Vancomycin hydrochloride
[CAS# 1404-93-9]

Identification

• Classification: API >> Antibiotics >> Peptide drug
• Name: Vancomycin hydrochloride
• Synonyms: (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;hydrochloride
• Molecular Formula: C₆₆H₇₅Cl₂N₉O₂₄.HCl
• Molecular Weight: 1485.72
• CAS Registry Number: 1404-93-9
• EC Number: 604-193-8
• 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.Cl

Properties

• Density: 1.7±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.735, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H317-H319-H35
• Safety Statements: P261-P264-P264+P265-P271-P272-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P333+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - single exposure	STOT SE	3	H335
Eye irritation	Eye Irrit.	2	H319
Skin irritation	Skin Irrit.	2	H315
Respiratory sensitization	Resp. Sens.	1	H334
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H302
Acute toxicity	Acute Tox.	4	H312
Respiratory sensitization	Resp. Sens.	1B	H334

Discovery and Applications

Vancomycin, a potent antibiotic, was discovered in the 1950s by Edmund Kornfeld and coworkers at Eli Lilly and Company. It was isolated from a soil sample collected in Borneo, Malaysia. The discovery of vancomycin marked a significant advancement in the treatment of bacterial infections, particularly those caused by gram-positive bacteria resistant to other antibiotics.

Vancomycin hydrochloride is primarily used for the treatment of serious infections caused by gram-positive bacteria, including methicillin-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus (VRE). It is particularly effective against infections such as bloodstream infections, pneumonia, skin and soft tissue infections, bone and joint infections, and endocarditis. Vancomycin is often used as empirical therapy in hospital settings for suspected or confirmed infections in patients with severe illnesses or compromised immune systems. It is commonly prescribed for patients with healthcare-associated infections, surgical site infections, and infections in critically ill patients where MRSA or other resistant bacteria are suspected. Vancomycin is considered a first-line treatment for Clostridioides difficile infection (CDI), a common cause of antibiotic-associated diarrhea. Vancomycin disrupts the growth of C. difficile by inhibiting cell wall synthesis, leading to bacterial cell death. It is particularly effective in severe cases of CDI or in patients who cannot tolerate or fail to respond to other treatment options. Vancomycin may be used prophylactically in certain surgical procedures to prevent surgical site infections caused by MRSA or other resistant bacteria. Given the emergence of vancomycin-resistant strains of bacteria, prudent use of vancomycin is essential to preserve its efficacy and prevent the development of resistance. Antibiotic stewardship programs promote judicious use of vancomycin and encourage appropriate dosing, duration, and monitoring to minimize the risk of resistance and adverse effects.

References

1979. Relapse of Pseudomembranous Colitis after Vancomycin Therapy. The New England journal of medicine. W. Lance George, Nicholas A. Volpicelli, Dana B. Stiner, Douglas D. Richman, E. Joseph Liechty, Henry Y. I. Mok, Rial D. Rolfe, Sydney M. Finegold.
DOI: 10.1056/nejm197908233010806

2024. Comparison of Vancomycin AUC24 Calculation Methods for Neonates and Infants. European Journal of Drug Metabolism and Pharmacokinetics. Tuomas Laitila, Ulla Sankilampi, Marjo Renko, Merja Kokki, Veli-Pekka Ranta.
DOI: 10.1007/s13318-024-00920-5

1987. Bactericidal activity and killing rate of serum against Gram-positive cocci in volunteers receiving imipenem, oxacillin, vancomycin or ampicillin plus gentamicin. The Journal of antimicrobial chemotherapy. P. Van der Auwera, Y. Van Laethem, J. Klastersky.
DOI: 10.1093/jac/20.2.239