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Identification
NameVancomycin
Accession NumberDB00512  (APRD01287, EXPT03217)
TypeSmall Molecule
GroupsApproved
DescriptionAntibacterial obtained from Streptomyces orientalis. It is a glycopeptide related to ristocetin that inhibits bacterial cell wall assembly and is toxic to kidneys and the inner ear. [PubChem]
Structure
Thumb
Synonyms
(1S,2R,18R,22S,25R,28R,40S)-22-(2-amino-2-Oxoethyl)-48-[2-O-(3-amino-2,3,6-trideoxy-3-methyl-alpha-L-lyxo-hexopyranosyl)-beta-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[26.14.2.2(3,6).2(14,17).1(8,12).1(29,33).0(10,25).0(34,39)]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid
(2.2Sp,3.5sa,2.6sp)-O(4.2),C(3.4):c(5.4),O(4.6):c(3.5),C(2.7)-tricyclo[N-methyl-D-leucyl-3-chloro-(R)-beta-hydroxy-D-tyrosyl-L-asparaginyl-D-2-(4-{[2-O-(3-amino-2,3,6-trideoxy-3-C-methyl-alpha-L-lyxo-hexopyranosyl)-beta-D-glucopyranosyl]oxy}phenyl)glycyl-D-2-(4-hydroxyphenyl)glycyl-3-chloro-(R)-beta-hydroxy-L-tyrosyl-L-2-(3,5-dihydroxyphenyl)glycine]
Vancocin
Vancomicina
Vancomycin
Vancomycine
Vancomycinum
External IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Vancomycin Hydrochloride71WO621TJD 1404-93-9LCTORFDMHNKUSG-XTTLPDOESA-NDetails
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Jamp-vancomycinPowder, for solution5 gIntravenousJamp Pharma Corporation2014-09-22Not applicableCanada
Jamp-vancomycinCapsule250 mgOralJamp Pharma Corporation2014-03-26Not applicableCanada
Jamp-vancomycinPowder, for solution10 gIntravenousJamp Pharma Corporation2014-06-06Not applicableCanada
Jamp-vancomycinPowder, for solution1 gIntravenousJamp Pharma Corporation2014-09-22Not applicableCanada
Jamp-vancomycinPowder, for solution500 mgIntravenousJamp Pharma Corporation2014-09-22Not applicableCanada
Jamp-vancomycinCapsule125 mgOralJamp Pharma Corporation2014-03-26Not applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPPowder, for solution500 mgIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPPowder, for solution10 gIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPPowder, for solution1 gIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPPowder, for solution5 gIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
PMS-vancomycinCapsule125 mgOralPharmascience IncNot applicableNot applicableCanada
PMS-vancomycinCapsule250 mgOralPharmascience Inc2015-03-18Not applicableCanada
PMS-vancomycin 1 GPowder, for solution1.0 gIntravenousPharmascience Inc2000-10-30Not applicableCanada
PMS-vancomycin 500 mgPowder, for solution500 mgIntravenousPharmascience Inc2000-10-30Not applicableCanada
Sterile Vancomycin HCl 5.0gm/vialPowder, for solution5 gIntravenousLyphomed, Division Of Fujisawa Canada Inc.1992-12-311996-09-10Canada
Sterile Vancomycin HCl USP 1.0gm/vialPowder, for solution1 gIntravenousLyphomed, Division Of Fujisawa Canada Inc.1992-12-311996-09-10Canada
Sterile Vancomycin HCl USP 500mg/vialPowder, for solution500 mgIntravenousLyphomed, Division Of Fujisawa Canada Inc.1992-12-311996-09-10Canada
Sterile Vancomycin Hydrochloride, USPPowder, for solution1 gIntravenousPartners Health Care, Inc.1987-12-312008-02-15Canada
Sterile Vancomycin Hydrochloride, USPPowder, for solution500 mgIntravenousPartners Health Care, Inc.1959-12-312008-02-15Canada
Val-vancomycinPowder, for solution1 gIntravenousValeant Canada Lp Valeant Canada S.E.C.2010-09-23Not applicableCanada
Val-vancomycinPowder, for solution5 gIntravenousValeant Canada Lp Valeant Canada S.E.C.Not applicableNot applicableCanada
Val-vancomycinPowder, for solution10 gIntravenousValeant Canada Lp Valeant Canada S.E.C.2013-06-12Not applicableCanada
Val-vancomycinPowder, for solution500 mgIntravenousValeant Canada Lp Valeant Canada S.E.C.2010-09-23Not applicableCanada
VancocinCapsule125 mgOralMerus Labs International Inc.1989-12-31Not applicableCanada
VancocinCapsule250 mg/1OralViro Pharma1986-04-152016-10-13Us
VancocinCapsule125 mg/1OralCardinal Health1986-04-152016-10-13Us
VancocinCapsule250 mg/1OralCardinal Health1986-04-152016-10-13Us
VancocinCapsule125 mg/1OralANI Pharmaceuticals, Inc.2014-11-17Not applicableUs
VancocinCapsule250 mg/1OralANI Pharmaceuticals, Inc.2014-11-17Not applicableUs
VancocinCapsule250 mgOralMerus Labs International Inc.1989-12-31Not applicableCanada
VancocinCapsule125 mg/1OralViro Pharma1986-04-152016-10-13Us
Vancocin Cp Add-vantage Inj 500mg/vialPowder, for solution500 mgIntravenousEli Lilly & Co. Ltd.1989-12-312002-07-26Canada
Vancocin Inj 1gm/vial AdvantagePowder1 gIntravenousEli Lilly & Co. Ltd.1989-12-312002-07-26Canada
Vancomycin HydrochlorideInjection, solution500 mg/100mLIntravenousBaxter Laboratories1958-11-14Not applicableUs
Vancomycin HydrochlorideCapsule125 mg/1OralANI Pharmaceuticals, Inc.2015-10-26Not applicableUs
Vancomycin HydrochlorideInjection, solution750 mg/150mLIntravenousBaxter Laboratories1958-11-14Not applicableUs
Vancomycin HydrochlorideCapsule125 mg/1OralPrasco, Laboratories2012-04-10Not applicableUs
Vancomycin HydrochlorideCapsule250 mg/1OralANI Pharmaceuticals, Inc.2015-10-26Not applicableUs
Vancomycin HydrochlorideInjection, solution1 g/200mLIntravenousBaxter Laboratories1958-11-14Not applicableUs
Vancomycin HydrochlorideCapsule250 mg/1OralPrasco, Laboratories2012-04-10Not applicableUs
Vancomycin HydrochlorideInjection, solution500 mg/100mLIntravenousBaxter Laboratories1958-11-14Not applicableUs
Vancomycin HydrochlorideInjection, solution1 g/200mLIntravenousBaxter Laboratories1958-11-14Not applicableUs
Vancomycin HydrochlorideInjection, solution750 mg/150mLIntravenousBaxter Laboratories1958-11-14Not applicableUs
Vancomycin Hydrochloride Capsules, USPCapsule125 mgOralFresenius Kabi2012-07-16Not applicableCanada
Vancomycin Hydrochloride Capsules, USPCapsule250 mgOralFresenius Kabi2012-07-16Not applicableCanada
Vancomycin Hydrochloride Capsules, USPCapsule125 mgOralStrides Arcolab LimitedNot applicableNot applicableCanada
Vancomycin Hydrochloride Capsules, USPCapsule250 mgOralStrides Arcolab LimitedNot applicableNot applicableCanada
Vancomycin Hydrochloride for InjectionPowder, for solution500 mgIntravenousSterimax Inc2013-09-30Not applicableCanada
Vancomycin Hydrochloride for InjectionPowder, for solution10 gIntravenousSterimax Inc2013-09-30Not applicableCanada
Vancomycin Hydrochloride for InjectionPowder, for solution1000 mgIntravenousSterimax Inc2013-01-30Not applicableCanada
Vancomycin Hydrochloride for Injection USPPowder, for solution500 mgIntravenousGeneric Medical Partners IncNot applicableNot applicableCanada
Vancomycin Hydrochloride for Injection USPPowder, for solution1000 mgIntravenousGeneric Medical Partners IncNot applicableNot applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution1 gIntravenousFresenius Kabi1992-12-31Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution1000 mgIntravenousHospira, Inc.2000-03-31Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution10 gIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution1 gIntravenousSandoz Canada Incorporated2014-03-18Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution5 gIntravenousFresenius Kabi1996-08-14Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution5 gIntravenousHospira, Inc.2015-11-17Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution5 gIntravenousMylan Pharmaceuticals2013-12-28Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution10 gIntravenousFresenius Kabi2000-07-10Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution10 gIntravenousHospira, Inc.2015-10-05Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution5 gIntravenousSandoz Canada Incorporated2013-02-14Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution500 mgIntravenousMylan Pharmaceuticals2014-03-10Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution10 gIntravenousSandoz Canada Incorporated2013-02-14Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution10 gIntravenousPartners Health Care, Inc.1993-12-312008-02-15Canada
Vancomycin Hydrochloride for Injection, USPPowder, for solution1 gIntravenousMylan Pharmaceuticals2014-03-10Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution500 mgIntravenousFresenius Kabi1992-12-31Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution500 mgIntravenousHospira, Inc.2000-03-31Not applicableCanada
Vancomycin Hydrochloride for Injection, USPPowder, for solution500 mgIntravenousSandoz Canada Incorporated2014-03-18Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Sterile Vancomycin HydrochlorideInjection, powder, lyophilized, for solution5 g/100mLIntravenousAkorn Strides Llc2008-12-312016-10-13Us
Sterile Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousGeneral Injectables & Vaccines2010-09-01Not applicableUs
Sterile Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousRebel Distributors2008-12-31Not applicableUs
Sterile Vancomycin HydrochlorideInjection, powder, lyophilized, for solution5 g/100mLIntravenousPfizer Laboratories Div Pfizer Inc.2011-05-10Not applicableUs
Sterile Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousAkorn Strides Llc2008-12-312016-10-13Us
Sterile Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousAkorn Strides Llc2008-12-312016-10-13Us
VancomycinInjection, powder, lyophilized, for solution5 g/100mLIntravenousSagent Pharmaceuticals2012-09-20Not applicableUs
VancomycinInjection, powder, lyophilized, for solution10 g/100mLIntravenousSagent Pharmaceuticals2012-09-20Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousHospira, Inc.1990-12-21Not applicableUs
Vancomycin HydrochlorideInjection10 g/100mLIntravenousXellia Pharmaceuticals, Ap S2015-02-10Not applicableUs
Vancomycin HydrochlorideCapsule125 mg/1OralLupin Pharmaceuticals2015-03-27Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousCardinal Health2010-06-04Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousFresenius Kabi2000-09-01Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution750 mg/250mLIntravenousHospira, Inc.1988-08-04Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousMylan Institutional2008-12-31Not applicableUs
Vancomycin HydrochlorideCapsule250 mg/1OralAkorn2012-04-09Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousHospira, Inc.1988-08-04Not applicableUs
Vancomycin HydrochlorideCapsule125 mg/1OralAkorn2012-04-09Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousAuro Medics Pharma Llc2016-03-31Not applicableUs
Vancomycin HydrochlorideCapsule250 mg/1OralLupin Pharmaceuticals2015-03-27Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousCardinal Health2010-06-04Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousFresenius Kabi2000-09-20Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/100mLIntravenousHospira, Inc.1992-10-29Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousMylan Institutional2008-12-31Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousPfizer Laboratories Div Pfizer Inc.2011-05-10Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousHospira, Inc.1988-08-04Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousGland Pharma Limited2016-02-23Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution5 g/100mLIntravenousMylan Institutional2008-12-31Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousMylan Institutional2008-12-31Not applicableUs
Vancomycin HydrochlorideCapsule250 mg/1OralAlvogen, Inc.2012-04-09Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousAuro Medics Pharma Llc2016-03-31Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution750 mg/15mLIntravenousFresenius Kabi2016-08-17Not applicableUs
Vancomycin HydrochlorideCapsule125 mg/1OralAPP Pharmaceuticals, Inc.2012-06-18Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution5 g/100mLIntravenousHeritage2011-11-25Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousPfizer Laboratories Div Pfizer Inc.2011-05-10Not applicableUs
Vancomycin HydrochlorideCapsule125 mg/1OralWatson Pharmaceuticals2012-04-092016-10-13Us
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/250mLIntravenousHospira, Inc.1992-10-29Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousGland Pharma Limited2016-02-23Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution10 g/100mLIntravenousMylan Institutional2011-09-19Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousMylan Institutional2008-12-31Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/250mLIntravenousCardinal Health2010-07-29Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution5 g/1IntravenousAuro Medics Pharma Llc2016-03-29Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution100 g/1IntravenousSamson Medical Technologies Llc2016-06-01Not applicableUs
Vancomycin HydrochlorideCapsule250 mg/1OralAPP Pharmaceuticals, Inc.2012-06-18Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/1IntravenousXellia Pharmaceuticals, Ap S2014-04-10Not applicableUs
Vancomycin HydrochlorideCapsule250 mg/1OralWatson Pharmaceuticals2012-04-092016-10-13Us
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousAthenex Pharmaceutical Division, Llc.2017-01-01Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/4mLIntravenousHeritage2013-11-15Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution10 g/100mLIntravenousAGILA SPECIALTIES PRIVATE LIMITED2011-07-02Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution5 g/100mLIntravenousMylan Institutional2008-12-31Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/100mLIntravenousCardinal Health2010-07-29Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution10 g/1IntravenousAuro Medics Pharma Llc2016-03-29Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution5 g/100mLIntravenousFresenius Kabi2001-07-17Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousMylan Institutional2008-06-30Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution10 g/100mLIntravenousPfizer Laboratories Div Pfizer Inc.2011-05-10Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/1IntravenousXellia Pharmaceuticals, Ap S2014-04-10Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousSandoz2010-04-27Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousAthenex Pharmaceutical Division, Llc.2017-01-01Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/8mLIntravenousHeritage2013-11-15Not applicableUs
Vancomycin HydrochlorideInjection5 g/100mLIntravenousXellia Pharmaceuticals, Ap S2015-02-10Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution10 g/100mLIntravenousMylan Institutional2011-09-19Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/250mLIntravenousCardinal Health2010-07-29Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution100 mg/mLIntravenousHospira, Inc.2009-04-29Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution10 g/100mLIntravenousFresenius Kabi2004-11-30Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution500 mg/10mLIntravenousMylan Institutional2012-01-10Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution10 g/100mLIntravenousPfizer Laboratories Div Pfizer Inc.2011-09-19Not applicableUs
Vancomycin HydrochlorideCapsule125 mg/1OralAlvogen, Inc.2012-04-09Not applicableUs
Vancomycin HydrochlorideInjection, powder, lyophilized, for solution1 g/20mLIntravenousSandoz2010-04-27Not applicableUs
Vancomycin HydroclorideInjection, powder, lyophilized, for solution10 g/80mLIntravenousHeritage2011-11-29Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Vancomycin HClInjection, solution4.2 mg/mLIntravenousCantrell Drug Company2013-05-01Not applicableUs
Vancomycin HClInjection, solution5 mg/mLIntravenousCantrell Drug Company2012-05-25Not applicableUs
Vancomycin HClInjection, solution6 mg/mLIntravenousCantrell Drug Company2012-05-25Not applicableUs
International Brands
NameCompany
COVANCNucleus
VancoledNot Available
Brand mixturesNot Available
Categories
UNII6Q205EH1VU
CAS number1404-90-6
WeightAverage: 1449.254
Monoisotopic: 1447.430199787
Chemical FormulaC66H75Cl2N9O24
InChI KeyMYPYJXKWCTUITO-LYRMYLQWSA-N
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
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-(carbamoylmethyl)-5,47-dichloro-2,18,32,35,37-pentahydroxy-19-[(2R)-4-methyl-2-(methylamino)pentanamido]-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-3,5,8,10,12(48),14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid
SMILES
CN[[email protected]](CC(C)C)C(=O)N[C@@H]1[[email protected]](O)C2=CC=C(OC3=C(O[C@@H]4O[[email protected]](CO)[C@@H](O)[[email protected]](O)[[email protected]]4O[[email protected]]4C[C@](C)(N)[[email protected]](O)[[email protected]](C)O4)C4=CC(=C3)[C@@H](NC(=O)[[email protected]](CC(N)=O)NC1=O)C(=O)N[C@@H]1C3=CC(=C(O)C=C3)C3=C(O)C=C(O)C=C3[[email protected]](NC(=O)[C@@H](NC1=O)[[email protected]](O)C1=CC(Cl)=C(O4)C=C1)C(O)=O)C(Cl)=C2
Pharmacology
IndicationFor the treatment of serious or severe infections caused by susceptible strains of methicillin-resistant (beta-lactam-resistant) staphylococci.
Structured Indications
PharmacodynamicsVancomycin is a branched tricyclic glycosylated nonribosomal peptide produced by the fermentation of the Actinobacteria species Amycolatopsis orientalis (formerly Nocardia orientalis). It is often reserved as the "drug of last resort", used only after treatment with other antibiotics had failed. Vancomycin has been shown to be active against most strains of the following microorganisms, both in vitro and in clinical infections: Listeria monocytogenes, Streptococcus pyogenes, Streptococcus pneumoniae (including penicillin-resistant strains), Streptococcus agalactiae, Actinomyces species, and Lactobacillus species. The combination of vancomycin and an aminoglycoside acts synergistically in vitro against many strains of Staphylococcus aureus, Streptococcus bovis, enterococci, and the viridans group streptococci.
Mechanism of actionThe bactericidal action of vancomycin results primarily from inhibition of cell-wall biosynthesis. Specifically, vancomycin prevents incorporation of N-acetylmuramic acid (NAM)- and N-acetylglucosamine (NAG)-peptide subunits from being incorporated into the peptidoglycan matrix; which forms the major structural component of Gram-positive cell walls. The large hydrophilic molecule is able to form hydrogen bond interactions with the terminal D-alanyl-D-alanine moieties of the NAM/NAG-peptides. Normally this is a five-point interaction. This binding of vancomycin to the D-Ala-D-Ala prevents the incorporation of the NAM/NAG-peptide subunits into the peptidoglycan matrix. In addition, vancomycin alters bacterial-cell-membrane permeability and RNA synthesis. There is no cross-resistance between vancomycin and other antibiotics. Vancomycin is not active in vitro against gram-negative bacilli, mycobacteria, or fungi.
TargetKindPharmacological actionActionsOrganismUniProt ID
D-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycanGroupyes
inhibitor
Gram-positive bacterianot applicabledetails
dTDP-epi-vancosaminyltransferaseProteinno
other
Amycolatopsis orientalisP96558 details
Serum albuminProteinunknownNot AvailableHumanP02768 details
D-alanyl-D-alanine dipeptidaseProteinunknownNot AvailableEnterococcus faeciumQ06241 details
Related Articles
AbsorptionPoorly absorbed from gastrointestinal tract, however systemic absorption (up to 60%) may occur following intraperitoneal administration.
Volume of distributionNot Available
Protein bindingApproximately 55% serum protein bound.
MetabolismNot Available
Route of eliminationIn the first 24 hours, about 75% of an administered dose of vancomycin is excreted in urine by glomerular filtration.
Half lifeHalf-life in normal renal patients is approximately 6 hours (range 4 to 11 hours). In anephric patients, the average half-life of elimination is 7.5 days.
Clearance
  • 0.06 L/kg/h
ToxicityThe oral LD50 in mice is 5000 mg/kg. The median lethal intravenous dose is 319 mg/kg in rats and 400 mg/kg in mice.
Affected organisms
  • Enteric bacteria and other eubacteria
  • Corynebacterium diphtheriae
  • Treponema pallidum
  • Streptococcus pyogenes
  • Chlamydia pneumoniae
  • Chlamydia trachomatis
  • Mycoplasma pneumoniae
  • Neisseria gonorrhoeae
  • Legionella pneumophila
  • Bordetella pertussis
  • Chlamydia psittaci
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
AceclofenacThe serum concentration of Vancomycin can be increased when it is combined with Aceclofenac.Approved
Acetylsalicylic acidThe serum concentration of Vancomycin can be increased when it is combined with Acetylsalicylic acid.Approved, Vet Approved
AclarubicinVancomycin may increase the nephrotoxic activities of Aclarubicin.Investigational
AdapaleneThe serum concentration of Vancomycin can be increased when it is combined with Adapalene.Approved
AmikacinVancomycin may increase the nephrotoxic activities of Amikacin.Approved, Vet Approved
AmrubicinVancomycin may increase the nephrotoxic activities of Amrubicin.Approved, Investigational
AntipyrineThe serum concentration of Vancomycin can be increased when it is combined with Antipyrine.Approved
ApramycinVancomycin may increase the nephrotoxic activities of Apramycin.Experimental, Vet Approved
ApremilastThe serum concentration of Vancomycin can be increased when it is combined with Apremilast.Approved, Investigational
ArbekacinVancomycin may increase the nephrotoxic activities of Arbekacin.Approved
Atracurium besylateVancomycin may increase the neuromuscular blocking activities of Atracurium besylate.Approved
AzapropazoneThe serum concentration of Vancomycin can be increased when it is combined with Azapropazone.Withdrawn
AzelastineThe serum concentration of Vancomycin can be increased when it is combined with Azelastine.Approved
BalsalazideThe serum concentration of Vancomycin can be increased when it is combined with Balsalazide.Approved, Investigational
BenoxaprofenThe serum concentration of Vancomycin can be increased when it is combined with Benoxaprofen.Withdrawn
BromfenacThe serum concentration of Vancomycin can be increased when it is combined with Bromfenac.Approved
CarprofenThe serum concentration of Vancomycin can be increased when it is combined with Carprofen.Approved, Vet Approved, Withdrawn
CastanospermineThe serum concentration of Vancomycin can be increased when it is combined with Castanospermine.Experimental
CelecoxibThe serum concentration of Vancomycin can be increased when it is combined with Celecoxib.Approved, Investigational
ChloroquineThe serum concentration of Vancomycin can be increased when it is combined with Chloroquine.Approved, Vet Approved
CholestyramineThe therapeutic efficacy of Vancomycin can be decreased when used in combination with Cholestyramine.Approved
Cisatracurium besylateVancomycin may increase the neuromuscular blocking activities of Cisatracurium besylate.Approved
ClonixinThe serum concentration of Vancomycin can be increased when it is combined with Clonixin.Approved
ColesevelamThe therapeutic efficacy of Vancomycin can be decreased when used in combination with Colesevelam.Approved
ColestipolThe therapeutic efficacy of Vancomycin can be decreased when used in combination with Colestipol.Approved
ColistimethateVancomycin may increase the nephrotoxic activities of Colistimethate.Approved, Vet Approved
DaunorubicinVancomycin may increase the nephrotoxic activities of Daunorubicin.Approved
DecamethoniumVancomycin may increase the neuromuscular blocking activities of Decamethonium.Approved
DiclofenacThe serum concentration of Vancomycin can be increased when it is combined with Diclofenac.Approved, Vet Approved
DiflunisalThe serum concentration of Vancomycin can be increased when it is combined with Diflunisal.Approved
Domoic AcidVancomycin may increase the neuromuscular blocking activities of Domoic Acid.Experimental
Doxacurium chlorideVancomycin may increase the neuromuscular blocking activities of Doxacurium chloride.Approved
DoxorubicinVancomycin may increase the nephrotoxic activities of Doxorubicin.Approved, Investigational
DroxicamThe serum concentration of Vancomycin can be increased when it is combined with Droxicam.Approved
EpirizoleThe serum concentration of Vancomycin can be increased when it is combined with Epirizole.Approved
EpirubicinVancomycin may increase the nephrotoxic activities of Epirubicin.Approved
EtanerceptThe serum concentration of Vancomycin can be increased when it is combined with Etanercept.Approved, Investigational
EtodolacThe serum concentration of Vancomycin can be increased when it is combined with Etodolac.Approved, Investigational, Vet Approved
EtofenamateThe serum concentration of Vancomycin can be increased when it is combined with Etofenamate.Approved
EtoricoxibThe serum concentration of Vancomycin can be increased when it is combined with Etoricoxib.Approved, Investigational
FenbufenThe serum concentration of Vancomycin can be increased when it is combined with Fenbufen.Approved
FenoprofenThe serum concentration of Vancomycin can be increased when it is combined with Fenoprofen.Approved
FloctafenineThe serum concentration of Vancomycin can be increased when it is combined with Floctafenine.Approved, Withdrawn
FlurbiprofenThe serum concentration of Vancomycin can be increased when it is combined with Flurbiprofen.Approved, Investigational
FramycetinVancomycin may increase the nephrotoxic activities of Framycetin.Approved
Gallamine TriethiodideVancomycin may increase the neuromuscular blocking activities of Gallamine Triethiodide.Approved
GeneticinVancomycin may increase the nephrotoxic activities of Geneticin.Experimental
GentamicinVancomycin may increase the nephrotoxic activities of Gentamicin.Approved, Vet Approved
GENTAMICIN C1AVancomycin may increase the nephrotoxic activities of GENTAMICIN C1A.Experimental
HMPL-004The serum concentration of Vancomycin can be increased when it is combined with HMPL-004.Investigational
IbuprofenThe serum concentration of Vancomycin can be increased when it is combined with Ibuprofen.Approved
IbuproxamThe serum concentration of Vancomycin can be increased when it is combined with Ibuproxam.Withdrawn
IcatibantThe serum concentration of Vancomycin can be increased when it is combined with Icatibant.Approved
IdarubicinVancomycin may increase the nephrotoxic activities of Idarubicin.Approved
IndomethacinThe serum concentration of Vancomycin can be increased when it is combined with Indomethacin.Approved, Investigational
IndoprofenThe serum concentration of Vancomycin can be increased when it is combined with Indoprofen.Withdrawn
IsoxicamThe serum concentration of Vancomycin can be increased when it is combined with Isoxicam.Withdrawn
KanamycinVancomycin may increase the nephrotoxic activities of Kanamycin.Approved, Vet Approved
KebuzoneThe serum concentration of Vancomycin can be increased when it is combined with Kebuzone.Experimental
KetoprofenThe serum concentration of Vancomycin can be increased when it is combined with Ketoprofen.Approved, Vet Approved
KetorolacThe serum concentration of Vancomycin can be increased when it is combined with Ketorolac.Approved
LeflunomideThe serum concentration of Vancomycin can be increased when it is combined with Leflunomide.Approved, Investigational
LornoxicamThe serum concentration of Vancomycin can be increased when it is combined with Lornoxicam.Approved
LoxoprofenThe serum concentration of Vancomycin can be increased when it is combined with Loxoprofen.Approved
LumiracoxibThe serum concentration of Vancomycin can be increased when it is combined with Lumiracoxib.Approved, Investigational
Magnesium salicylateThe serum concentration of Vancomycin can be increased when it is combined with Magnesium salicylate.Approved
MasoprocolThe serum concentration of Vancomycin can be increased when it is combined with Masoprocol.Approved
Meclofenamic acidThe serum concentration of Vancomycin can be increased when it is combined with Meclofenamic acid.Approved, Vet Approved
Mefenamic acidThe serum concentration of Vancomycin can be increased when it is combined with Mefenamic acid.Approved
MeloxicamThe serum concentration of Vancomycin can be increased when it is combined with Meloxicam.Approved, Vet Approved
MesalazineThe serum concentration of Vancomycin can be increased when it is combined with Mesalazine.Approved
MetamizoleThe serum concentration of Vancomycin can be increased when it is combined with Metamizole.Withdrawn
MetocurineVancomycin may increase the neuromuscular blocking activities of Metocurine.Approved
Metocurine IodideVancomycin may increase the neuromuscular blocking activities of Metocurine Iodide.Withdrawn
MetrizamideVancomycin may increase the nephrotoxic activities of Metrizamide.Approved
MivacuriumVancomycin may increase the neuromuscular blocking activities of Mivacurium.Approved
Mycophenolate mofetilThe serum concentration of Vancomycin can be increased when it is combined with Mycophenolate mofetil.Approved, Investigational
Mycophenolic acidThe serum concentration of Vancomycin can be increased when it is combined with Mycophenolic acid.Approved
NabumetoneThe serum concentration of Vancomycin can be increased when it is combined with Nabumetone.Approved
NafamostatThe serum concentration of Vancomycin can be increased when it is combined with Nafamostat.Approved, Investigational
NaftifineThe serum concentration of Vancomycin can be increased when it is combined with Naftifine.Approved
NaproxenThe serum concentration of Vancomycin can be increased when it is combined with Naproxen.Approved, Vet Approved
NCX 4016The serum concentration of Vancomycin can be increased when it is combined with NCX 4016.Investigational
NeamineVancomycin may increase the nephrotoxic activities of Neamine.Experimental
NeomycinVancomycin may increase the nephrotoxic activities of Neomycin.Approved, Vet Approved
NepafenacThe serum concentration of Vancomycin can be increased when it is combined with Nepafenac.Approved
NetilmicinVancomycin may increase the nephrotoxic activities of Netilmicin.Approved
Niflumic AcidThe serum concentration of Vancomycin can be increased when it is combined with Niflumic Acid.Approved
NimesulideThe serum concentration of Vancomycin can be increased when it is combined with Nimesulide.Approved, Withdrawn
OlopatadineThe serum concentration of Vancomycin can be increased when it is combined with Olopatadine.Approved
OlsalazineThe serum concentration of Vancomycin can be increased when it is combined with Olsalazine.Approved
OxaprozinThe serum concentration of Vancomycin can be increased when it is combined with Oxaprozin.Approved
OxyphenbutazoneThe serum concentration of Vancomycin can be increased when it is combined with Oxyphenbutazone.Withdrawn
PancuroniumVancomycin may increase the neuromuscular blocking activities of Pancuronium.Approved
ParecoxibThe serum concentration of Vancomycin can be increased when it is combined with Parecoxib.Approved
ParomomycinVancomycin may increase the nephrotoxic activities of Paromomycin.Approved, Investigational
PhenylbutazoneThe serum concentration of Vancomycin can be increased when it is combined with Phenylbutazone.Approved, Vet Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Vancomycin.Approved
PimecrolimusThe serum concentration of Vancomycin can be increased when it is combined with Pimecrolimus.Approved, Investigational
PipecuroniumVancomycin may increase the neuromuscular blocking activities of Pipecuronium.Approved
PiperacillinPiperacillin may increase the nephrotoxic activities of Vancomycin.Approved
PirarubicinVancomycin may increase the nephrotoxic activities of Pirarubicin.Investigational
PirfenidoneThe serum concentration of Vancomycin can be increased when it is combined with Pirfenidone.Investigational
PiroxicamThe serum concentration of Vancomycin can be increased when it is combined with Piroxicam.Approved, Investigational
PlicamycinVancomycin may increase the nephrotoxic activities of Plicamycin.Approved, Withdrawn
PropacetamolThe serum concentration of Vancomycin can be increased when it is combined with Propacetamol.Approved
PTC299The serum concentration of Vancomycin can be increased when it is combined with PTC299.Investigational
PuromycinVancomycin may increase the nephrotoxic activities of Puromycin.Experimental
RapacuroniumVancomycin may increase the neuromuscular blocking activities of Rapacuronium.Withdrawn
ResveratrolThe serum concentration of Vancomycin can be increased when it is combined with Resveratrol.Experimental, Investigational
RibostamycinVancomycin may increase the nephrotoxic activities of Ribostamycin.Approved
RocuroniumVancomycin may increase the neuromuscular blocking activities of Rocuronium.Approved
RofecoxibThe serum concentration of Vancomycin can be increased when it is combined with Rofecoxib.Investigational, Withdrawn
SalicylamideThe serum concentration of Vancomycin can be increased when it is combined with Salicylamide.Approved
Salicylic acidThe serum concentration of Vancomycin can be increased when it is combined with Salicylic acid.Approved, Vet Approved
SalsalateThe serum concentration of Vancomycin can be increased when it is combined with Salsalate.Approved
SP1049CVancomycin may increase the nephrotoxic activities of SP1049C.Investigational
SpectinomycinVancomycin may increase the nephrotoxic activities of Spectinomycin.Approved, Vet Approved
SRT501The serum concentration of Vancomycin can be increased when it is combined with SRT501.Investigational
StreptomycinVancomycin may increase the nephrotoxic activities of Streptomycin.Approved, Vet Approved
StreptozocinVancomycin may increase the nephrotoxic activities of Streptozocin.Approved
SuccinylcholineVancomycin may increase the neuromuscular blocking activities of Succinylcholine.Approved
SulfasalazineThe serum concentration of Vancomycin can be increased when it is combined with Sulfasalazine.Approved
SulindacThe serum concentration of Vancomycin can be increased when it is combined with Sulindac.Approved
SuprofenThe serum concentration of Vancomycin can be increased when it is combined with Suprofen.Approved, Withdrawn
TenoxicamThe serum concentration of Vancomycin can be increased when it is combined with Tenoxicam.Approved
TeriflunomideThe serum concentration of Vancomycin can be increased when it is combined with Teriflunomide.Approved
Tiaprofenic acidThe serum concentration of Vancomycin can be increased when it is combined with Tiaprofenic acid.Approved
TobramycinVancomycin may increase the nephrotoxic activities of Tobramycin.Approved, Investigational
Tolfenamic AcidThe serum concentration of Vancomycin can be increased when it is combined with Tolfenamic Acid.Approved
TolmetinThe serum concentration of Vancomycin can be increased when it is combined with Tolmetin.Approved
TranilastThe serum concentration of Vancomycin can be increased when it is combined with Tranilast.Approved, Investigational
Trisalicylate-cholineThe serum concentration of Vancomycin can be increased when it is combined with Trisalicylate-choline.Approved
TubocurarineVancomycin may increase the neuromuscular blocking activities of Tubocurarine.Approved
ValdecoxibThe serum concentration of Vancomycin can be increased when it is combined with Valdecoxib.Investigational, Withdrawn
ValrubicinVancomycin may increase the nephrotoxic activities of Valrubicin.Approved
VecuroniumVancomycin may increase the neuromuscular blocking activities of Vecuronium.Approved
ZaltoprofenThe serum concentration of Vancomycin can be increased when it is combined with Zaltoprofen.Approved
ZileutonThe serum concentration of Vancomycin can be increased when it is combined with Zileuton.Approved, Investigational, Withdrawn
ZomepiracThe serum concentration of Vancomycin can be increased when it is combined with Zomepirac.Withdrawn
ZorubicinVancomycin may increase the nephrotoxic activities of Zorubicin.Experimental
Food InteractionsNot Available
References
Synthesis Reference
  1. Boger DL. Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic studies. Med Res Rev. 2001 Sep;21(5):356-81. Pubmed
General References
  1. Levine DP: Vancomycin: a history. Clin Infect Dis. 2006 Jan 1;42 Suppl 1:S5-12. [PubMed:16323120 ]
  2. Small PM, Chambers HF: Vancomycin for Staphylococcus aureus endocarditis in intravenous drug users. Antimicrob Agents Chemother. 1990 Jun;34(6):1227-31. [PubMed:2393284 ]
  3. Gonzalez C, Rubio M, Romero-Vivas J, Gonzalez M, Picazo JJ: Bacteremic pneumonia due to Staphylococcus aureus: A comparison of disease caused by methicillin-resistant and methicillin-susceptible organisms. Clin Infect Dis. 1999 Nov;29(5):1171-7. [PubMed:10524959 ]
  4. Sivagnanam S, Deleu D: Red man syndrome. Crit Care. 2003 Apr;7(2):119-20. Epub 2002 Dec 23. [PubMed:12720556 ]
  5. Cantu TG, Yamanaka-Yuen NA, Lietman PS: Serum vancomycin concentrations: reappraisal of their clinical value. Clin Infect Dis. 1994 Apr;18(4):533-43. [PubMed:8038306 ]
External Links
ATC CodesA07AA09J01XA01
AHFS Codes
  • 08:12.28.16
PDB Entries
FDA labelDownload (57.8 KB)
MSDSDownload (73 KB)
Clinical Trials
Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceBMI >30 kg/m2 / Diabetes / Inflammatory processes / Osteoporosis1
0CompletedTreatmentBacterial Resistance / Respiratory Failure / Respiratory Infections1
0Enrolling by InvitationBasic ScienceDietary Modifications / Nutrition1
1CompletedSupportive CareCritical Illness / Methicillin-Resistant Staphylococcus Aureus (MRSA) / Sepsis 1
1CompletedTreatmentBiliary Atresia / Primary Sclerosing Cholangitis (PSC)1
1CompletedTreatmentCystic Fibrosis (CF) / Healthy Volunteers1
1CompletedTreatmentPrimary Sclerosing Cholangitis (PSC)1
1RecruitingTreatmentBiliary Atresia / Primary Sclerosing Cholangitis (PSC)1
1RecruitingTreatmentDialysis therapy / Pediatric Continuous Renal Replacement Therapy / Renal Failure1
1SuspendedPreventionSurgical Site Infections1
1Unknown StatusTreatmentCystic Fibrosis (CF) / Methicillin-Resistant Staphylococcus Aureus (MRSA)1
1WithdrawnPreventionNeurosurgery1
1, 2CompletedTreatmentAutism Spectrum Disorder (ASD) / Gastrointestinal Problems1
2Active Not RecruitingTreatmentChronic Constipation / Slow Transit Constipation1
2CompletedTreatmentClostridium Difficile Infection (CDI)2
2CompletedTreatmentClostridium Difficile Infection (CDI) / Diarrhea1
2CompletedTreatmentInfection NOS / Infections, Bacterial1
2CompletedTreatmentInfections, Bacterial1
2CompletedTreatmentModerate Clostridium Difficile Infection1
2CompletedTreatmentOsteomyelitis1
2CompletedTreatmentRecurrent C. Difficile Infection1
2CompletedTreatmentSkin and Subcutaneous Tissue Bacterial Infections1
2CompletedTreatmentSoft Tissues Infections1
2CompletedTreatmentStaphylococcal Skin Infections1
2Enrolling by InvitationPreventionInfection NOS1
2RecruitingTreatmentBacteremia1
2RecruitingTreatmentClostridium Difficile1
2RecruitingTreatmentCrohn's Disease (CD)1
2RecruitingTreatmentLate Onset Neonatal Sepsis1
2RecruitingTreatmentMethicillin-Resistant Staphylococcus Aureus (MRSA) / Pneumonia, Staphylococcal1
2RecruitingTreatmentOsteomyelitis1
2RecruitingTreatmentPre-Diabetes1
2TerminatedTreatmentBacteremia Due to Staphylococcus Aureus1
2TerminatedTreatmentEndocarditis, Bacterial / Infective Endocarditis1
2TerminatedTreatmentFebrile Neutropenia / Neoplasms1
2TerminatedTreatmentHealth-Care-Associated Pneumonia / Pneumonia, Hospital-Acquired / Ventilator-Associated Pneumonia (VAP)1
2TerminatedTreatmentInfected Spacers / Prosthetic Joint Infections of Hip / Prosthetic Joint Infections of Knee1
2Unknown StatusPreventionWound Infections1
2Unknown StatusTreatmentHip Prosthetic Joint Infection1
2, 3CompletedTreatmentArthropathy of Knee Joint / Revision, Knee Joint1
2, 3Not Yet RecruitingTreatmentClostridium Difficile Infection (CDI)1
2, 3RecruitingTreatmentClostridium Difficile1
2, 3TerminatedTreatmentClostridium difficile infection recurrence / Laboratory Confirmed Clostridium Difficile Infection1
3Active Not RecruitingTreatmentClostridium Difficile Infection (CDI)1
3Active Not RecruitingTreatmentPrimary Sclerosing Cholangitis (PSC)1
3CompletedSupportive CareBone Marrow Suppression / Fever, Sweats, and Hot Flashes / Infection NOS / Leukemias / Lymphoma NOS / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes / Unspecified Adult Solid Tumor, Protocol Specific / Unspecified Childhood Solid Tumor, Protocol Specific1
3CompletedTreatmentAbscesses / Cellulitis / Surgical Site Infections / Wound Infections2
3CompletedTreatmentAbscesses / Cellulitis / Systemic Inflammation / Wound Infections2
3CompletedTreatmentAcute Hematogenous Osteomyelitis1
3CompletedTreatmentBacteremia / Infections, Bacterial / Infections, Gram-Positive Bacterial1
3CompletedTreatmentClostridium Difficile1
3CompletedTreatmentClostridium Difficile Infection (CDI)3
3CompletedTreatmentClostridium Infections / Diarrhea2
3CompletedTreatmentComplicated Skin and Soft Tissue Infection1
3CompletedTreatmentFebrile Neutropenia1
3CompletedTreatmentInfection caused by staphylococci1
3CompletedTreatmentInfection caused by staphylococci / Meningitis / Pneumonia / Sepsis 1
3CompletedTreatmentInfections, Bacterial1
3CompletedTreatmentInfectious / Skin Diseases1
3CompletedTreatmentNosocomial Neonatal Sepsis1
3CompletedTreatmentPneumonia, Bacterial2
3CompletedTreatmentSkin Diseases, Bacterial / Skin Diseases, Infectious / Staphylococcal Skin Infections1
3CompletedTreatmentSkin Structures and Soft Tissue Infections1
3CompletedTreatmentSkin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections1
3CompletedTreatmentSkin and Subcutaneous Tissue Bacterial Infections1
3CompletedTreatmentStaphylococcal Skin Infections2
3Not Yet RecruitingTreatmentClostridium Difficile2
3RecruitingPreventionGeneral Surgery / Infection NOS / Nervous System Diseases1
3RecruitingTreatmentBacteremia1
3RecruitingTreatmentClostridium Difficile Infection (CDI)1
3RecruitingTreatmentClostridium Difficile-Associated Diarrhea (CDAD)1
3RecruitingTreatmentConjunctivitis, Bacterial1
3RecruitingTreatmentSkin Diseases, Bacterial / Skin Diseases, Infectious1
3RecruitingTreatmentSkin Structures and Soft Tissue Infections1
3RecruitingTreatmentStaphylococcus Aureus Infections1
3TerminatedTreatmentBacteremia / Infections, Gram-Positive Bacterial1
3TerminatedTreatmentClostridium Infections1
3TerminatedTreatmentComplicated Skin and Soft Tissue Infection1
3TerminatedTreatmentDiabetic Foot1
3TerminatedTreatmentSkin Diseases, Infectious / Soft Tissues Infections1
4Active Not RecruitingPreventionArrythmias1
4CompletedNot AvailableComplicated Skin and Structure Infection / Hospital Acquired Pneumonia (HAP)1
4CompletedNot AvailableStaphylococcus Aureus1
4CompletedBasic ScienceCellulitis1
4CompletedPreventionAortic Valve Disorder / Congenital Heart Disease (CHD)1
4CompletedPreventionMRSA Infections1
4CompletedTreatmentCellulitis1
4CompletedTreatmentCellulitis / Skin Infections1
4CompletedTreatmentClostridium Difficile1
4CompletedTreatmentCoronary Artery Disease1
4CompletedTreatmentExtracorporeal Membrane Oxygenation1
4CompletedTreatmentFebrile Neutropenia / Infection NOS1
4CompletedTreatmentInfection NOS / Pneumonia1
4CompletedTreatmentMethicillin Resistant Staphylococcus Aureus (MRSA)1
4CompletedTreatmentMethicillin Resistant Staphylococcus Aureus (MRSA) / Skin/Soft Tissue Infections1
4CompletedTreatmentSkin Diseases, Infectious / Staphylococcal Skin Infections1
4CompletedTreatmentStaphylococcal Skin Infections1
4CompletedTreatmentVentilator-Associated Pneumonia (VAP)1
4Enrolling by InvitationPreventionFractures, Open / Infection, Postoperative Wound1
4Not Yet RecruitingPreventionClostridium Difficile Infection (CDI) / Prophylaxis / Vancomycin1
4Not Yet RecruitingTreatmentClostridium Difficile Infection (CDI)2
4Not Yet RecruitingTreatmentFebrile Neutropenia / Fevers1
4RecruitingNot AvailableC. Difficile / Diarrhea / Enterocolitis1
4RecruitingBasic ScienceInflammatory Bowel Diseases (IBD) / Primary Sclerosing Cholangitis (PSC)1
4RecruitingBasic ScienceNeonatal Infections1
4RecruitingPreventionCalcium Nephrolithiasis / Urinary Tract Infections (UTIs)1
4RecruitingPreventionClostridium Difficile Infection (CDI)1
4RecruitingPreventionSpinal Fusion Acquired1
4RecruitingPreventionSurgical Site Infections1
4RecruitingTreatmentAsthma1
4RecruitingTreatmentBacteremia1
4RecruitingTreatmentBlood Stream Infections / Endocarditis / MRSA1
4RecruitingTreatmentClostridium / Difficile / Fidaxomicin / Vancomycin1
4RecruitingTreatmentLiver Cirrhosis1
4RecruitingTreatmentPrimary Sclerosing Cholangitis (PSC)1
4TerminatedNot AvailableBacteremia / Pneumonia1
4TerminatedHealth Services ResearchComplicated Skin or Skin Structure Infection1
4TerminatedPreventionAcute Bacterial Skin and Skin Structure Infections / Bacteremia / Endocarditis / Health Care Associated Pneumonia / Osteomyelitis/Septic Arthritis1
4TerminatedPreventionInfection caused by staphylococci / Methicillin-Resistant Staphylococcus Aureus (MRSA)1
4TerminatedTreatmentBacteremia1
4TerminatedTreatmentClostridium Difficile1
4TerminatedTreatmentClostridium Difficile / Spinal Cord Injuries (SCI)1
4TerminatedTreatmentDiabetic Foot1
4TerminatedTreatmentRenal Impairments / S. Aureus Bacteremia / Skin and Subcutaneous Tissue Bacterial Infections1
4Unknown StatusPreventionClostridium Difficile Infection (CDI)1
4Unknown StatusTreatmentClostridium Difficile Infection (CDI)1
4Unknown StatusTreatmentInfective Endocarditis1
Not AvailableActive Not RecruitingNot AvailableFlu caused by Influenza1
Not AvailableActive Not RecruitingTreatmentClostridium Difficile Infection (CDI)1
Not AvailableCompletedNot AvailableAcinetobacter Infections1
Not AvailableCompletedNot AvailableAllogenic Blood Stem Cell Transplantation / Febrile Neutropenia1
Not AvailableCompletedNot AvailableEnd Stage Renal Disease (ESRD) / Infection NOS1
Not AvailableCompletedNot AvailableMethicillin-Resistant Staphylococcus Aureus (MRSA) / Pneumonia, Hospital-Acquired1
Not AvailableCompletedNot AvailableOsteomyelitis1
Not AvailableCompletedNot AvailablePeriodontal Diseases / Psoriatic Arthritis / Rheumatoid Arthritis1
Not AvailableCompletedNot AvailablePneumonia1
Not AvailableCompletedBasic ScienceEndotoxaemia1
Not AvailableCompletedBasic ScienceHealthy Volunteers / Sepsis 1
Not AvailableCompletedPreventionDental Caries1
Not AvailableCompletedPreventionProsthetic Joint Infection1
Not AvailableCompletedTreatmentAntibiotic Prophylaxis1
Not AvailableCompletedTreatmentClostridium Difficile Infection (CDI)1
Not AvailableCompletedTreatmentInfection caused by staphylococci1
Not AvailableCompletedTreatmentInfectious Diseases1
Not AvailableCompletedTreatmentPeritoneal Dialysis Associated Peritonitis1
Not AvailableCompletedTreatmentSkin and Soft Tissue Infections1
Not AvailableCompletedTreatmentUlcerative Colitis (UC)1
Not AvailableEnrolling by InvitationPreventionFractures, Closed / Infection NOS1
Not AvailableNot Yet RecruitingNot AvailableAcute Kidney Insufficiency / Anti-Infective Agent Toxicity1
Not AvailableNot Yet RecruitingTreatmentCataract operation / Endophthalmitis / Intracameral Antibiotics / Moxifloxacin / Phacoemulsification / Vancomycin1
Not AvailableNot Yet RecruitingTreatmentClostridium Difficile Infection (CDI)1
Not AvailableRecruitingNot AvailableCritical Illness / Infection NOS1
Not AvailableRecruitingPreventionAntibiotic Prophylaxis / Thoracic Surgery1
Not AvailableRecruitingPreventionPost- Orthotopic Liver Transplantation / Primary Sclerosing Cholangitis (PSC)1
Not AvailableRecruitingPreventionSurgical Site Infections1
Not AvailableRecruitingTreatmentBMI >30 kg/m2 / Infection NOS / Sepsis 1
Not AvailableTerminatedTreatmentColitis1
Not AvailableTerminatedTreatmentInfection NOS2
Not AvailableUnknown StatusBasic ScienceBMI >30 kg/m2 / Insulin Resistance1
Not AvailableUnknown StatusPreventionInfection NOS1
Not AvailableUnknown StatusPreventionLumbar Pain1
Not AvailableUnknown StatusTreatmentAcute Renal Failure / Postoperative / Sepsis 1
Not AvailableUnknown StatusTreatmentClostridium Difficile / Clostridium Difficile Infection (CDI)1
Not AvailableUnknown StatusTreatmentInfection NOS1
Not AvailableUnknown StatusTreatmentInfection, Postoperative Wound1
Not AvailableUnknown StatusTreatmentMethicillin-Resistant Staphylococcus Aureus (MRSA) / Osteomyelitis1
Not AvailableWithdrawnSupportive CareInfection NOS / Neutropenias / Unspecified Adult Solid Tumor, Protocol Specific / Unspecified Childhood Solid Tumor, Protocol Specific1
Pharmacoeconomics
Manufacturers
  • Viropharma inc
  • Lederle parenterals inc
  • Baxter healthcare corp
  • Baxter healthcare corp anesthesia and critical care
  • Akorn strides llc
  • App pharmaceuticals llc
  • Bioniche pharma usa llc
  • Hospira inc
  • Sandoz inc
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
CapsuleOral125 mg
CapsuleOral250 mg
Powder, for solutionIntravenous1.0 g
Powder, for solutionIntravenous500 mg
Injection, powder, lyophilized, for solutionIntravenous5 g/100mL
PowderIntravenous1 g
Injection, solutionIntravenous4.2 mg/mL
Injection, solutionIntravenous5 mg/mL
Injection, solutionIntravenous6 mg/mL
CapsuleOral125 mg/1
CapsuleOral250 mg/1
InjectionIntravenous10 g/100mL
InjectionIntravenous5 g/100mL
Injection, powder, lyophilized, for solutionIntravenous1 g/8mL
Injection, powder, lyophilized, for solutionIntravenous1 g/20mL
Injection, powder, lyophilized, for solutionIntravenous1 g/250mL
Injection, powder, lyophilized, for solutionIntravenous1 g/1
Injection, powder, lyophilized, for solutionIntravenous10 g/100mL
Injection, powder, lyophilized, for solutionIntravenous10 g/1
Injection, powder, lyophilized, for solutionIntravenous100 g/1
Injection, powder, lyophilized, for solutionIntravenous100 mg/mL
Injection, powder, lyophilized, for solutionIntravenous5 g/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/10mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/100mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/4mL
Injection, powder, lyophilized, for solutionIntravenous750 mg/250mL
Injection, powder, lyophilized, for solutionIntravenous750 mg/15mL
Injection, solutionIntravenous1 g/200mL
Injection, solutionIntravenous500 mg/100mL
Injection, solutionIntravenous750 mg/150mL
Powder, for solutionIntravenous1000 mg
Powder, for solutionIntravenous1 g
Powder, for solutionIntravenous10 g
Powder, for solutionIntravenous5 g
Injection, powder, lyophilized, for solutionIntravenous10 g/80mL
Prices
Unit descriptionCostUnit
Vancocin HCl 20 250 mg capsule Box1019.87USD box
Vancomycin hcl powder85.68USD g
Pms-Vancomycin 1 g/vial61.98USD vial
Vancocin hcl 250 mg pulvule40.97USD each
Pms-Vancomycin 500 mg/vial32.62USD vial
Vancocin HCl 125 mg capsule27.66USD capsule
Vancocin hcl 125 mg pulvule22.22USD each
Vancomycin 1 gm vial7.0USD vial
Vancomycin hcl 750 mg vial5.72USD vial
Vancomycin 500 mg vial3.74USD vial
Vancomycin-ns 1.5 g/150 ml0.24USD ml
Vancomycin-ns 1.25 g/150 ml0.21USD ml
Vancomycin hcl 1 g/200 ml bag0.17USD ml
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PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP-3.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.225 mg/mLALOGPS
logP1.11ALOGPS
logP-4.4ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)2.99ChemAxon
pKa (Strongest Basic)9.93ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count24ChemAxon
Hydrogen Donor Count19ChemAxon
Polar Surface Area530.49 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity346.61 m3·mol-1ChemAxon
Polarizability138.7 Å3ChemAxon
Number of Rings10ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7876
Blood Brain Barrier-0.991
Caco-2 permeable-0.7094
P-glycoprotein substrateSubstrate0.8562
P-glycoprotein inhibitor INon-inhibitor0.8781
P-glycoprotein inhibitor IINon-inhibitor0.9636
Renal organic cation transporterNon-inhibitor0.9503
CYP450 2C9 substrateNon-substrate0.8535
CYP450 2D6 substrateNon-substrate0.8323
CYP450 3A4 substrateSubstrate0.6686
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7268
Ames testNon AMES toxic0.5927
CarcinogenicityNon-carcinogens0.8826
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5856 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9987
hERG inhibition (predictor II)Non-inhibitor0.8098
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Cyclic alpha peptide
  • Phenolic glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Diaryl ether
  • Alpha-amino acid or derivatives
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Amino saccharide
  • Oxane
  • Benzenoid
  • Aryl chloride
  • Aryl halide
  • Cyclic carboximidic acid
  • Secondary alcohol
  • Amino acid
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Acetal
  • Oxacycle
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid
  • Azacycle
  • Secondary aliphatic amine
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Ether
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Secondary amine
  • Polyol
  • Organic oxide
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Carbonyl group
  • Primary aliphatic amine
  • Alcohol
  • Organic oxygen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Primary amine
  • Amine
  • Primary alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

1. D-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan
Kind
Group
Organism
Gram-positive bacteria
Pharmacological action
yes
Actions
inhibitor
References
  1. Reynolds PE: Structure, biochemistry and mechanism of action of glycopeptide antibiotics. Eur J Clin Microbiol Infect Dis. 1989 Nov;8(11):943-50. [PubMed:2532132 ]
  2. Reynolds PE, Somner EA: Comparison of the target sites and mechanisms of action of glycopeptide and lipoglycodepsipeptide antibiotics. Drugs Exp Clin Res. 1990;16(8):385-9. [PubMed:2151441 ]
  3. Boger DL: Vancomycin, teicoplanin, and ramoplanin: synthetic and mechanistic studies. Med Res Rev. 2001 Sep;21(5):356-81. [PubMed:11579438 ]
Kind
Protein
Organism
Amycolatopsis orientalis
Pharmacological action
no
Actions
other
General Function:
Transferase activity, transferring hexosyl groups
Specific Function:
Catalyzes the attachment of 4-epi-vancosamine from a TDP donor to the beta-OH-Tyr-6 of the aglycone cosubstrate in the biosynthesis of glycopeptide antibiotic chloroeremomycin, a member of the vancomycin group of antibiotics. Strongly prefers devancoaminyl-vancomycin (DVV) as substrate rather than the heptapeptide vancomycin aglycone (AGV). Acts downstream of GtfB.
Gene Name:
gtfA
Uniprot ID:
P96558
Molecular Weight:
41661.965 Da
References
  1. Mulichak AM, Lu W, Losey HC, Walsh CT, Garavito RM: Crystal structure of vancosaminyltransferase GtfD from the vancomycin biosynthetic pathway: interactions with acceptor and nucleotide ligands. Biochemistry. 2004 May 11;43(18):5170-80. [PubMed:15122882 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Baneres-Roquet F, Gualtieri M, Villain-Guillot P, Pugniere M, Leonetti JP: Use of a surface plasmon resonance method to investigate antibiotic and plasma protein interactions. Antimicrob Agents Chemother. 2009 Apr;53(4):1528-31. doi: 10.1128/AAC.00971-08. Epub 2009 Jan 21. [PubMed:19164148 ]
Kind
Protein
Organism
Enterococcus faecium
Pharmacological action
unknown
General Function:
Zinc ion binding
Specific Function:
Catalyzes hydrolysis of the D-alanyl-D-alanine dipeptide.
Gene Name:
vanX
Uniprot ID:
Q06241
Molecular Weight:
23379.995 Da
References
  1. Hill CM, Krause KM, Lewis SR, Blais J, Benton BM, Mammen M, Humphrey PP, Kinana A, Janc JW: Specificity of induction of the vanA and vanB operons in vancomycin-resistant enterococci by telavancin. Antimicrob Agents Chemother. 2010 Jul;54(7):2814-8. doi: 10.1128/AAC.01737-09. Epub 2010 Apr 19. [PubMed:20404117 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]
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Drug created on June 13, 2005 07:24 / Updated on December 08, 2016 11:11