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Vancomycin (Standard)

CAT: 0804-HY-B0671R-05Size: 100 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-B0671R-05Size:100 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Vancomycin (Standard) is the analytical standard of Vancomycin. This product is intended for research and analytical applications. Vancomycin is an antibiotic for the treatment of bacterial infections.
CAS Number
1404-90-6
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Antibiotic; Autophagy; Bacterial; Reference Standards
Type
Reference Standards
Related Pathways
Anti-infection; Autophagy; Others
Field of Research
Infection; Cancer
Assay Protocol
https://www.medchemexpress.com/vancomycin-standard.html
Purity
95.92
Smiles
O[C@@H]1[C@@H](O[C@@](O[C@@H](C)[C@H]2O)([H])C[C@@]2(N)C)[C@@H](O[C@H](CO)[C@H]1O)OC3=C(OC4=CC=C([C@H]([C@H]5NC([C@H](NC)CC(C)C)=O)O)C=C4Cl)C=C([C@](NC([C@@H](NC5=O)CC(N)=O)=O)([H])C(N[C@](C6=O)([H])C7=CC8=C(O)C=C7)=O)C=C3OC9=CC=C([C@H]([C@](C(N[C@@](C(O)=O)([H])C%10=C8C(O)=CC(O)=C%10)=O)([H])N6)O)C=C9Cl
Molecular Formula
C66H75Cl2N9O24
Molecular Weight
1449.25
Precautions
H302, H315, H319, H335
References & Citations
[1]Rybak MJ, et al. The pharmacokinetic and pharmacodynamic properties of vancomycin. Clin Infect Dis. 2006 Jan 1;42 Suppl 1:S35-9.|[2]Watanakunakorn C, et al. Mode of action and in-vitro activity of vancomycin. J Antimicrob Chemother. 1984 Dec;14 Suppl D:7-18.|[3]Warren CA, et al. Vancomycin treatment's association with delayed intestinal tissue injury, clostridial overgrowth, and recurrence of Clostridium difficile infection in mice. Antimicrob Agents Chemother. 2013 Feb;57 (2) :689-96.|[4]Juan He, et al. Vitamin C reduces vancomycin-related nephrotoxicity through the inhibition of oxidative stress, apoptosis, and inflammation in mice. Ann Transl Med. 2021 Aug; 9 (16) : 1319.|[5]Ping Yu, et al. N-acetylcysteine Ameliorates Vancomycin-induced Nephrotoxicity by Inhibiting Oxidative Stress and Apoptosis in the in vivo and in vitro Models. Int J Med Sci. 2022; 19 (4) : 740–752.
Shipping Conditions
Blue Ice
Storage Conditions
4°C, sealed and dry storage, away from light and moisture
Scientific Category
Reference Standards

Chemical Information

Vancomycin

Vancomycin is a complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile. It has a role as an antimicrobial agent, an antibacterial drug and a bacterial metabolite. It is functionally related to a vancomycin aglycone. It is a conjugate base of a vancomycin(1+).

CAS Number1404-90-6
PubChem CID14969
IUPAC Name(1S,2R,18R,19R,22S,25R,28R,40S)-48-[(2S,3R,4S,5S,6R)-3-[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-(2-amino-2-oxoethyl)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34(39),35,37,46,49-pentadecaene-40-carboxylic acid
Molecular FormulaC66H75Cl2N9O24
Molecular Weight1449.2
XLogP-2.6
Topological Polar Surface Area530
Hydrogen Bond Donor Count19
Hydrogen Bond Acceptor Count26
Rotatable Bond Count13
Heavy Atom Count101
Formal Charge0
Complexity2960
SMILES
C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)[C@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
InChI
InChI=1S/C66H75Cl2N9O24/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)/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-/m0/s1
InChIKey
MYPYJXKWCTUITO-LYRMYLQWSA-N
Chemical Structure
2D Structure
2D structure of Vancomycin
CAS: 1404-90-6
CID: 14969
Formula: C66H75Cl2N9O24
MW: 1449.2
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1449.2
XLogP3-2.6
Hydrogen Bond Donor Count19
Hydrogen Bond Acceptor Count26
Rotatable Bond Count13
Exact Mass1447.4301997
Monoisotopic Mass1447.4301997
Topological Polar Surface Area530 Ų
Heavy Atom Count101
Formal Charge0
Complexity2960
Isotope Atom Count0
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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