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Merck

V8138

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
NACRES:
NA.76
PubChem Substance ID:
24278773
UNSPSC Code:
51282703
Beilstein/REAXYS Number:
3704657

Key Documents

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InChI key

LCTORFDMHNKUSG-XTTLPDOESA-N

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

biological source

Streptomyces orientalis

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

Quality Level

200

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Related Categories

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

signalword

Danger

hcodes

H317,H334

Hazard Classifications

Resp. Sens. 1 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000519658
0000519657
0000519657
0000519658
0000506800

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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
David W Eyre et al.
The Journal of infectious diseases, 209(9), 1446-1451 (2013-11-13)
Whole-genome sequencing was used to determine whether the reductions in recurrence of Clostridium difficile infection observed with fidaxomicin in pivotal phase 3 trials occurred by preventing relapse of the same infection, by preventing reinfection with a new strain, or by
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
Wessam Abdelhady et al.
The Journal of infectious diseases, 209(8), 1231-1240 (2014-01-10)
Staphylococcus aureus is the most common cause of endovascular infections. The staphylococcal accessory regulator A locus (sarA) is a major virulence determinant that may potentially impact methicillin-resistant S. aureus (MRSA) persistence in such infections via its influence on biofilm formation.
G Ralph Corey et al.
The New England journal of medicine, 370(23), 2180-2190 (2014-06-05)
Oritavancin is a lipoglycopeptide with bactericidal activity against gram-positive bacteria. Its concentration-dependent activity and prolonged half-life allow for single-dose treatment. We conducted a randomized, double-blind trial in which adults with acute bacterial skin and skin-structure infections received either a single
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