Bacitracin

Title: Bacitracin
CAS Registry Number: 1405-87-4
Trademarks: Ak-Tracin (Akorn); Baciim (Pharma-Tek); Fortracin (CPC); Ocu-Tracin (Ocumed)
Literature References: Antibiotic polypeptide complex produced by Bacillus subtilis and B. licheniformis; mixture of at least nine bacitracins of which bacitracin A is the major component. Isoln: Johnson et al., Science 102, 376 (1945); Anker et al., J. Bacteriol. 55, 249 (1948). Purification of bacitracin by carrier displacement method: Porath, Acta Chem. Scand. 6, 1237 (1952). Purification with ion exchange resin: Chaiet, Cochrane, US 2915432 (1959 to Merck & Co.). Production: Johnson, Meleney, US 2498165 (1950 to the U.S. Secy. of War); Freaney, Allen, US 2828246 (1958 to Commercial Solvents). Solubilities: Weiss et al., Antibiot. Chemother. 7, 374 (1957). Preliminary structure studies: Hausmann et al., J. Am. Chem. Soc. 77, 723 (1955); Lockhart et al., Biochem. J. 61, 534 (1955); Stoffel, Craig, J. Am. Chem. Soc. 83, 145 (1961). Structure of bacitracin A: Ressler, Kashelikar, ibid. 88, 2025 (1966); Galardy et al., Biochemistry 10, 2429 (1971). Synthetic studies: Munekata et al., Bull. Chem. Soc. Jpn. 46, 3187, 3835 (1973). Mechanism of action: Storm, Ann. N.Y. Acad. Sci. 235, 387 (1974). Comprehensive description: G. A. Brewen, Anal. Profiles Drug Subs. 9, 1-69 (1980). Reviews: Craig et al., "Bacitracin" in G. E. W. Wolstenholme, C. M. O'Connor, Ciba Foundation Symposium on Amino Acids and Peptides with Antimetabolic Activity (Little, Brown, Boston, 1958) pp 226-246; E. D. Weinberg in Antibiotics, D. Gottlieb, P. D. Shaw, Eds. (Springer-Verlag, New York, 1967) I, pp 90-99; II, pp 240-245; D. R. Storm, W. A. Toscano, Jr. in Antibiotics vol. 5, pt. 1, F. E. Hahn, Ed. (Springer-Verlag, New York, 1979) pp 1-17.
Properties: Grayish-white powder. Very bitter taste. Sol in water, alcohol. Practically insol in ether, chloroform, acetone. Stable in acid soln; unstable in alkaline solns. Potency loss probably due to transformation of bacitracin A to bacitracin F, latter having little antimicrobial activity.
Therap-Cat: Antibacterial.
Therap-Cat-Vet: Antibacterial.
Keywords: Antibacterial (Antibiotics); Polypeptides.
Bacitracin Methylenedisalicylate Bacitracin Zinc Baclofen Bactericidal Permeability-Increasing Protein Bacteriorhodopsin

Bacitracin
Systematic (IUPAC) name
(4R)-4-[(2S)-2-({2-[(1S)-1-amino-2-methylbutyl]- 4,5-dihydro-1,3-thiazol-5-yl}formamido)-4-methylpentanamido]-4-{[(1S)- 1-{[(3S,6R,9S,12R,15S,18R,21S)- 18-(3-aminopropyl)-12-benzyl-15-(butan-2-yl)-3-(carbamoylmethyl)- 6-(carboxymethyl)-9-(1H-imidazol-5-ylmethyl)-2,5,8,11,14,17,20- heptaoxo-1,4,7,10,13,16,19-heptaazacyclopentacosan-21-yl]carbamoyl}- 2-methylbutyl]carbamoyl}butanoic acid
Clinical data
Trade names Baciim
AHFS/Drugs.com monograph
Legal status OTC/℞-only
Routes Topical, intramuscular
Identifiers
CAS number 1405-87-4 YesY
ATC code D06AX05 J01XX10 R02AB04 QA07AA93
PubChem CID 439542
DrugBank DB00626
ChemSpider 10481985 YesY
UNII 58H6RWO52I YesY
KEGG D00128 N
ChEMBL CHEMBL1200558 N
Chemical data
Formula C66H103N17O16S 
Mol. mass 1422.69 g/mol
 N (what is this?)  (verify)

Bacitracin is a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy, first isolated in 1945. These peptides disrupt both gram positive and gram negative bacteria by interfering with cell wall and peptidoglycan synthesis.

Bacitracin is used as a topical preparation (since it is toxic and has poor oral bioavailability). In terms of adverse reactions only, in comparison with bacitracin, white petrolatum possesses an equally low infection rate and minimal risk for induction of allergy.[1]

The widespread use of bacitracin, even for minor wounds where it is not useful, contributes to antibiotic resistance.[2][3] This widespread use has contributed to the emergence of MRSA bacteria,[4] specifically the highly lethal ST8:USA300 strain.[5]