Chemical: Drug
sulfisoxazole

PharmGKB contains no dosing guidelines for this . To report known genotype-based dosing guidelines, or if you are interested in developing guidelines, click here.


Annotated Labels

  1. FDA Label for erythromycin,sulfisoxazole and G6PD
  2. HCSC Label for erythromycin,sulfisoxazole and G6PD



PharmGKB contains no Clinical Variants that meet the highest level of criteria.

Disclaimer: The PharmGKB's clinical annotations reflect expert consensus based on clinical evidence and peer-reviewed literature available at the time they are written and are intended only to assist clinicians in decision-making and to identify questions for further research. New evidence may have emerged since the time an annotation was submitted to the PharmGKB. The annotations are limited in scope and are not applicable to interventions or diseases that are not specifically identified.

The annotations do not account for individual variations among patients, and cannot be considered inclusive of all proper methods of care or exclusive of other treatments. It remains the responsibility of the health-care provider to determine the best course of treatment for a patient. Adherence to any guideline is voluntary, with the ultimate determination regarding its application to be made solely by the clinician and the patient. PharmGKB assumes no responsibility for any injury or damage to persons or property arising out of or related to any use of the PharmGKB clinical annotations, or for any errors or omissions.

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Overview

Generic Names
  • Sulfadimethylisoxazole
  • Sulfafurazol
  • Sulfafurazole
  • Sulfaisoxazole
  • Sulfasoxazole
  • Sulfisonazole
  • Sulfisoxasole
  • Sulfisoxazol
  • Sulfisoxazole Dialamine
  • Sulfisoxazole Diolamine
  • Sulfofurazole
  • Sulphafurazol
  • Sulphafurazole
  • Sulphafurazolum
  • Sulphaisoxazole
  • Sulphisoxazol
  • Sulphofurazole
Trade Names
  • Accuzole
  • Alphazole
  • Amidoxal
  • Astrazolo
  • Azo Gantrisin
  • Azosulfizin
  • Bactesulf
  • Barazae
  • Chemouag
  • Cosoxazole
  • Dorsulfan
  • Dorsulfan Warthausen
  • Entusil
  • Entusul
  • G-Sox
  • Ganda
  • Gantrisin
  • Gantrisine
  • Gantrisona
  • Gantrosan
  • Isoxamin
  • J-Sul
  • Koro-Sulf
  • Neazolin
  • Neoxazol
  • Norilgan-S
  • Novazolo
  • Novosaxazole
  • Pancid
  • Renosulfan
  • Resoxol
  • Roxosul
  • Roxosul Tablets
  • Roxoxol
  • SI
  • Saxosozine
  • Sk-Soxazole
  • Sodizole
  • Sosol
  • Soxamide
  • Soxazole
  • Soxisol
  • Soxitabs
  • Soxo
  • Soxomide
  • Stansin
  • Sulbio
  • Sulfagan
  • Sulfagen
  • Sulfalar
  • Sulfapolar
  • Sulfasan
  • Sulfasol
  • Sulfazin
  • Sulfisin
  • Sulfizin
  • Sulfizol
  • Sulfizole
  • Sulfoxol
  • Suloxsol
  • Sulphafuraz
  • Sulsoxin
  • Thiasin
  • Tl-Azole
  • Unisulf
  • Urisoxin
  • Uritrisin
  • Urogan
  • V-Sul
  • Vagilia
Brand Mixture Names
  • Pediazole (Erythromycin (Erythromycin Ethylsuccinate) + Sulfisoxazole Acetyl)
  • Renazone Plus Tab (Ammonium Chloride + Atropine Sulfate + Hyoscyamine Hydrobromide + Scopolamine Hydrobromide + Sulfisoxazole)

PharmGKB Accession Id

PA164748964

Type(s):

Drug

Description

A short-acting sulfonamide antibacterial with activity against a wide range of gram- negative and gram-positive organisms.

Source: Drug Bank

Indication

For the treatment of severe, repeated, or long-lasting urinary tract infections, meningococcal meningitis, acute otitis media, trachoma, inclusion conjunctivitis, nocardiosis, chancroid, toxoplasmosis, malaria and other bacterial infections.

Source: Drug Bank

Other Vocabularies

Information pulled from DrugBank has not been reviewed by PharmGKB.

Pharmacology, Interactions, and Contraindications

Mechanism of Action

Sulfisoxazole is a competitive inhibitor of the enzyme dihydropteroate synthetase. It inhibits bacterial synthesis of dihydrofolic acid by preventing the condensation of the pteridine with para-aminobenzoic acid (PABA), a substrate of the enzyme dihydropteroate synthetase. The inhibited reaction is necessary in these organisms for the synthesis of folic acid.

Source: Drug Bank

Pharmacology

Sulfisoxazole is a sulfonamide antibiotic. The sulfonamides are synthetic bacteriostatic antibiotics with a wide spectrum against most gram-positive and many gram-negative organisms. However, many strains of an individual species may be resistant. Sulfonamides inhibit multiplication of bacteria by acting as competitive inhibitors of p-aminobenzoic acid in the folic acid metabolism cycle. Bacterial sensitivity is the same for the various sulfonamides, and resistance to one sulfonamide indicates resistance to all. Most sulfonamides are readily absorbed orally. However, parenteral administration is difficult, since the soluble sulfonamide salts are highly alkaline and irritating to the tissues. The sulfonamides are widely distributed throughout all tissues. High levels are achieved in pleural, peritoneal, synovial, and ocular fluids. Although these drugs are no longer used to treat meningitis, CSF levels are high in meningeal infections. Their antibacterial action is inhibited by pus.

Source: Drug Bank

Absorption, Distribution, Metabolism, Elimination & Toxicity

Toxicity

LD 50=6800 mg/kg (Orally in mice)

Source: Drug Bank

Route of Elimination

The mean urinary excretion recovery following oral administration of sulfisoxazole is 97% within 48 hours, of which 52% is intact drug, with the remaining as the N4-acetylated metabolite. It is excreted in human milk.

Source: Drug Bank

Chemical Properties

Chemical Formula

C11H13N3O3S

Source: Drug Bank

Isomeric SMILES

Cc1c(noc1NS(=O)(=O)c2ccc(cc2)N)C

Source: OpenEye

Canonical SMILES

CC1=NOC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1C

Source: Drug Bank

Average Molecular Weight

267.304

Source: Drug Bank

Monoisotopic Molecular Weight

267.067761987

Source: Drug Bank

SMILES

CC1=NOC(NS(=O)(=O)C2=CC=C(N)C=C2)=C1C

Source: Drug Bank

InChI String

InChI=1S/C11H13N3O3S/c1-7-8(2)13-17-11(7)14-18(15,16)10-5-3-9(12)4-6-10/h3-6,14H,12H2,1-2H3

Source: Drug Bank

Genes that are associated with this drug in PharmGKB's database based on (1) variant annotations, (2) literature review, (3) pathways or (4) information automatically retrieved from DrugBank, depending on the "evidence" and "source" listed below.

Curated Information ?

EvidenceGene
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
CYP3A4
No Dosing Guideline available DL No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
G6PD
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available VIP No VIP available
NR1I2
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
UGT1A1

Drug Interactions

Interaction Description
chlorpropamide - sulfisoxazole Sulfonamide/sulfonylurea: possible hypoglycemia (source: Drug Bank )
methotrexate - sulfisoxazole The sulfamide increases the toxicity of methotrexate (source: Drug Bank )
tamoxifen - sulfisoxazole Sulfisoxazole may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Sulfisoxazole is initiated, discontinued or dose changed. (source: Drug Bank )
tamoxifen - sulfisoxazole Sulfisoxazole may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Sulfisoxazole is initiated, discontinued or dose changed. (source: Drug Bank )
tolbutamide - sulfisoxazole Tolbutamide and Sulfisoxazole are strong CYP2C9 inhibitors and substrates. Decreased metabolism and clearance of both agents may occur during concomitant therapy. Consider alternate therpy or monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose(s) changed. (source: Drug Bank )
tolbutamide - sulfisoxazole Tolbutamide and Sulfisoxazole are strong CYP2C9 inhibitors and substrates. Decreased metabolism and clearance of both agents may occur during concomitant therapy. Consider alternate therpy or monitor for changes in the therapeutic and adverse effects of both agents if concomitant therapy is initiated, discontinued or dose(s) changed. (source: Drug Bank )
torasemide - sulfisoxazole Sulfisoxazole, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Sulfisoxazole is initiated, discontinued or dose changed. (source: Drug Bank )
trimethoprim - sulfisoxazole The strong CYP2C9 inhibitor, Sulfisoxazole, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Sulfisoxazole is initiated, discontinued or dose changed. (source: Drug Bank )
voriconazole - sulfisoxazole Sulfisoxazole, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of voriconazole if sulfisoxazole is initiated, discontinued or dose changed. (source: Drug Bank )
warfarin - sulfisoxazole Sulfisoxazole, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if sulfisoxazole is initiated, discontinued or dose changed. (source: Drug Bank )
zafirlukast - sulfisoxazole Sulfisoxazole, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of zafirlukast. Consider alternate therapy or monitor for changes in zafirlukast therapeutic and adverse effects if sulfisoxazole is initiated, discontinued or dose changed. (source: Drug Bank )

Curated Information ?

Relationships from National Drug File - Reference Terminology (NDF-RT)

May Treat
Contraindicated With

Publications related to sulfisoxazole: 4

No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Medications and glucose-6-phosphate dehydrogenase deficiency: an evidence-based review. Drug safety : an international journal of medical toxicology and drug experience. 2010. Youngster Ilan, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. Drug metabolism and disposition: the biological fate of chemicals. 2008. Yasuda Kazuto, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Glucose-6-phosphate dehydrogenase deficiency. Lancet. 2008. Cappellini M D, et al. PubMed
No Dosing Guideline available No Drug Label available No Clinical Annotation available No Variant Annotation available No VIP available No VIP available
Glucose-6-phosphate dehydrogenase deficiency. WHO Working Group. Bulletin of the World Health Organization. 1989. PubMed

LinkOuts

Web Resource:
Wikipedia
National Drug Code Directory:
0004-1003-28
DrugBank:
DB00263
ChEBI:
102484
KEGG Compound:
C07318
KEGG Drug:
D00450
PubChem Compound:
5344
PubChem Substance:
46505342
9526
Drugs Product Database (DPD):
363774
BindingDB:
50034452
ChemSpider:
5151
Therapeutic Targets Database:
DAP001203
FDA Drug Label at DailyMed:
2da604ea-01c4-44f3-852f-e6e55f140360

Clinical Trials

These are trials that mention sulfisoxazole and are related to either pharmacogenetics or pharmacogenomics.

No trials loaded.

NURSA Datasets

provided by nursa.org

No NURSA datasets available.

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Sources for PharmGKB drug information: DrugBank, PubChem.