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V8138

Sigma-Aldrich

Vancomycin hydrochloride from Streptomyces orientalis

meets USP testing specifications

Synonym(s):

Vancomycin, Vancomycin HCL, Vancomycin Hydrochloride

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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:
51282703
PubChem Substance ID:
24278773
NACRES:
NA.76

biological source

Streptomyces orientalis

Quality Level

200

Agency

USP/NF
meets USP testing specifications

storage condition

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

concentration

≥900 μg/mg (as vancomycin base)

antibiotic activity spectrum

Gram-positive bacteria

application(s)

pharmaceutical (small molecule)

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

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
0000395353
0000368641
0000354968
0000354968
0000368641

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Jacqueline C Y Lai et al.
Antimicrobial agents and chemotherapy, 64(3) (2019-12-11)
Infection is correlated with increased risk of neurodevelopmental sequelae in preterm infants. In modeling neonatal brain injury, Toll-like receptor agonists have often been used to mimic infections and induce inflammation. Using the most common cause of bacteremia in preterm infants
Celine Vidaillac et al.
The Journal of infectious diseases, 208(1), 67-74 (2013-03-30)
We used 2 in vitro experimental systems to compare phenotypic and genotypic changes that accompany selection of mutants of methicillin-resistant Staphylococcus aureus (MRSA) strain JH1 with low-level vancomycin resistance similar to the type found in vancomycin-intermediate S. aureus (VISA). The
Lukas P Zebala et al.
The Journal of bone and joint surgery. American volume, 96(1), 46-51 (2014-01-03)
Surgical site infection remains a complication of spine surgery despite routine use of prophylactic antibiotics. Retrospective clinical studies of intrawound vancomycin use have documented a decreased prevalence of surgical site infection after spine surgery. The purpose of the present study
Christopher J Rudnisky et al.
Ophthalmology, 121(4), 835-841 (2013-12-12)
To determine the 8-year incidence of endophthalmitis after cataract surgery and to determine which surgical practices were associated with higher rates of endophthalmitis. Case-control study. A total of 75 318 eyes undergoing cataract extractions, performed by 26 different surgeons at 4 public
Thomas M Schmelzer et al.
The American surgeon, 79(11), 1185-1190 (2013-10-30)
Current guidelines for the empiric treatment of ventilator-associated pneumonia (VAP) recommend that vancomycin is dosed 15 mg/kg and administered twice daily for a target trough level of 15 to 20 μg/mL. This study compared conventional intermittent vancomycin infusion (IVI) with
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