Bacitracin

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Bacitracin

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Catalog Number	PR1405874
CAS	1405-87-4
Description	Bacitracin is a combination of at least 9 bacitracins. 60-80% of commercially prepared bacitracin is bacitracin A.
IUPAC Name	(4S)-4-[[(2S)-2-[[(4R)-2-[(1R,2R)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2R,3S)-1-[[(3R,6R,9R,12R,15R,18R,21R)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2R)-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
Molecular Weight	1421.68
Molecular Formula	C66H102N17O16S
InChI	CLKOFPXJLQSYAH-YBVXDRQKSA-N
InChI Key	InChI=1S/C66H103N17O16S/c1-9-35(6)52(69)66-81-48(32-100-66)63(97)76-43(26-34(4)5)59(93)74-42(22-23-50(85)86)58(92)83-53(36(7)10-2)64(98)75-40-20-15-16-25-71-55(89)46(29-49(68)84)78-62(96)47(30-51(87)88)79-61(95)45(28-39-31-70-33-72-39)77-60(94)44(27-38-18-13-12-14-19-38)80-65(99)54(37(8)11-3)82-57(91)41(21-17-24-67)73-56(40)90/h12-14,18-19,31,33-37,40-48,52-54H,9-11,15-17,20-30,32,67,69H2,1-8H3,(H2,68,84)(H,70,72)(H,71,89)(H,73,90)(H,74,93)(H,75,98)(H,76,97)(H,77,94)(H,78,96)(H,79,95)(H,80,99)(H,82,91)(H,83,92)(H,85,86)(H,87,88)/t35-,36+,37-,40-,41-,42+,43+,44-,45-,46-,47-,48+,52-,53-,54-/m1/s1
Drug Categories	Acids, Carbocyclic; Amino Acids, Peptides, and Proteins; Anti-Bacterial Agents; Anti-Infective Agents; Anti-Infective Agents, Local; Antibacterials for Systemic Use; Antibiotics for Topical Use; Antiinfectives for Systemic Use; Bacitracins; Benzene Derivatives; Benzoates; Decreased Cell Wall Synthesis & Repair; Dermatologicals; Hydroxy Acids; Hydroxybenzoates; Nephrotoxic agents; Ophthalmologicals; Peptides; Peptides, Cyclic; Phenols; Sensory Organs; Throat Preparations
Drug Interactions	Abacavir-Bacitracin may decrease the excretion rate of Abacavir which could result in a higher serum level. Aceclofenac-The risk or severity of nephrotoxicity can be increased when Bacitracin is combined with Aceclofenac. Acemetacin-The risk or severity of nephrotoxicity can be increased when Bacitracin is combined with Acemetacin. Acenocoumarol-The risk or severity of bleeding can be increased when Bacitracin is combined with Acenocoumarol. Acetaminophen-Bacitracin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
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
Standard	BP
Type	Small Molecule
Therapeutic Category	Ophthalmic Agents

Pharmacology

Indications

Bacitracin is primarily indicated for use in topical formulations to treat acute and chronic localized skin infections. In some cases, it is also administered intramuscularly, specifically for infantile streptococcal pneumonia and empyema. In over-the-counter formulations, bacitracin is often combined with neomycin and polymyxin B as an ointment. An additional formulation includes hydrocortisone, making it suitable for treating corticosteroid-responsive dermatoses with secondary infections.

Pharmacodynamics

Bacitracin consists of a mixture of polypeptides that impede bacterial cell wall synthesis and function by oxidatively cleaving DNA. Its therapeutic action is short-lived, necessitating topical administration every three to four hours. Notably, when bacitracin is administered intramuscularly, it exhibits nephrotoxicity, which can potentially lead to renal failure.

Absorption

When applied in topical, ophthalmic, or oral formulations, bacitracin demonstrates poor systemic absorption. However, when administered via intramuscular injection, bacitracin is completely and readily absorbed into the system.

Metabolism

The specifics of bacitracin metabolism in humans are not thoroughly documented. Given that bacitracin is a protein, it is anticipated to undergo metabolism into smaller polypeptides and amino acids. Nevertheless, the unique structure of bacitracin may confer some degree of protection against proteolytic enzymes.

Mechanism of Action

Bacitracin functions by interacting with divalent metal ions, including manganese (Mn), cobalt (Co), nickel (Ni), copper (Cu), or zinc (Zn), forming complexes that are pivotal in its mechanism of action. These complexes specifically target and bind to C55-isoprenyl pyrophosphate, thereby inhibiting the hydrolysis of lipid dolichol pyrophosphate. This action effectively disrupts the synthesis of the bacterial cell wall, impeding bacterial growth and proliferation. Moreover, the bacitracin-metal ion complexes have the ability to bind to DNA, leading to its oxidative cleavage, which further contributes to its antibacterial efficacy.

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