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V1130

Sigma-Aldrich

Vancomycin hydrochloride from Streptomyces orientalis

BioReagent, suitable for plant cell culture

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About This Item

Empirical Formula (Hill Notation):
C66H75Cl2N9O24 · HCl
CAS Number:
1404-93-9
Molecular Weight:
1485.71
Beilstein:
3704657
UNSPSC Code:
10171502
NACRES:
NA.72

biological source

Streptomyces orientalis

Quality Level

200

product line

BioReagent

form

powder

storage condition

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

concentration

≥900 μg/mg (as vancomycin base)

technique(s)

cell culture | plant: suitable

color

, off-white to brown or White to orange-brown

solubility

H2O: 50 mg/mL, clear, colorless to dark yellow (and Very Faint Orange to Faint Orange)

antibiotic activity spectrum

Gram-positive bacteria

application(s)

agriculture

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

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General description

Chemical structure: glycopeptide
Vancomycin is a heptapeptide.

Application

Vancomycin hydrochloride from Streptomyces orientalis has been used as:
  • an antibiotic in screening: minimal inhibitory concentrations (MICs) Streptomyces coelicolor
  • in treating Leishmania infected sand flies
  • in combined antibiotic treatment in asthma induced mice

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 is used for treating methicillin-resistant Staphylococcus aureus (MRSA) infections and shunt-associated Staphylococcal ventriculitis. It may lead to hypersensitivity reactions like anaphylaxis and red man syndrome. Vanomycin is also used to treat thrombocytopenia and induces drug reaction with eosinophilia and systemic symptoms (DRESS) on usage.

Other Notes

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

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H317,H334

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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T Asano et al.
Phytopathology, 89(4), 314-319 (2008-10-24)
ABSTRACT Resting spores of Plasmodiophora brassicae were surface-disinfested by treatment with 2% chloramine-T for 20 min and then with an antibiotic solution (1,000 ppm of colistin sulfate, 1,000 ppm of vancomycin hydrochloride, and 6,000 ppm of cefotaxime sodium) for 1
Red man syndrome
Sivagnanam S and Deleu D
Critical Care, 7(2), 119-119 (2002)
Vancomycin-Induced Drug Reaction with Eosinophilia and Systemic Symptoms (DRESS) Syndrome Masquerading as Elusive Sepsis
Roy S, et al.
Case reports in immunology, 2019, 119-119 (2019)
Optimization of fermentation conditions for production of glycopeptide antibiotic vancomycin by Amycolatopsis orientalis
Padma PN, et al.
Applied Biochemistry and Biotechnology, 102(1-6), 395-405 (2002)
Jyot D Antani et al.
eLife, 10 (2021-01-26)
The canonical chemotaxis network modulates the bias for a particular direction of rotation in the bacterial flagellar motor to help the cell migrate toward favorable chemical environments. How the chemotaxis network in Helicobacter pylori modulates flagellar functions is unknown, which
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