A cyclic polypeptide antibiotic
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Bacitracin (zinc)

Item No. 21212

Technical Information
CAS Number
1405-89-6
Synonyms
  • Bacifarmin
Molecular Formula
C66H101N17O16S • Zn
Formula Weight
Purity
≥70% (Bacitracin A,B1,B3 mixture)
A crystalline solid
DMSO: Slightly Soluble
SMILES
CC[C@@H]([C@H]1C(N[C@H](CC2=CC=CC=C2)C(N[C@@H](CC3=CN=CN3)C(N[C@H](CC([O-])=O)C(N[C@@H](CC(N)=O)C(NCCCC[C@H](NC([C@@H](NC([C@H](NC([C@@H](NC(C4=NC(C(C(CC)C)N)SC4)=O)CC(C)C)=O)CCC([O-])=O)=O)[C@H](CC)C)=O)C(N[C@H](CCCN)C(N1)=O)=O)=O)=O)=O)=O)=O)C.[Zn+2]
InChi Code
InChI=1S/C66H103N17O16S.Zn/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;/h12-14,18-19,31,33-37,40-47,52-54,66H,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);/q;+2/p-2/t35?,36-,37-,40-,41+,42+,43-,44+,45-,46-,47+,52?,53-,54-,66?;/m0./s1
InChi Key
YDUPIJIVLKNJJG-DAQOJNSOSA-L
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Bacitracin is a cyclic polypeptide antibiotic that was first isolated from B. licheniformis.1 Formulations containing bacitracin, often combined with other antibiotics, are used for topical treatment of infections in humans and animals.2,3 The activity of bacitracin can be enhanced by zinc.4 Bacitracin sequesters C55-isopropyl pyrophosphate (IPP), a lipid carrier in peptidoglycan synthesis, and in this way disrupts cell wall biosynthesis.2,3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Katz, E., and Demain, A.L. The peptide antibiotics of Bacillus: Chemistry, biogenesis, and possible functions. Bacteriol. Rev. 41(2), 449-474 (1977).

    2. Butaye, P., Devriese, L.A., and Haesebrouck, F. Antimicrobial growth promoters used in animal feed: Effects of less well known antibiotics on gram-positive bacteria. Clin. Microbiol. Rev. 16(2), 175-188 (2003).

    3. Chancey, S.T., Zähner, H., and Stephens, D.S. Acquired inducible antimicrobial resistance in Gram-positive bacteria. Future Microbiol. 7(8), 959-978 (2012).

    4. Astiazarán-García, H., Iñigo-Figueroa, G., Quihui-Cota, L., et alCrosstalk between zinc status and Giardia infection: A new approach. Nutrients 7(6), 4438-4452 (2015).