Bacitracin A

Base Information

• Chemical Name: Bacitracin A
• CAS No.: 1405-87-4
• Deprecated CAS: 12640-37-8,1405-75-0,60454-67-3
• Molecular Formula: C66H103N17O16S
• Molecular Weight: 1422.69
• Hs Code.: 29419090
• European Community (EC) Number: 245-115-9
• UNII: DDA3RRX0P7
• Nikkaji Number: J286.255G
• Wikidata: Q424319
• NCI Thesaurus Code: C76238
• RXCUI: 1291
• Metabolomics Workbench ID: 42952
• ChEMBL ID: CHEMBL1200558
• Mol file: 1405-87-4.mol

Synonyms:bacitracin A

Chemical Property of Bacitracin A

Chemical Property:

• Appearance/Colour: white to almost white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 221-225 °C
• Refractive Index: 1.655
• Boiling Point: 1750.1 °C at 760 mmHg
• Flash Point: 1012.2 °C
• PSA: 556.17000
• Density: 1.43 g/cm³
• LogP: 3.72410
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL, clear to very slightly hazy, deep yellow
• Water Solubility.: soluble
• XLogP3: -4.1
• Hydrogen Bond Donor Count: 17
• Hydrogen Bond Acceptor Count: 21
• Rotatable Bond Count: 31
• Exact Mass: 1421.74894144
• Heavy Atom Count: 100
• Complexity: 2850

Purity/Quality:

98%min ^*data from raw suppliers

Bacitracin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 20/21/22
• Safety Statements: 22-24/25-45-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC(C)C1C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NCCCCC(C(=O)NC(C(=O)N1)CCCN)NC(=O)C(C(C)CC)NC(=O)C(CCC(=O)O)NC(=O)C(CC(C)C)NC(=O)C2CSC(=N2)C(C(C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
• Isomeric SMILES: CC[C@H](C)[C@H]1C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)NCCCC[C@@H](C(=O)N[C@@H](C(=O)N1)CCCN)NC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](CCC(=O)O)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H]2CSC(=N2)[C@H]([C@@H](C)CC)N)CC(=O)N)CC(=O)O)CC3=CN=CN3)CC4=CC=CC=C4
• Description: 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.
• Uses: Polypeptide antibacterial. 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. antibiotic agent effective against gram-positive organisms and spirochetes; in products for topieal treatment, ear medications and ophthalmie drugs
• Indications: This polypeptide antibiotic, which is produced from Bacillus subtilis, interferes with bacterial cell wall growth and is bactericidal against many grampositive organisms such as streptococci, staphylococci, and pneumococci but is inactive against most gram-negative organisms. All anaerobic cocci, Neisseria, and the tetanus and diphtheria bacilli are also sensitive to bacitracin. Resistance is rare, but some staphylococcal strains are inherently resistant. Hypersensitivity reactions are uncommon. Bacitracin is stable in petrolatum (but not water-miscible preparations) and is available as an ointment or as a component of antibiotic mixtures. Sensitization to bacitracin has been reported more recently, particularly in patients with leg ulcers.
• Therapeutic Function: Antibacterial
• Clinical Use: Bacitracin is mainly used topically for the treatment of skin, eye and ear infections, and the prevention of wound infections. It is especially employed for minor skin injuries, such as cuts, scrapes, or burns. Although it has been in use for almost half a century, it has only quite recently been recognized as a potent sensitizer, with occasional anaphylaxis. Thus, bacitracin should be used with caution. The value of bacitracin in the prevention of wound infections following clean surgical procedures is doubtful. A randomized, doubleblind study that evaluated approximately 1200 surgical wounds and compared bacitracin with white petrolatum for postoperative dressings demonstrated petrolatum to be equally as effective for postoperative wound care as bacitracin. The important advantage of white petrolatum over bacitracin was that its application led to a significantly lower rate of contact allergy. Other studies that have compared topical antimicrobial agents for use on clean surgical wounds have confirmed that such protocols do not improve healing or reduce the infection rate. Bacitracin is predominantly active against Gram-positive microorganisms, and parenteral use is limited to IM injection for infants with pneumonia and empyema caused by staphylococci resistant to other agents. It is rather neuro- and nephrotoxic and, therefore, is used in this manner with caution. Bacitracin also is widely employed topically to prevent infection in minor cuts, scrapes, and burns.