Vancomycin

Summary

Vancomycin (CHEMBL262777) is an approved small-molecule antimicrobial agent (ATC S01AA28); indicated across 52 conditions including skin disorder and bacterial infectious disease.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: S01AA28 (+2 more)
• Indications: 52 conditions
• Clinical trials: 326
• Chemistry: 1449.2 Da · C66H75Cl2N9O24

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL262777
Name	Vancomycin
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	14969
ChEBI	CHEBI:28001
ATC	S01AA28, A07AA09, J01XA01
Molecular formula	C66H75Cl2N9O24
Molecular weight	1449.2
InChIKey	MYPYJXKWCTUITO-LYRMYLQWSA-N

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

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-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

ChEBI definition: A complex glycopeptide from Streptomyces orientalis. It inhibits a specific step in the synthesis of the peptidoglycan layer in the Gram-positive bacteria Staphylococcus aureus and Clostridium difficile.

Pharmacological roles (ChEBI): antimicrobial agent, antibacterial drug.

Other ChEBI roles (chemical / environmental): bacterial metabolite.

Also known as: Vancomicina, Vancomycin, Vancomycine, Tuberactinomycin Analogue, Viomycin derivative, vancomycin, Mannopeptimycin Glycopeptide, Vancomycin Aglycon Analogue, Glycopeptide antibiotic, Mannopeptimycin glycopeptide analogue, Chloroorienticin B derivative, Poly ethylene glycol derivative

Parent form; salt/anhydrous children: CHEMBL1200628

Patent coverage: 30,077 distinct patent families (100,538 SureChEMBL compound mentions), from 4 matched compound structure(s). One matched structure accounts for 99,340 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 8 (assay-derived). Sample: D-alanyl-D-alanine dipeptidase, Alpha-2A adrenergic receptor, Adrenergic receptor alpha-1, Adrenergic receptor alpha-2, Sodium-dependent serotonin transporter, Albumin, UDP-N-acetylglucosamine–N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferase, Phospho-N-acetylmuramoyl-pentapeptide-transferase/UDP-N-acetylglucosamine–N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferase.

Bioactivity

ChEMBL activities: 6 potent at pChembl ≥ 5 of 8 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P31652	7.3	Ki	50.12	nM	CHEMBL_ACT_251025
ADRA2A	7.3	Ki	50.12	nM	CHEMBL_ACT_251027
P19328	6.9	Ki	125.9	nM	CHEMBL_ACT_251024
P15823	6	Ki	1000	nM	CHEMBL_ACT_251023
P0A6W3	5.05	IC50	9000	nM	CHEMBL_ACT_15663596
P17443	5	IC50	10000	nM	CHEMBL_ACT_15663645

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

52 indications (9 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
skin disorder	4	MONDO:0005093	EFO:0000701
bacterial infectious disease	4	MONDO:0005113	EFO:0000771
diarrheal disease	4	MONDO:0001673	HP:0002014
eye infectious disorder	4	MONDO:0043885	EFO:1001888
endocarditis	4	MONDO:0005025	MONDO:0000565
enterocolitis	4	MONDO:0009172	EFO:1001481
respiratory tract infectious disorder	4	MONDO:0024355	MONDO:0024355
cellulitis	3	MONDO:0005230	EFO:0003035
sclerosing cholangitis	3	MONDO:0018646	EFO:0004268
bacterial pneumonia	3	MONDO:0004652	EFO:1001272
bacterial conjunctivitis	3	MONDO:0006668	EFO:1000829
abscess	3	MONDO:0005227	EFO:0003030
bacterial infectious disease with sepsis	3	MONDO:0005229	EFO:0003033
osteomyelitis	3	MONDO:0005246	EFO:0003102
pneumonia	3	MONDO:0005249	EFO:0003106
staphylococcus aureus infection	3	MONDO:0005545	EFO:0005681
Clostridium infectious disease	3	MONDO:0024388	EFO:1000874
staphylococcal infection	3	MONDO:0024313	EFO:1001849
gram-positive bacterial infections	3	MONDO:0021679	MONDO:0021679
nosocomial infection	3	MONDO:0043544	MONDO:0043544
ulcerative colitis	2	MONDO:0005101	EFO:0000729
Crohn disease	2	MONDO:0005011	EFO:0000384
obesity disorder	2	MONDO:0011122	EFO:0001073
chronic kidney disease	2	MONDO:0005300	EFO:0003884
graft versus host disease	2	MONDO:0013730	EFO:0004599
prediabetes syndrome	2	MONDO:0006920	EFO:1001121
constipation disorder	2	MONDO:0002203	HP:0002019
hepatocellular carcinoma	2	MONDO:0007256	EFO:0000182
staphylococcal pneumonia	2	MONDO:0005970	EFO:0007496
arthropathy	2	MONDO:0006816	HP:0003040
cystic fibrosis	2	MONDO:0009061	MONDO:0009061
hematopoietic and lymphoid system neoplasm	2	MONDO:0002334	MONDO:0044881
injury	2	MONDO:0021178	EFO:0000546
bone fracture	2	MONDO:0005315	EFO:0003931
autism spectrum disorder	1	MONDO:0005258	EFO:0003756
metastatic melanoma	1	MONDO:0005191	EFO:0002617
non-small cell lung carcinoma	1	MONDO:0005233	EFO:0003060
infectious peritonitis	1	MONDO:0004522	EFO:0008588
kidney failure	1	MONDO:0001106	EFO:1002048
sinusitis	1	MONDO:0005961	EFO:0007486
osteoarthritis	1	MONDO:0005178	MONDO:0005178
multiple sclerosis	1	MONDO:0005301	MONDO:0005301

10 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 326.

Phase distribution

Phase	Trials
PHASE4	82
Not specified	64
PHASE3	62
PHASE2	61
PHASE1	30
PHASE2/PHASE3	14
PHASE1/PHASE2	8
EARLY_PHASE1	5

Top trials by phase / activity

NCT	Phase	Status	Title
NCT02096536	PHASE4	RECRUITING	Exploring Vancomycin Disposition in Neonates
NCT03765567	PHASE4	RECRUITING	Placement of Antibiotic Powder in Wounds During the Emergency Room
NCT04825522	PHASE4	RECRUITING	The Effect of Intrawound Vancomycin Powder in Spine Surgery
NCT05137119	PHASE4	RECRUITING	Staphylococcus Aureus Network Adaptive Platform Trial
NCT05571722	PHASE4	RECRUITING	Linezolid or Vancomycin Surgical Site Infection Prophylaxis
NCT06148025	PHASE4	RECRUITING	Antibiotics and Vaccine Immune Responses Study
NCT06384651	PHASE4	RECRUITING	Intraosseous vs. Intravenous Vancomycin Administration in Total Ankle Arthroplasty
NCT06504992	PHASE4	NOT_YET_RECRUITING	Powdered Intrawound Vancomycin in Open Fractures Trial
NCT06567808	PHASE4	NOT_YET_RECRUITING	Prevention of Infections in Cardiac Surgery (PICS): a Cluster-randomized Factorial Cross-over Trial
NCT06637332	PHASE4	RECRUITING	Daptomycin vs. Vancomycin for the Treatment of Methicillin Resistant S. Aureus Bacteremia
NCT06794944	PHASE4	NOT_YET_RECRUITING	Use of Fidaxomicin Compared to Vancomycin for Decolonization of C. Difficile in Patients With Inflammatory Bowel Disease
NCT06954129	PHASE4	RECRUITING	A Pragmatic Clinical Trial Comparing the Risk of Acute Kidney Injury During Treatment With Vancomycin and Piperacillin-Tazobactam vs. Vancomycin and Cefepime in Hospitalized Patients
NCT07220967	PHASE4	RECRUITING	A Study of Antibiotic Delivery to Prevent Infection After Breast Tissue Expander Placement
NCT07282782	PHASE4	RECRUITING	A Prospective, Randomized Parallel Group Study of the Efficacy of Vancomycin Administered Through Intraarticular Injection Versus Intraosseous Injection Versus Intravenous Infusion in Patients Undergoing Total Knee Arthroplasty
NCT07338773	PHASE4	RECRUITING	Intraosseous vs. Intravenous Vancomycin Prophylaxis for Diabetic Foot Amputations: A Randomized Trial
NCT07547826	PHASE4	NOT_YET_RECRUITING	Efficacy and Cost-Effectiveness of Topical Vancomycin Powder in Preventing Pediatric Ventriculoperitoneal Shunt Infections Across Different Etiologies
NCT00084266	PHASE4	COMPLETED	Nosocomial Pneumonia With Suspected Or Proven Methicillin-Resistant Staphylococcus Aureus (MRSA)
NCT00087490	PHASE4	COMPLETED	Skin Structure Infections With Suspected or Proven Methicillin-Resistant Staphylococcus Aureus (MRSA)
NCT00281281	PHASE4	COMPLETED	Pharmacokinetics of Vancomycin in Adults Receiving ECMO
NCT00295178	PHASE4	COMPLETED	Study Comparing CUBICIN® (Daptomycin for Injection) With Vancomycin in Cellulitis or Erysipelas
NCT00304811	PHASE4	COMPLETED	Vancomycin vs. Vancomycin Plus Gentamycin in Treatment of MRSA Infection
NCT00454272	PHASE4	COMPLETED	Comparison of Teicoplanin and Vancomycin in Initial Empirical Antibiotic Regimen for Febrile Neutropenic Patients
NCT00572559	PHASE4	COMPLETED	Microbiologic Response With Linezolid And Vancomycin In Ventilator-Associated Pneumonia Due To Methicillin Resistant Staphylococcus Aureus
NCT00871104	PHASE4	COMPLETED	Fosfomycin Plus Imipenem for Treatment of Infective Endocarditis
NCT01104662	PHASE4	TERMINATED	Study of Daptomycin Safety and Efficacy for Complicated Skin and Skin Structure Infections (cSSSI) and Bacteremia in Renal Impairment
NCT01133600	PHASE4	TERMINATED	Outpatient Treatment of Gram Positive Wound Infections in the Diabetic Foot: A Pharmaco-economic Comparison of Daptomycin vs. Vancomycin Based Regimens
NCT01175707	PHASE4	TERMINATED	Study Comparing Cubicin With Vancomycin in Treatment of Participants With Complicated Skin and Skin Structure Infections in a Home Infusion Setting
NCT01196169	PHASE4	TERMINATED	Daptomycin Use for Antimicrobial Prophylaxis in Methicillin Resistant Staphylococcus Aureus (MRSA) Colonized Adult Patients Undergoing Primary Elective Hip, Knee, or Shoulder Arthroplasty
NCT01287832	PHASE4	TERMINATED	Vancomycin Versus Daptomycin for the Treatment of Methicillin-resistant Staphylococcus Aureus Bacteremia Due to Isolates With High Vancomycin Minimum Inhibitory Concentrations (MICs)
NCT01419184	PHASE4	COMPLETED	Daptomycin Versus Vancomycin in Participants With Skin Infections Due to MRSA
NCT01549613	PHASE4	COMPLETED	Evaluation of Daptomycin for the Emergency Department Treatment of Complicated Skin and Skin Structure Infections
NCT01626560	PHASE4	COMPLETED	The Effects of Daptomycin and Cytokines Production in Comparison With Vancomycin
NCT01669980	PHASE4	COMPLETED	Safety and Efficacy Study of Ceftaroline Versus a Comparator in Pediatric Subjects With Complicated Community Acquired Pneumonia (CABP)
NCT01734694	PHASE4	TERMINATED	Safety and Efficacy of Strategy to Prevent Drug-Induced Nephrotoxicity in High-Risk Patients
NCT01775397	PHASE4	TERMINATED	A Post-marketing, Blinded Study to Investigate How Effective Fidaxomicin is Compared to Vancomycin in the Sustained Cure of Clostridium Difficile Infection in Adults That Are Receiving Therapy to Suppress the Immune System
NCT01818141	PHASE4	COMPLETED	Study to Assess Inhibition of Spore Production in Patients With C. Difficile Infections: Fidaxomicin Versus Vancomycin
NCT01820026	PHASE4	UNKNOWN	Empirical vs 2nd Line Antibiotic Therapy in Health-care Associated Infections in Cirrhosis
NCT01952834	PHASE4	COMPLETED	Effect of Probiotic Supplementation on Endothelial Function
NCT01977989	PHASE4	UNKNOWN	Vancomycin in Spine Surgery
NCT02057198	PHASE4	COMPLETED	Impact of Oral Antibiotic Treatment on C. Difficile

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 2 clinical and 45 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).