기본 정보
- 표준 SMILES
CC[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- InChIKey
CLKOFPXJLQSYAH-ABRJDSQDSA-N- 분자식
- C66H103N17O16S
- 평균 분자량
- 1,422.7 g/mol
개요
Bacitracin A is a homodetic cyclic peptide consisting of (4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carboxylic acid attached head-to-tail to L-leucyl,D-glutamyl, L-lysyl, D-ornityl, L-isoleucyl, D-phenylalanyl, L-histidyl. D-aspartyl and L-asparaginyl residues coupled in sequence and cyclised by condensation of the side-chain amino group of the L-lysyl residue with the C-terminal carboxylic acid group. It is the major component of bacitracin. It has a role as an antimicrobial agent and an antibacterial agent. It is a polypeptide and a homodetic cyclic peptide.
이름 및 식별자
- 우선 이름
- Bacitracin
- IUPAC
- (4R)-4-[[(2S)-2-[[(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2S,3S)-1-[[(3S,6R,9S,12R,15S,18R,21S)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-6-(carboxymethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclopentacos-21-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid
이름 및 동의어
이름 더 보기
데이터베이스 식별자
- CAS
1405-87-4、22601-59-8- PubChem CID
- 10909430
- ChEMBL
CHEMBL1200558、CHEMBL1790520- ChEBI
CHEBI:35862- UNII
- DDA3RRX0P7
- EC Number
- 215-786-2、245-115-9
물성
구조 계산 물성
- XLogP
- -4.1
- 극성 표면적
- 556 Ų
- 수소 결합 공여자 수
- 17
- 수소 결합 수용자 수
- 21
- 회전 가능 결합 수
- 31
- 무거운 원자 수
- 100
- 형식 전하
- 0
- 복잡도
- 2,850
실험 및 물리화학적 성질
Color/Form
White to pale buff powder
Grayish-white powder
Solubility
Freely soluble
White 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 water
Soluble in methanol, alcohol, glacial acetic acid; practically insoluble in acetone, chloroform, ether
2.45e-02 g/L
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-Infective Agents, Local; Antibacterial Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal Drugs
FDA approved animal drugs -> Active ingredient
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
안전 및 규제
GHS 분류
GHS Classification
This chemical does not meet GHS hazard criteria for 10.8% (4 of 37) of reports.
Warning
H315 (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
유해성 정보
FDA Requirements
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.
Hazard Classes and Categories
Skin Irrit. 2 (10.8%)
Not Classified
안전 및 보호
Fire Fighting Procedures
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.
Storage Conditions
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.
Cleanup Methods
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.
Disposal Methods
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 Measures
Appropriate 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.
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.
독성 정보
Interactions
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 Symptoms
Selected 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.
Environmental Fate
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).
Toxicity Summary
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 (CDAD; also 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 topically; however, 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.
Ecotoxicity Excerpts
/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/Mobility
Bacitracin 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).
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 Sources
Bacitracin'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 Biodegradation
AEROBIC: 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 6.0-6.3; clay 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 Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Bacitracin
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
규제 정보
FDA Requirements
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.
화학 및 산업
약리 정보
ATC Code
R - Respiratory system
D - Dermatologicals
J - Antiinfectives for systemic use
S - Sensory organs
QA - Alimentary tract and metabolism
QD - Dermatologicals
Pharmacodynamics
Bacitracin is a mixture of polypeptides that prevent the formation of the bacterial cell wall and oxidatively cleave DNA. It has a short duration of action as it must be given every 3 to 4 hours topically. Bacitracin is nephrotoxic when given intramuscularly and may lead to renal failure.
Mechanism of Action
Bacitracin binds to a divalent metal ion such as Mn(II), Co(II), Ni(II), Cu(II), or Zn(II). These complexes bind C<sub>55</sub>-isoprenyl pyrophosphate, preventing the hydrolysis of a lipid dolichol pyrophosphate, which finally inhibits cell wall synthesis. Bacitracin metal complexes also bind and oxidatively cleave DNA.
Bacitracin interferes with bacterial cell wall synthesis by blocking the function of the lipid carrier molecule that transfers cell wall subunits across the cell membrane. It is active against many gram positive bacteria including staphylococci, streptococci (particularly group A streptococci), corynebacteria, and clostridia. It is also active against Actinomyces, Treponema pallidum and some gram negative species such as Neisseria and Haemophilus influenzae, although most Gram-negative organisms are resistant. .
Bacitracin may be bactericidal or bacteriostatic in action, depending on the concentration of the drug attained at the site of infection and the susceptibility of the infecting organism. Bacitracin inhibits bacterial cell wall synthesis by preventing the incorporation of amino acids and nucleotides into the cell wall. The drug probably interferes with the final dephosphorylation step in the phospholipid carrier cycle and in this manner bacitracin prevents the transfer of the mucopeptide to the growing cell wall. Bacitracin also damages the bacterial plasma membrane and is active against protoplasts.
Bacitracin is a polypeptide antibiotic active against Gram-positive bacterial strains. Its mechanism of action postulates disturbing the cell wall synthesis by inhibiting dephosphorylation of the lipid carrier. We have discovered that bacitracin induces degradation of nucleic acids, being particularly active against RNA. In the examination of the nucleolytic activity of bacitracin several model RNA and DNA oligomers were used. The oligomers were labeled at their 5' ends with (32)P radioisotope and following treatment with bacitracin the cleavage sites and efficiency were determined. Bacitracin induces degradation of RNA at guanosine residues, preferentially in single-stranded RNA regions. Bacitracin is also able to degrade DNA to some extent but comparable effects to those observed with RNA require its 10-fold higher concentration. The sites of degradation in DNA are very infrequent and preferentially occur near cytidine residues. Free radicals are not involved in the reaction, and which probably proceeds via a hydrolytic mechanism. The phosphate groups at the cleavage sites are present at the 3' ends of RNA products and at the 5' ends of DNA fragments. Importantly, the presence of EDTA does not influence RNA degradation but completely inhibits the degradation of DNA. For DNA degradation divalent metal ions like Mg(2+), Mn(2+) or Zn(2+) are absolutely necessary. The ability of bacitracin to degrade nucleic acids via a hydrolytic mechanism was a surprising observation, and it is of interest whether these properties can contribute to its mechanisms of action during antibiotic treatment.
Biological Half-Life
Data regarding the half life of bacitracin in humans is not readily available.
The half-life of bacitracin in serum was 1.5 hr ... .
Metabolism/Metabolites
Data regarding the metabolism of bacitracin in humans is not readily available. Because bacitracin is a protein it is expected to be metabolized into smaller polypeptides and amino acids. However, the structure of bacitracin may afford it some protection from the action of proteases.
Bacitracin is metabolized to amino acids and smaller peptides via the main metabolite desamidobacitracin, which is microbiologically inactive. Main metabolites in feces are bacitracin A, B1, B2, F, desamidobacitracin and catabolic peptides. In urine and bile only hydrolytic cleavage products (di- and tripeptides) are present.
FDA Pharmacological Classification
58H6RWO52I
BACITRACIN
Physiologic Effects [PE] - Decreased Cell Wall Synthesis & Repair
The physiologic effect of bacitracin is by means of Decreased Cell Wall Synthesis & Repair.
BACITRACIN
Decreased Cell Wall Synthesis & Repair [PE]
MeSH Pharmacological Classification
Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects.
Substances that inhibit the growth or reproduction of BACTERIA.
Absorption, Distribution and Excretion
Topical, ophthalmic, and oral formulations of bacitracin are poorly absorbed systemically. Intramuscular bacitracin is readily and completely absorbed.
Bacitracin is mainly excreted renally with 87% of and intramuscular dose being recovered in the urine after 6 hours.
Data regarding the volume of distribution of bacitracin in humans is not readily available.
Data regarding the clearance of bacitracin in humans has not been well studied. A study of 9 subjects in 1947 shows a renal clearance of 105-283mL/min with an average renal clearance of 159mL/min.
Bacitracin is excreted in feces following oral administration. After IM administration, 10-40% of the dose is excreted slowly by glomerular filtration and appears in the urine within 24 hours. A considerable amount of bacitracin has not been accounted for and is thought to be either retained or destroyed in the body.
/MILK/ It is not known whether bacitracin is distributed into milk.
용도 및 제조
Uses
Bacitracin ... has been incorporated as an additive in feed for various purposes of growth and disease control at a concentration of from 1-100 g/900 kg feed.
... Effective against many gram-positive bacteria, but ineffective against most aerobic gram-negative bacteria.
... Food additive permitted in food for human consumption.
Veterinary: Used locally in wound powders and ointments, dermatologic preparations, eye and ear ointments, and as feed additives in swine and poultry rations for growth promotion /Bacitracins/
For more Uses (Complete) data for BACITRACIN (8 total), please visit the HSDB record page.
Use (kg; approx.) in Germany (2009): >10
Methods of Manufacturing
Antibiotic polypeptide complex produced by Bacillus subtilis and Bacillus licheniformis; mixture of at least nine bacitracins of which bacitracin A is a major component.
Production: Johnson, Meleney, USA patent 2498165 (1950 to the United States Secretary of War); Freaney, Allen, USA patent 2828246 (1958 to Commercial Solvents0.
Formulations/Preparations
Table: Bacitracin Combination Preparations [Table#5964]
Table: Bacitracin Preparations [Table#5965]
Table: Bacitracin Zinc Preparations [Table#5966]
Ophthalmic: Ointment, 500 units/g, Bacitracin Ophthalmic Ointment.
For more Formulations/Preparations (Complete) data for BACITRACIN (13 total), please visit the HSDB record page.
Use Classification
Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
General Manufacturing Information
Bacitracin: ACTIVE
The stability of bacitracin and neomycin in powder and ointment preparations was studied. The ointment preparation exhibited a progressive and gradual incr in spreadability during storage. The content of the powder and ointment bacitracin was acceptable for the first six months, yielding more than 90% of the antibiotic. Neomycin content in both dosage forms decreased after 12 months to less than 90%. The decomposition rate was a first order kinetic rate for both antibiotics. There was no difference in stability between bacitracin and neomycin in both preparations. The expiration date for the products was determined to be 24 mo.
Purification of bacitracin by carrier displacement method; ... purification with ion exchange resin.
As an aid in preventing outbreaks of cecal ... and intestinal ... coccidiosis, and for increased rate of weight gain and improved feed efficiency in broiler chickens /Bacitracin zinc/
관련 반응
연결된 노트
불러오는 중…