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Identification
Name Bacitracin
Accession Number DB00626 (APRD00816)
Type small molecule
Groups approved
Description

Bacitracin is a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy. Its unique name derives from the fact that the bacillus producing it was first isolated in 1943 from a knee scrape from a girl named Margaret Tracy. As a toxic and difficult-to-use antibiotic, bacitracin doesn’t work well orally. However, it is very effective topically.

Bacitracin is synthesised via the so-called nonribosomal peptide synthetases (NRPSs), which means that ribosomes are not involved in its synthesis.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Baciguent
  • Baciim
  • Bacitracin Bacillus licheniformis
Brand name mixtures
  • Antibiotic Ointment (Bacitracin + Polymyxin B (Polymyxin B Sulfate))
  • Aurex Rotenone Drops (Bacitracin + Penicillin + Rotenone + Streptomycin (Streptomycin Sulfate) + Undecylenic Acid)
  • Baciguent Plus Pain Reliever Ont (Bacitracin + Lidocaine)
  • Bacitracin-Neomycin Polymyxin Ont (Bacitracin Zinc + Neomycin Sulfate + Polymyxin B Sulfate)
  • Bacitracin-Neomycin-Polymixin Ont (Bacitracin Zinc + Neomycin Sulfate + Polymyxin B Sulfate)
  • Bacitracin-Neomycin-Polymyxin Oph Ont (Bacitracin Zinc + Neomycin Sulfate + Polymyxin B Sulfate)
  • Band-Aid-S-1 (Bacitracin Zinc + Polymyxin B Sulfate)
  • Emercreme No4 Ont Efa (Bacitracin + Benzocaine + Cetylpyridinium Chloride + Diphenylpyraline Hydrochloride + Tyrothricin)
  • First Aid Antibiotic (Bacitracin Zinc + Polymyxin B Sulfate)
  • First Aid Antibiotic Ointment (Bacitracin Zinc + Polymyxin B Sulfate)
  • Gercillin (Bacitracin + Benzocaine + Polymyxin B Sulfate + Tyrothricin)
  • Lanabiotic Ont (Bacitracin + Polymyxin B Sulfate)
  • Mycitracin Oph Ont (Bacitracin + Neomycin Sulfate + Polymyxin B Sulfate)
  • Neo Bace Ophthalmic Ointment (Bacitracin + Polymyxin B Sulfate)
  • Neosporin Ointment (Bacitracin (Bacitracin Zinc) + Neomycin (Neomycin Sulfate) + Polymyxin B (Polymyxin B Sulfate))
  • Neosporin Ophthalmic Ointment (Bacitracin (Bacitracin Zinc) + Neomycin (Neomycin Sulfate) + Polymyxin B (Polymyxin B Sulfate))
  • Neotopic Ointment (Bacitracin (Bacitracin Zinc) + Neomycin (Neomycin Sulfate) + Polymyxin B (Polymyxin B Sulfate))
  • Ozonol Antibiotic Plus - Ointment (Bacitracin + Lidocaine Hydrochloride + Polymyxin B (Polymyxin B Sulfate))
  • Ozonol Antibiotic Plus Ont (Bacitracin + Lidocaine Hydrochloride + Polymyxin B Sulfate)
  • Polycidin Ophthalmic Ointment (Bacitracin (Bacitracin Zinc) + Polymyxin B (Polymyxin B Sulfate))
  • Polyderm Antibiotic Ointment (Bacitracin + Lidocaine Hydrochloride + Polymyxin B Sulfate)
  • Polysporin Antibiotic Ointment (Bacitracin + Polymyxin B (Polymyxin B Sulfate))
  • Polysporin Sterile Ophthalmic Ointment (Bacitracin (Bacitracin Zinc) + Polymyxin B (Polymyxin B Sulfate))
  • Polysporin Topical First Aid Antibiotic Ointment (Bacitracin + Polymyxin B (Polymyxin B Sulfate))
  • Polysporin Triple Antibiotic Ointment (Bacitracin + Gramicidin + Polymyxin B (Polymyxin B Sulfate))
  • Polytopic Ont (Bacitracin + Polymyxin B (Polymyxin B Sulfate))
  • Polytracin Ont (Bacitracin Zinc + Polymyxin B (Polymyxin B Sulfate))
  • Sandoz Cortimyxin (Bacitracin (Bacitracin Zinc) + Hydrocortisone + Neomycin (Neomycin Sulfate) + Polymyxin B (Polymyxin B Sulfate))
Categories
  • Anti-Bacterial Agents
  • Anti-Infective Agents, Local
CAS number 1405-87-4
Weight Average: 1422.693
Monoisotopic: 1421.748941023
Chemical Formula C66H103N17O16S
InChI Key InChIKey=CLKOFPXJLQSYAH-ABRJDSQDSA-N
InChI
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-/m0/s1
Plain Text
IUPAC Name
(4R)-4-[(2S)-2-{[(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazol-4-yl]formamido}-4-methylpentanamido]-4-{[(1S,2S)-1-{[(3S,6R,9S,12R,15S,18R,21S)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-3-(carbamoylmethyl)-6-(carboxymethyl)-9-(1H-imidazol-4-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
SMILES
CC[C@H](C)[C@H](N)C1=N[C@@H](CS1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@H]1CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(O)=O)NC(=O)[C@H](CC2=CNC=N2)NC(=O)[C@@H](CC2=CC=CC=C2)NC(=O)[C@@H](NC(=O)[C@@H](CCCN)NC1=O)[C@@H](C)CC
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the treatment of infants with pneumonia and empyema caused by staphylococci shown to be susceptible to the drug. Also 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. Used against gram positive bacteria. Bacitracin is also used as an inhibitor of proteases and other enzymes. However, specific activity of bactracin's inhibition of protein disulfide isomerase has been called into question.
Pharmacodynamics Bacitracin is a mixture of related cyclic polypeptides produced by organisms of the licheniformis group of Bacillus subtilis var Tracy. As a polypeptide, toxic, and difficult to use chemical, bacitracin doesn't work well orally, however is very effective topically. Bacitracin exerts pronounced antibacterial action in vitro against a variety of gram-positive and a few gram-negative organisms. However, among systemic diseases, only staphylococcal infections qualify for consideration of bacitracin therapy.
Mechanism of action Bacitracin intereferes with the dephosphorylation of the 55-carbon, biphosphate lipid transport molecule C55-isoprenyl pyrophosphate (undecaprenyl pyrophosphate), which carries the building blocks of the peptidoglycan bacterial cell wall outside the inner membrane for construction. Bacitracin binds divalent transition metal ions (Mn(II), Co(II), Ni(II), Cu(II), and Zn(II)) which binds and oxidatively cleave DNA.
Absorption Absorption of bacitracin following intramuscular injection is rapid and complete. Absorption from the gastrointestinal tract following oral administration is not appreciable. Absorption following topical application is negligible.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination The drug is excreted slowly by glomerular filtration.
Half life Not Available
Clearance Not Available
Toxicity Oral, mouse: LD50 = >3750 mg/kg.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • X gen pharmaceuticals inc
  • App pharmaceuticals llc
  • Pfizer laboratories div pfizer inc
  • Pharmacia and upjohn co
  • Sagent pharmaceuticals inc
  • Altana inc
  • Eli lilly and co
  • Pharmaderm div altana inc
  • Pharmafair inc
  • Combe inc
  • Naska pharmacal co inc div rugby darby group cosmetics
  • Apothekernes laboratorium a/s
  • Paddock laboratories inc
Packagers
Dosage forms
Form Route Strength
Ointment Topical
Powder, for solution Intramuscular
Prices
Unit description Cost Unit
Bacitracin 5mm unit powder 126.0 USD each
Baciim strl 50000 unit vial 19.8 USD vial
Bacitracin 50000 unit vial 13.31 USD vial
Bacitracin 500 unit/gm ointmnt 9.69 USD g
CVS Pharmacy bacitracin 500 unit/gm oin 0.15 USD g
Sm first aid bacitracin ointmn 0.1 USD g
Patents Not Available
Properties
State solid
Melting point 221 - 225 oC
Experimental Properties
Property Value Source
water solubility Freely soluble PhysProp
logP -0.8 PhysProp
Predicted Properties
Property Value Source
water solubility 2.45e-02 g/l ALOGPS
logP -2.89 ALOGPS
logP -6.83751987876902 ChemAxon Molconvert
logS -4.76 ALOGPS
pKa 3.8138918645352446 ChemAxon Molconvert
hydrogen acceptor count 20 ChemAxon Molconvert
hydrogen donor count 17 ChemAxon Molconvert
polar surface area 530.8699999999998 ChemAxon Molconvert
rotatable bond count 31 ChemAxon Molconvert
refractivity 363.1393000000003 ChemAxon Molconvert
polarizability 147.14847372555454 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Tay WM, Epperson JD, da Silva GF, Ming LJ: 1H NMR, mechanism, and mononuclear oxidative activity of the antibiotic metallopeptide bacitracin: the role of D-Glu-4, interaction with pyrophosphate moiety, DNA binding and cleavage, and bioactivity. J Am Chem Soc. 2010 Apr 28;132(16):5652-61. Pubmed
  2. Karala AR, Ruddock LW: Bacitracin is not a specific inhibitor of protein disulfide isomerase. FEBS J. 2010 Jun;277(11):2454-62. Epub 2010 Apr 30. Pubmed
External Links
Resource Link
KEGG Drug D00128 Link_out
KEGG Compound C01667 Link_out
ChEBI 28669 Link_out
ChEMBL 28669 Link_out
Therapeutic Targets Database DAP000710 Link_out
PharmGKB PA448531 Link_out
Drug Product Database 2237196 Link_out
RxList http://www.rxlist.com/cgi/generic3/bacit.htm Link_out
Drugs.com http://www.drugs.com/cdi/bacitracin-ointment.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Bacitracin Link_out
ATC Codes
  • D06AX05
  • R02AB04
AHFS Codes
  • 84:04.04
  • 08:12.28.08
PDB Entries Not Available
FDA label Not Available
MSDS show (71.6 KB)
Interactions
Drug Interactions
Drug Interaction
Food Interactions Not Available
Targets

1. C55-isoprenyl pyrophosphate

Pharmacological action: yes
Actions: antagonist

References:
  1. Stone KJ, Strominger JL: Mechanism of action of bacitracin: complexation with metal ion and C 55 -isoprenyl pyrophosphate. Proc Natl Acad Sci U S A. 1971 Dec;68(12):3223-7. Pubmed

2. Insulin-degrading enzyme

Pharmacological action: yes
Actions: inhibitor

May play a role in the cellular processing of insulin. May be involved in intercellular peptide signaling

Organism class: human
UniProt ID: P14735 Link_out
Gene: IDE Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  2. Medina V, Kesner L, Stracher A: Purification of nonantibiotic insulinase inhibitors from bacitracin. Biochem Med Metab Biol. 1993 Apr;49(2):255-64. Pubmed

3. Alpha-2-macroglobulin

Pharmacological action: unknown
Actions: inhibitor

Is able to inhibit all four classes of proteinases by a unique 'trapping' mechanism. This protein has a peptide stretch, called the 'bait region' which contains specific cleavage sites for different proteinases. When a proteinase cleaves the bait region, a conformational change is induced in the protein which traps the proteinase. The entrapped enzyme remains active against low molecular weight substrates (activity against high molecular weight substrates is greatly reduced). Following cleavage in the bait region a thioester bond is hydrolyzed and mediates the covalent binding of the protein to the proteinase

Organism class: human
UniProt ID: P01023 Link_out
Gene: A2M Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Maxfield FR, Davies PJ, Klempner L, Willingham MC, Pastan I: Epidermal growth factor stimulation of DNA synthesis is potentiated by compounds that inhibit its clustering in coated pits. Proc Natl Acad Sci U S A. 1979 Nov;76(11):5731-5. Pubmed
  2. Dickson RB, Willingham MC, Pastan I: Binding and internalization of 125I-alpha 2-macroglobulin by cultured fibroblasts. J Biol Chem. 1981 Apr 10;256(7):3454-9. Pubmed
  3. Dickson RB, Willingham MC, Gallo M, Pastan I: Inhibition by bacitracin of high affinity binding of 125I-alpha 2M to plasma membranes. FEBS Lett. 1981 Apr 20;126(2):265-8. Pubmed
  4. Hanover JA, Cheng S, Willingham MC, Pastan IH: alpha 2-Macroglobulin binding to cultured fibroblasts. Solubilization and partial purification of binding sites. J Biol Chem. 1983 Jan 10;258(1):370-7. Pubmed
  5. Gliemann J, Larsen TR, Sottrup-Jensen L: Cell association and degradation of alpha 2-macroglobulin-trypsin complexes in hepatocytes and adipocytes. Biochim Biophys Acta. 1983 Mar 31;756(2):230-7. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on October 06, 2011 16:28

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.