CHEBI:28001 - vancomycin

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ChEBI Name vancomycin
ChEBI ID CHEBI:28001
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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:49941, CHEBI:9931, CHEBI:27276
Supplier Information No supplier information found for this compound.
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Vancomycin is a glycopeptide antibiotic medication used to treat certain bacterial infections. It is administered intravenously (injection into a vein) to treat complicated skin infections, bloodstream infections, endocarditis, bone and joint infections, and meningitis caused by methicillin-resistant Staphylococcus aureus. Blood levels may be measured to determine the correct dose. Vancomycin is also taken orally (by mouth) to treat Clostridioides difficile infections. When taken orally, it is poorly absorbed. Common side effects include pain in the area of injection and allergic reactions. Occasionally, hearing loss, low blood pressure, or bone marrow suppression occur. Safety in pregnancy is not clear, but no evidence of harm has been found, and it is likely safe for use when breastfeeding. It is a type of glycopeptide antibiotic and works by blocking the construction of a cell wall. Vancomycin was approved for medical use in the United States in 1958. It is on the World Health Organization's List of Essential Medicines. The WHO classifies vancomycin as critically important for human medicine. It is available as a generic medication. Vancomycin is made by the soil bacterium Amycolatopsis orientalis.
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Formula C66H75Cl2N9O24
Net Charge 0
Average Mass 1449.25336
Monoisotopic Mass 1447.43020
InChI InChI=1S/C66H75Cl2N9O24/c1-23(2)12-34(71-5)58(88)76-49-51(83)26-7-10-38(32(67)14-26)97-40-16-28-17-41(55(40)101-65-56(54(86)53(85)42(22-78)99-65)100-44-21-66(4,70)57(87)24(3)96-44)98-39-11-8-27(15-33(39)68)52(84)50-63(93)75-48(64(94)95)31-18-29(79)19-37(81)45(31)30-13-25(6-9-36(30)80)46(60(90)77-50)74-61(91)47(28)73-59(89)35(20-43(69)82)72-62(49)92/h6-11,13-19,23-24,34-35,42,44,46-54,56-57,65,71,78-81,83-87H,12,20-22,70H2,1-5H3,(H2,69,82)(H,72,92)(H,73,89)(H,74,91)(H,75,93)(H,76,88)(H,77,90)(H,94,95)/t24-,34+,35-,42+,44-,46+,47+,48-,49+,50-,51+,52+,53+,54-,56+,57+,65-,66-/m0/s1
InChIKey MYPYJXKWCTUITO-LYRMYLQWSA-N
SMILES CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)c2ccc(Oc3cc4cc(Oc5ccc(cc5Cl)[C@@H](O)[C@@H]5NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(N)=O)NC1=O)c1ccc(O)c(c1)-c1c(O)cc(O)cc1[C@H](NC5=O)C(O)=O)c3O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1)c(Cl)c2
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
bacterial metabolite
Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
antimicrobial agent
A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.
Application(s): antibacterial drug
A drug used to treat or prevent bacterial infections.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing vancomycin (CHEBI:28001) has functional parent vancomycin aglycone (CHEBI:47724)
vancomycin (CHEBI:28001) has role antibacterial drug (CHEBI:36047)
vancomycin (CHEBI:28001) has role antimicrobial agent (CHEBI:33281)
vancomycin (CHEBI:28001) has role bacterial metabolite (CHEBI:76969)
vancomycin (CHEBI:28001) is a glycopeptide (CHEBI:24396)
vancomycin (CHEBI:28001) is conjugate base of vancomycin(1+) (CHEBI:76842)
Incoming telavancin (CHEBI:71229) has functional parent vancomycin (CHEBI:28001)
vancomycin(1+) (CHEBI:76842) is conjugate acid of vancomycin (CHEBI:28001)
IUPAC Name
(3S,6R,7R,11R,23S,26S,30aS,36R,38aR)-44-[2-O-(3-amino-2,3,6-trideoxy-3-C-methyl-α-L-lyxo-hexopyranosyl)-β-D-glucopyranosyloxy]-3-(carbamoylmethyl)-10,19-dichloro-2,3,4,5,6,7,23,25,26,36,37,38,38a-tetradecahydro-7,22,28,30,32-pentahydroxy-6-(N-methyl-D-leucyl)-2,5,24,38,39-pentaoxo-1H,22H-23,36-(epiminomethano)-8,11:18,21-dietheno-13,16:31,35-di(metheno)[1,6,9]oxadiazacyclohexadecino[4,5-m][10,2,16]benzoxadiazacyclotetracosine-26-carboxylic acid
INNs Sources
vancomicina ChemIDplus
vancomycin ChemIDplus
vancomycine ChemIDplus
vancomycinum ChemIDplus
Synonyms Sources
(1S,2R,18R,22S,25R,28R,40S)-22-(2-amino-2-oxoethyl)-48-[2-O-(3-amino-2,3,6-trideoxy-3-methyl-α-L-lyxo-hexopyranosyl)-β-D-glucopyranosyloxy]-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[(N-methyl-D-leucyl)amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[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),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid ChEBI
(2.2Sp,3.5Sa,2.6Sp)-O4.2,C3.4:C5.4,O4.6:C3.5,C2.7-tricyclo[N-methyl-D-leucyl-3-chloro-(R)-β-hydroxy-D-tyrosyl-L-asparaginyl-D-2-(4-{[2-O-(3-amino-2,3,6-trideoxy-3-C-methyl-α-L-lyxo-hexopyranosyl)-β-D-glucopyranosyl]oxy}phenyl)glycyl-D-2-(4-hydroxyphenyl)glycyl-3-chloro-(R)-β-hydroxy-L-tyrosyl-L-2-(3,5-dihydroxyphenyl)glycine] JCBN
vancomicin
Note: (2015-03-23) An uncommon spelling variant.
ChEBI
Vancomycin KEGG COMPOUND
VANCOMYCIN PDBeChem
Brand Name Source
Vancocin KEGG DRUG
Manual Xrefs Databases
2807 DrugCentral
C00016052 KNApSAcK
C06689 KEGG COMPOUND
CPD-12245 MetaCyc
D00212 KEGG DRUG
DB00512 DrugBank
US3067099 Patent
VAN PDBeChem
Vancomycin Wikipedia
View more database links
Registry Numbers Types Sources
1404-90-6 CAS Registry Number KEGG COMPOUND
1404-90-6 CAS Registry Number ChemIDplus
3132 Reaxys Registry Number Reaxys
Citations
Hwang JH, Lee JH, Moon MK, Kim JS, Won KS, Lee CS (2012)
The usefulness of arbekacin compared to vancomycin.
European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology 31, 1663-1666 [PubMed:22124537]
[show Abstract]
Popescu M, Vialet R, Loundou A, Peyron F, Buès-Charbit M (2011)
[Imprecision of vancomycin prepared for intravenous administration at the bedside in a neonatal intensive care unit].
Annales francaises d'anesthesie et de reanimation 30, 726-729 [PubMed:21719238]
[show Abstract]
Entenza JM, Veloso TR, Vouillamoz J, Giddey M, Moreillon P (2011)
Failure of vancomycin continuous infusion against experimental endocarditis due to vancomycin-intermediate Staphylococcus aureus.
Antimicrobial agents and chemotherapy 55, 385-387 [PubMed:20956604]
[show Abstract]
Zegbeh H, Bleyzac N, Berhoune C, Bertrand Y (2011)
[Vancomycin: what dosages are needed to achieve efficacy in paediatric hematology/oncology?].
Archives de pediatrie : organe officiel de la Societe francaise de pediatrie 18, 850-855 [PubMed:21664803]
[show Abstract]
Schweizer ML, Furuno JP, Harris AD, Johnson JK, Shardell MD, McGregor JC, Thom KA, Cosgrove SE, Sakoulas G, Perencevich EN (2011)
Comparative effectiveness of nafcillin or cefazolin versus vancomycin in methicillin-susceptible Staphylococcus aureus bacteremia.
BMC infectious diseases 11, 279 [PubMed:22011388]
[show Abstract]
Xing B, Jiang T, Bi W, Yang Y, Li L, Ma M, Chang CK, Xu B, Yeow EK (2011)
Multifunctional divalent vancomycin: the fluorescent imaging and photodynamic antimicrobial properties for drug resistant bacteria.
Chemical communications (Cambridge, England) 47, 1601-1603 [PubMed:21109901]
[show Abstract]
Jobson S, Moise PA, Eskandarian R (2011)
Retrospective observational study comparing vancomycin versus daptomycin as initial therapy for Staphylococcus aureus infections.
Clinical therapeutics 33, 1391-1399 [PubMed:22015328]
[show Abstract]
Lazar HL, Barlam T, Cabral H (2011)
The effect of topical vancomycin applied to sternotomy incisions on postoperative serum vancomycin levels.
Journal of cardiac surgery 26, 461-465 [PubMed:21951032]
[show Abstract]
Commandeur D, Giacardi C, Danguy Des Deserts M, Huynh S, Buguet-Brown ML, Ould-Ahmed M, Drouillard I (2011)
[Monitoring vancomycin in an intensive care unit: A retrospective survey on 66 patients].
Medecine et maladies infectieuses 41, 410-414 [PubMed:21458937]
[show Abstract]
van Maarseveen EM, Man WH, Touw DJ, Bouma AW, van Zanten AR (2011)
[Continuous and intermittent infusion of vancomycin equally effective: review of the literature].
Nederlands tijdschrift voor geneeskunde 155, A2667 [PubMed:22027450]
[show Abstract]
Jelassi ML, Benlmouden A, Lefeuvre S, Mainardi JL, Billaud EM, Groupe Suivi Therapeutique Pharmacologique de la Societe Francaise de Pharmacologie et de Therapeutique (2011)
[Level of evidence for therapeutic drug monitoring of vancomycin].
Therapie 66, 29-37 [PubMed:21466775]
[show Abstract]
Shah RA, Musthaq A, Khardori N (2009)
Vancomycin-induced thrombocytopenia in a 60-year-old man: a case report.
Journal of medical case reports 3, 7290 [PubMed:19830166]
[show Abstract]
Kaakeh Y, Phan H, DeSmet BD, Pasko DA, Glenn DK, Stevenson JG (2008)
Enhanced photoemission spectroscopy for verification of high-risk i.v. medications.
American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 65, 49-54 [PubMed:18159039]
[show Abstract]
Yao N, Wu CY, Xiao W, Lam KS (2008)
Discovery of high-affinity peptide ligands for vancomycin.
Biopolymers 90, 421-432 [PubMed:18260149]
[show Abstract]
Stryjewski ME, Chambers HF (2008)
Skin and soft-tissue infections caused by community-acquired methicillin-resistant Staphylococcus aureus.
Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 46 Suppl 5, S368-77 [PubMed:18462092]
[show Abstract]
Tverdek FP, Crank CW, Segreti J (2008)
Antibiotic therapy of methicillin-resistant Staphylococcus aureus in critical care.
Critical care clinics 24, 249-60, vii-viii [PubMed:18361944]
[show Abstract]
Chaudhuri A, Martinez-Martin P, Kennedy PG, Andrew Seaton R, Portegies P, Bojar M, Steiner I, EFNS Task Force (2008)
EFNS guideline on the management of community-acquired bacterial meningitis: report of an EFNS Task Force on acute bacterial meningitis in older children and adults.
European journal of neurology 15, 649-659 [PubMed:18582342]
[show Abstract]
Zhang LF, Yang DJ, Chen HC, Sun R, Xu L, Xiong ZC, Govender T, Xiong CD (2008)
An ionically crosslinked hydrogel containing vancomycin coating on a porous scaffold for drug delivery and cell culture.
International journal of pharmaceutics 353, 74-87 [PubMed:18162343]
[show Abstract]
Japoni A, Farshad S, Alborzi A, Kalani M, Rafaatpour N, Oboodi B, Pourabbas B (2008)
Epidemiology and antibacterial susceptibility patterns of bloodstream infections, 2001-2004: an experience with BACTEC 9240 in Southern Iran.
Pakistan journal of biological sciences : PJBS 11, 422-427 [PubMed:18817166]
[show Abstract]
Khorvash F, Mostafavizadeh K, Mobasherizadeh S, Behjati M, Naeini AE, Rostami S, Abbasi S, Memarzadeh M, Khorvash FA (2008)
Antimicrobial susceptibility pattern of microorganisms involved in the pathogenesis of surgical site infection (SSI); A 1 year of surveillance.
Pakistan journal of biological sciences : PJBS 11, 1940-1944 [PubMed:18983037]
[show Abstract]
Oldfield EC (2008)
Infectious disease. Vancomycin should be the drug of choice for severe Clostridium difficile-associated diarrhea.
Reviews in gastroenterological disorders 8, 270-271 [PubMed:19107100]
Radin S, Ducheyne P (2007)
Controlled release of vancomycin from thin sol-gel films on titanium alloy fracture plate material.
Biomaterials 28, 1721-1729 [PubMed:17184835]
[show Abstract]
Lodise TP, McKinnon PS (2007)
Burden of methicillin-resistant Staphylococcus aureus: focus on clinical and economic outcomes.
Pharmacotherapy 27, 1001-1012 [PubMed:17594206]
[show Abstract]
Hong S, Valderrama E, Mattana J, Shah HH, Wagner JD, Esposito M, Singhal PC (2007)
Vancomycin-induced acute granulomatous interstitial nephritis: therapeutic options.
The American journal of the medical sciences 334, 296-300 [PubMed:18030187]
[show Abstract]
Maclayton DO, Hall RG (2007)
Pharmacologic treatment options for nosocomial pneumonia involving methicillin-resistant Staphylococcus aureus.
The Annals of pharmacotherapy 41, 235-244 [PubMed:17299012]
[show Abstract]
Kitazawa T, Ota Y, Kada N, Morisawa Y, Yoshida A, Koike K, Kimura S (2006)
Successful vancomycin desensitization with a combination of rapid and slow infusion methods.
Internal medicine (Tokyo, Japan) 45, 317-321 [PubMed:16596002]
[show Abstract]
Kleinschmidt SL, Munckhof WJ, Nimmo GR (2006)
In vitro exposure of community-associated methicillin-resistant Staphylococcus aureus (MRSA) strains to vancomycin: does vancomycin resistance occur?
International journal of antimicrobial agents 27, 168-170 [PubMed:16420976]
[show Abstract]
Bingen E, Mariani-Kurkdjian P, Nebbad B (2006)
[Optimal vancomycin serum level in Staphylococcus aureus infections?].
Medecine et maladies infectieuses 36, 439-442 [PubMed:17027219]
[show Abstract]
Cadle RM, Mansouri MD, Darouiche RO (2006)
Vancomycin-induced elevation of liver enzyme levels.
The Annals of pharmacotherapy 40, 1186-1189 [PubMed:16720708]
[show Abstract]
Ariano RE, Fine A, Sitar DS, Rexrode S, Zelenitsky SA (2005)
Adequacy of a vancomycin dosing regimen in patients receiving high-flux hemodialysis.
American journal of kidney diseases : the official journal of the National Kidney Foundation 46, 681-687 [PubMed:16183423]
[show Abstract]
de Macedo JL, Santos JB (2005)
Bacterial and fungal colonization of burn wounds.
Memorias do Instituto Oswaldo Cruz 100, 535-539 [PubMed:16184232]
[show Abstract]
Samra Z, Ofer O, Shmuely H (2005)
Susceptibility of methicillin-resistant Staphylococcus aureus to vancomycin, teicoplanin, linezolid, pristinamycin and other antibiotics.
The Israel Medical Association journal : IMAJ 7, 148-150 [PubMed:15792257]
[show Abstract]
Mory F, Fougnot S, Rabaud C, Schuhmacher H, Lozniewski A (2005)
In vitro activities of cefotaxime, vancomycin, quinupristin/dalfopristin, linezolid and other antibiotics alone and in combination against Propionibacterium acnes isolates from central nervous system infections.
The Journal of antimicrobial chemotherapy 55, 265-268 [PubMed:15590714]
[show Abstract]
Kimura T, Sunakawa K, Matsuura N, Kubo H, Shimada S, Yago K (2004)
Population pharmacokinetics of arbekacin, vancomycin, and panipenem in neonates.
Antimicrobial agents and chemotherapy 48, 1159-1167 [PubMed:15047516]
[show Abstract]
Babalola CP, Patel KB, Nightingale CH, Nicolau DP (2004)
Synergistic activity of vancomycin and teicoplanin alone and in combination with streptomycin against Enterococcus faecalis strains with various vancomycin susceptibilities.
International journal of antimicrobial agents 23, 343-348 [PubMed:15081082]
[show Abstract]
King DW, Smith MA (2004)
Proliferative responses observed following vancomycin treatment in renal proximal tubule epithelial cells.
Toxicology in vitro : an international journal published in association with BIBRA 18, 797-803 [PubMed:15465645]
[show Abstract]
Wunderink RG, Rello J, Cammarata SK, Croos-Dabrera RV, Kollef MH (2003)
Linezolid vs vancomycin: analysis of two double-blind studies of patients with methicillin-resistant Staphylococcus aureus nosocomial pneumonia.
Chest 124, 1789-1797 [PubMed:14605050]
[show Abstract]
Pituch H, Obuch-Woszczatyński P, Glinka D, Łazińska B, Meisel-Mikołajczyk F, Łuczak M (2003)
[Assessment of susceptibility to metronidazole and vancomycin of Clostridium difficile strains isolated between 1998-2002].
Medycyna doswiadczalna i mikrobiologia 55, 253-258 [PubMed:14702667]
[show Abstract]
Du B, Chen DC, Liu DW (2003)
[Efficacy and nephrotoxicity of vancomycin in the treatment of Gram positive infections].
Zhongguo wei zhong bing ji jiu yi xue = Chinese critical care medicine = Zhongguo weizhongbing jijiuyixue 15, 32-34 [PubMed:12852813]
[show Abstract]
Blum R, Seymour JF, Toner G (2002)
Significant impairment of high-dose methotrexate clearance following vancomycin administration in the absence of overt renal impairment.
Annals of oncology : official journal of the European Society for Medical Oncology 13, 327-330 [PubMed:11886013]
[show Abstract]
Peláez T, Alcalá L, Alonso R, Rodríguez-Créixems M, García-Lechuz JM, Bouza E (2002)
Reassessment of Clostridium difficile susceptibility to metronidazole and vancomycin.
Antimicrobial agents and chemotherapy 46, 1647-1650 [PubMed:12019070]
[show Abstract]
Georges B, Roche C, Archambaud M, Decun JF, Cougot P, Conil JM, Chaminade B, Andrieu P, Saivin S, Bonnet E, Chabanon G, Houin G, Samii K, Virenque C (2002)
[Importance of a cefpirome-vancomycin combination on bactericidal kinetics in severe MRSA infections in intensive care].
Pathologie-biologie 50, 161-168 [PubMed:11980329]
[show Abstract]
Martínez-Lacasa J, Cabellos C, Martos A, Fernández A, Tubau F, Viladrich PF, Liñares J, Gudiol F (2002)
Experimental study of the efficacy of vancomycin, rifampicin and dexamethasone in the therapy of pneumococcal meningitis.
The Journal of antimicrobial chemotherapy 49, 507-513 [PubMed:11864951]
[show Abstract]
Aarestrup FM, Seyfarth AM, Emborg HD, Pedersen K, Hendriksen RS, Bager F (2001)
Effect of abolishment of the use of antimicrobial agents for growth promotion on occurrence of antimicrobial resistance in fecal enterococci from food animals in Denmark.
Antimicrobial agents and chemotherapy 45, 2054-2059 [PubMed:11408222]
[show Abstract]
Liñares J (2001)
The VISA/GISA problem: therapeutic implications.
Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 7 Suppl 4, 8-15 [PubMed:11688538]
[show Abstract]
Liu F, Zhou S, Zhang S, Deng Q, Zhang L, Xu Y, Wang J (2001)
[Research of drug resistance and detection of methicillin-resistant Staphylococcus aureus in chronic maxillary sinusitis].
Lin chuang er bi yan hou ke za zhi = Journal of clinical otorhinolaryngology 15, 341-343 [PubMed:12541895]
[show Abstract]
Moreillon P (2000)
[Means of bacterial resistance].
Revue medicale de la Suisse romande 120, 641-650 [PubMed:11028184]
[show Abstract]
HIGGINS HM, HARRISON WH, WILD GM, BUNGAY HR, McCORMICK MH (1957)
Vancomycin, a new antibiotic. VI. Purification and properties of vancomycin.
Antibiotics annual 5, 906-914 [PubMed:13521912]
GERACI JE, HEILMAN FR, NICHOLS DR, ROSS GT, WELLMAN WE (1956)
Some laboratory and clinical experiences with a new antibiotic, vancomycin.
Proceedings of the staff meetings. Mayo Clinic 31, 564-582 [PubMed:13370625]
Last Modified
22 February 2017
General Comment
2015-04-23 Vancomycin is a member of the class of glycopeptide antibiotics.