V2002

Vancomycin hydrochloride from Streptomyces orientalis

≥900 μg per mg (as vancomycin base)

• Synonym(s): Vancomycin, Vancomycin HCL
• Empirical Formula (Hill Notation): C₆₆H₇₅Cl₂N₉O₂₄ · HCl
• CAS Number: 1404-93-9
• Molecular Weight: 1485.71
• Beilstein: 3704657
• UNSPSC Code: 51282703
• PubChem Substance ID: 24900723
• NACRES: NA.85

Properties

• biological source: Streptomyces orientalis
• Quality Level: 200
• form: powder
• storage condition: (Keep container tightly closed in a dry and well-ventilated place.)
• concentration: ≥900 μg/mg (as vancomycin base)
• color: , off-white to brown or White to orange-brown
• antibiotic activity spectrum: Gram-positive bacteria
• Mode of action: cell wall synthesis | interferes
• storage temp.: 2-8°C
• SMILES string: Cl[H].CO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]1O[C@H]2C[C@](C)(N)[C@@H](O)[C@@H](C)O2.CN[C@H](CC(C)C)C(=O)NC3[C@H](O)c4ccc(Oc5cc6Oc7ccc(cc7Cl)[C@@H](O)[C@H]8NC(=O)[C@H](NC(=O)[C@H](NC(=O)[C@H](CC(N)=O)NC3=O)c(c5)c6)c9ccc(O)c(c9)-c%10c(O)cc(O)cc%10[C@@H](NC8=O)C(O)=O)c(Cl)c4
• InChI: 1S/C66H75Cl2N9O24.ClH/c1-23(2)12-34(71-5)58(88)76-49-51(83)26-7-10-38(32(67)14-26)97-40-16-28-17-41(55(40)101-65-56(54(86)53(85)42(22-78)99-65)100-44-21-66(4,70)57(87)24(3)96-44)98-39-11-8-27(15-33(39)68)52(84)50-63(93)75-48(64(94)95)31-18-29(79)19-37(81)45(31)30-13-25(6-9-36(30)80)46(60(90)77-50)74-61(91)47(28)73-59(89)35(20-43(69)82)72-62(49)92;/h6-11,13-19,23-24,34-35,42,44,46-54,56-57,65,71,78-81,83-87H,12,20-22,70H2,1-5H3,(H2,69,82)(H,72,92)(H,73,89)(H,74,91)(H,75,93)(H,76,88)(H,77,90)(H,94,95);1H/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-;/m0./s1
• InChI key: LCTORFDMHNKUSG-XTTLPDOESA-N

Description

General description

Vancomycin is a nonribosomal glycopeptide antibiotic characterized by its branched, tricyclic, and glycosylated structure. Unlike beta-lactam antibiotics, vancomycin operates by inhibiting bacterial cell wall synthesis at an earlier stage. Its spectrum of activity is primarily directed against aerobic and anaerobic gram-positive bacteria, encompassing a wide range of isolates, including those that exhibit resistance to β-lactams. Vancomycin is notably effective against Gram-positive organisms such as Clostridium difficile, Listeria monocytogenes, Streptococcus pyogenes, Streptococcus pneumoniae, Streptococcus agalactiae, Streptococcus viridans, Streptococcus bovis, Staphylococcus epidermidis, Actinomyces species, and Lactobacillus species. It demonstrates exceptional efficacy in combating methicillin-resistant Staphylococcus aureus (MRSA). Furthermore, vancomycin is a valuable tool for preventing the proliferation of bacterial contaminants in studies related to cell biology and biochemistry.

Application

Vancomycin hydrochloride from Streptomyces orientalis has been used:

• in the research the effects of antibiotic-induced depletion of Firmicutes and Bacteroidetes on dysregulation of energy homeostasis in obesity[1]
• in the research of non-O157 Shiga toxin-producing Escherichia coli Isolates from Bovine Farms[2]
• to research the antimicrobial susceptibility of Bifidobacterium strains in various organisms[3]

Biochem/physiol Actions

Mode of action: Inhibits incorporation of terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides.

Antimicrobial Spectrum: Active against Gram-positive bacteria

Vancomycin exerts its antibacterial effects by forming noncovalent bonds with undecaprenyl-(muramyl-glucosaminyl)-pentapeptide, a crucial precursor in the biosynthesis of bacterial cell walls. This interaction disrupts the synthesis of peptidoglycan, interfering with the transglycosylation and transpeptidation processes that are essential for bacterial cell wall construction. Consequently, the cell wall′s integrity is compromised, leading to cell lysis. Furthermore, Vancomycin augments the permeability of the bacterial cell wall and hinders RNA synthesis.

Vancomycin is a glycopeptide antibiotic that blocks bacterial cell wall biosynthesis at the level of peptidoglycan biosynthesis. It inhibits incorporation of terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides. It is effective against Gram-positive bacteria. Vancomycin also alters bacterial-cell-membrane permeability and RNA synthesis.

Features and Benefits

• Effective against a wide range of Gram-positive bacteria, including MRSA
• Commonly used in Cell Biology and Biochemical applications

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Keep container tightly closed in a dry and well-ventilated place.

Safety Information

• Pictograms: GHS08
• Signal Word: Danger
• Hazard Statements: H317,H334
• Precautionary Statements: P261 - P272 - P280 - P284 - P302 + P352 - P333 + P313
• Hazard Classifications: Resp. Sens. 1 - Skin Sens. 1
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 2
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves