Bacitracin Zinc
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MedKoo CAT#: 574449

CAS#: 1405-89-6

Description: Bacitracin Zinc is a cyclic polypeptide antibiotic. Formulations containing bacitracin, often combined with other antibiotics, are used for topical treatment of infections in humans and animals. The activity of bacitracin can be enhanced by zinc. Bacitracin sequesters C55-isopropyl pyrophosphate (IPP), a lipid carrier in peptidoglycan synthesis, and in this way disrupts cell wall biosynthesis.


Chemical Structure

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Bacitracin Zinc
CAS# 1405-89-6

Theoretical Analysis

MedKoo Cat#: 574449
Name: Bacitracin Zinc
CAS#: 1405-89-6
Chemical Formula: C66H101N17O16SZn
Exact Mass: 1483.6624
Molecular Weight: 1486.08
Elemental Analysis: C, 53.34; H, 6.85; N, 16.02; O, 17.23; S, 2.16; Zn, 4.40

Price and Availability

Size Price Availability Quantity
1.0g USD 200.0 2 Weeks
5.0g USD 380.0 2 Weeks
10.0g USD 610.0 2 Weeks
25.0g USD 950.0 2 Weeks
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Synonym: Bacitracin zinc; Bacifarmin; Bacifarmin (zinc)

IUPAC/Chemical Name: 4-[[2-[[2-(1-amino-2-methylbutyl)-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[1-[[3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-butan-2-yl-6-(carboxymethyl)-9-(4H-imidazol-4-ylmethyl)-2,5,8,11,14,17,20-heptaoxo-1,4,7,10,13,16,19-heptazacyclopentacos-21-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-5-oxopentanoic acid;zinc

InChi Key: DFCFJNHVZXJGQP-UHFFFAOYSA-L

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(

SMILES Code: 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+]

Appearance: Solid powder

Purity: ≥70% (Bacitracin A,B1,B3 mixture)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >3 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Product Data:

Biological target: Bacitracin Zinc is a dephosphorylation of the C55-isoprenyl pyrophosphate interference for inhibition of cleavage of Tyr from Met-enkephalin with IC50 of 10 μM.
In vitro activity: To investigate the effect of Bacitracin (Bac) on the intoxication of cells with the binary actin ADP-ribosylating C2 toxin, HeLa cells were incubated with recombinantly expressed C2 toxin in the absence and presence of Bac. After different incubation periods, the number of round cells was determined as a specific and highly sensitive endpoint for the C2 toxin–mediated destruction of the actin cytoskeleton of the cells. As shown in Fig. 1A, the number of round cells was significantly reduced in the presence of Bac, indicating that Bac protects cells from the intoxication with recombinant C2 toxin. Reference: FASEB J. 2019 Apr;33(4):5755-5771. https://faseb.onlinelibrary.wiley.com/doi/10.1096/fj.201802453R
In vivo activity: The effects of protease inhibitor bacitracin on brain beta-endorphin content and analgesia, were examined in vivo. Male Sprague-Dawley rats were injected with bacitracin intracerebroventricularly and sacrificed by microwave irradiation 15 and 30 min after injection. Brain beta-endorphin levels were 27% higher in bacitracin treated rats than in controls. A second group of bacitracin injected rats was subjected to continuous intermittent 55 degrees C hot plate exposure. Bacitracin-injected rats exhibited total analgesia 15 min after bacitracin injection. At 30 min, this analgesic effect subsided. Control rats exhibited no analgesia. These results suggest that bacitracin induced analgesia might be due to the elevated levels of brain beta-endorphin caused by a decrease in its breakdown by bacitracin. Reference: Brain Res. 1982 Jun 17;242(1):119-23. https://www.sciencedirect.com/science/article/abs/pii/0006899382905017?via%3Dihub

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 50.5 33.98
1M HCl 50.0 33.65
Water 1.0 0.67

Preparing Stock Solutions

The following data is based on the product molecular weight 1486.08 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Schnell L, Felix I, Müller B, Sadi M, von Bank F, Papatheodorou P, Popoff MR, Aktories K, Waltenberger E, Benz R, Weichbrodt C, Fauler M, Frick M, Barth H. Revisiting an old antibiotic: bacitracin neutralizes binary bacterial toxins and protects cells from intoxication. FASEB J. 2019 Apr;33(4):5755-5771. doi: 10.1096/fj.201802453R. Epub 2019 Jan 30. PMID: 30699302. 2. Zhu Z, Schnell L, Müller B, Müller M, Papatheodorou P, Barth H. The Antibiotic Bacitracin Protects Human Intestinal Epithelial Cells and Stem Cell-Derived Intestinal Organoids from Clostridium difficile Toxin TcdB. Stem Cells Int. 2019 Aug 5;2019:4149762. doi: 10.1155/2019/4149762. PMID: 31467562; PMCID: PMC6701344. 3. Sikand G, Havlicek V. Bacitracin produces analgesia by increasing brain immunoreactive beta-endorphin (beta-E) content. Brain Res. 1982 Jun 17;242(1):119-23. doi: 10.1016/0006-8993(82)90501-7. PMID: 7104723.
In vitro protocol: 1. Schnell L, Felix I, Müller B, Sadi M, von Bank F, Papatheodorou P, Popoff MR, Aktories K, Waltenberger E, Benz R, Weichbrodt C, Fauler M, Frick M, Barth H. Revisiting an old antibiotic: bacitracin neutralizes binary bacterial toxins and protects cells from intoxication. FASEB J. 2019 Apr;33(4):5755-5771. doi: 10.1096/fj.201802453R. Epub 2019 Jan 30. PMID: 30699302. 2. Zhu Z, Schnell L, Müller B, Müller M, Papatheodorou P, Barth H. The Antibiotic Bacitracin Protects Human Intestinal Epithelial Cells and Stem Cell-Derived Intestinal Organoids from Clostridium difficile Toxin TcdB. Stem Cells Int. 2019 Aug 5;2019:4149762. doi: 10.1155/2019/4149762. PMID: 31467562; PMCID: PMC6701344.
In vivo protocol: 1. Sikand G, Havlicek V. Bacitracin produces analgesia by increasing brain immunoreactive beta-endorphin (beta-E) content. Brain Res. 1982 Jun 17;242(1):119-23. doi: 10.1016/0006-8993(82)90501-7. PMID: 7104723.

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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 al. Crosstalk between zinc status and Giardia infection: A new approach. Nutrients 7(6), 4438-4452 (2015).