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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-{[(1 S)- 1-{[(3S,6R,9S,12R,15S,18 R,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
Identifiers
CAS number 1405-87-4
ATC code D06AX05 J01XX10 R02AB04 QA07AA93
PubChem 439542
DrugBank APRD00816
ChemSpider 10481985
Chemical data
Formula C 66H103N17O16S 
Mol. mass 1422.69 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status OTC/℞-only
Routes Topical, intramuscular
 Yes check.svgY(what is this?)  (verify)
A tube of bacitracin ointment for eyes

Bacitracin is a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy, isolation of which was first reported in 1945.

As a toxic and difficult-to-use antibiotic, bacitracin doesn't work well orally. However, it is very effective topically. Its action is on gram positive cell walls.

Contents

History

The drug's unique name derives from the fact that it was isolated by John T. Goorley from a girl named Tracy:

One strain isolated from tissue debrided from a compound fracture of the tibia was particularly active. We named this growth-antagonistic strain for the patient, "Tracy I." When cell-free filtrates of broth cultures of this bacillus proved to possess strong antibiotic activity and to be non-toxic, further study seemed warranted. We have called this active principle "Bacitracin."[1]

It was approved by FDA in 1948.

Synthesis

Bacitracin is synthesised via the so-called nonribosomal peptide synthetases (NRPSs), which means that ribosomes are not involved in its synthesis.

bacABC is involved in synthesis.[2]

Mechanism of action

Bacitracin interferes with the dephosphorylation of the C55-isoprenyl pyrophosphate, a molecule which carries the building blocks of the peptidoglycan bacterial cell wall outside of the inner membrane [3].

Bacitracin is a protein disulfide isomerase inhibitor.[4]

Clinical use

Bacitracin is used in human medicine as a polypeptide antibiotic and is "approved by the U.S. Food and Drug Administration (FDA) for use in chickens and turkeys."[5]

As bacitracin zinc salt, and in combination with other topical antibiotics (usually polymyxin B and neomycin), it is used in ointment form for topical treatment of a variety of localized skin and eye infections, as well as for the prevention of wound infections. In the United States a popular brand name Neosporin contains Bacitracin as one of its antibiotic agents along with Neomycin and Polymyxin B. Bacitracin can also be bought in pure form for those with allergies.

It is also commonly used as an aftercare antibiotic on tattoos. It is preferred over Neosporin because of its fewer ingredients, which lowers chances of an allergic reaction.[6]

In infants, it is sometimes administered intramuscularly for the treatment of pneumonias, but in most cases, it has been replaced by other antibiotics. This formulation is sold under the brand name Baciim.

Clinical note: This is a good alternative to silver sulfadiazine (Silvadene) for burn patients with a sulfa allergy.

Bacitracin can be used to distinguish Streptococcus pyogenes from Streptococcus agalactiae,[7] with S. pyogenes being sensitive and S. agalactiae being resistant to bacitracin.

It was voted Allergen of the Year in 2003 by the American Contact Dermatitis Society.

References

  1. ^ Johnson B, Anker H, Meleney F (1945). "Bacitracin: a new antibiotic produced by a member of the B. subtilis group".Science 102 (2650): 376–377.
  2. ^ Murphy, T.; Roy, I.; Harrop, A.; Dixon, K.; Keshavarz, T. (2007). "Effect of oligosaccharide elicitors on bacitracin a production and evidence of transcriptional level control". Journal of biotechnology 131 (4): 397–403. doi:10.1016/j.jbiotec.2007.07.943. PMID 17825450.   edit
  3. ^ Mechanism of Action of Bacitracin: Complexation with Metal Ion and C55-Isoprenyl Pyrophosphate K. John Stone and Jack L. Strominger
  4. ^ Weston, B.; Wahab, N.; Roberts, T.; Mason, R. (2001). "Bacitracin inhibits fibronectin matrix assembly by mesangial cells in high glucose". Kidney international 60 (5): 1756–1764. doi:10.1046/j.1523-1755.2001.00991.x. PMID 11703593.   edit
  5. ^ Antibiotic use on the farm hurts people—and doesn’t help the bottom line. Discover Magazine. Accessed on September 16, 2007.
  6. ^ Tattoo Aftercare Contradictions
  7. ^ "Streptococci". http://pathmicro.med.sc.edu/fox/streptococci.htm. Retrieved 2008-11-07.  







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