戻る
化工社化工社 化学情報印刷レポート · 研究参考用
HCID 5333作成日:2026年10月23日

Sulfanilamide

https://huagongshe.com/ja/chemical/5333

Sulfanilamide の分子構造式

識別子と物理属性

CAS No.63-74-1
分子式C6H8N2O2S
平均分子量172.21 g/mol
単同位体質量172.03064868 g/mol
SMILESNc1ccc(S(N)(=O)=O)cc1
InChIKeyFDDDEECHVMSUSB-UHFFFAOYSA-N
PubChem CID5333
ChEMBLCHEMBL21
ChEBICHEBI:45373
EC No.200-563-4
DTXSIDDTXSID4023622

化学・物理的性質

XLogP-0.6
極性表面積94.6
水素結合供与体数2
水素結合受容体数4
回転可能結合数1
重原子数11
形式電荷0
複雑度211
pHNEUTRAL TO LITMUSPH OF 0.5% AQ SOLN: 5.8-6.1
LogP(分配係数)-0.62log Kow = -0.62-0.8
LogS-1.36
密度1.08 at 68 °F (NTP, 1992) - Denser than waterwill sink1.08 @ 25 °C1.08 @25 °C
Color/FormLEAFLETS FROM AQ ALCOHOLCRYSTALS
溶解度0.1 to 1.0 mg/mL at 72 °F (NTP, 1992)7500IN WATER: 7.5 G/L AT 25 °C & 477 G/L AT 100 °C1 G DISSOLVES IN ABOUT 37 ML OF ALC & ABOUT 5 ML ACETONEINSOL IN CHLOROFORM, ETHER, BENZENE & PETROLEUM ETHERSOL IN GLYCEROL, PROPYLENE GLYCOL, HYDROCHLORIC ACID, SOLN OF POTASSIUM AND SODIUM HYDROXIDESOL IN ETHANOL
融点329 to 331 °F (NTP, 1992)165.5165.5 °C
蒸気圧0.0000073 [mmHg]
Physical DescriptionSulfanilamide is a white powder. pH of 0.5% aqueous solution: 5.8-6.1. (NTP, 1992)Solid[Merck Index]
Stability/Shelf LifeSENSITIVE TO LIGHT
Ionization EfficiencyPositive2.76Agilent XCTElectrospray ionizationformic acid (5.3nM)
Dissociation Constants10.6 (at 20 °C)pKa = 10.43, pKb = 11.63pKa = 10.58

安全性と法規制

GHS 分類This chemical does not meet GHS hazard criteria for 41.6% (121 of 291) of reports.WarningH315 (58.4%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (58.4%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (57%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract 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 291 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 121 of 291 reports by companies.There are 12 notifications provided by 170 of 291 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.
規制情報Chemical: Benzenesulfonamide, 4-amino-Regulation (EC) No 1107/2009 (amended)Status: Active Update: 11-07-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/24237Sulphanilamide: Does not have an individual approval but may be used under an appropriate group standard
輸送ラベル(DOT)Corrosive
火災危険Flash point data for this chemical are not available but it is probably combustible. (NTP, 1992)
健康有害性SYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin, eyes and mucous membranes, nausea, vomiting, fever, diarrhea, jaundice, headache, crystalluria, acidosis, ataxia, convulsions, cyanosis, dizziness, dermatitis, paralysis and respiratory failure. It has been implicated in aplastic anemia.ACUTE/CHRONIC HAZARDS: This material may cause irritation of the skin on contact. (NTP, 1992)
有害性の概要Photoallergic contact dermatitis reportedSulfanilamide may induce photosensitivity in patients taking sulfanilamide systemically (photodrug reaction). [Marks, p. 201-3] In a 1946 report, occupational asthma was induced by sulfathiazole (72-14-0). [Malo] See Sulfathiazole.
FDA 要件Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended21 U.S.C. 321-392).
反応性グループSulfonates, Phosphonates, and Thiophosphonates, OrganicAmines, Aromatic
Reactivity ProfileSULFANILAMIDE is an amino acid. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May react with azo and diazo compounds to generate toxic gases.
Air and Water ReactionsMay be unstable if exposed for long periods air and light (NTP, 1992). Slightly water soluble.
Hazard Classes and CategoriesSkin Irrit. 2 (58.4%)Eye Irrit. 2 (58.4%)STOT SE 3 (57%)
消火Fires involving this compound can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
応急処置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.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)
非火災時の漏出対応SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, you should dampen the solid spill material with acetone, then transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone 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 acetone followed by washing with a strong soap and water solution. Do not reenter the contaminate area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.STORAGE PRECAUTIONS: You should protect this container from exposure to light. Keep the container tightly closed under an inert atmosphere and store under refrigerated temperatures. (NTP, 1992)
処分方法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.
Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024)
Protective Action Criteria (PAC)3.0 [mg/m3]140 [mg/m3]830 [mg/m3]
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)
相互作用The most important interactions of the sulfonamides involve those with 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.PENTOBARBITAL /SRP: CNS DEPRESSION/ IN MICE WAS ENHANCED AFTER PRE-TREATMENT WITH... SULFANILAMIDE... INCR /SRP: CNS DEPRESSION/ APPEARED TO BE DUE TO RELEASE OF PENTOBARBITAL FROM SERUM-PROTEIN BINDING, RESULTING IN HIGHER CEREBRAL CONCN, RATHER THAN DUE TO INHIBITION OF METABOLISM.INTRAGASTRIC FORMATION OF /A/ TRIAZENE OCCURRED IN SYRIAN GOLDEN HAMSTERS BY CONCURRENT ADMIN OF SULFANILAMIDE AND SODIUM NITRITE/.
環境中動態TERRESTRIAL FATE: Based on a recommended classification scheme(1), an estimated Koc value of 11(SRC), determined from an experimental log Kow(2) and a recommended regression-derived equation(3), indicates that sulfanilamide should have very high mobility in soil(SRC). The adsorptivity of sulfanilamide is expected to be sensitive to pH since sulfanilamide has a pKa of 10.58(7). Also, studies have shown that covalent binding of ring-substituted anilines, such as sulfanilamide(SRC), to humates involves a reversible equilibrium which is followed by a very slow and relatively irreversible reaction(9) which may reduce sulfanilamide's mobility in soil(SRC). Volatilization of sulfanilamide should not be important from moist soil surfaces(SRC) given an estimated Henry's Law constant of 1.5X10-10 atm-cu m/mole(4,SRC), or from dry soil surfaces(SRC) based on an estimated vapor pressure of 7.3X10-6 mm Hg(5,SRC). Sulfanilamide may be susceptible to direct photolysis on soil surfaces based on its absorption of light at wavelengths >290 nm(6,SRC). Although aniline was able to degrade quickly, sulfanilamide degraded very slowly by aniline-acclimated activated sludge in a 200 hour Warburg Run(8), suggesting that biodegradation in soil will be slow(SRC).AQUATIC FATE: An estimated Koc value of 11(SRC), determined from an experimental log Kow(1) and a recommended regression-derived equation(2), indicates that sulfanilamide should not adsorb to suspended solids and sediment(SRC) in the water(2,SRC). Sulfanilamide will be essentially non-volatile from water surfaces based on an estimated Henry's Law constant of 1.5X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). An estimated BCF value of 0.2(2,SRC), from an experimental log Kow(1), suggests that sulfanilamide will not bioconcentrate in aquatic organisms(SRC) according to a recommended classification scheme(4). Although aniline was able to degrade quickly, sulfanilamide degraded very slowly by aniline-acclimated activated sludge in a 200 hour Warburg Run(5), suggesting that biodegradation in water will be slow(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulfanilamide, which has an estimated vapor pressure of 7.3X10-6 mm Hg at 25 °C(2,SRC) will exist as both a vapor and particulate in the ambient atmosphere. Vapor-phase sulfanilamide 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 about 17 hours(3,SRC). Particulate-phase sulfanilamide may be physically removed from the air by wet deposition(SRC).
有害作用Dermatotoxin - PACD (photoallergic contact dermatitis).
Soil Adsorption/MobilityThe Koc of sulfanilamide is estimated as approximately 11(SRC), using an experimental log Kow of -0.62(1,SRC) and a regression-derived equation(2,SRC). According to a recommended classification scheme(3), this estimated Koc value suggests that sulfanilamide should have high mobility in soil(SRC). The adsorptivity of sulfanilamide is expected to be sensitive to pH since sulfanilamide has a pKa of 10.58(4). Also, studies have shown that covalent binding of ring-substituted anilines, such as sulfanilamide(SRC), to humates involves a reversible equilibrium which is followed by a very slow and relatively irreversible reaction(5) which may reduce sulfanilamide's mobility in soil(5).
Human Toxicity ExcerptsRetinal and preretinal hemorrhages have in very rare instances been observed following administration of sulfanilamide ... .Visual distrubances have in a few cases been attributed to effects of sulfonamides on the optic nerve or retina. /Sulfonamide drugs/Sulfonamide drugs have been held responsible for several types of ocular disturbance, including acute transient myopia, conjunctivitis, and keratitis associated with skin reactions, rarely disturbances of the optic nerve and retina, and temporary impairment of depth perception. /Sulfonamide drugs/
Artificial Pollution SourcesSulfanilamide's production and use as an antibacterial and an antimicrobial agent(1) may result in its release to the environment through various waste streams(SRC).
Environmental BiodegradationAlthough aniline was able to degrade quickly, sulfanilamide degraded very slowly by aniline-acclimated activated sludge in a 200 hour Warburg Run(1), suggesting that biodegradation in water will be slow(SRC).
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)sulfanilamideDILI PositiveVaginalDOI:10.1016/j.drudis.2019.09.022
Environmental BioconcentrationAn estimated BCF value of 0.2 was calculated for sulfanilamide(SRC), using an experimental log Kow of -0.62(1) and a recommended regression-derived equation(2). According to a recommended classification scheme(3), this BCF value suggests that bioconcentration in aquatic organisms will not be an important fate process(SRC).
Volatilization from Water/SoilThe Henry's Law constant for sulfanilamide is estimated as 1.5X10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This value indicates that sulfanilamide will be essentially nonvolatile from water surfaces(2,SRC). Sulfanilamide's vapor pressure, 7.3X10-6 mm Hg(3,SRC) and Henry's Law constant(1,SRC) indicate that volatilization from dry or moist soil surfaces should not occur(SRC).
Non-Human Toxicity ExcerptsLETHAL DOSES IN ANIMALS PRODUCE ATAXIA, CLONIC CONVULSIONS, PARALYSIS AND DEATH FROM RESPIRATORY FAILURE.COWS SHOWED...VARIABLE SUSCEPTIBILITY...IN SOME ANIMALS SINGLE DOSES OF 220 MG/KG PRODUCED DIARRHEA. LARGER DOSES 440 MG/KG BROUGHT ABOUT DROP IN MILK YIELD, INAPPETENCE, SLEEPINESS & SOME INCOORDINATION OF MOVEMENTDIARRHEA WAS ALSO SOMETIMES SEEN.DAILY DOSING...TO HORSES AT RATE OF 0.44 G/KG (0.2 G/LB) PRODUCED...ANOREXIA, WEAK PULSE & GENERAL DEBILITY... AT LOWER DOSE RATE OF 0.17 G/KG DAILY... GENERAL DEPRESSION, MUSCLE RIGIDITY & EDEMA /WERE OBSERVED/IF ADMIN WAS CONTINUED ANIMALS DIED.IN HORSE A SINGLE DOSE /ORALLY ADMIN/ AT RATE OF 440 MG/KG CAUSED SOME LISTLESSNESS & DISINCLINATION TO FEED.For more Non-Human Toxicity Excerpts (Complete) data for SULFANILAMIDE (9 total), please visit the HSDB record page.
Environmental Abiotic DegradationThe rate constant for the vapor-phase reaction of sulfanilamide with photochemically produced hydroxyl radicals has been estimated as 2.3X10-11 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1,SRC). This corresponds to an atmospheric half-life of about 17 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Sulfanilamide may be susceptible to direct photolysis on soil surfaces based on its absorption of light at wavelengths >290 nm(2,SRC). UV photolysis of an aqueous solution of sulfanilamide, with a 1 kw Xe Arc lamp equipped with an infrared filter (intensity of 1.22 kw/sq-m), yielded the following radicals: C6H4SO2NH2, C6H5SO2, SO2NH2, and SO3.-(3).