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Sulfafurazol
SULFAFURAZOLE · SULFISOXAZOL · SIZ · sulphisoxazole · 4-AMINO-N-(3,4-DIMETHYL-5-ISOXAZOLYL)BENZENESULFONAMIDE · Sosol · vagilia · Sulsoxin
Identifikatoren & physikalische Daten
| CAS No. | 127-69-5 |
|---|---|
| Summenformel | C11H13N3O3S |
| Durchschnittliche Molmasse | 267,31 g/mol |
| Monoisotopische Masse | 267,06776228 g/mol |
| SMILES | Cc1noc(NS(=O)(=O)c2ccc(N)cc2)c1C |
| InChIKey | NHUHCSRWZMLRLA-UHFFFAOYSA-N |
| PubChem CID | 5344 |
| ChEMBL | CHEMBL453 |
| ChEBI | CHEBI:102484 |
| EC No. | 204-858-9 |
| DTXSID | DTXSID6021292 |
| Lokaler Name | Sulfafurazol |
Chemische & physikalische Eigenschaften
| XLogP | 1 |
|---|---|
| Polarare Oberfläche (TPSA) | 107 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 18 |
| Formalladung | 0 |
| Komplexität | 373 |
| Arzneimittel | PharmaceuticalPharmaceuticals -> AntibioticsPharmaceuticals -> Antibiotics (Sulfonamide)Pharmaceuticals -> Listed in ZINC15 |
| pH | ACID TO LITMUS |
| LogP (Verteilungskoeffizient) | log Kow = 1.010.90.83 |
| Geruch | Odorless |
| Geschmack | Bitter |
| Color/Form | Colorless prismsWhite to slightly yellowish crystalline powder |
| Löslichkeit | less than 1 mg/mL at 72.5 °F (NTP, 1992)White to off-white, odorless, crystalline powder. Sol in alcoholfreely sol in water. /Diethanolamine salt/Soluble in alcoholSOL IN DIETHYL ETHER (1 IN 800)SOL IN 5% AQ SODIUM BICARBONATE (1 IN 30)1 G IN ABOUT 6700 ML WATERSOL IN DIL HYDROCHLORIC ACID1 G IN ABOUT 10 ML BOILING ALCOHOLacetone: complete50 mg/ml<0.1 g/100 mL at 22.5 ºC |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsSulfonamidesFDA approved drugs -> Active ingredientPharmaceuticals |
| Animal Drugs | Active Ingredients (Sulfisoxazole) -> FDA Greenbook |
| Decomposition | When heated to decomposition it emits very toxic fumes of sulfoxides and nitroxides. |
| Schmelzpunkt | 383 to 388 °F (NTP, 1992)194 °CMP: 191 °CMP: 195-198 °C195°C |
| Physical Description | Sulfisoxazole is an odorless white to yellowish crystalline powder. Slightly bitter taste. Acid to litmus. (NTP, 1992)Solid |
| Siedepunkt | 482.2±55.0 °C(Predicted) |
| Dichte | 1.3486 (rough estimate) |
| Brechungsindex | 1.6630 (estimate) |
| Lagerbedingungen | Keep in dark place,Inert atmosphere,2-8°C |
| pKa (Säurekonstante) | 5.0(at 25℃) |
| Aggregatzustand | Solid |
| Farbe | White to Light Brown |
| Merck | 14,8952 |
| BRN | 6737262 |
| Henry-Konstante | 6.2×106 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | forensics and toxicologypharmaceutical (small molecule) |
| 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 |
| InChIKey | NHUHCSRWZMLRLA-UHFFFAOYSA-N |
| SMILES | Cc1noc(NS(=O)(=O)c2ccc(N)cc2)c1C |
| CAS Datenbank | 127-69-5(CAS DataBase Reference) |
| NIST chemische Informationen | Benzenesulfonamide, 4-amino-N-(3,4-dimethyl-5-isoxazolyl)-(127-69-5) |
| EPA chemische Informationen | Sulfisoxazole (127-69-5) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (95.6%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 45 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Sulfisoxazole: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzenesulfonamide, 4-amino-N-(3,4-dimethyl-5-isoxazolyl)-: Environment tier I assessment |
| Brandgefahren | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992) |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this chemical include anaphylaxis, generalized allergic reactions, angioneurotic edema, arteritis, vasculitis, myocarditis, serum sickness, conjunctival and scleral injection, periarteritis nodosa, systemic lupus erythematosus, tachycardia, palpitations, syncope, cyanosis, rash, urticaria, pruritus, erythema multiforme, Stevens-Johnson syndrome, toxi epidermal necrolysis, exfoliative dermatitis, photosensitivity, goiter production, diuresis, hypoglycemia, nausea, emesis, abdominal pain, anorexia, diarrhea, glossitis, stomatitis, flatulence, salivary gland enlargement, gastrointestinal hemorrhage, pseudomembranous enterocolitis, melena, pancreatitis, hepatic dysfunction, jaundice, hepatocellular necrosis, crystalluria, hematuria, creatinine elevation, nephritis and toxic nephrosis with oliguria and anurialeukopenia, agranulocytosis, aplastic anemia, eosino philia, clotting disorders, arthralgia, chest pain, myalgia, headache, dizziness, peripheral neuritis, paresthesia, convulsions, tinnitus, vertigo, ataxia edema, pyrexia, drowsiness, weakness, fatigue, rigors, lassitude, flushing, hearing loss, insomnia and pneumonitis. It may cause blood dyscrasias, sore throat, fever, cough, shortness of breath, pallor, pulmonary infiltrates and death. Other symptoms may include colic, vomiting, unconsciousness, thrombocytopenia, purpura, hemolytic anemia, intracranial hypertension, psychosis, hallucinations, disorientation, depression, anxiety, hypersensitivity reactions, blood disorders, acute renal failure and urinary retention. |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl sulfisoxazole, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.Oral dosage form new animal drugs. Sulfisoxazole tablets. ... Specifications. Each tablet contains 260 milligrams (4 grains) of sulfisoxazole. ... Indications for use. Use in dogs and cats as an aid in treatment of bacterial pneumonia and bacterial enteritis when caused by organisms sensitive to sulfisoxazole..The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Sulfisoxazole is included on this list. |
| Reaktive Gruppe | Amines, Phosphines, and Pyridines |
| Special Reports | NTP TR No 138Route: oral, gavageSpecies: rats and mice. NTIS No PB288779/AS.[NTPDivision of Toxicology Research and TestingManagement Status Report07/07/93p.27]Storer RD et alMutation Research 368 (2): 59-101 1996. Revalidation of the in vitro alkaline elution/rat hepatocyte assay for DNA damage: Improved criteria for assessment of cytotoxicity and genotoxicity and results for 81 compounds.Berman SNew England Journal of Medicine 332: 1560-1565 June 8, 1995. Otitis media in children.Miyagawa M et alMutation Research 343 (2-3): 157-183 1995. The in vivo-in vitro replicative DNA synthesis (RDS) test with hepatocytes prepared from male B6C3F1 mice as an early prediction assay for putative nongenotoxic (Ames-negative) mouse hepatocarcinogens.For more Special Reports (Complete) data for SULFISOXAZOLE (19 total), please visit the HSDB record page. |
| Air and Water Reactions | May be sensitive to prolonged exposure to air and light. Sensitive to heat. Slightly soluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (95.6%) |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992) |
| Erste Hilfe | EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
| Personal Protective Equipment (PPE) | RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992) |
| Wechselwirkungen | It has been reported that sulfisoxazole may prolong the prothrombin time in patients who are receiving anticoagulants, including warfarin. This interaction should be kept in mind when /sulfisoxazole/ is given to patients already on anticoagulant therapy, and prothrombin time or other suitable coagulation test should be monitored.It has been proposed that sulfisoxazole competes with thiopental for plasma protein binding. In one study involving 48 patients, intravenous sulfisoxazole resulted in a decrease in the amount of thiopental required for anesthesia and in a shortening of the awakening time. It is not known whether chronic oral doses of sulfisoxazole would have a similar effect.Sulfonamides can displace methotrexate from plasma protein-binding sites, thus increasing free methotrexate concentrations. Studies in man have shown sulfisoxazole infusions to decrease plasma protein-bound methotrexate by one-fourth.These medications /coumarin- or indandione-derivative anticoagulantshydantoin anticonvulsants or oral antidiabetic agents/ may be displaced from protein binding sites and/or their metabolism may be inhibited by some sulfonamides, resulting in increased or prolonged effects and/or toxicitydosage adjustments may be necessary during and after sulfonamide therapy. /Sulfonamides/For more Interactions (Complete) data for SULFISOXAZOLE (17 total), please visit the HSDB record page. |
| Ökotoxizitätswerte | LC50Species: Ictalurus punctatus (Channel catfish)Conditions: freshwater, static, 17 °C, hardness 42 mg/L CaCO3Concentration: < or =100 mg/L for 48 hrSpecies: Lepomis macrochirus (Bluegill)Conditions: freshwater, static, 12 °C, hardness 42 mg/L CaCO3Species: Oncorhynchus mykiss (Rainbow trout)Species: Salmo trutta (Brown trout)For more Ecotoxicity Values (Complete) data for SULFISOXAZOLE (6 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 58(2), indicates that sulfisoxazole is expected to have very high mobility in soil(SRC). Volatilization from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.1X10-12 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Sulfisoxazole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.1X10-18 mm Hg(SRC), determined from a fragment constant method(4). In general, sulfonamide antimicrobials are not readily biodegraded and persist in soils(5).AQUATIC FATE: Based on a classification scheme(1), a Koc value of 58(SRC), determined from a structure estimation method(2), indicates that sulfisoxazole is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.1X10-12 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(6), an estimated BCF of one(SRC), from its log Kow of 1.01(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Sulfisoxazole is expected to be readily photodegraded in most natural waters as the anionic form is susceptible to direct photodegradation(5). In general, sulfonamide antimicrobials are not readily biodegraded(9).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulfisoxazole, which has an estimated vapor pressure of 5.08X10-8 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase sulfisoxazole is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC)the half-life for this reaction in air is estimated to be 12 hours(SRC), calculated from its rate constant of 3.2X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). The anionic form is susceptible to direct photodegradation(4). |
| Milk Concentrations | Six lactating women, ages 19-27 yr, were given 4 oral doses of sulfisoxazole, one g every 6 hr, during the first 24 hr of the collection period. Half-lives in milk were 7.2 hr for sulfisoxazole (I) and 8.9 hr for its major metabolite, N4-acetylsulfisoxazole (II). The milk to serum ratio for II was approximately fourfold that for I, reflecting the greater diffusion of the metabolite into milk. Total I recovered in breast milk during the 48 hr collection period accounted for less than 1% of the maternal dose in all patients, with a mean recovery of 0.45%. The drug was secreted predominantly as the acetylated metabolite, which comprised 77% of total drug recovered, whereas 23% appeared as the parent compound.Because sulfonamides are distributed into milk, and because of the potential for serious adverse reactions from the drugs in nursing infants, a decision should be made whether to discontinue nursing or to discontinue the drug, taking into account the importance of the drug to the woman. Because of the risk of kernicterus in infants younger than 2 months of age, use of sulfonamides is contraindicated in lactating women who are nursing such infants. /Sulfonamides//Sulfisoxazole/ is excreted in human milk. |
| Ongoing Test Status | The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical. [http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=127-69-5] |
| Effluent Concentrations | Sulfisoxazole was detected at a maximum concentration of 0.034 ug/L, median concentration of 0.019 ug/L, in final effluents of five of eight wastewater treatment plants located in five Canadian cities, sampled during 2002(1). |
| Soil Adsorption/Mobility | The Koc of sulfisoxazole using a clay loam (pH 6.2, organic content 3.1%) was reported as 58, Kd = 1.5(1). According to a classification scheme(2), this Koc value suggests that sulfisoxazole is expected to have very high mobility in soil. The pKa1 and pKa2 of sulfisoxazole are 1.5 and 5.0(3), respectively, indicating that this compound will partially exist in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). However, aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that mobility may be much lower in some soils(SRC). |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ /Investigators/ identified 40 patients (25 men and 15 women) who developed calculi composed totally or partially of sulfonamides (acetylsulfamethoxazole, sulfadiazine, and acetylsulfisoxazole) between 1980 and 1987. The incidence of sulfonamide stones is less than 1% of stones. Patient characteristics were determined from questionnaires sent to the patients and attending physicians. The majority of patients developed symptoms 1 to 4 weeks after beginning sulfonamide therapy. The bladder was the most common stone location. Obstruction of the urinary system by the acetyl derivatives of the drug is the most serious consequence of sulfonamide therapy. Early recognition of drug-related stones is essential to protect patients from recurrences, reduce the risk of renal complications, and avoid continuing ineffective therapeutic regimens./HUMAN EXPOSURE STUDIES/ Adverse reactions severe enough to require discontinuation of sulfafurazole administration occurred with an incidence of 3.1% in a series of 1002 treated patients. Skin rashes, eosinophilia and drug fever were the common manifestations./SIGNS AND SYMPTOMS/ The amount of a single dose of sulfisoxazole that is associated with symptoms of overdosage or is likely to be life-threatening has not been reported. Signs and symptoms of overdosage reported with sulfonamides include anorexia, colic, nausea, vomiting, dizziness, headache, drowsiness and unconsciousness. Pyrexia, hematuria and crystalluria may be noted. Blood dyscrasias and jaundice are potential late manifestations of overdosage./CASE REPORTS/ A 35-year-old man demonstrated sulfisoxazole diolamine-induced photosensitivity during treatment for staphylococcal blepharitis. This reaction was easily avoided by applying the ointment at bedtime and covering the eyelids during sun-bathing while in therapy. A drug-induced photosensitivity reaction should be considered in cases of staphylococcal blepharitis resistant to or aggravated by eyelid-margin therapy with sulfonamides.For more Human Toxicity Excerpts (Complete) data for SULFISOXAZOLE (15 total), please visit the HSDB record page. |
| Artificial Pollution Sources | Sulfisoxazole's production and use as a human and veterinary antibiotic(1) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: In general, sulfonamide antimicrobials are not readily biodegraded and persist in soils(1). |
| Carcinogen Classification | Sulfafurazole (Sulfisoxazole)Group 3: Not classifiable as to its carcinogenicity to humansVolume 24: (1980) Some Pharmaceutical Drugs1987 |
| Environmental Bioconcentration | An estimated BCF of 1 was calculated in fish for sulfisoxazole(SRC), using a log Kow of 1.01(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC). |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29350030 |
| RTECS-Nr. | WO9100000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | LD50 orally in mice: 6800 mg/kg (Seki) |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | IRRITANTEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 127-69-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Sulfisoxazole is a sulfonamide based antibacterial that exhibits activity against wide spectrum of gram-negative and gram-positive bacterium.