Drug/Small Molecule:

sulfamethoxazole

Overview

IUPAC Name:	4-amino-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
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)

Indication

For the treatment of bronchitis, prostatitis and urinary tract infections.

ATC Therapeutic Category

• J01EC:Intermediate-acting sulfonamides

Pharmacology and Interactions

Mechanism Of Action

Sulfonamides inhibit bacterial dihydrofolate synthetase, causing interference in the conversion of p-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.

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.

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.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Hepatic. The metabolism of sulfamethoxazole occurs predominately by N4-acetylation, although the glucuronide conjugate has been identified.

Protein Binding

70%

Absorption

Rapidly absorbed following oral administration.

Half Life

10 hours

Chemical Properties

Chemical Formula:

C₁₀H₁₁N₃O₃S

SMILES Code:

c1cnc(nc1)NS(=O)(=O)c2ccc(cc2)N

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

253.278 / 253.0521

Curated Information

The following genes are in curated knowledge about this drug.

	Gene	Relationship	Evidence
	CYP2C9	PK	Publications
	HLA-B	CO          GN	Publications
	KCNE2	CO       FA GN	Publications
	NAT1	FA	Publications
	NAT2	PK    GN	Publications
	SCN5A	PD	Publications

Non-Curated Information

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

Metabolizing Enzymes

• CYP2C9

Non-Curated Information

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
	Heart Arrest	PD	Publications
	Long QT Syndrome	CO       FA GN	Publications
	Seizures	PD	Publications
	Stevens-Johnson Syndrome	CO          GN	Publications
	sulfamethoxazole idiosyncratic adverse drug reactions	FA	Publications
	Syncope	PD	Publications
	Tachycardia, Ventricular	PD	Publications
	Torsades de Pointes	PD	Publications
	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.

1. Drug-Induced Long QT Intervals

   • 
   • 
   • 
   • 
   • PD

   Submitted by Dan Roden, MD involving ADRB1, ADRB2, KCNE1, KCNE2, KCNH2, KCNQ1, SCN5A, almokalant, amiodarone, amitriptyline, bretylium, bupivacaine, cisapride, disopyramide, dofetilide, encainide, fluconazole, haloperidol, hydroquinidine, isoflurane, itraconazole, ketoconazole, lithium, loratadine, metoclopramide, nortriptyline, procainamide, quinidine, sematilide, sotalol, sulfamethoxazole, thioridazine, trimethoprim, , Long QT Syndrome, Proarrhythmia and Torsades de Pointes

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

You must sign in before you can download data.

LinkOuts

Common Searches

Search PubMed
Search Medline Plus
Search PubChem
Search CTD

Non-Curated Publications

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