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Vancomycin

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Identification
Molecular formula
C66H75Cl2N9O24
CAS number
1404-93-9
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-dimethyl-tetrahydropyran-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-22-(2-amino-2-oxo-ethyl)-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
State
State

Vancomycin is a solid at room temperature and is typically available as a powder for injection or in capsule form for oral administration.

Melting point (Celsius)
140.00
Melting point (Kelvin)
413.15
Boiling point (Celsius)
0.00
Boiling point (Kelvin)
0.00
General information
Molecular weight
1485.71g/mol
Molar mass
1 485.7000g/mol
Density
1.3000g/cm3
Appearence

Vancomycin is typically a white to off-white powder that is crystalline in appearance. It is often provided and used in its hydrochloride salt form, which helps enhance its solubility in water.

Comment on solubility

Solubility of the Compound

The solubility of the compound (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-dimethyl-tetrahydropyran-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-22-(2-amino-2-oxo-ethyl)-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 can be influenced by various factors:

  • Polarity: As a compound rich in hydroxyl and amino groups, it likely exhibits significant polarity, which may enhance its solubility in polar solvents such as water.
  • Hydrogen Bonding: The presence of multiple hydroxyl and amine functionalities allows for extensive hydrogen bonding with the solvent, which can further facilitate solubility.
  • pH Influence: Given that it contains carboxylic acid functionality, variations in pH may affect its ionization state, influencing solubility. For example, at higher pH, the carboxylic acid may deprotonate, increasing its water solubility.
  • Molecular Weight: The compound's complex and large structure might challenge solubility in certain organic solvents, despite its polar character.
  • Crystallinity: If the compound tends to crystallize, it may exhibit reduced solubility due to a stable lattice structure, inhibiting dissolution.

In summary, while the compound possesses characteristics that suggest it can be soluble in polar solvents, the actual solubility is likely to be dependent on its environmental conditions and molecular interactions. As a general observation, compounds with a high degree of complexity and multiple functional groups can present unique solubility profiles that warrant further experimental investigation.

Interesting facts

Interesting Facts about the Compound

This remarkable compound, often referred to in scientific literature, presents a rich tapestry of chemical interactions and biological significance. It belongs to a class of molecules known for their complexity and potential therapeutic applications. Here are some fascinating insights:

  • Structural Complexity: The compound boasts a highly intricate structure, with multiple stereocenters, indicating that its three-dimensional arrangement plays a crucial role in its biological activity.
  • Biological Relevance: Many compounds with similar structural features have been studied for their pharmaceutical potential. They often exhibit antimicrobial or antiviral properties, making them targets for drug discovery.
  • Functional Groups: The presence of various functional groups, such as amino, hydroxyl, and carbonyl groups, enhances the compound's reactivity and enables it to participate in diverse biochemical reactions.
  • Chirality: The compound's chirality signifies that it may exist in multiple enantiomeric forms, which can lead to different biological responses. Understanding the chiral nature is essential in developing effective drugs.
  • Potential Applications: Given its structural attributes, the compound could be researched further for applications in fields such as:
    • Pharmaceuticals for treating resistant infections
    • Anticancer therapies
    • Bioconjugation in drug delivery systems
  • Natural Sources: Compounds of this nature are often derived from natural products, leading to interesting studies on biosynthesis pathways in microorganisms and plants.

Overall, this compound exemplifies the intricate interplay of chemistry and biology, highlighting the importance of molecular structure in determining function and potential utility in health-related applications. As we venture further into the world of chemical compounds, understanding such intricate structures will pave the way for innovative discoveries.

Synonyms
VANCOMYCIN
1404-90-6
Vancomicina
Vancomycine
Vancomycinum
vancomicin
HSDB 3262
Vancomycine [INN-French]
Vancomycinum [INN-Latin]
Vancomicina [INN-Spanish]
EINECS 215-772-6
UNII-6Q205EH1VU
6Q205EH1VU
CHEBI:28001
Vancomycin [USP:INN:BAN]
DTXSID0042664
Vancomycine (INN-French)
Vancomycinum (INN-Latin)
Vancomicina (INN-Spanish)
VANCOMYCIN (MART.)
VANCOMYCIN [MART.]
Vancomycin (USP:INN:BAN)
VANCOMYCIN (USP IMPURITY)
VANCOMYCIN [USP IMPURITY]
VANCOMYCIN (USP MONOGRAPH)
VANCOMYCIN [USP MONOGRAPH]
Vancomycinum (Latin)
A07AA09
J01XA01
S01AA28
DTXCID401031367
215-772-6
(1s,2r,18r,22s,25r,28r,40s)-22-(2-amino-2-oxoethyl)-48-(2-o-(3-amino-2,3,6-trideoxy-3-methyl-alpha-l-lyxo-hexopyranosyl)-beta-d-glucopyranosyloxy)-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-((n-methyl-d-leucyl)amino)-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo(26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39))pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid
(2.2sp,3.5sa,2.6sp)-o(4.2),c(3.4):c(5.4),o(4.6):c(3.5),c(2.7)-tricyclo(n-methyl-d-leucyl-3-chloro-(r)-beta-hydroxy-d-tyrosyl-l-asparaginyl-d-2-(4-((2-o-(3-amino-2,3,6-trideoxy-3-c-methyl-alpha-l-lyxo-hexopyranosyl)-beta-d-glucopyranosyl)oxy)phenyl)glycyl-d-2-(4-hydroxyphenyl)glycyl-3-chloro-(r)-beta-hydroxy-l-tyrosyl-l-2-(3,5-dihydroxyphenyl)glycine)
(3s,6r,7r,11r,23s,26s,30as,36r,38ar)-44-(2-o-(3-amino-2,3,6-trideoxy-3-c-methyl-alpha-l-lyxo-hexopyranosyl)-beta-d-glucopyranosyloxy)-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(n-methyl-d-leucyl)-2,5,24,38,39-pentaoxo-1h,22h-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)(1,6,9)oxadiazacyclohexadecino(4,5-m)(10,2,16)benzoxadiazacyclotetracosine-26-carboxylic acid
Vancocin
Vancoled
VANCOR
CHEMBL262777
Vancomycin ( >85%)
Vancomycin (USP)
vanomycin
Vancomycin hydrochloride from Streptomyces orientalis
Viomycin derivative
[(2S,3R,4S,5S,6R)-3-[(2S,4S,5S,6S)-4-amino-5-hydroxy-4,6-dimethyl-tetrahydropyran-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-(2-amino-2-oxo-ethyl)-dichloro-pentahydroxy-[[(2R)-4-methyl-2-(methylamino)pentanoyl]amino]-pentaoxo-[?]carboxylic acid
Vancomycin (Standard)
Glycopeptide Antibiotic
C06689
D00212
VANCOMYCIN [MI]
VANCOMYCIN [INN]
Prestwick0_000497
Prestwick1_000497
Prestwick2_000497
VANCOMYCIN [HSDB]
SCHEMBL3177
VANCOMYCIN [WHO-DD]
Chloroorienticin B derivative
Lopac0_001267
N-demethylvancomycin derivative
SPBio_002314
CHEMBL3735877
SCHEMBL25297175
VANCOMYCIN [ORANGE BOOK]
GTPL10932
HY-B0671R
HY-B0671
BDBM50335519
s5784
AKOS030526092
CCG-205340
CS-3242
DB00512
SDCCGSBI-0051233.P002
NCGC00162383-04
NCGC00162383-11
FV152644
NS00001544
4-Naphthalen-2-ylmethyl-4,5-dihydro-1H-imidazole
Q424027
SR-01000076194-5
BRD-K91065602-001-01-8
BRD-K91065602-003-04-8
BRD-K91065602-003-05-5
(2.2Sp,3.5Sa,2.6Sp)-O4.2,C3.4:C5.4,O4.6:C3.5,C2.7-tricyclo[N-methyl-D-leucyl-3-chloro-(R)-beta-hydroxy-D-tyrosyl-L-asparaginyl-D-2-(4-{[2-O-(3-amino-2,3,6-trideoxy-3-C-methyl-alpha-L-lyxo-hexopyranosyl)-beta-D-glucopyranosyl]oxy}phenyl)glycyl-D-2-(4-hydroxyphenyl)glycyl-3-chloro-(R)-beta-hydroxy-L-tyrosyl-L-2-(3,5-dihydroxyphenyl)glycine]
(S)-3,6-Diamino-hexanoic acid {(3S,9S,12S,15S)-3-((S)-6-hydroxy-2-imino-hexahydro-pyrimidin-4-yl)-9,12-bis-hydroxymethyl-2,5,8,11,14-pentaoxo-6-[1-ureido-meth-(Z)-ylidene]-1,4,7,10,13pentaaza-cyclohexadec-15-yl}-amide