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Sulfathiazol
ST · NORSULFAZOLE · Sulphathiazole · 2-SULFANILAMIDOTHIAZOLE · Norsulfazol · SULFATHIAZOL · Sulfathiazloe · Sulfanilamidothiazole
Identifikatoren & physikalische Daten
| CAS No. | 72-14-0 |
|---|---|
| Summenformel | C9H9N3O2S2 |
| Durchschnittliche Molmasse | 255,3 g/mol |
| Monoisotopische Masse | 255,01361853 g/mol |
| SMILES | Nc1ccc(S(=O)(=O)Nc2nccs2)cc1 |
| InChIKey | JNMRHUJNCSQMMB-UHFFFAOYSA-N |
| PubChem CID | 5340 |
| ChEMBL | CHEMBL437 |
| ChEBI | CHEBI:9337 |
| EC No. | 200-771-5 |
| DTXSID | DTXSID8026068 |
| Lokaler Name | Sulfathiazol |
Chemische & physikalische Eigenschaften
| XLogP | 0,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 122 |
| H-Brücken-Donoren | 2 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 3 |
| Schwere Atome | 16 |
| Formalladung | 0 |
| Komplexität | 320 |
| Stoffklassen | Other Uses -> Pharmaceuticals |
| Arzneimittel | Pharmaceuticals -> AntibioticsPharmaceuticals -> Antibiotics (Sulfonamide)Pharmaceuticals -> Listed in ZINC15 |
| SpringerMaterials Properties | Crystal structure |
| LogP (Verteilungskoeffizient) | log Kow = 0.050.43 |
| Color/Form | Brown plates, rods or powder from 45% alcoholYellowish-white prismatic rods and six sided plates and prisms |
| Löslichkeit | Insoluble (<1 mg/ml at 70 °F) (NTP, 1992)Amorphous powder. Practically insol in water /Polymer with formaldehyde/Soly at 26 °C (mg/100 mL): water 60 (pH 6.03)alcohol 525. Sol in acetone, dil mineral acids, KOH and NaOH solns, ammonia water. Sparingly soluble in ethanol. Practically insoluble in chloroform, ether.Slightly soluble in dimethyl sulfoxide.In water, 373 mg/L at 25 °C0.5g/lInsoluble (<0.1 g/100 mL at 21 ºC) |
| Human Drugs | Pharmaceuticals |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Decomposition | When heated to decomposition it emits very toxic fumes of /nitrogen and sulfur oxides/. |
| Schmelzpunkt | 396.5 °F (Form I)347 °F (Form II) (NTP, 1992)175 °C (form a)202 °C (form b)189 °C200-202 °C (lit.) |
| Physical Description | Sulfathiazole is a white crystalline powder. Is dimorphous: form I is consists of prismatic rods and form II of six-sided plates and prisms. Insoluble in water and soluble in dil aqueous acid and aqueous base.White solid[HSDB] |
| Stability/Shelf Life | The stability of sulfamethazine (sulfadimidine) sulfathiazole, sulfameter (sulfamethoxydiazine), and sulfacetamide during acid hydrolysis in one mol/L of hydrochloric acid under increased temperature was examined using high pressure liquid chromatography. Kinetic characteristics of the process of decomposition were calculated from the found values of the concentration of undecomposed sulfonamide in relation to time. The calculated values of activation energy for the individual sulfonamides are given. The paper stresses the illustrativeness of HPLC in the examination of decomposition products. |
| Siedepunkt | 479.5±47.0 °C(Predicted) |
| Dichte | 1.4629 (rough estimate) |
| Brechungsindex | 1.6560 (estimate) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | 7.2(at 25℃) |
| Aggregatzustand | Solid |
| Farbe | White |
| Merck | 14,8943 |
| BRN | 226178 |
| Henry-Konstante | 1.7×108 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| Hauptanwendungen | clinical testing |
| InChI | 1S/C9H9N3O2S2/c10-7-1-3-8(4-2-7)16(13,14)12-9-11-5-6-15-9/h1-6H,10H2,(H,11,12) |
| InChIKey | JNMRHUJNCSQMMB-UHFFFAOYSA-N |
| SMILES | Nc1ccc(cc1)S(=O)(=O)Nc2nccs2 |
| CAS Datenbank | 72-14-0(CAS DataBase Reference) |
| NIST chemische Informationen | Sulfathiazole(72-14-0) |
| EPA chemische Informationen | Sulfathiazole (72-14-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 5.8% (5 of 86) of reports.WarningH315 (91.9%): 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 86 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Sulphathiazole: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzenesulfonamide, 4-amino-N-2-thiazolyl-: Human health tier I assessment |
| Brandgefahren | Flash point data for this compound are not available, but it is probably combustible. (NTP, 1992) |
| Gefahrenübersicht | Liver necrosis has been rarely reported during therapy[HSDB] Occupational asthma confirmed in two hospital workers[Malo] |
| FDA-Anforderungen | A tolerance of 0.1 part per million is established for negligible residues of sulfathiazole in the uncooked edible tissues of swine.The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies discontinued drug products. Sulfathiazole is included on this list.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. Sulfathiazole is included on this list.The following drug products were withdrawn or removed from the market because such drug products or components of such drug products were found to be unsafe or not effective. The following drug products may not be compounded under the exemptions provided by section 503A(a) of the Federal Food, Drug, and Cosmetic Act: All drug products containing sulfathiazole (except those formulated for vaginal use).New animal drugs for use in animal feeds. Chlortetracycline, sulfathiazole, penicillin. Type A medicated articles: (1) 20 grams of chlortetracycline hydrochloride, 4.4 percent (20 grams) sulfathiazole, and procaine penicillin equivalent to 10 grams of penicillin per pound to No. 046573 in section 510.600(c) of this chapter. (2) 40 grams of chlortetracycline hydrochloride, 8.8 percent (40 grams) sulfathiazole and procaine penicillin equivalent in activity to 20 grams of penicillin per pound to No. 046573 in section 510.600(c) of this chapter. ... Indications for use: For reduction of incidence of cervical abscesses. Treatment of bacterial enteritis (salmonellosis or necrotic enteritis caused by Salmonella choleraesuis and vibrionic dysentery). Maintenance of weight gains in the presence of atrophic rhinitis. Swine 10 pounds of body weight to 6 weeks post-weaning: Increased rate of weight gain and improved feed efficiency. Swine 6 to 16 weeks post-weaning: Increased rate of weight gain. ... Limitations: For swine raised in confinement (dry-lot) or on limited pasture. Feed as sole ration. Withdraw 7 days prior to slaughter. |
| Reaktive Gruppe | Amines, Phosphines, and Pyridines |
| Special Reports | Anwar J et alJ Pharm Sci 78: 337-342 Apr 1989. Polymorphism of sulfathiazole.Burger A and RD DialerPharm Acta Helv 58: 72-78 Mar 1983. New investigational results of sulfathiazole polymorphism.Alpar HD and JA HerseyFarmaco Ed Prat 34: 532-541 Dec 1979. Effect of suspending agents on the bioavailability of suspensions of sulfathiazole. |
| Reactivity Profile | SULFATHIAZOLE is an amino acid. |
| History and Incidents | The beginning of modern standards for good manufacturing practices can be traced to an incident that began in December 1940, when the Winthrop Chemical Company of New York put on the market sulfathiazole tablets contaminated with phenobarbital. Hundreds of deaths and injuries resulted. FDA's investigation into Winthrop's sulfathiazole production and the agency's efforts to retrieve the Winthrop drug remaining on the market revealed numerous control deficiencies in the plant and serious irregularities in the firm's attempt to recall the tainted tablets. The incident prompted FDA to require detailed controls in sulfathiazole production at Winthrop and throughout the industry, an approach that became the basis for production control standards for all pharmaceuticals. |
| Air and Water Reactions | May be sensitive to heat, air and light during long-term storage (NTP, 1992). Insoluble in water. |
| Hazard Classes and Categories | Skin Irrit. 2 (91.9%) |
| Hazardous Reactivities and Incompatibilities | Sulfonamide solutions are incompatible with calcium- or other polyionic-containing fluids as well as many other preparations. /Sulfonamides/ |
| Brandbekämpfung | Fires involving this compound should 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. If symptoms (such as redness or irritation) develop, immediately transport the victim to a hospital. |
| Lagerbedingungen | Solutions of the sodium salts of most sulfonamides are strongly basic and deteriorate rapidly. Most sulfonamides slowly darken on exposure to light and should be stored in tight, light-resistant containers. /Sulfonamides/ |
| Freisetung ohne Brand | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol 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 | Since salicylates and other nonsteroidal anti-inflammatory agents (e.g., fenoprofen, indomethacin, meclofenamate) are highly protein bound, these drugs theoretically could be displaced from binding sites by sulfonamides, or could displace sulfonamides from binding sites. Although no clinically important drug interactions have been reported, patients receiving sulfonamides concomitantly with nonsteroidal anti-inflammatory agents should be observed for adverse effects. /Sulfonamides/Because...sulfathiazole may form insoluble precipitates with formaldehyde in the urine, their concomitant administration with methenamine compounds (eg, methenamine mandelate [mandelamine]) should be avoided.The most important interactions of the sulfonamides involve those with the oral anticoagulants, the sulfonylurea hypoglycemic agents, and the hydantoin anticonvulsants. In each case, sulfonamides can potentiate the effects of the other drug by mechanisms that appear to involve primarily inhibition of metabolism and, possibly, displacement from albumin. Dosage adjustment may be necessary when a sulfonamide is given concurrently. /Sulfonamides/Antacids tend to inhibit the GI absorption of sulfonamides. /Sulfonamides/For more Interactions (Complete) data for SULFATHIAZOLE (7 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 200(2) and 97(3) indicate that sulfathiazole is expected to have moderate to high mobility in soil(SRC). The pKa of sulfathiazole is 7.24(4), indicating that this compound will exist partially 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(5). Volatilization from moist soil surfaces is not expected to be an important fate process for the neutral species based upon an estimated Henry's Law constant of 5.8X19-14 atm-cu m/mole(SRC), using a fragment constant estimation method(6). Sulfathiazole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 4.2X10-8 mm Hg(SRC), determined from a fragment constant method(7). In general, sulfonamide antimicrobials are not readily biodegraded and persist in soils(8).AQUATIC FATE: Based on a classification scheme(1), Koc values of 200(2) and 97(3) indicate that sulfathiazole is not expected to adsorb to suspended solids and sediment(SRC). The Henry's Law constant for the neutral species of sulfathiazole is estimated as 5.8X10-14 atm-cu m/mole(SRC) using a fragment constant estimation method(4). This Henry's Law constant indicates that the neutral species is expected to be essentially nonvolatile from water surfaces(5). A pKa of 7.2(6) indicates sulfathiazole will exist partially in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(7). Volatilization from water surfaces is not expected to be an important fate process for the neutral species based upon an estimated Henry's Law constant of 5.8X19-14 atm-cu m/mole(SRC), developed using a fragment constant estimation method(8). According to a classification scheme(9), an estimated BCF of 3(SRC), from an estimated log Kow of 0.05(10) and a regression-derived equation(11), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Sulfathaizole is expected to be readily photodegraded in most natural waters as the anionic form is most susceptible to direct photodegradation(6). A biodegradation rate in soil of 50 kg/wk as part of a land treatment study(12) suggests that biodegradation is not an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulfathiazole, which has an estimated vapor pressure of 4.2X10-8 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 sulfathiazole 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 7 hrs(SRC), calculated from its rate constant of 5.4X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase sulfathiazole may be removed from the air by wet or dry deposition(SRC). Sulfathiazole contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC). |
| Lebensmitteluntersuchungswerte | Sulfathiazole residues were tested for in 2,363 farm and fish samples on the market from 1994 to 1998 in Slovenia(1). Sulfonamides were not detected in 99.37% of samples (detection limit = 0.01 mg/kg)no residues were found in poultry samples and half of the positive samples belong to pig tissues(1). Sulfathiazole was detected in one unspecified sample at a concentration between 10 and 50 ng/g wet weight(1). |
| Unerwünschte Wirkungen | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Milk Concentrations | 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/ |
| Ökotoxizitätsauszüge | /AQUATIC SPECIES/ The photocatalytic degradation of sulfacetamide, sulfathiazole, sulfamethoxazole and sulfadiazine in water solutions during their illumination of UV radiation (gmma max 366 nm) with TiO2 catalyst was examined. The growth-inhibition effect of sulfonamides and intermediate products theirs photodegradation was investigated in aqueous solution with the green alga Chlorella vulgaris. The biodegradability of the investigated compounds was determined in the illuminated solutions and is expressed as Biochemical Oxygen Demand. It was found that all of the investigated sulfonamides in the initial solutions were resistant to biodegradation and were toxic relative to C. vulgaris. The toxicity (EC50 values) relative to C. vulgaris increased in the following order sulfacetamide, sulfathiazole, sulfamethoxazole, sulfadiazine. All of the investigated sulfonamides undergo photocatalytic degradation. The toxicity of intermediate products of the sulfonamides degradation was significantly lower than the toxicity of sulfonamides in the initial solutions and was dependent on illumination time and degradation rate. The intermediate products of photocatalysis in contrast to the initial sulfonamides, might be mineralized using biological methods. |
| 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=72-14-0][Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=72-14-0] |
| Effluent Concentrations | Leachate samples were collected on September 6, 2000, down gradient from the Norman Municipal Landfill research site in central Oklahomathe landfill was established in the 1920s and closed in 1985(1). Sulfathiazole was tested for but not detected, reporting limit 0.10 ug/L(1). The average concentration in daily flushwater of a US swine confined feeding operation was 971 ug/L assuming 2500 head, average weight of 180 lbs, average administration of 496 mg/day/animal(2). Sulfathiazole was not detected in final effluents of eight wastewater treatment plants in five Canadian cities, sampled in 2002detection limit 0.004 ug/L(3). The compound has been found up to the low ug/L-level in unspecified sewage samples(4). |
| Soil Adsorption/Mobility | A Koc of 200 (Kd 4.9) has been reported for sulfathiazole using a loamy sand soil with a pH of 5.2(1). A Koc of 97 was reported using a clay loam soil (pH 6.0, organic content 3.1%)(2). According to a classification scheme(3), these Koc values suggests that sulfathiazole is expected to have moderate to high mobility in soil. The pKa values of sulfathiazole are 2.2 and 7.2(4), indicating that this compound will exist partially 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(5). 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(6,7), suggesting that mobility may be much lower in some soils(SRC). Treated waste water effluent containing sulfathiazole was applied to soil columns over 23 daysthe compound was not detected (detection limit 0.05 ug/L) in the drainage samples(8). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ The physician should be alert to the signs, including high fever, severe headache, stomatitis, conjunctivitis, rhinitis, urethritis, and balanitis, which may precede the onset of the cutaneous lesions of the Stevens-Johnson syndrome. If a rash develops during therapy, the sulfonamide should be discontinued at once. In rare instances, a skin rash may precede a more serious reaction such as Stevens-Johnson syndrome, toxic epidermal necrolysis, hepatic necrosis, and/or serious blood disorders. /Sulfonamides//EPIDEMIOLOGY STUDIES/ In the Collaborative Perinatal Project, the frequency of congenital anomalies was no greater than expected among children of 100 women who were treated with sulfathiazole during the first four lunar months of pregnancy or among the children of 124 women treated with this drug anytime in pregnancy. |
| Artificial Pollution Sources | Sulfathiazole's production and use as both a human(1) and veterinary antibiotic(2) may result in its release to the environment through various waste streams(SRC). |
| Environmental Biodegradation | AEROBIC: A biodegradation rate of 50 kg/wk was reported following the addition of 10,000 ppm added to soil, as part of an analysis of land treatment capacity for effective biodegradation of waste effluent(1). This rate was slow to moderate in comparison to other organo-sulfur compounds tested, the most rapid being sodium-taurocholate at 950 kg/wk and the slowest being sodium-diethyldithiocarbamate at 10 kt/wk(1). Biodegradation of organic sulfur compounds may result in lower soil pH as a result of sulfur mineralization(1). In general, sulfonamide antimicrobials are not readily biodegraded and persist in soils(2). |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3249 |
| Zollcode | 29350090 |
| RTECS-Nr. | WP2360000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36 |
| Gefahrenklasse | 6.1(b)Aquatic Chronic 3Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrstoffdaten | 72-14-0(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Sulfonamide antibacterial.