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:
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99%, *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
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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.
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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
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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.
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Therapeutic Function
Antibacterial
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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.
