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Product Description
Mechanism of action
Bacitracin is a cyclic polypeptide antibiotic that inhibits bacterial cell‑wall synthesis by interfering with the dephosphorylation of bactoprenol pyrophosphate, a lipid carrier responsible for shuttling peptidoglycan precursors across the cytoplasmic membrane. By preventing regeneration of the bactoprenol carrier, bacitracin effectively halts polymerisation of the cell wall. The compound exhibits strong activity against Gram‑positive organisms.
Benefits and advantages
Widely used in cell‑wall biosynthesis research, membrane transport studies, peptidoglycan precursor trafficking models and investigations into lipid‑cycle antibiotics. Its mechanism provides key insights into carrier‑lipid biochemistry.
Side effects and risks
Bacitracin may cause nephrotoxicity, allergic dermatitis and local irritation. In concentrated form, it requires biological‑agent containment and careful dermal protection.
Datasheet
| Molecular Formula | C66H103N17O16S |
|---|---|
| Molecular Weight | 1422.7 g/mol |
| CAS Number | 1405-87-4 |
| Storage Condition | Bacitracin ophthalmic ointment should be stored at 15-30 °C. |
| Solubility | Freely soluble |
| Purity | Purity information is available upon request (COA). |
| Synonym | Fortracin; Bacitracina; Bacitracine; Bacitracinum; Parentracin |
| IUPAC/Chemical Name | (4R)-4-[[(2S)-2-[[(4R)-2-[(1S,2S)-1-amino-2-methylbutyl]-4,5-dihydro-1,3-thiazole-4-carbonyl]amino]-4-methylpentanoyl]amino]-5-[[(2S,3S)-1-[[(3S,6R,9S,12R,15S,18R,21S)-3-(2-amino-2-oxoethyl)-18-(3-aminopropyl)-12-benzyl-15-[(2S)-butan-2-yl]-6-(carboxymethyl)-9-(1H-imidazol-5-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 |
| InChl Key | CLKOFPXJLQSYAH-ABRJDSQDSA-N |
| InChl Code | 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 |
| References |
3D Conformer.
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