults 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017377s074lbl.pdf	Curative	Approved 7997	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
Shigellosis 2 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017377s074lbl.pdf	Curative	Approved 7997	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
Pneumocystis jiroveci pneumonia 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017377s074lbl.pdf	Curative	Approved 7997	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
Travelers’ diarrhea 7 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/017377s074lbl.pdf	Curative	Approved 7997	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

C_max

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 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

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

T_1/2

Value	Dose	Co-administered	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

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 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

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 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

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1172 substrate 1470	inhibitor 1318 substrate 865	inhibitor 1421

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1268 CYP2A6 594 CYP2C8 761 CYP2C19 1215 CYP2E1 761

Drug as perpetrator

Target	Modality	Activity
CYP2C9 1362	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 5.0	moderate [Ki 271 uM]
CYP1A2 1406	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0	unlikely
CYP2A6 625	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0	unlikely
CYP2C19 1277	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0	unlikely
CYP2C8 810	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0	unlikely
CYP2D6 1455	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0	unlikely
CYP2E1 841	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0	unlikely
CYP3A4 1462	inhibitor 2614 Sources: https://pubmed.ncbi.nlm.nih.gov/12019187/ Page: 4.0	unlikely

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP3A4 1470	substrate 2752 Sources: https://pubmed.ncbi.nlm.nih.gov/9602961/ Page: 4.0	yes
CYP2C9 865	substrate 2752 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

Sourcing

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Recognition of sulfamethoxazole and its reactive metabolites by drug-specific CD4+ T cells from allergic individuals.	2000 Jun 15	10843725
The importance of the removal of the intrauterine device in genital colonization by actinomyces.	2001	11586040
Molecular characterization of Salmonella weltevreden isolated from poultry: evidence of conjugal transfer of plasmid and antibiotic resistance.	2001	11229656
Infrared studies on Co and Cd complexes of sulfamethoxazole.	2001 Apr	11374562
Persistence of sulphonamide resistance in Escherichia coli in the UK despite national prescribing restriction.	2001 Apr 28	11343738
Practice guidelines for the treatment of uncomplicated cystitis.	2001 Aug	12084260
Circadian changes in pharmacokinetics of sulfamethoxazole administered orally to rabbits.	2001 Aug	11534768
Pharmacokinetics of sulfadimethoxine and sulfamethoxazole in combination with trimethoprim after oral single- and multiple-dose administration to healthy pigs.	2001 Aug	11519678
Effect of lipopolysaccharide (LPS)-evoked host defense activation on hepatic microsomal formation and reduction of sulfamethoxazole hydroxylamine in the rat.	2001 Aug 15	11448455
Resistance to trimethoprim-sulfamethoxazole and modifications in genes coding for dihydrofolate reductase and dihydropteroate synthase in European Streptococcus pneumoniae isolates.	2001 Dec	11733486
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	11733467
Influence of reduced glutathione on the proliferative response of sulfamethoxazole-specific and sulfamethoxazole-metabolite-specific human CD4+ T-cells.	2001 Feb	11159714
Degeneracy and additional alloreactivity of drug-specific human alpha beta(+) T cell clones.	2001 Jul	11431418
Drug interactions as a cause of overanticoagulation on phenprocoumon or acenocoumarol predominantly concern antibacterial drugs.	2001 Jun	11406743
Impact of prophylaxis for Mycobacterium avium complex on bacterial infections in patients with advanced human immunodeficiency virus disease.	2001 Jun 1	11340534
Indirect potentiometric titration of sulphamethoxazole in the presence of trimethoprim in co-trimazole tablets using copper based mercury film electrode.	2001 Mar	11253916
Topical bactrim versus trimethoprim and sulfonamide against nocardia keratitis.	2001 Mar	11248825
Randomized intervention study comparing several regimens for the treatment of moderate anemia among refugee children in Kigoma Region, Tanzania.	2001 Mar-Apr	11442213
A suspected case of primary cutaneous actinomycosis on the buttock.	2001 May	11436367
Antigenicity and immunogenicity of sulphamethoxazole: demonstration of metabolism-dependent haptenation and T-cell proliferation in vivo.	2001 May	11350866
Determination of sulfametoxazole, sulfadiazine and associated compounds in pharmaceutical preparations by capillary zone electrophoresis.	2001 May 18	11403449
Paraplegia secondary to Burkholderia pseudomallei myelitis: a case report.	2001 Nov	11689986
Design and evaluation of drug-loaded wound dressing having thermoresponsive, adhesive, absorptive and easy peeling properties.	2001 Nov	11575474
Plasmid mediated antibiotic resistance in Klebsiella pneumoniae.	2001 Oct	12035355
Antimicrobial susceptibility and plasmids from Escherichia coli isolated from rats.	2001 Oct	11921594
Possible interaction between gliclazide, fluconazole and sulfamethoxazole resulting in severe hypoglycaemia.	2001 Oct	11678792
Cotrimoxazole treatment for rheumatoid arthritis.	2001 Oct	11590583
Antimicrobial susceptibility of Haemophilus influenzae among children in Beijing, China, 1999-2000.	2002	11951998
Determination of selected sulfonamide antibiotics and trimethoprim in manure by electrospray and atmospheric pressure chemical ionization tandem mass spectrometry.	2002	11921244
Transfer and distribution profiles of dietary sulphonamides in the tissues of the laying hen.	2002 Apr	11962694
Inhibition by atovaquone of CYP2C9-mediated sulphamethoxazole hydroxylamine formation.	2002 Apr	11956677
Pneumocystis carinii infection in bilateral aural polyps in a human immunodeficiency virus-positive patient.	2002 Apr	11945191
Drug specific cytotoxic T-cells in the skin lesions of a patient with toxic epidermal necrolysis.	2002 Apr	11918724
Prevalence and predictors of trimethoprim-sulfamethoxazole resistance among uropathogenic Escherichia coli isolates in Michigan.	2002 Apr 15	11914994
Quantification of veterinary antibiotics (sulfonamides and trimethoprim) in animal manure by liquid chromatography-mass spectrometry.	2002 Apr 5	12064522
Determination of anti-microbial susceptibilities of Haemophilus influenzae, Streptococcus pneumoniae and Moraxella catarrhalis.	2002 Feb	12073719
Role of endotoxin in 6-sulfanilamidoindazole(6SAI)-induced arthritis in rats.	2002 Feb	11926286
Folic acid antagonism of sulfa drug treatments.	2002 Feb	11832284
Bacterial infections in cirrhosis: epidemiological changes with invasive procedures and norfloxacin prophylaxis.	2002 Jan	11786970
Liquid chromatographic determination of multiple sulfonamides, nitrofurans, and chloramphenicol residues in pasteurized milk.	2002 Jan-Feb	11878601
Sensitivity and resistance of antibiotics in common infection of male and female.	2002 Jan-Mar	12043324
Current treatment options for chronic granulomatous disease.	2002 Jul	12083986
Ofuji's disease: a report on 20 patients with clinical and histopathologic analysis.	2002 Jun	12063478
Second derivative spectrophotometric determination of trimethoprime and sulfamethoxazole in the presence of hydroxypropyl-beta-cyclodextrin (HP-beta-CD).	2002 Jun 20	12062664
Septicaemic pasteurellosis in ostriches (Struthio camelus) in central Saudi Arabia.	2002 Mar	12093199
Pharmacokinetics of sulfamethoxazole and trimethoprim in donkeys, mules, and horses.	2002 Mar	11911569
Iminodibenzyl as a novel coupling agent for the spectrophotometric determination of sulfonamide derivatives.	2002 Mar	11880002
[Characterization of Vibrio cholerae eltor in the city of Kazan in 2001].	2002 Mar-Apr	12043149

Patents

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).

Name

Type

Language

SULFAMETHOXAZOLE

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

SULFAMETHOXAZOLE [USP]

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 [WHO-DD]

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 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 COMPONENT OF AZO GANTANOL

Common Name

English

SULFAMETHOXAZOLE [HSDB]

Common Name

English

SMX

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)