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HCID 10909430作成日:2026年10月26日

バシトラシン標準品

バシ-ジェル · シロトラシン · ズトラシン · フォルトラシン · アイフィビン · バシトラシン · トピトラシン · ペニトラシン

https://huagongshe.com/ja/chemical/10909430

バシトラシン標準品 の分子構造式

識別子と物理属性

CAS No.1405-87-4
分子式C66H103N17O16S
平均分子量1,422.7 g/mol
SMILESCC[C@H](C)[C@H](N)C1=N[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(=O)O)C(=O)N[C@H](C(=O)N[C@H]2CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(=O)O)NC(=O)[C@H](Cc3cnc[nH]3)NC(=O)[C@@H](Cc3ccccc3)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCCN)NC2=O)[C@@H](C)CC)CS1
InChIKeyCLKOFPXJLQSYAH-ABRJDSQDSA-N
PubChem CID10909430
ChEMBLCHEMBL1200558
ChEBICHEBI:35862
EC No.215-786-2
現地名バシトラシン標準品

化学・物理的性質

XLogP-4.1
極性表面積556
水素結合供与体数17
水素結合受容体数21
回転可能結合数31
重原子数100
形式電荷0
複雑度2,850
物質分類Other Uses -> Pharmaceuticals
pHA solution containing 10000 units per ml has a pH of 5.5-7.5.
LogP(分配係数)-0.8
臭いOdorless無臭または塩臭
味Very bitter taste
Color/FormWhite to pale buff powderGrayish-white powder
溶解度Freely solubleWhite to grayish-white powder. Slightly disagreeable odor. Somewhat less bitter than bacitracin. UV max (dilute acetic acid): 318 nm, min: 280 nm. Solubility in water about 50 mg/mL. pH of saturated aqueous solution 3.5 to 5.0. Soluble in pyridine, ethanol, less soluble or insoluble in acetone, ether, chloroform, pentane, benzene. Soluble in dilute aqueous alkali at pH 6 and higher, increasingly insoluble at pH 6 to 3. /Bacitracin methylenedisalicylate/Freely soluble in waterSoluble in methanol, alcohol, glacial acetic acidpractically insoluble in acetone, chloroform, ether2.45e-02 g/LH2O: 50mg/mL、透明からわずかに濁った、濃い黄色溶ける
Human DrugsBreast FeedingLactationMilk, HumanAnti-Infective Agents, LocalAntibacterial AgentsFDA approved drugs -> Active ingredient
Animal DrugsFDA approved animal drugs -> Active ingredientPharmaceuticals -> Animal Drugs -> Approved in Taiwan
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
融点221 - 225 °C221-225°C
蒸気圧Infitesimally low vapor pressure over the temperature range at which bacitracins are stable
密度1.0166 (rough estimate)
屈折率1.6700 (estimate)
貯蔵条件Keep in dark place,Inert atmosphere,2-8°C
外観・状態粉
色白~ほんのりベージュ
Merck13,936
InChIKeyQSNOBVJFKSQBBD-UHFFFAOYSA-N
LogP(分配係数)-0.050 (est)
EPAの化学物質情報Bacitracin (1405-87-4)

化学的特性

Bacitracin is a white to light tan powder which is odorless or having a slight odor and very bitter taste.

安全性と法規制

GHS 分類This chemical does not meet GHS hazard criteria for 10.8% (4 of 37) of reports.WarningH315 (10.8%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P272, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P333+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 37 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Not Classified
規制情報Bacitracin: 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 - Bacitracin: Human health tier I assessment
有害性の概要Allergic contact dermatitis and contact urticaria reported in patients using the antibiotic topically[Marks, p. 186-8]
FDA 要件Bacitracin methylenedisalicylate. ... (1) Growing turkeys ... Indications for use. Aid in the control of transmissible enteritis complicated by organisms susceptible to bacitracin methylenedisalicylate. ... (2) Broiler and replacement chickens ... Indications for use. Aid in the prevention of necrotic enteritis caused by Clostridium perfringens susceptible to bacitracin methylenedisalicylate. ... Indications for use. Treatment of necrotic enteritis caused by C. perfringens susceptible to bacitracin methylenedisalicylate. ... (3) Swine ... Indications for use. Treatment of swine dysentery associated with Brachyspira hyodysenteriae. ... (4) Growing quail ... Indications for use. For prevention of ulcerative enteritis due to Clostridium colinum susceptible to bacitracin methylenedisalicylate. /Bacitracin methylenedisalicylate/Bacitracin methylene disalicylate and streptomycin sulfate powder. ... Indications for use /in dogs/. For the treatment of bacterial enteritis caused by pathogens susceptible to bacitracin and streptomycin such as Escherichia coli, Proteus spp., Staphylococcus spp., and Streptococcus spp., and for the symptomatic treatment of associated diarrhea. /Bacitracin methylene disalicylate/Bacitracin zinc soluble powder. ... (1) Broiler chickens ... Indications for use. Prevention of necrotic enteritis caused by Clostridium perfringens susceptible to bacitracin zinc. ... Indications for use. Control of necrotic enteritis caused by Clostridium perfringens susceptible to bacitracin zinc. ... (2) Growing quail ... Indications for use. Control of ulcerative enteritis caused by Clostridium spp. susceptible to bacitracin zinc. /Bacitracin zinc soluble powder/Bacitracin, neomycin, and polymyxin B ophthalmic ointment. ... Indications for use /in dogs and cats/. Treatment of superficial bacterial infections of the eyelid and conjunctiva of dogs and cats when due to susceptible organisms.For more FDA Requirements (Complete) data for BACITRACIN (12 total), please visit the HSDB record page.
Toxic Combustion ProductsSpecial hazards arising from the substance or mixture include Carbon oxides, nitrogen oxides (NOx), Sulfur oxides.
Hazard Classes and CategoriesSkin Irrit. 2 (10.8%)Not Classified
Hazardous Reactivities and IncompatibilitiesIncompatible materials: Strong oxidizing agents.
消火手順Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
保管条件Bacitracin ophthalmic ointment should be stored at 15-30 °C.Aqueous solutions ... are stable for 1 week when stored at 2-8 °C. ... Bacitracin powder should be stored at 2-15 °C and should be protected from direct sunlight. Bacitracin topical ointment should be stored at 15-30 °C.Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2-8 °C Keep in a dry place. Keep in a dry place.
清掃方法Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Avoid breathing dust. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.
処分方法SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.
Preventive MeasuresAppropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.Precautions for safe handling: Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.
Allowable TolerancesThe tolerance for residues of bacitracin from zinc bacitracin or bacitracin methylene disalicylate in uncooked edible tissues of cattle, swine, chickens, turkeys, pheasants, and quail, and in milk and eggs is 0.5 part per million.
Personal Protective Equipment (PPE)Skin protection: Handle with gloves.Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).Body Protection: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place. The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.
相互作用Bacitracin is believed to inhibit neuromuscular transmission. Parenterally administered bacitracin may increase or prolong skeletal muscle relaxation produced by neuromuscular blocking agents and/or anesthetics if the antibiotic is administered during surgery, or may reinstate neuromuscular blockade if administered parenterally postoperatively.Since nephrotoxic effects may be additive, concurrent use of other nephrotoxic drugs, particularly aminoglycosides (streptomycin, kanamycin, neomycin, viomycin (not commercially available in the US)), polymyxin B, and colistimethate/colistin, should be avoided.
Skin SymptomsSelected as the 2003 American Contact Dermatitis Society Allergen of the Year. The authors note that Bacitracin can cause allergic contact dermatitis, urticarial reactions, and near-fatal anaphylaxis. Also, Bacitracin was the ninth most common allergen in 1998 to 2000 according to the North American Contact Dermatitis Group.
環境中動態TERRESTRIAL FATE: Bacitracin is a high molecular weight, ionic peptide that may exist as a dipolar molecule(1). In acid solution it can be a cation(1) which absorb strongly to soil and under basic conditions(3) it can exist as an anion(1) and is mobile in soil(3). The estimated pKa values for bacitracin range from 3.19 to 13.26(2). Volatilization from moist soil is not expected because the compound exists as an ion and ions do not volatilize. Bacitracin is not expected to volatilize from dry soil surfaces as bacitracin has an infitesimally low vapor pressure(1). A Pseudomonid was isolated from a soil-poultry feces mixture that was capable of degrading bacitracin(4).AQUATIC FATE: Bacitracin is a high molecular weight, ionic peptide that may exist as a dipolar molecule(1). It may or may not adsorb to suspended solids and sediment due to its dipolar chemistry(SRC). The estimated pKa values for bacitracin range from 3.19 to 13.26(2), indicating that bacitracin will exist almost entirely in the ion form at pH values of 5 to 9. Therefore, volatilization from water surfaces and bioconcentration are not expected to be important fate processes(SRC). Biodegradation data in water were not available(SRC, 2015).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), bacitracin, which has an infitesimally low vapor pressure(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase bacitracin may be removed from the air by wet and dry deposition(SRC). Bacitracin contains chromophores that absorb at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).
有害作用Skin Sensitizer - An agent that can induce an allergic reaction in the skin.
毒性の概要IDENTIFICATION AND USE: Bacitracin is greyish white powder formulated into both a human and animal medicinal agent. It is an antibacterial veterinary medicine agent used in wound powders and ointments, dermatologic preparations, eye and ear ointments, as well as feed additives in swine and poultry rations for growth promotion. In humans, IM bacitracin has been used in infants for the treatment of pneumonia and empyema caused by staphylococci susceptible to the drug. Bacitracin is also used topically alone or in combination with other anti-infectives for the prevention or treatment of superficial skin infections caused by susceptible organisms. Bacitracin has been used orally for the treatment of Clostridium difficile-associated diarrhea and colitis (CDADalso known as antibiotic-associated diarrhea and colitis or pseudomembranous colitis). It is also used alone or in combination with other anti-infective agents in the short-term topical treatment of superficial infections of the eye caused by susceptible bacteria. HUMAN EXPOSURE AND TOXICITY: Bacitracin has a low order of toxicity when applied topicallyhowever, rashes and allergic anaphylactoid reactions have occurred in some patients. Anaphylactoid reactions have ranged from generalized itching, swelling of the lips and face, sweating, and tightness of the chest, to hypotension, unconsciousness, apnea, and cardiac arrest. Anaphylaxis has also been reported in a patient after irrigation and packing of an infected pacemaker pocket with a bacitracin solution. IM bacitracin is nephrotoxic and may cause renal failure due to renal tubular and glomerular necrosis. Albuminuria, hematuria, cylindruria, and rising blood concentrations of the drug may occur initially, followed eventually by oliguria, azotemia, and renal failure. Infants are much less prone to this toxicity than are older children and adults, and substantial renal toxicity usually does not occur in infants. Nephrotoxicity may also occur after local application over the site of abdominal operations or after instillation into infected cavities. Zinc bacitracin was negative in in vitro tests for chromosomal aberrations in human peripheral lymphocytes. ANIMAL STUDIES: In two studies, rats received feed-grade and/or pure zinc bacitracin by gavage at doss of 0, 36, 72, 144, 250, 500, and 1000 mg/kg bw/day for 28 days (range-finding study), or 0, 11, 34,150, 250, and 500 mg/kg bw/day for 13 weeks. In these studies the most relevant effects were post-dosing salivation, loose feces, decreased food utilization and (13-week study only) minor pathological changes in the stomach. In the 13-week study post-dosing salivation (brown facial staining) was observed at all dose levels, as well as over-excitation in females from all treated groups. In a 1-year study, rats received feed-grade zinc bacitracin in their diet at doses equivalent to 0, 1, 10, and 50 mg/kg bw/day. The rats that were not sacrificed received control feed and their fertility and reproduction was examined. No toxic effects were observed up to the highest dose tested. There were no signs of nephrotoxicity, which is known to occur after systemic administration of bacitracin. Compared to controls, there was no increase in neoplasms, and the ability to reproduce was not adversely affected. In a teratogenicity study, rats received feed-grade and/or pure zinc bacitracin by gavage at dose levels of 0, 11, 34, 150, 250 and 500 mg/kg bw on days 7 to 17 of pregnancy. Zinc bacitracin had no adverse effects on embryo-fetal development, and did not produce irreversible structural malformation up to the highest dose tested. In dams, post-dosing salivation, soft feces, increased water intake, and slightly decreased body weight gain were noted. Zinc bacitracin was negative in in vitro tests for gene mutations in Salmonella typhimurium, gene mutations, in mouse lymphoma cells and in in vivo tests for chromosomal aberrations in rate bone marrow cells, unscheduled DNA synthesis in rat spleen cells. ECOTOXICITY STUDIES: Referenced to control soil, nitrification was accelerated in soil exposed to 100 mg/kg zinc bacitracin.
生態毒性抜粋/OTHER TERRESTRIAL SPECIES/ A field experiment was initiated whereby a series of replicated plots received annual applications of ivermectin, monensin, and zinc bacitracin, either singly or in a mixture. Pharmaceuticals were added at concentrations of 0.1 mg/kg soil or 10 mg/kg soil. The authors collected soil samples in 2013, before and after the fourth annual application of pharmaceuticals. In addition, a 30-day laboratory experiment was undertaken with the same soil and same pharmaceuticals, but at concentrations of 100 mg/kg soil. The impact of the pharmaceuticals on nitrification rates, on the abundance of ammonia-oxidizing bacteria (AOB), and on the abundance of ammonia-oxidizing archaea (AOA) was assessed. None of the pharmaceuticals at 0.1 mg/kg had any effect on nitrification. Referenced to control soil, nitrification was accelerated in soil exposed to 100 mg/kg zinc bacitracin or 10 mg/kg of the pharmaceutical mixture, but none of the treatments inhibited nitrification. Neither AOB abundance nor AOA abundance was affected by the pharmaceuticals at 0.1 mg/kg. At 10 mg/kg, monensin, zinc bacitracin, and a mixture of all 3 pharmaceuticals suppressed the abundance of AOB, and zinc bacitracin and the mixture increased AOA abundance. The decrease in AOB abundance and increase in AOA abundance when exposed to 10 mg/kg soil suggests that AOB are more sensitive to these chemicals and that AOA populations can expand to occupy the partially vacated niche. /Zinc bacitracin/
Soil Adsorption/MobilityBacitracin is a high molecular weight, ionic peptide that may exist as a dipolar molecule. In acid solution it can be cationic and under basic conditions it can exist as an anion(1). Bacitracin has been shown to be unstable in the presence of alkaline clays(1). Low values of adsorption of bacitracin by vermiculite and illite have been attributed to the anionic behavior resulting from the clay alkalinity at pH range of 7.9-8.2(1). The estimated pKa values for bacitracin range from 3.19 to 13.26(2).
Natural Pollution SourcesAntibiotic polypeptide complex produced by Bacillus subtilis and B. licheniformismixture of at least nine bacitracins of which bacitracin A is the major component
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ Topical medicaments are a common cause of allergic contact dermatitis. This study will evaluate the prevalence of contact allergy to a wide array of topical medicaments at the Ottawa Patch Test Clinic. The objectives of this study are to report the results of positive patch testing to topical medicaments at the Ottawa Patch Test Clinic and identify common sensitizers in topical medicaments. Patients were tested with the standard North American Contact Dermatitis screening series of 70 allergens plus supplementary allergens when indicated. A retrospective chart review of patients positive to topical medicaments between January 1, 2000, and September 30, 2010, was undertaken. The average age of patients was 49.5 years. Thirty-four percent were atopic. Common sensitizers included topical antibiotics (58%), steroids (30%), anesthetics (6%), and antifungals (6%). Patch testing showed that 61% of patients tested positive to antibiotics, 21% to topical steroids, 17% tested positive to topical anesthetics, and 1% tested positive to topical antifungals. The most common reactions were to bacitracin (44%) and neomycin (29%). The most common steroid screener was tixocortol-17-pivalate (group A) (19%), and the most common local anesthetic was lidocaine (12%)./HUMAN EXPOSURE STUDIES/ We report the results of patch testing 85 patients with either long-standing venous ulceration or eczema complicating their leg ulcers. As previously reported, lanolin and its derivatives and topical antibiotics were the most frequent sensitizers. However, unlike previously published data, we found bacitracin to be the most potent sensitizer of all topical antibiotics tested. There were no positive reactions in a control group of patients, although we were unable to repeat the patch tests in patients with a positive reaction to bacitracin. In the past 10 years, our department has used a proprietary mixture of polymyxin and bacitracin in treating infected leg ulcers and other dermatoses. It is therefore possible that chronic usage of topical bacitracin on leg ulcers carries a significant risk of contact sensitization./SIGNS AND SYMPTOMS/ When administered by intramuscular injection, bacitracin can be nephrotoxic. Nephrotoxicity may also occur after local application over the site of abdominal operations or after instillation into infected cavities. Local application of bacitracin has been associated with severe allergic disorders./SIGNS AND SYMPTOMS/ IM bacitracin is nephrotoxic and may cause renal failure due to renal tubular and glomerular necrosis. Albuminuria, hematuria, cylindruria, and rising blood concentrations of the drug may occur initially, followed eventually by oliguria, azotemia, and renal failure. Infants are much less prone to this toxicity than are older children and adults, and substantial renal toxicity usually does not occur in infants.For more Human Toxicity Excerpts (Complete) data for BACITRACIN (17 total), please visit the HSDB record page.
Artificial Pollution SourcesBacitracin's administration and use as an antibiotic(1) may result in its release to the environment through various waste streams(SRC). Its use as an animal feed supplement for growth promotion(1,2) will result in its direct release to the environment(SRC). Bacitracin can be released to the environment from bathing, washing, laundering following dermal application of formulations containing bacitracin. Disposal of unused medicine by flushing into sewers is a secondary route of environmental release(3).
Environmental BiodegradationAEROBIC: Bacitracin, present as the zinc salt at 62.8 units/mg and mixed with chicken feces, was 77% biodegraded in 30 days at 4 °C and 67% biodegraded at 20 °C, using a sandy loam soil (pH 6.0-6.3clay 16.3%sand 60.0%silt 27.3%) incubated at 35 °C(1). The soil had no prior history of agricultural use. The half-lives of bacitracin in soil were reported as 22.5 and 12 days at 20 and 30 °C, respectively(1-4). Bacitracin-zinc, present at 25 ug/g was 90% degraded (half-life 2 days), when incubated in poultry manure. It was 100 % degraded (half-life of 7 days), when incubated in manure plus soil(3). /Bacitracin-zinc/PURE CULTURE: A Pseudomonid was isolated from a soil-poultry feces mixture that was capable of degrading bacitracin(1).
Drug Induced Liver InjuryDrug Induced Liver Injury Rank (DILIrank 2.0)BacitracinvNo-DILI-concernNo matchDOI:10.1016/j.drudis.2016.02.015
F21
水環境危害等級(WGK)2
TSCA 収載状態TSCA listed
RTECS 番号CP0175000
毒性LD50 oral in guinea pig: 2gm/kg
税関コード29419090
危険文句(R)20/21/22
危険表示Xn
安全措置(S)22-24/25-45-36
貯蔵分類11 - Combustible Solids
有害物質データ1405-87-4(Hazardous Substances Data)

用途

解説

バシトラシンA,バシトラシンエー.Bacillus subtilis var Tracyなどの生産する環状ペプチド系抗生物質の主成分.白色または淡灰色の粉末.[α]D25"+5°(0.02 mol L-1 塩酸).λmax 252 nm(水).水,エタノールに可溶.細菌の細胞壁合成系に作用する.グラム陽性菌およびナイセリアの発育を阻止する.感染性口内炎治療薬に用いられる.LD50 190 mg/kg(ラット,静注).

用途

細胞同定用ディスク及び培地添加用。

用途

ペプチド系抗生物質です。細 菌の細胞壁ペプチドグリカン生合成系を阻害 することで、抗菌作用を示します。ほとん どはバシトラシン A ですが、バシトラシン A,B,C,D,E など少なくとも 9 種以上の混合物 です。

説明

Bacitracin is a mixture of similar peptides produced by fermentation of the bacterium Bacillus subtil is. The A-type component predominates. Its mode of action is to inhibit both peptidoglycan biosynthesis at a late stage (probably at the dephosphorylation of the phospholipid carrier step) and disruptions of plasma membrane function.

使用

Bacitracin is a peptide antibiotic effective against gram-postive bacteria. Bacitracin is an inhibitor of peptidoglycan synthesis. Bacitracin disrupts bacterial cell wall synthesis by inhibiting depho sphorylation of lipid pyrophosphate. Bacitracin also strongly inhibits proline endopeptidase from human muscle.

使用用途

バシトラシンは、主としてグラム陽性細菌に対し強い抗菌作用を示すため、医薬品として用いられます。細菌の細胞壁の形成を阻害し、DNAを酸化切断することで殺菌作用を示します。作用時間が短く、1日数回の局所投与が必要です。 バシトラシンは筋肉内に投与すると腎毒性を示し、腎不全を引き起こす可能性があります。また、経口摂取でも強い毒性を示すことから、傷口などに局所的に用いるトローチや軟膏などの剤形で利用されます。

製法・合成法

純化方法

Bacitracin has been purified by carrier displacement using n-heptanol, n-octanol and n-nonanol as carriers and 50% EtOH in 0.1 N HCl. The pure material gives one spot with RF ~0.5 on paper chromatography using AcOH:n-BuOH:H2O (4:1:5). [Porath Acta Chem Scand 6 1237 1952.] It has also been purified by ion-exchange chromatography. It is a white powder soluble in H2O and EtOH but insoluble in Et2O, CHCl3 and Me2CO. It is stable in acidic solution but unstable in base. It is a strong antibacterial. [Abraham & Bewton Biochem J 47 257 1950, Synthesis: Munekata et al. Bull Chem Soc Jpn 46 3187, 3835 1973, Beilstein 27 III/IV 5746.]