Bacitracin
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Bacitracin
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| 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 | |
| Identifiers | |
| CAS number | |
| ATC code | D06 R02 QA07 |
| PubChem | |
| DrugBank | |
| ChemSpider | |
| Chemical data | |
| Formula | C66H103N17O16S |
| Mol. mass | 1422.69 g/mol |
| SMILES | & |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status |
OTC/℞-only |
| Routes | Topical, intramuscular |
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.
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[edit] 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.
[edit] Synthesis
Bacitracin is synthesised via the so-called nonribosomal peptide synthetases (NRPSs), which means that ribosomes are not involved in its synthesis.
[edit] 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 [2].
[edit] 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."[3]
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.[4]
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.[5]
It was voted Allergen of the Year in 2003 by the American Contact Dermatitis Society.
[edit] References
- ^ 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.
- ^ Mechanism of Action of Bacitracin: Complexation with Metal Ion and C55-Isoprenyl Pyrophosphate K. John Stone and Jack L. Strominger
- ^ Antibiotic use on the farm hurts people—and doesn’t help the bottom line. Discover Magazine. Accessed on September 16, 2007.
- ^ Tattoo Aftercare Contradictions
- ^ "Streptococci". http://pathmicro.med.sc.edu/fox/streptococci.htm. Retrieved on 2008-11-07.
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