Vancomycin and glycopeptides

Vancomycin (Vancocin and generics); teicoplanin (Targocid); dalbavancin (Dalvance US / Xydalba EU); oritavancin (Orbactiv, Kimyrsa); telavancin (Vibativ). The last three are "lipoglycopeptides"

Antimicrobial & antiviral

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Note on this profile. Vancomycin and its relatives are approved prescription antibiotics used in hospitals for serious Gram-positive infections. This page explains the published science. Community or self-directed use is essentially none documented. Misuse of antibiotics drives resistance and is a public-health problem, not a personal one.

Summary

Class: Glycopeptide antibiotics: a heptapeptide (seven amino acids, several non-proteinogenic and aromatic) cross-linked into a rigid tricyclic or tetracyclic scaffold and decorated with sugars. Lipoglycopeptides (dalbavancin, oritavancin, telavancin) add a lipophilic side chain. Natural products of Amycolatopsis and Actinoplanes soil bacteria, or semi-synthetic derivatives
Mechanism: Bind the D-alanyl-D-alanine end of peptidoglycan precursors, physically blocking the enzymes that build the bacterial cell wall; lipoglycopeptides additionally anchor to and disrupt the membrane
Routes studied: Intravenous (systemic infection); oral vancomycin (gut-only, for C. difficile; not absorbed); intraperitoneal, intrathecal, inhaled and intraocular in special situations
Half-life: Vancomycin ~4–6 h (normal kidneys; much longer in renal failure); teicoplanin ~70–100 h; dalbavancin ~8.5 days (~204 h); oritavancin ~245 h; telavancin ~8 h
Storage: Lyophilised vials at room temperature; reconstituted vancomycin refrigerated up to 14 days (pharmacy data) †; premixed bags per label
Regulatory status: All approved medicines; dalbavancin and oritavancin approved US 2014, EU 2015 (dalbavancin) and 2015 (oritavancin, later withdrawn from the EU market for commercial reasons †)

Doses are as reported in studies or by the community — never recommendations.

1What it is

Vancomycin was isolated in 1953 from a soil bacterium in a Borneo mud sample and approved in 1958. Early impure batches ("Mississippi mud") caused kidney and hearing damage, so it was shelved while better-tolerated penicillins dominated. It returned to prominence in the 1980s as methicillin-resistant Staphylococcus aureus (MRSA) spread, and for decades it has been the default treatment for serious MRSA infection. It is chemically a peptide, but a highly unusual one: seven amino acids, five of them aromatic, cross-linked into a cup-shaped cage and glycosylated. Human enzymes cannot break it down and the gut cannot absorb it.

Teicoplanin (1988, Europe and elsewhere; never approved in the US) is a related natural glycopeptide with a longer . The lipoglycopeptides are semi-synthetic 2000s–2010s derivatives designed for once-weekly or single-dose treatment of skin infections. Vancomycin-resistant enterococci (VRE) and intermediate-resistance staphylococci emerged in the late 1980s–1990s and are now a global concern.

2How it's thought to work

The peptide cage binds the terminal D-Ala-D-Ala of lipid II and nascent peptidoglycan chains with high affinity, sterically blocking transglycosylation and transpeptidation so the wall cannot be cross-linked. The weakened wall fails under osmotic pressure.

Because the target is outside the inner membrane but inside the outer membrane of Gram-negative bacteria, glycopeptides are too large to reach it in Gram-negatives; the spectrum is Gram-positive only.

Resistance (VanA, VanB and related gene clusters) swaps D-Ala-D-Ala for D-Ala-D-lactate, which reduces binding roughly a thousand-fold. Oritavancin and telavancin partly overcome this through a second mechanism: their lipid tail anchors them to the membrane and dimerises them, disrupting membrane potential and increasing target affinity.

Dalbavancin's lipid tail mainly serves to bind albumin, extending the to about a week.

Vancomycin caps the D-alanyl-D-alanine end of the peptidoglycan building block rather than blocking an enzyme. With the end covered, the cross-links that tie the bacterial wall together cannot be made, and the wall fails under its own pressure.Schematic — not to scale

3What the research shows

MRSA bacteraemia and endocarditis

Vancomycin has been the standard comparator in essentially every MRSA trial since the 1980s. Daptomycin was non-inferior to vancomycin plus gentamicin (Fowler 2006, NEJM). Linezolid was not superior for bacteraemia. Adjunctive combination with an anti-staphylococcal β-lactam shortened bacteraemia but increased kidney injury in CAMERA2 (Tong 2020, JAMA). Vancomycin failure rates rise when the MIC approaches 2 mg/L, and AUC-guided dosing is now recommended over trough-only dosing (Rybak 2020, Am J Health Syst Pharm — consensus guideline). [1][2][3]

Skin and skin-structure infections

Dalbavancin (DISCOVER 1 and 2, 1,312 patients; Boucher 2014, NEJM) and oritavancin (SOLO I and II, 1,987 patients; Corey 2014, NEJM) were each non-inferior to 7–10 days of twice-daily vancomycin with a single dose or two doses. Telavancin was non-inferior to vancomycin (ATLAS trials; Stryjewski 2008, Clin Infect Dis). [4][5]

Hospital-acquired and ventilator-associated pneumonia

Telavancin was non-inferior to vancomycin (ATTAIN; Rubinstein 2011, Clin Infect Dis) but with higher mortality in patients with pre-existing kidney impairment, leading to a restricted indication. Linezolid showed a higher clinical success rate than vancomycin in MRSA pneumonia in ZEPHyR (Wunderink 2012, Clin Infect Dis), though mortality was equal. [6][8]

Clostridioides difficile infection (oral vancomycin)

Oral vancomycin was superior to metronidazole for severe infection (Zar 2007, Clin Infect Dis) and is a guideline first-line option alongside fidaxomicin. The drug stays in the gut lumen, which is the whole point. [7]

Osteomyelitis and prosthetic-joint infection

Dalbavancin has observational and small randomised support for bone and joint infection (Rappo 2019, Open Forum Infect Dis), and is widely used off-label for this.

4Reported side effects and interactions

Literature-reported

Nephrotoxicity is vancomycin's main problem: acute kidney injury in roughly 5–15% of courses, rising sharply with troughs above 15–20 mg/L, with piperacillin-tazobactam co-therapy, with aminoglycosides, and in critical illness. Vancomycin infusion reaction (formerly "red man syndrome"): flushing, itching and hypotension from histamine release when infused too fast; prevented by infusing over at least 60 minutes. Ototoxicity is rare with modern preparations. Neutropenia and thrombocytopenia with prolonged courses; drug fever; DRESS and linear IgA bullous dermatosis are rare but documented. Teicoplanin causes less kidney injury but more drug fever and rash. Dalbavancin and oritavancin: nausea, headache, infusion reactions; oritavancin artificially prolongs laboratory clotting times (aPTT, PT/INR) for up to 5 days by binding phospholipid reagents, so heparin monitoring by aPTT is unreliable. Telavancin: taste disturbance, foamy urine, nephrotoxicity, QT prolongation, and a boxed warning against use in pregnancy from animal developmental data.

Community-reported

none documented.

Theoretical. selection of VRE and vancomycin-intermediate S. aureus with widespread use.

Interactions. additive nephrotoxicity with aminoglycosides, piperacillin-tazobactam, amphotericin B, NSAIDs, contrast and ciclosporin; additive ototoxicity with loop diuretics and aminoglycosides; oritavancin interferes with coagulation assays and inhibits CYP2C9/2C19 and induces CYP3A4 modestly, with a warning about warfarin.

Markers researchers commonly monitor

Per guidelines and labels:

Marker	Why it's watched
Serum vancomycin levels (AUC/MIC or trough)	the central monitoring tool; current consensus targets an AUC/MIC of 400–600 for serious MRSA infection, using Bayesian software where available.
Serum creatinine and eGFR	at baseline and at least twice weekly during IV vancomycin, more often in critical illness.
Full blood count	neutropenia and thrombocytopenia with courses longer than about a week.
Blood cultures	repeated until clearance in bacteraemia.
Audiometry	only in prolonged high-dose therapy or with other ototoxic drugs.
Coagulation tests	unreliable for up to 5 days after oritavancin; relevant if heparin is being monitored.
Teicoplanin trough levels	in deep-seated infection, targeting 20–40 mg/L †.

Free for everyone. Safety information is never behind a paywall.

5Reconstitution and handling

Hospital-pharmacy products. Vancomycin vials (500 mg to 10 g) are with sterile water and diluted to 5 mg/mL or less for infusion over at least 60 minutes, or longer for doses above 1 g; continuous infusion is used in some centres. Lipoglycopeptides are reconstituted and diluted in 5% dextrose (oritavancin must not be mixed with saline) and infused over 30 minutes (dalbavancin) to 3 hours (oritavancin). Oral vancomycin is given as capsules or a pharmacy-prepared solution. The calculator does not apply.

6Commonly studied alongside

Compared head-to-head with daptomycin, linezolid, ceftaroline and tedizolid. Combined with rifampicin or gentamicin in device infections, and with β-lactams in MRSA bacteraemia trials. Related peptide antimicrobials: daptomycin, polymyxins, bacitracin, gramicidin, and the echinocandins (profile #226) for fungi.

Informational cross-links. Not stack recommendations.

7Regulatory status by region

Region	Status (checked —)
United States	Vancomycin FDA-approved (1958, many generics; oral capsules for C. difficile). Dalbavancin (2014), oritavancin (2014; Kimyrsa one-hour formulation 2021) and telavancin (2009) approved. Teicoplanin never approved
European Union	Vancomycin and teicoplanin authorised (teicoplanin nationally since 1988). Dalbavancin (Xydalba) EMA-authorised 2015. Oritavancin authorised 2015, marketing authorisation later withdrawn by the company †. Telavancin authorisation withdrawn 2018 †
United Kingdom	Vancomycin, teicoplanin and dalbavancin MHRA-licensed
Australia	Vancomycin and teicoplanin TGA-registered. Dalbavancin †; oritavancin and telavancin not registered †
South Africa	Vancomycin and teicoplanin SAHPRA-registered. Lipoglycopeptides †
Sport (WADA)	Not prohibited

8Open questions

Is AUC-guided dosing truly superior to trough-based dosing for outcomes, or only for reducing kidney injury?
Whether single-dose lipoglycopeptides can safely replace weeks of IV therapy for bone, joint and endovascular infection; are underway.
The clinical significance of "MIC creep" in S. aureus, and when to abandon vancomycin for an alternative.

9References

1Rybak MJ et al. (2020). Therapeutic monitoring of vancomycin for serious methicillin-resistant Staphylococcus aureus infections: a revised consensus guideline and review. Am J Health Syst Pharm. PubMed
2Fowler VG Jr et al. (2006). Daptomycin versus standard therapy for bacteremia and endocarditis caused by Staphylococcus aureus. NEJM. PubMed · DOI
3Tong SYC et al. (2020). Effect of vancomycin or daptomycin with vs without an antistaphylococcal β-lactam on mortality, bacteremia, relapse, or treatment failure in patients with MRSA bacteremia (CAMERA2). JAMA. PubMed · DOI
4Boucher HW et al. (2014). Once-weekly dalbavancin versus daily conventional therapy for skin infection (DISCOVER 1 and 2). NEJM. PubMed · DOI
5Corey GR et al. (2014). Single-dose oritavancin in the treatment of acute bacterial skin infections (SOLO I). NEJM. PubMed · DOI
6Rubinstein E et al. (2011). Telavancin versus vancomycin for hospital-acquired pneumonia due to Gram-positive pathogens (ATTAIN). Clin Infect Dis. PubMed · DOI
7Zar FA et al. (2007). A comparison of vancomycin and metronidazole for the treatment of Clostridium difficile-associated diarrhea, stratified by disease severity. Clin Infect Dis. PubMed · DOI
8Wunderink RG et al. (2012). Linezolid in methicillin-resistant Staphylococcus aureus nosocomial pneumonia: a randomized, controlled study (ZEPHyR). Clin Infect Dis. PubMed · DOI
9Levine DP (2006). Vancomycin: a history. Clin Infect Dis. PubMed · DOI
10Zeng D et al. (2016). Approved glycopeptide antibacterial drugs: mechanism of action and resistance. Cold Spring Harb Perspect Med. PubMed · DOI

References are being resolved to PubMed/DOI identifiers; links search PubMed for the citation until then.

† Being confirmed by our reviewers against current sources.

10Community

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Self-reported side effects Phase 2

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11Page history

31 Oct 2026Profile published — awaiting medical review

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