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V1130

Sigma-Aldrich

Vancomycin hydrochloride from Streptomyces orientalis

BioReagent, suitable for plant cell culture

Empirical Formula (Hill Notation):
C66H75Cl2N9O24 · HCl
CAS Number:
Molecular Weight:
1485.71
Beilstein:
3704657
NACRES:
NA.72

biological source

Streptomyces orientalis

Quality Level

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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This Item
V2002V813894747
product line

BioReagent

product line

-

product line

-

product line

-

form

powder

form

powder

form

-

form

powder

storage condition

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

storage condition

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

storage condition

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

storage condition

-

concentration

≥900 μg/mg (as vancomycin base)

concentration

≥900 μg/mg (as vancomycin base)

concentration

≥900 μg/mg (as vancomycin base)

concentration

-

technique(s)

cell culture | plant: suitable

technique(s)

-

technique(s)

-

technique(s)

-

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

Signal Word

Danger

Hazard Statements

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

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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)
Complete genome sequence and comparative genomic analyses of the vancomycin-producing Amycolatopsis orientalis
Xu L, et al.
BMC Genomics, 15(1), 363-363 (2014)
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
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)
Red man syndrome
Sivagnanam S and Deleu D
Critical Care, 7(2), 119-119 (2002)

Articles

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