Bacitracin

Bacitracin
Clinical data
Trade namesBaciguent, Baciim, others
AHFS/Drugs.comMonograph
Pregnancy
category
  • AU: D
Routes of
administration		Topical, intramuscular, Ophthalmic drug administration
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: OTC / Rx-only
Identifiers
  • (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
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC66H103N17O16S
Molar mass1422.71 g·mol−1
3D model (JSmol)
  • CCC(C)C(N)NC4=NC(C(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@@H](C(C)CC)C(=O)N[C@H]3CCCCNC(=O)[C@H](CC(N)=O)NC(=O)[C@@H](CC(O)=O)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H](Cc2ccccc2)NC(=O)[C@H](C(C)CC)NC(=O)[C@@H](CCCN)NC3=O)CS4
  • 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 checkY
  • Key:CLKOFPXJLQSYAH-NVOBBBONSA-N checkY
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Bacitracin[1] is a polypeptide antibiotic. It is a mixture of related cyclic peptides produced by Bacillus licheniformis bacteria, that was first isolated from the variety "Tracy I" (ATCC 10716) in 1945.[2] These peptides disrupt Gram-positive bacteria by interfering with cell wall and peptidoglycan synthesis.

Bacitracin is primarily used as a topical preparation, as it can cause kidney damage when used internally.[3] It is generally safe when used topically, but in rare cases may cause hypersensitivity, allergic or anaphylactic reactions, especially in people allergic to neomycin.[4][5]

In 2021, it was the 300th most commonly prescribed medication in the United States, with more than 400,000 prescriptions.[6][7]

  1. ^ Elks J, Ganellin CR (1990). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 119–. ISBN 978-1-4757-2085-3.
  2. ^ Originally grouped under B. subtilis, but nomenclature has since changed. See Podstawka A. "Bacillus licheniformis Tracy I | DSM 603, ATCC 10716, CCM 2181, IFO 12199, NBRC 12199, NCIB 8874, FDA BT1 | BacDiveID:686". bacdive.dsmz.de. Archived from the original on 7 February 2022. Retrieved 7 February 2022.
  3. ^ Zintel HA, Ma RA (October 1949). "The absorption, distribution, excretion and toxicity of bacitracin in man". The American Journal of the Medical Sciences. 218 (4): 439–445. doi:10.1097/00000441-194910000-00012. PMID 18140540. S2CID 2371497.
  4. ^ Spann CT, Taylor SC, Weinberg JM (July 2004). "Topical antimicrobial agents in dermatology". Disease-a-Month. 50 (7): 407–421. doi:10.1016/j.disamonth.2004.05.011. PMID 15280871.
  5. ^ Trookman NS, Rizer RL, Weber T (March 2011). "Treatment of minor wounds from dermatologic procedures: a comparison of three topical wound care ointments using a laser wound model". Journal of the American Academy of Dermatology. 64 (3 Suppl): S8-15. doi:10.1016/j.jaad.2010.11.011. PMID 21247665.
  6. ^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  7. ^ "Bacitracin - Drug Usage Statistics". ClinCalc. Retrieved 14 January 2024.