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化工社化工社 化学情報印刷レポート · 研究参考用
HCID 5338作成日：2026年10月27日

スルファキノキサリン

2-スルファニルアミドキノキサリン · スルキン · 化合物3-120 · ウルソコキサリン · スルファキノキサリン · スルファリン · イタルキナ · 4-アミノ-N-(2-キノキサリニル)ベンゼンスルホンアミド

https://huagongshe.com/ja/chemical/5338

スルファキノキサリン の分子構造式

識別子と物理属性

CAS No.59-40-5
分子式C14H12N4O2S
平均分子量300.34 g/mol
単同位体質量300.06809662 g/mol
SMILESNc1ccc(S(=O)(=O)Nc2cnc3ccccc3n2)cc1
InChIKeyNHZLNPMOSADWGC-UHFFFAOYSA-N
PubChem CID5338
ChEMBLCHEMBL1437847
ChEBICHEBI:94719
EC No.200-423-2
DTXSIDDTXSID8042424
現地名スルファキノキサリン

化学・物理的性質

XLogP1.7
極性表面積106
水素結合供与体数2
水素結合受容体数6
回転可能結合数3
重原子数21
形式電荷0
複雑度442
物質分類Nitrogen Compounds -> Other Aromatics (Nitrogen)
医薬品Pharmaceuticals -> AntibioticsPharmaceuticals -> Antibiotics (Sulfonamide)
LogP（分配係数）log Kow = 1.681.0
Color/FormMinute crystals
溶解度Mol wt: 322.32. Very sol in waterpH of 1% aqueous solution is about 10. The amorphous salt is deliquescent and absorbs carbon dioxide which liberates the practically insoluble sulfaquinoxaline /Sodium salt/Solubility = 730 mg/L in 95% alcohol and 4,300 mg/L in acetone. Soluble in aqueous sodium bicarbonate and sodium hydroxide solutions.In water, 7.5 mg/L at pH 7 / room temp/>45.1 [ug/mL] (The mean of the results at pH 7.4)DMSO（微量）、メタノール（微量）、水（微量）
Animal DrugsFDA approved animal drugs -> Active ingredientPharmaceuticals -> Animal Drugs -> Approved in Taiwan
融点247.5 °C247 - 248 °C247-2480C
Physical DescriptionSolid[Merck Index]
Stability/Shelf LifeStable under storage and application conditions.
Collision Cross Section167.8 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID8042424]164.8 Ų [M+H]+ [CCS Type: TW]155.78 Ų [M+H-H2O]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]168.94 Ų [M-H]-
沸点551.1±60.0 °C(Predicted)
密度1.3196 (rough estimate)
屈折率1.6440 (estimate)
貯蔵条件Refrigerator
pKa（酸解離定数）5.65±0.10(Predicted)
外観・状態Solid
色淡い黄色から黄色
Merck13,9025
BRN290026
主な用途農業環境
InChIInChI=1S/C14H12N4O2S/c15-10-5-7-11(8-6-10)21(19,20)18-14-9-16-12-3-1-2-4-13(12)17-14/h1-9H,15H2,(H,17,18)
InChIKeyNHZLNPMOSADWGC-UHFFFAOYSA-N
SMILESC1(S(NC2C=NC3C(N=2)=CC=CC=3)(=O)=O)=CC=C(N)C=C1
LogP（分配係数）1.680
CAS データベース59-40-5(CAS DataBase Reference)
EPAの化学物質情報Sulfaquinoxaline (59-40-5)

化学的特性

Crystalline Solid

安全性と法規制

GHS 分類This chemical does not meet GHS hazard criteria for 2.1% (1 of 48) of reports.DangerH302 (97.9%): Harmful if swallowed [Warning Acute toxicity, oral]P233, P260, P261, P264, P270, P271, P272, P280, P284, P301+P317, P302+P352, P304+P340, P321, P330, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 48 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報Sulphaquinoxaline: Does not have an individual approval but may be used under an appropriate group standard
その他の安全情報IMAP assessments - Benzenesulfonamide, 4-amino-N-2-quinoxalinyl-: Environment tier I assessment
有害性の概要A flock of chickens treated with 0.05% in feed for 2-3 days, removed 2 days, and treated again for 2-3 days had 47% mortality with hemorrhages, bone marrow pallor, and septicemiaEmergency treatment: SulfonamidesSulfonamides are used as antibioticsThey can cause hypersensitivity reactions including erythema multiforme and liver injuryMethemoglobinemia and renal failure may occur after toxic ingestions[HSDB] Causes changes in renal tubules in 26-week, intermittent, oral study of rats (9100 mg/kg)Causes hemorrhage in 14 day intermittent study of dogs (1400 mg/kg)[RTECS] May cause irritationMay cause skin and respiratory sensitization[Aldrich MSDS]
FDA 要件Oral dosage form new animal drugs. Sulfamerazine, sulfamethazine, and sulfaquinoxaline powder. ... Conditions of use: (1) Chickens ...(A) As an aid in the control of coccidiosis caused by Eimeria tenella and E. necatrix susceptible to sulfamerazine, sulfamethazine, and sulfaquinoxaline ... (B) As an aid in the control of acute fowl cholera caused by Pasteurella multocida susceptible to sulfamerazine, sulfamethazine, and sulfaquinoxaline ... (2) Turkeys ... (A) As an aid in the control of coccidiosis caused by Eimeria meleagrimitis and E. adenoeides susceptible to sulfamerazine, sulfamethazine, and sulfaquinoxaline ... (B) As an aid in the control of acute fowl cholera caused by Pasteurella multocida susceptible to sulfamerazine, sulfamethazine, and sulfaquinoxaline ... .Oral dosage new animal drugs. Sulfaquinoxaline drinking water. ... Conditions of use. It is used in drinking water as follows: (1) Chickens. (i) As an aid in the control of outbreaks of coccidiosis caused by Eimeria tenella, E. necatrix, E. acervulina, E. maxima, and E. brunetti. ... (2) Turkeys. (i) As an aid in the control of outbreaks of coccidiosis caused by Eimeria meleagrimitis and E. adenoeides. ... 3) Chickens and turkeys. (i) As an aid in the control of acute fowl cholera caused by Pasteurella multocida susceptible to sulfaquinoxaline and fowl typhoid caused by Salmonella gallinarum susceptible to sulfaquinoxaline. ... (4) Cattle and calves. (i) For the control and treatment of outbreaks of coccidiosis caused by Eimeria bovis or E. zurnii.
Oral dosage new animal drugs. Sulfaquinoxaline drench. ... Conditions of uses: ... For the control and treatment of outbreaks of coccidiosis in cattle and calves caused by Eimeria bovis or E. zurnii.
A tolerance of 0.1 part per million is established for negligible residues of sulfaquinoxaline in the uncooked edible tissues of chickens, turkeys, calves, and cattle.
For more FDA Requirements (Complete) data for SULFAQUINOXALINE (7 total), please visit the HSDB record page.
FIFRA 要件As the federal pesticide law FIFRA directs, EPA is conducting a comprehensive review of older pesticides to consider their health and environmental effects and make decisions about their future use. Under this pesticide reregistration program, EPA examines health and safety data for pesticide active ingredients initially registered before November 1, 1984, and determines whether they are eligible for reregistration. In addition, all pesticides must meet the new safety standard of the Food Quality Protection Act of 1996. Pesticides for which EPA had not issued Registration Standards prior to the effective date of FIFRA '88 were divided into three lists based upon their potential for human exposure and other factors, with List B containing pesticides of greater concern and List D pesticides of less concern. Sulfaquinoxaline is found on List C. Case No:3135Pesticide type:RodenticideCase Status:Cancelled - No products containing the pesticide are actively registered. Therefore, we are characterizing the case as cancelled. Under FIFRA, pesticide producers may voluntarily cancel their registered products. EPA also may cancel pesticide registrations if registrants fail to pay required fees or make/meet certain reregistration commitments, or if EPA reaches findings of unreasonable adverse effects.Active ingredient (AI):N 1-(2-Quinoxaliny)sulfanilamideAI Status: Cancelled - The active ingredient is no longer contained in any registered pesticide product. Thus, we characterize it as cancelled.
Hazard Classes and CategoriesAcute Tox. 4 (97.9%)
保管条件Store below 40 °C (104 °F), preferably between 15 and 30 °C (59 and 86 °F), unless otherwise specified by manufacturer. Protect from moisture.
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.
Preventive MeasuresPeople who handle this medication should avoid contact with eyes, skin, or clothing to prevent eye and skin burns. In case of contact, the areas affected should be flushed for at least fifteen minutesmedical attention should be sought for eye exposure. Keep out of the reach of children.
Allowable TolerancesA tolerance of 0.1 part per million is established for negligible residues of sulfaquinoxaline in the uncooked edible tissues of chickens, turkeys, calves, and cattle.
相互作用The most important interactions of the sulfonamides involve those with the oral anticoagulants, the sulfonylurea hypoglycemic agents, and the hydantoin acticonvulsants. In each case, sulfonamides can potentiate the effects of the other drug by metabolism and, possibly, displacement from albumin. Dosage adjustment may be necessary when a sulfonamide is given concurrently. /Sulfonamides/One of the most active agents that exerts a synergistic effect when used with a sulfonamide is trimethoprim. This cmpd is a potent and selective competitive inhibitor of microbial dihydrofolate reductase, the enzyme that reduces dihydrofolate to tetrahydrofolate. It is this reduced form of folic acid that is required for one-carbon transfer reactions. The simultaneous admin of a sulfonamide and trimethoprim ... introduces sequential blocks in the pathway by which microorganisms synthesize tetrahydrofolate from precursor molecules. The ... synergistic antimicrobial effects has been realized both in vitro and in vivo. /Sulfonamides/Para-aminobenzoic acid (PABA) is most prominent sulfonamide antagonists. Certain local anesthetics, such as procaine, that are esters of PABA antagonize these drugs in vitro and in vivo. /Sulfonamides/
環境中動態TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 200(SRC), determined from a log Kow of 1.68(2) and a regression-derived equation(3), indicates that sulfaquinoxaline is expected to have moderate mobility in soil(SRC). However, aromatic amines may bind strongly to humus and organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils(SRC). An estimated pKa of 5.1 (sulfonamide nitrogen)(6), indicates that this compound will exist primarily as an anion in the environment. Volatilization of sulfaquinoxaline from moist soil surfaces is not expected to be an important fate process(SRC) because anions do not volatilize. Sulfaquinoxaline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.0X10-10 mm Hg(SRC), determined from a fragment constant method(7). Biodegradation data were not available(SRC, 2006).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 200(SRC), determined from a log Kow of 1.68(2) and a regression-derived equation(3), indicates that sulfaquinoxaline is not expected to adsorb to suspended solids and sediment(SRC). However, aromatic amines may bind strongly to organic matter due to the high reactivity of the aromatic amino group(4,5). An estimated pKa of 5.1 (sulfonamide nitrogen)(SRC), calculated using a method based on linear free energy relationships and perturbed molecular orbital theory(6), indicates that this compound will exist primarily as an anion in the environment. Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 4.4X10-15 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). The estimated pKa of sulfaquinoxaline is 5.1(5), indicating that this compound will primarily exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(6). According to a classification scheme(7), an estimated BCF of 11(SRC), from its log Kow(2) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2006).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), sulfaquinoxaline, which has an estimated vapor pressure of 3.0X10-10 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase sulfaquinoxaline may be removed from the air by wet or dry deposition(SRC). Sulfaquinoxaline absorbs light at wavelengths >290 nm (lambda max = 360 nm)(3) and therefore may be susceptible to direct photolysis by sunlight(4).
有害作用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 ConcentrationsSulfonamides are distributed into milkhowever, the sulfonamides that are clinically relevant to food-producing animals are distributed into milk in concentrations too low to be therapeutic but high enough to produce residues. Sulfadiazine and sulfanilamide are more efficiently distributed into milk than most sulfonamides, but are not used in dairy cattle. For many sulfonamides, 0.5 to 2% of the total dose is found in the milk. Distribution into milk varies depending on the amount of non-protein -bound sulfonamide present in the blood and the amount of the nonionized and therefore liposoluble form of the medication present. Sulfonamides with higher pKa values produce a higher proportion of drug in the blood that is non-ionized, and if other factors, such as the rate of biotransformation, also support it, may be distributed more easily into milk. /Sulfonamides/
生態毒性抜粋/AQUATIC SPECIES/ The short-term toxicity (EC50 respectively LC50 after 2 or 4 days) of 13 feed additives was determined to 4 freshwater organisms of different trophical levels: Chlorella pyrenoidosa, Daphnia magna, Lebistes reticulatus and Salmo gairdneri. The most toxic (LC(EC)50 less than 1 mg/L) were robenidine (to all tested organisms) and stenorol (to Daphnia)moderately toxic (1 less than LC(EC)50 less than 10 mg/1) was pyrimethamine. Amprolium, ethopabate, furazolidone and zoalene proved to be little toxic (LC(EC)50 greater than 10 mg/L)whereas buquinolate, carbadox, clopidol, decoquinate, grofas and sulfaquinoxaline were under the experimental conditions not toxic for the tested organisms.
Soil Adsorption/MobilityThe Koc of sulfaquinoxaline is estimated as 200(SRC), using a log Kow of 1.68(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that sulfaquinoxaline is expected to have moderate mobility in soil. However, aromatic amines may bind strongly to humus and organic matter in soils due to the high reactivity of the aromatic amino group(4,5), suggesting that mobility may be much lower in some soils(SRC).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Complete suppression of bone-marrow activity with profound anemia, granulocytopenia, and thrombocytopenia is an extremely rare occurrence with sulfonamide therapy. It probably results from a direct myelotoxic effect and may be fatal. /Sulfonamides//SIGNS AND SYMPTOMS/ Focal or diffuse necrosis of the liver due to direct drug toxicity or sensitization occurs in fewer than 0.1% of patients. Headache, nausea, vomiting, fever, hepatomegaly, jaundice, and laboratory evidence of hepatocellular dysfunction usually appear 3 to 5 days after sulfonamide administration is started, and the syndrome may progress to acute yellow atrophy and death. /Hypersensitivity reactions to sulfonamides//SIGNS AND SYMPTOMS/ The admin of sulfonamides to newborn infants, especially if premature, may lead to the displacement of bilirubin from plasma albumin. In newborn infants, free bilirubin can become deposited in the basal ganglia and subthalamic nuclei of the brain, causing an encephalopathy called kernicterus. /Sulfonamides//SIGNS AND SYMPTOMS/ Short-term depression /of serum cholinesterase activity/ is caused by ... sulfanilamides ... /Sulfanilamides//OTHER TOXICITY INFORMATION/ Human beings, nonhuman primates, guinea pig and chicken /are resistant to/ thyroperoxidase (TPO) inhibition by sulfonamidesrat, mouse, dog and pig /are sensitive to/ TPO inhibition by sulfonamides. /From table/
Artificial Pollution SourcesSulfaquinoxaline's production and use for the treatment of coccidiosis in chickens, turkeys, and cattle(1) may result in its release to the environment through various waste streams(SRC).
Environmental BioconcentrationAn estimated BCF of 11 was calculated for sulfaquinoxaline(SRC), using a log Kow of 1.68(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).
Volatilization from Water/SoilAn estimated pKa of 5.1 (sulfonamide nitrogen)(1), calculated using a method based on linear free energy relationships and perturbed molecular orbital theory(2), indicates that sulfaquinoxaline will exist primarily as an anion in the environment. Volatilization of sulfaquinoxaline from moist soil or water surfaces is not expected to be an important fate process(SRC) since anions do not volatilize. Sulfaquinoxaline is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.0X10-10 mm Hg(SRC), determined from a fragment constant method(3).
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ Mortality of 47% occurred in a commercial flock of 20-week-old leghorn pullets treated with 0.05% sulfaquinoxaline in the feed. The drug was given for 2-3 days, removed for 2 days, and fed again for 2-3 days. Gross lesions consisted of disseminated hemorrhages, bone marrow pallor, a variety of changes suggesting septicemia, and overwhelming bacterial infection. Experimental feeding of sulfaquinoxaline at 0.05% in the feed at a schedule of 3 days on, 3 days off, and 2 days on successfully reproduced the essential features and gross lesions of the field toxicosis. Mortalities of 32.5% and 43.5% were observed in sulfaquinoxaline-treated groups. A high incidence of gangrenous dermatitis occurred in chickens with the experimental toxicosis, but it was not observed in the field case.
Populations at Special Risk... Sulfonamides ... may produce acute hemolysis in patients with glucose-6-phosphate dehydrogenase deficiency. /Sulfonamides/The admin of sulfonamides to newborn infants, especially if premature, may lead to the displacement of bilirubin from plasma albumin. In newborn infants, free bilirubin can become deposited in the basal ganglia and subthalamic nuclei of the brain, causing an encephalopathy called kernicterus. Sulfonamides should not be given to pregnant women near term because these drugs pass through the placenta and are secreted in milk. /Sulfonamides/... Patients with acute pyelonephritis with high fever and other severe constitutional manifestations are at risk of bacteremia and shock and should not be treated with a sulfonamide. /Sulfonamides for urinary tract infections/
水環境危害等級（WGK）3
TSCA 収載状態TSCA listed
RTECS 番号WP2100000
税関コード29350090
危険文句（R）22-42/43
化審法一般化学物質
危険表示Xn
安全措置（S）22-36/37-45
危険等級Acute Tox. 4 OralResp. Sens. 1Skin Sens. 1
貯蔵分類11 - Combustible Solids
有害物質データ59-40-5(Hazardous Substances Data)