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[Pharmacology](https://durgical.com/en/pharmacology/) · Class

# Glycopeptides

Large antibiotics that block cell-wall building in gram-positive bacteria, including MRSA; vancomycin is the classic member.

Updated 2026-11-01

## What they are

Glycopeptides and their lipid-bearing relatives (lipoglycopeptides) act only on gram-positive bacteria. They are the main option for methicillin-resistant Staphylococcus aureus (MRSA) and for patients who cannot receive β-lactams.

## Mechanism of action

They bind tightly, without a covalent bond, to the D-alanyl–D-alanine end of the peptidoglycan building block. Sitting on that end, they physically block both the polymerization step (transglycosylation) and the cross-linking step (transpeptidation), so the wall cannot grow. They are too large to cross the outer membrane of gram-negative bacteria.

Target: D-Ala–D-Ala terminus of peptidoglycan precursors

## Key points

- No activity against gram-negative bacteria: the molecule is too big to pass their outer membrane.
- Enterococcal resistance (VRE) comes from changing the D-Ala–D-Ala end to D-Ala–D-lactate or D-Ala–D-serine, which glycopeptides bind poorly (vanA, vanB genes).
- Rapid vancomycin infusion releases histamine from mast cells (vancomycin infusion reaction, once called «red man syndrome»): it is not an allergy and is prevented by infusing slowly.
- Oral vancomycin is not absorbed, so it is used only for Clostridioides difficile colitis.
- Dalbavancin and oritavancin have very long half-lives, allowing weekly or single-dose treatment of skin infections.

## Drugs in this class

- [**Vancomycin** An intravenous glycopeptide for serious gram-positive infections such as MRSA; given by mouth only for C. difficile… D-Ala–D-Ala terminus of the peptidoglycan precursor](https://durgical.com/en/pharmacology/vancomycin/)
- [**Dalbavancin** A long-acting lipoglycopeptide for gram-positive skin infections, including MRSA, given as one or two infusions. D-Ala–D-Ala terminus of the peptidoglycan precursor](https://durgical.com/en/pharmacology/dalbavancin/)

## Others in the class

- teicoplanin
- oritavancin (lipoglycopeptide)
- telavancin (lipoglycopeptide)

## Test yourself

Think of the answer, then tap the question to see it.

## Which molecular target do glycopeptides bind?

The D-alanyl–D-alanine end of the peptidoglycan precursor; by covering it they block polymerization and cross-linking of the cell wall.

## Why are glycopeptides useless against Escherichia coli?

They are too large to cross the outer membrane of gram-negative bacteria, so they never reach the cell wall.

## How do vancomycin-resistant enterococci escape the drug?

They replace D-Ala–D-Ala with D-Ala–D-lactate (or D-Ala–D-serine), a terminus that vancomycin binds poorly.

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Educational content on how drugs work; not a prescribing guide and no substitute for a health professional's advice. No doses are given.

Sources: Goodman & Gilman's The Pharmacological Basis of Therapeutics, 14th ed., ch. 58 (McGraw Hill, 2023); [DailyMed - VANCOMYCIN HYDROCHLORIDE injection, powder, lyophilized, for solution](https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=b79d9671-02dd-40e2-97fb-a6c7be85cda1) (DailyMed (U.S. National Library of Medicine), 2026); [RCSB PDB - 1FVM: Complex of vancomycin with DI-acetyl-LYS-D-ALA-D-ALA](https://www.rcsb.org/structure/1FVM) (RCSB Protein Data Bank, 2026).

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Representative model, for educational purposes only.

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