Drug/Small Molecule:
sulfamethoxazole

2D structure

Overview

Trade Names: Apo-Sulfamethoxazole; Azo Gantanol; Azo-Gantanol; Bactrimel; Gamazole; Gantanol; Gantanol-DS; Metoxal; Radonil; SIM; Septran; Simsinomin; Sinomin; Sulfamethalazole; Sulfamethoxazol; Sulfamethoxizole; Sulfamethylisoxazole; Sulfisomezole; Sulpha-Methoxizole; Sulphamethalazole; Sulphamethoxazol; Sulphamethoxazole; Sulphamethoxazole BP 98; Sulphamethylisoxazole; Sulphisomezole; Trib; Urobak
Brand Mixtures: Apo Sulfatrim DS Tab (Sulfamethoxazole + Trimethoprim); Apo Sulfatrim Pediatric (Sulfamethoxazole + Trimethoprim); Apo Sulfatrim Tab (Sulfamethoxazole + Trimethoprim); Bactrim DS Roche Tab (Sulfamethoxazole + Trimethoprim); Bactrim Roche Inj (Sulfamethoxazole + Trimethoprim); Bactrim Roche Suspension Paediatric (Sulfamethoxazole + Trimethoprim); Bactrim Roche Tab (Sulfamethoxazole + Trimethoprim); Novo-Trimel DS Tab (Sulfamethoxazole + Trimethoprim); Novo-Trimel Oral Sus (Sulfamethoxazole + Trimethoprim); Novo-Trimel Tab (Sulfamethoxazole + Trimethoprim); Protrin DF Tab (Sulfamethoxazole + Trimethoprim); Protrin Tab (Sulfamethoxazole + Trimethoprim); Riva-Sep DS (Sulfamethoxazole + Trimethoprim); Roubac Tab 160/800 (Sulfamethoxazole + Trimethoprim); Roubac Tab 80/400 (Sulfamethoxazole + Trimethoprim); Septra (Sulfamethoxazole + Trimethoprim); Septra DS Tablets (Sulfamethoxazole + Trimethoprim); Septra Injection (Sulfamethoxazole + Trimethoprim); Septra Pediatric Suspension (Sulfamethoxazole + Trimethoprim); Sulfamethoxazole and Trimethoprim Tablets (Sulfamethoxazole + Trimethoprim)
PharmGKB Accession Id: PA451544

Description

A bacteriostatic antibacterial agent that interferes with folic acid synthesis in susceptible bacteria. Its broad spectrum of activity has been limited by the development of resistance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p208) (source: Drug Bank)

Indication

For the treatment of bronchitis, prostatitis and urinary tract infections. (source: Drug Bank)

ATC Therapeutic Category

  • J01EC:Intermediate-acting sulfonamides

Pharmacology, Interactions, and Contraindications

Mechanism Of Action

Sulfonamides inhibit bacterial dihydrofolate synthetase, causing interference in the conversion of <i>p</i>-aminobenzoic acid (PABA) into folic acid. As folic acid is a coenzyme responsible for the transport of one-carbon fragments from one molecule to another, it is an essential component of bacterial development. Pyrimethamine and trimethoprim inhibit dihydrofolate reductase, the immediate next step, and therefore act synergistically with the sulfonamides. (source: Drug Bank)

Pharmacology

Sulfamethoxazole is a sulfonamide drug that inhibits bacterial synthesis of dihydrofolic acid by competing with para-aminobenzoic acid (PABA). Sulfamethoxazole is normally given in combination with Trimethoprim (a dihydrofolate reductase inhibitor). Studies have shown that bacterial resistance develops more slowly with the combination of the two drugs than with either Trimethoprim or Sulfamethoxazole alone. (source: Drug Bank)

Food Interactions

Do not take calcium, aluminium, magnesium or iron supplements within 2 hours of taking this medication.
Take on empty stomach: 1 hour before or 2 hours after meals.
Take with a full glass of water. (source: Drug Bank)

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic. The metabolism of sulfamethoxazole occurs predominately by N4-acetylation, although the glucuronide conjugate has been identified. (source: Drug Bank)

Protein Binding

70% (source: Drug Bank)

Absorption

Rapidly absorbed following oral administration. (source: Drug Bank)

Isomeric SMILES Code:

c1cnc(nc1)NS(=O)(=O)c2ccc(cc2)N (source: Drug Bank)

The following genes are in curated knowledge about this drug.

  Gene Relationship Evidence
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP2C9
  •   
  •   
  • PK
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  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
CYP3A4
  •   
  •   
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
HLA-B
  • CO
  •   
  •   
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
KCNE2
  • CO
  •   
  •   
  • FA
  • GN
Publications
No phenotype data Genotype Data Available Literature annotations available Not annotated
NAT1
  •   
  •   
  •   
  • FA
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
NAT2
  •   
  •   
  • PK
  •   
  • GN
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
NR1I2
  •   
  •   
  •   
  • FA
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Has annotations
SCN5A
  •   
  • PD
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  •   
  •   
Publications

A list of non-curated publications that mention this drug along with other genes is available.

A list of non-curated publications that mention this drug along with other drugs is available.

Curated Information

The following diseases are in curated knowledge about this drug.

  Disease Relationship Evidence
No phenotype data No genotype data Literature annotations available Not annotated
Heart Arrest
  •   
  • PD
  •   
  •   
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
Long QT Syndrome
  • CO
  •   
  •   
  • FA
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Seizures
  •   
  • PD
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  •   
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Stevens-Johnson Syndrome
  • CO
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  •   
  •   
  • GN
Publications
No phenotype data No genotype data Literature annotations available Not annotated
sulfamethoxazole idiosyncratic adverse drug reactions
  •   
  •   
  •   
  • FA
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Syncope
  •   
  • PD
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  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Tachycardia, Ventricular
  •   
  • PD
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  •   
  •   
Publications
Phenotype data available Genotype Data Available Literature annotations available Not annotated
Torsades de Pointes
  •   
  • PD
  •   
  •   
  •   
Publications
No phenotype data No genotype data Literature annotations available Not annotated
Ventricular Fibrillation
  •   
  • PD
  •   
  •   
  •   
Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Curated Phenotype Datasets

These datasets are sorted alphabetically by title.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

  1. Genetic Associations in Drug-induced QT Prolongation and Torsades
  2. Physicochemical determinants of human renal clearance
  3. Serious Adverse Events Consortium (SAEC) Serious Skin Rash Study (v1.0)
  4. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

Downloads

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LinkOuts

Web Resource:
Wikipedia
DrugBank:
DB01015
ChEBI ID:
9332
KEGG Compound ID:
C07315
KEGG Drug ID:
D00447
PubChem Compound ID:
5329
PubChem Substance ID:
156228

Common Searches

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Non-Curated Publications

A list of non-curated publications that mention this drug is available.

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