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Compound Detail

CHEMBL262777

VANCOMYCIN
💊 Approved Drug
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💊 Approved Drug
CN[C@H](CC(C)C)C(=O)N[C@H]1C(=O)N[C@@H](CC(N)=O)C(=O)N[C@H]2C(=O)N[C@H]3C(=O)N[C@H](C(=O)N[C@H](C(=O)O)c4cc(O)cc(O)c4-c4cc3ccc4O)[C@H](O)c3ccc(c(Cl)c3)Oc3cc2cc(c3O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@H]2C[C@](C)(N)[C@H](O)[C@H](C)O2)Oc2ccc(cc2Cl)[C@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL262777
Name VANCOMYCIN
Phase Approved
Structure Type MOL
InChI Key MYPYJXKWCTUITO-LYRMYLQWSA-N
Therapeutic ✓ Yes

Known Names

Vancomicina Vancomycin Vancomycine
16
Targets
32
Activities
4
Assay Types
30
PK Parameters
20
Publications
3
Known Names
20
Indications
1
Mechanisms

Molecular Properties

1449.3
MW (Da)

Drug Information

Molecule Type Small molecule
First Approval 1964
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral Parenteral

Flags

Black Box Warning Natural Product
USAN Stem -mycin

Extended Properties

Molecular Formula C66H75Cl2N9O24
MW 1449.27

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Peptidoglycan inhibitor INHIBITOR Peptidoglycan ✓ ✓

Indications

Bacterial Infections Diarrhea Endocarditis Enterocolitis Eye Infections Respiratory Tract Infections Sepsis Skin Diseases Skin Diseases Abscess Bacteremia Cellulitis Cholangitis, Sclerosing Clostridium Infections Clostridium Infections Conjunctivitis, Bacterial Cross Infection Diabetic Foot Gram-Positive Bacterial Infections Infections

ATC Classification

A07AA09
vancomycin
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIDIARRHEALS, INTESTINAL ANTIINFLAMMATORY/ANTIINFECTIVE AGENTS
J01XA01
vancomycin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
S01AA28
vancomycin
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Drug Warnings

Black Box Warning
teratogenicity
Country: United States

Activity Summary

IC50 19 meas. best 9.4
Ki 6 meas. best 7.8
EC50 5 meas. best 6.28
Kd 2 meas. best 5.47

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Staphylococcus aureus
CHEMBL352
 IC50 9.4 6.98 0.4 4
Norepinephrine transporter
CHEMBL304
 Ki 7.8 7.8 15.8 1
Escherichia coli
CHEMBL354
 IC50 7.4 6.06 40.0 3
Alpha-2A adrenergic receptor
CHEMBL1867
 Ki 7.3 7.3 50.1 1
Sodium-dependent serotonin transporter
CHEMBL313
 Ki 7.3 7.3 50.1 1
Streptococcus pneumoniae
CHEMBL347
 IC50 6.92 6.8767 120.0 3
Adrenergic receptor alpha-2
CHEMBL2093864
 Ki 6.9 6.9 125.9 1
Staphylococcus aureus
CHEMBL352
 EC50 6.28 6.2225 520.0 4
Enterococcus faecium
CHEMBL357
 EC50 6.22 6.22 600.0 1
Adrenergic receptor alpha-1
CHEMBL1907610
 Ki 6.0 6.0 1000.0 1
Enterococcus faecalis
CHEMBL362
 IC50 5.58 5.58 2600.0 1
Mycolicibacterium smegmatis
CHEMBL613088
 IC50 5.5 5.0767 3180.0 6
Unchecked
CHEMBL612545
 Kd 5.47 5.47 3390.0 1
Phospho-N-acetylmuramoyl-pentapeptide-transferase/UDP-N-acetylglucosamine--N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferase
CHEMBL3885618
 IC50 5.05 5.05 9000.0 1
UDP-N-acetylglucosamine--N-acetylmuramyl-(pentapeptide) pyrophosphoryl-undecaprenol N-acetylglucosamine transferase
CHEMBL3596078
 IC50 5.0 5.0 10000.0 1
Albumin
CHEMBL3253
 Kd 4.92 4.92 12000.0 1
D-alanyl-D-alanine dipeptidase
CHEMBL1681622
 Ki 4.21 4.21 62000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 78800.0 ng.hr.mL-1 Rattus norvegicus
AUC 358600.0 ng.hr.mL-1 Homo sapiens
AUC 101000.0 ng.hr.mL-1 Oryctolagus cuniculus
AUC 298800.0 ng.hr.mL-1 Oryctolagus cuniculus
AUC 1829.17 ng.hr.mL-1 Rattus norvegicus
AUC 2142.33 ng.hr.mL-1 Rattus norvegicus
AUC 58000.0 ng.hr.mL-1 Oryctolagus cuniculus
AUC 127000.0 ng.hr.mL-1 Mus musculus
AUC 261000.0 ng.hr.mL-1 Mus musculus
AUC 358600.0 ng.hr.mL-1 Homo sapiens
AUC 101.0 uM.hr/ml Oryctolagus cuniculus
AUC 5.96 ug ml-1 Staphylococcus aureus
AUC 6.65 ug ml-1 Staphylococcus aureus
AUC 391300.0 ng.hr.mL-1 -
AUC 192880.0 ng.hr.mL-1 Staphylococcus aureus
AUC 139.8 ng.hr.mL-1 Mus musculus
AUC 13715.0 ng.hr.mL-1 Mus musculus
AUC 1242.0 ng.hr.mL-1 Mus musculus
AUC 1271.0 ng.hr.mL-1 Mus musculus
CL 10.7 mL.min-1.kg-1 Rattus norvegicus
CL 1.3 mL.min-1.kg-1 Homo sapiens
CL 1.3 mL.min-1.kg-1 Homo sapiens
CL 0.3 mL.min-1.kg-1 Homo sapiens
CL 1.3 mL.min-1.kg-1 Homo sapiens
CL 11.7 mL.min-1.kg-1 Mus musculus
CL 68.7 mL.min-1.kg-1 Mus musculus
Cmax 111780.41 nM Rattus norvegicus
Cmax 26082.1 nM Rattus norvegicus
Cmax 35880.13 nM Homo sapiens
Cmax 31740.12 nM Oryctolagus cuniculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Staphylococcus aureus IC50 = 0.4 nM 9.4 Antimicrobial activity against methicillin-resistant Staphylococcus aureus ATCC ... 31287681
Norepinephrine transporter Ki = 15.85 nM 7.8 In vitro binding affinity was determined against NA (noradrenaline) reuptake sit... 11262089
Escherichia coli IC50 = 40.0 nM 7.4 Antimicrobial activity against Escherichia coli ATCC 35218 assessed as inhibitio... 31287681
Sodium-dependent serotonin transporter Ki = 50.12 nM 7.3 In vitro binding affinity was determined against serotonin reuptake site of rat ... 11262089
Alpha-2A adrenergic receptor Ki = 50.12 nM 7.3 Binding affinity for human alpha-2 adrenergic receptor expressed in CHO cell 11262089
Streptococcus pneumoniae IC50 = 120.0 nM 6.92 Antibacterial activity against Streptococcus pneumoniae ATCC 700904 32146051
Adrenergic receptor alpha-2 Ki = 125.89 nM 6.9 In vitro binding affinity against alpha-2 adrenergic receptor of rat in presence... 11262089
Streptococcus pneumoniae IC50 = 130.0 nM 6.89 Antibacterial activity against Streptococcus pneumoniae ATCC BAA1663 32146051
Streptococcus pneumoniae IC50 = 150.0 nM 6.82 Antibacterial activity against Streptococcus pneumoniae ATCC 49617 32146051
Staphylococcus aureus IC50 = 400.0 nM 6.4 Inhibitory concentration required against cell wall synthesis in Staphylococcus ... 11354364
Staphylococcus aureus EC50 = 520.0 nM 6.28 Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC ... 30392371
Staphylococcus aureus EC50 = 540.0 nM 6.27 Antibiofilm activity against Staphylococcus aureus Rosenbach ATCC 25923 after 24... 30392371
Enterococcus faecium EC50 = 600.0 nM 6.22 Antibacterial activity against Enterococcus faecium ATCC 19434 after 24 hrs by b... 30392371
Staphylococcus aureus EC50 = 670.0 nM 6.17 Antibacterial activity against Staphylococcus aureus ATCC 25923 after 6 to 8 hrs... 30392371
Staphylococcus aureus EC50 = 670.0 nM 6.17 Bactericidal activity against planktonic growth of Staphylococcus aureus Rosenba... 30392371
Staphylococcus aureus IC50 = 839.0 nM 6.08 Concentration that inhibits 50% growth of methicillin resistant Staphylococcus a... 14643347
Staphylococcus aureus IC50 = 910.0 nM 6.04 Antibacterial activity against methicillin-resistant Staphylococcus aureus ATCC ... 20973551
Adrenergic receptor alpha-1 Ki = 1000.0 nM 6.0 In vitro binding affinity against alpha-1 adrenergic receptor of rat in presence... 11262089
Enterococcus faecalis IC50 = 2600.0 nM 5.58 Compound was evaluated for inhibition of peptidoglycan synthesis in Enterococcus... 11055331
Mycolicibacterium smegmatis IC50 = 3180.0 nM 5.5 Antimycobacterial activity against Mycobacterium smegmatis grown in Luria-Bertan... 19786608

Literature References

PubMed DOI Target Context # Activities
20547791 10.1128/aac.00269-10 Staphylococcus aureus 816
- 10.6019/CHEMBL3885881 Rattus norvegicus 333
18955526 10.1128/aac.00441-08 NON-PROTEIN TARGET 166
19581457 10.1128/aac.00908-08 NON-PROTEIN TARGET 108
19433566 10.1128/aac.00183-09 Staphylococcus aureus 107
28061346 10.1016/j.ejmech.2016.12.054 Staphylococcus aureus 104
17875997 10.1128/aac.00550-07 Staphylococcus aureus 82
19015334 10.1128/aac.01009-08 Staphylococcus aureus 79
16980961 10.1038/nchembio820 Staphylococcus aureus 75
20404122 10.1128/aac.01516-09 Staphylococcus aureus 62
30347327 10.1016/j.ejmech.2018.10.039 Staphylococcus aureus 56
18710909 10.1128/aac.00676-08 Staphylococcus aureus 55
19546358 10.1128/aac.00206-09 Staphylococcus aureus 54
19289525 10.1128/aac.01135-08 Staphylococcus aureus 44
20308374 10.1128/aac.01797-09 Streptococcus pneumoniae 41
19188385 10.1128/aac.01619-08 Staphylococcus aureus 36
19933800 10.1128/aac.00434-09 Staphylococcus aureus 33
17502406 10.1128/aac.00209-07 Staphylococcus aureus 33
20585126 10.1128/aac.00452-10 Staphylococcus aureus 31
29126733 10.1016/j.ejmech.2017.10.018 Staphylococcus aureus 30

Data from ChEMBL 36 via Core Engine