General
Preferred name
Acetyl sulfisoxazole
Synonyms
SULFISOXAZOLE ACETYL ()
Sulfafurazole acetyl ()
Acetylsulfafurazole ()
Acetyl sulfafurazole ()
Sulfisoxizole acetyl ()
Lipo Gantrisin ()
NSC-759138 ()
Gantrisin Pediatric ()
Gantrisin ()
Acetylsulfisoxazole ()
P&D ID
PD071672
CAS
80-74-0
Tags
available
prodrug
drug
Approved by
FDA
First approval
1953
Drug Status
approved
vet_approved
Max Phase
Phase 4
Drug indication
Antibacterial
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ROE The mean urinary excretion recovery following oral administration of sulfisoxazole is 97% within 48 hours, of which 52% is the parent drug, and the remaining as the N4-acetylated metabolite. It is excreted in human milk [L2793].; ; Sulfisoxazole and its acetylated metabolites are excreted primarily by the kidneys through glomerular filtration [L2804].
ABSORPTION Readily absorbed from the gastrointestinal tract [L2793].; ; In a pharmacokinetic study, the adjustments for variable renal clearances between oral and intravenous administration and using the unbound plasma concentrations, the bioavailability for an oral dose of sulfisoxazole was found to be 0.95 +/- 0.04 [L2800].
INDICATION Acute, recurrent or chronic urinary tract infections (primarily pyelonephritis, pyelitis and cystitis) due to susceptible organisms (usually Escherichia coli, Klebsiella-Enterobacter, staphylococcus, Proteus mirabilis and, less frequently, Proteus vulgaris) in the absence of obstructive uropathy or foreign bodies [L2804]; ; Meningococcal meningitis where the organism has been demonstrated to be susceptible. Haemophilus influenzae meningitis as adjunctive therapy with parenteral streptomycin [L2804]; ; Meningococcal meningitis prophylaxis [L2804].; ; Acute otitis media due to Haemophilus influenzae when used concomitantly with adequate doses of penicillin or erythromycin (see appropriate labeling for prescribing information) [L2804].; ; Trachoma, inclusion conjunctivitis, nocardiosis, chancroid, toxoplasmosis as adjunctive therapy with pyrimethamine. Malaria due to chloroquine-resistant strains of Plasmodium falciparum, when used as adjunctive therapy [L2804].; ; Currently, the increasing frequency of resistant organisms is a limitation of the usefulness of antibacterial agents including the sulfonamides, especially in the treatment of chronic and recurrent urinary tract infections [L2804].
TOXICITY LD50=6800 mg/kg (Orally in mice) [L2806].; ; Sulfonamide-induced hypersensitivity reactions, although uncommon, can be severe. They can include rare life-threatening cutaneous reactions such as erythema multiform (Stevens-Johnson syndrome) and toxic epidermal necrolysis. Crystalluria may result in dysuria, renal colic, haematuria and acute renal obstruction [L2803].; ; Other infrequent reactions include granulocytopenia, agranulocytosis, aplastic anemia, thrombocytopenic purpura and toxic hepatitis. Rarely, hemolysis may occur in individuals deficient in glucose-6-phosphate dehydrogenase [L2803].; ; The severe or irreversible adverse effects of sulfisoxazole, which give rise to more complications which may include: nephrotoxicity, blood dyscrasias, interstitial nephritis, hematuria, crystalluria, oliguria, anuria, lumbar pain, and tubular necrosis [L2803].; ; The symptomatic adverse reactions produced by sulfisoxazole are more or less tolerable and if severe, may be treated symptomatically, these include anorexia, diarrhea, rashes, pruritus, nausea and vomiting, hypersensitivity reactions, Photosensitivity reactions [L2793].; ; **Overdosage:** Continuously forced diuresis may be beneficial and an alkaline urine should be initiated [L2793].
METABOLISM Sulfisoxazole acetyl is a prodrug of _sulfisoxazole_. The acetyl group is added to make the drug poorly water-soluble and is hydrolyzed in vivo to the active drug [L2804], [L2807].; ; N1-acetyl sulfisoxazole is metabolized to sulfisoxazole by digestive enzymes in the gastrointestinal tract and is absorbed as sulfisoxazole. This enzymatic splitting is thought to be responsible for slower absorption and lower peak blood concentrations are achieved after administration of an equal oral dose of sulfisoxazole. With sustained administration of acetyl sulfisoxazole, blood concentrations approximate those of sulfisoxazole. Following a single 4 gram dose of acetyl sulfisoxazole to healthy volunteers, maximum plasma concentrations of sulfisoxazole ranged from 122 to 282 mcg/mL (mean, 181 mcg/mL) for the pediatric suspension and occurred between 2 and 6 hours postadministration of sulfisoxazole, in a pharmacokinetic study [L2804].
Compound Sets
9
ChEMBL Approved Drugs
CHEMBL1200910
ChEMBL Drugs
CHEMBL1200910
Drug Repurposing Hub
DrugBank
DB14033
DrugBank Approved Drugs
DB14033
DrugCentral
4458
DrugCentral Approved Drugs
4458
DrugMatrix
ReFrame library
External IDs
25
Properties
(calculated by RDKit )
Molecular Weight
309.08
Hydrogen Bond Acceptors
6
Hydrogen Bond Donors
1
Rotatable Bonds
3
Ring Count
2
Aromatic Ring Count
2
cLogP
1.62
TPSA
106.5
Fraction CSP3
0.23
Chiral centers
0.0
Largest ring
6.0
QED
0.86
Structural alerts
0
No structural alerts detected
Custom attributes
(extracted from source data)
Disease Area
infectious disease, otolaryngology
Indication
meningitis, urinary tract infections, otitis, trachoma
MOA
folic acid antagonist
Source data