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Vancomycin

Vancomycin is an antibacterial compound obtained from Streptomyces orientalis. It is a glycopeptide related to ristocetin that inhibits bacterial cell wall assembly.

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CAT No: 10-101-103

CAS No: 1404-90-6

Synonyms/Alias: Vancocin; Vancomycine; Vancomycinum; Vancomicina; HSDB 3262; Vancomycin; EINECS 215-772-6; LS-161387; LS161387; Diatracin; Vancocine

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M.F/FormulaC66H75Cl2N9O24
M.W/Mr.1449.25
Labeling TargetD-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan
ApplicationVancomycin is an antibiotic used to treat a number of bacterial infections. It is a member of the glycopeptide antibiotic class and is effective mostly against Gram-positive bacteria.
AppearanceWhite to off-white solid powder
Purity>98% (or refer to the Certificate of Analysis)
Biological ActivityVancomycin is an antibiotic for the treatment of bacterial infections.
Areas of InterestCardiovascular System & Diseases
Pituitary & Hypothalamic Hormones
TargetAntimicrobial
Source#Synthetic
Long-term Storage ConditionsSoluble in water
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage ConditionsDry, dark and at 0 - 4 °C
Solubility-20 °C
OrganismGram-positive bacteria
InChIInChI=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
InChI KeyMYPYJXKWCTUITO-LYRMYLQWSA-N
Isomeric SMILESC[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=C9[C@H](NC(=O)[C@H]([C@@H](C1=CC(=C(O4)C=C1)Cl)O)NC7=O)C(=O)O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
BoilingPointN/A
ShelfLife>2 years if stored properly
References

Vancomycin (VCM) is a tricyclic glycopeptide antibiotic produced by Streptococcus orientalis. Widely used in hospitals, it is indicated to fight severe infections caused by Gram-positive bacteria, especially with the advent of MRSA (methicillin-resistant Staphylococcus aureus), penicillin-resistant pneumococci among others. Furthermore, it is indicated for the treatment of patients allergic to penicillins and cephalosporins. Dose recommendations, dilution rates and types of infusion are controversial and also result in toxic effects. Aim of this paper was to perform a literature review showing the therapeutic and adverse effects of vancomycin.

Bruniera, F. R., Ferreira, F. M., Saviolli, L. R., Bacci, M. R., Feder, D., da Luz Goncalves Pedreira, M., ... & Fonseca, F. L. A. (2015). The use of vancomycin with its therapeutic and adverse effects: a review. Eur Rev Med Pharmacol Sci, 19(4), 694-700.

Vancomycin became available for clinical use >50 years ago but was soon discarded in favor of other antibiotics that were deemed to be more efficacious and less toxic. The advent of pseudomembranous enterocolitis, coupled with the spread of methicillin-resistant Staphylococcus aureus, led to a resurgence in the use of vancomycin. Almost immediately, concerns arose with regard to its therapeutic utility. In addition, resistance to vancomycin developed, first in enterococci and later in staphylococci. Several types of resistance have now been identified, each with a unique effect on infections treated with vancomycin. Recent studies have rekindled interest in the best way to administer the antibiotic. The findings of future studies may result in a return to measuring levels of vancomycin in serum, to assure a successful therapeutic outcome.

Levine, D. P. (2006). Vancomycin: a history. Clinical Infectious Diseases, 42(Supplement_1), S5-S12.

Vancomycin is one of only a few antibiotics available to treat patients infected with methicillin-resistant Staphylococcus aureus and methicillin-resistant, coagulase-negative Staphylococcus species. Therefore, understanding the clinical implications of the pharmacokinetic and pharmacodynamic properties of vancomycin is a necessity for clinicians. Vancomycin is a concentration-independent antibiotic (also referred to as a "time-dependent" antibiotic), and there are factors that affect its clinical activity, including variable tissue distribution, inoculum size, and emerging resistance. This article reviews the pharmacokinetic and pharmacodynamic data related to vancomycin and discusses such clinical issues as toxicities and serum concentration monitoring.

Rybak, M. J. (2006). The pharmacokinetic and pharmacodynamic properties of vancomycin. Clinical Infectious Diseases, 42(Supplement_1), S35-S39.

Melting PointN/A
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