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Identification
NameVancomycin
Accession NumberDB00512  (APRD01287, EXPT03217)
TypeSmall Molecule
GroupsApproved
Description

Antibacterial 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 Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Jamp-vancomycinpowder for solution10 gintravenousJamp Pharma Corporation2014-06-06Not applicableCanada
Jamp-vancomycinpowder for solution5 gintravenousJamp Pharma Corporation2014-09-22Not applicableCanada
Jamp-vancomycinpowder for solution1 gintravenousJamp Pharma Corporation2014-09-22Not applicableCanada
Jamp-vancomycinpowder for solution500 mgintravenousJamp Pharma Corporation2014-09-22Not applicableCanada
Jamp-vancomycincapsule250 mgoralJamp Pharma Corporation2014-03-26Not applicableCanada
Jamp-vancomycincapsule125 mgoralJamp Pharma Corporation2014-03-26Not applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPpowder for solution5 gintravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPpowder for solution1 gintravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPpowder for solution500 mgintravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPpowder for solution10 gintravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
PMS-vancomycincapsule250 mgoralPharmascience Inc2015-03-18Not applicableCanada
PMS-vancomycincapsule125 mgoralPharmascience IncNot applicableNot 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 gintravenousPharmaceutical Partners Of Canada Inc1987-12-312008-02-15Canada
Sterile Vancomycin Hydrochloride, USPpowder for solution500 mgintravenousPharmaceutical Partners Of Canada Inc1959-12-312008-02-15Canada
Val-vancomycinpowder for solution1 gintravenousValeant Canada Lp Valeant Canada S.E.C.2010-09-23Not 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
Val-vancomycinpowder for solution5 gintravenousValeant Canada Lp Valeant Canada S.E.C.Not applicableNot applicableCanada
Vancocincapsule250 mgoralMerus Labs International Inc1989-12-31Not applicableCanada
Vancocincapsule250 mg/1oralANI Pharmaceuticals, Inc.2014-11-17Not applicableUs
Vancocincapsule125 mg/1oralANI Pharmaceuticals, Inc.2014-11-17Not applicableUs
Vancocincapsule250 mg/1oralCardinal Health1986-04-15Not applicableUs
Vancocincapsule250 mg/1oralViro Pharma1986-04-15Not applicableUs
Vancocincapsule125 mg/1oralCardinal Health1986-04-15Not applicableUs
Vancocincapsule125 mg/1oralViro Pharma1986-04-15Not applicableUs
Vancocincapsule125 mgoralMerus Labs International Inc1989-12-31Not applicableCanada
Vancocin Cp Add-vantage Inj 500mg/vialpowder for solution500 mgintravenousEli Lilly Canada Inc1989-12-312002-07-26Canada
Vancocin Inj 1gm/vial Advantagepowder1 gintravenousEli Lilly Canada Inc1989-12-312002-07-26Canada
Vancomycin Hydrochlorideinjection, solution500 mg/100mLintravenousBaxter Healthcare Corporation2015-12-18Not applicableUs
Vancomycin Hydrochlorideinjection, solution1 g/200mLintravenousBaxter Healthcare Corporation2015-12-18Not applicableUs
Vancomycin Hydrochlorideinjection, solution500 mg/100mLintravenousBaxter Healthcare Corporation1958-11-14Not applicableUs
Vancomycin Hydrochloridecapsule250 mg/1oralPrasco Laboratories2012-04-10Not applicableUs
Vancomycin Hydrochloridecapsule125 mg/1oralPrasco Laboratories2012-04-10Not applicableUs
Vancomycin Hydrochlorideinjection, solution750 mg/150mLintravenousBaxter Healthcare Corporation1958-11-14Not applicableUs
Vancomycin Hydrochloridecapsule250 mg/1oralANI Pharmaceuticals, Inc.2015-10-26Not applicableUs
Vancomycin Hydrochlorideinjection, solution750 mg/150mLintravenousBaxter Healthcare Corporation2015-12-18Not applicableUs
Vancomycin Hydrochlorideinjection, solution1 g/200mLintravenousBaxter Healthcare Corporation1958-11-14Not applicableUs
Vancomycin Hydrochloridecapsule125 mg/1oralANI Pharmaceuticals, Inc.2015-10-26Not applicableUs
Vancomycin Hydrochloride Capsules, USPcapsule250 mgoralStrides Arcolab LimitedNot applicableNot applicableCanada
Vancomycin Hydrochloride Capsules, USPcapsule125 mgoralStrides Arcolab LimitedNot applicableNot applicableCanada
Vancomycin Hydrochloride Capsules, USPcapsule250 mgoralFresenius Kabi Canada Ltd2012-07-16Not applicableCanada
Vancomycin Hydrochloride Capsules, USPcapsule125 mgoralFresenius Kabi Canada Ltd2012-07-16Not applicableCanada
Vancomycin Hydrochloride for Injectionpowder for solution1000 mgintravenousSterimax Inc2013-01-30Not applicableCanada
Vancomycin Hydrochloride for Injectionpowder for solution10 gintravenousSterimax Inc2013-09-30Not applicableCanada
Vancomycin Hydrochloride for Injectionpowder for solution500 mgintravenousSterimax Inc2013-09-30Not applicableCanada
Vancomycin Hydrochloride for Injection USPpowder for solution1000 mgintravenousGeneric Medical Partners IncNot applicableNot applicableCanada
Vancomycin Hydrochloride for Injection USPpowder for solution500 mgintravenousGeneric Medical Partners IncNot applicableNot applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution10 gintravenousMylan Pharmaceuticals UlcNot applicableNot applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution5 gintravenousFresenius Kabi Canada Ltd1996-08-14Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution10 gintravenousHospira Healthcare Corporation2015-10-05Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution1 gintravenousFresenius Kabi Canada Ltd1992-12-31Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution5 gintravenousHospira Healthcare Corporation2015-11-17Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution500 mgintravenousFresenius Kabi Canada Ltd1992-12-31Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution10 gintravenousSandoz Canada Incorporated2013-02-14Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution1000 mgintravenousHospira Healthcare Corporation2000-03-31Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution10 gintravenousPharmaceutical Partners Of Canada Inc1993-12-312008-02-15Canada
Vancomycin Hydrochloride for Injection, USPpowder for solution5 gintravenousSandoz Canada Incorporated2013-02-14Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution500 mgintravenousHospira Healthcare Corporation2000-03-31Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution5 gintravenousMylan Pharmaceuticals Ulc2013-12-28Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution1 gintravenousMylan Pharmaceuticals Ulc2014-03-10Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution1 gintravenousSandoz Canada Incorporated2014-03-18Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution500 mgintravenousMylan Pharmaceuticals Ulc2014-03-10Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution500 mgintravenousSandoz Canada Incorporated2014-03-18Not applicableCanada
Vancomycin Hydrochloride for Injection, USPpowder for solution10 gintravenousFresenius Kabi Canada Ltd2000-07-10Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Sterile Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution5 g/100mLintravenousAkorn Strides Llc2008-12-31Not applicableUs
Sterile Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousRebel Distributors Corp2008-12-31Not applicableUs
Sterile Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution5 g/100mLintravenousPfizer Laboratories Div Pfizer Inc2011-05-10Not applicableUs
Sterile Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/20mLintravenousAkorn Strides Llc2008-12-31Not applicableUs
Sterile Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousGeneral Injectables & Vaccines, Inc2010-09-01Not applicableUs
Sterile Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousAkorn Strides Llc2008-12-31Not applicableUs
Vancomycininjection, powder, lyophilized, for solution10 g/100mLintravenousSagent Pharmaceuticals2012-09-20Not applicableUs
Vancomycininjection, powder, lyophilized, for solution5 g/100mLintravenousSagent Pharmaceuticals2012-09-20Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousGland Pharma Limited2016-02-23Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/20mLintravenousMylan Institutional LLC2008-06-30Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/1intravenousXellia Pharmaceuticals, Ap S2014-04-10Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousSandoz Inc2010-04-27Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousMylan Institutional LLC2008-12-31Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution750 mg/250mLintravenousHospira, Inc.1988-08-04Not applicableUs
Vancomycin Hydrochloridecapsule250 mg/1oralAlvogen, Inc.2012-04-09Not applicableUs
Vancomycin Hydrochloridecapsule125 mg/1oralAkorn, Inc.2012-04-09Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousPfizer Laboratories Div Pfizer Inc2011-05-10Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousHospira, Inc.1990-12-21Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution5 g/100mLintravenousMylan Institutional LLC2008-12-31Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousCardinal Health2010-06-04Not applicableUs
Vancomycin Hydrochlorideinjection10 g/100mLintravenousXellia Pharmaceuticals Ap S2015-02-10Not applicableUs
Vancomycin Hydrochloridecapsule250 mg/1oralAPP Pharmaceuticals, LLC2012-06-18Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/1intravenousXellia Pharmaceuticals, Ap S2014-04-10Not applicableUs
Vancomycin Hydrochloridecapsule250 mg/1oralWatson Laboratories, Inc.2012-04-09Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/20mLintravenousMylan Institutional LLC2008-12-31Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/20mLintravenousCardinal Health2010-06-04Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution5 g/100mLintravenousHeritage Pharmaceuticals Inc.2011-11-25Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousHospira, Inc.1988-08-04Not applicableUs
Vancomycin Hydrochlorideinjection5 g/100mLintravenousXellia Pharmaceuticals Ap S2015-02-10Not applicableUs
Vancomycin Hydrochloridecapsule125 mg/1oralAPP Pharmaceuticals, LLC2012-06-18Not applicableUs
Vancomycin Hydrochloridecapsule125 mg/1oralWatson Laboratories, Inc.2012-04-09Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousMylan Institutional LLC2008-12-31Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution10 g/1intravenousAuro Medics Pharma Llc2016-03-29Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/250mLintravenousCardinal Health2010-07-29Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/8mLintravenousHeritage Pharmaceuticals Inc.2013-11-15Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution10 g/100mLintravenousPfizer Laboratories Div Pfizer Inc.2011-09-19Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution10 g/100mLintravenousAGILA SPECIALTIES PRIVATE LIMITED2011-07-02Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution10 g/100mLintravenousAPP Pharmaceuticals, LLC2004-11-30Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/250mLintravenousHospira, Inc.1992-10-29Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution10 g/100mLintravenousMylan Institutional LLC2011-09-19Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution5 g/1intravenousAuro Medics Pharma Llc2016-03-29Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/100mLintravenousCardinal Health2010-07-29Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/4mLintravenousHeritage Pharmaceuticals Inc.2013-11-15Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution10 g/100mLintravenousPfizer Laboratories Div Pfizer Inc2011-05-10Not applicableUs
Vancomycin Hydrochloridecapsule250 mg/1oralLupin Pharmaceuticals, Inc.2015-03-27Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution5 g/100mLintravenousAPP Pharmaceuticals, LLC2001-07-17Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/100mLintravenousHospira, Inc.1992-10-29Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution5 g/100mLintravenousMylan Institutional LLC2008-12-31Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/20mLintravenousAuro Medics Pharma Llc2016-03-31Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/250mLintravenousCardinal Health2010-07-29Not applicableUs
Vancomycin Hydrochloridecapsule125 mg/1oralLupin Pharmaceuticals, Inc.2015-03-27Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/20mLintravenousAPP Pharmaceuticals, LLC2000-09-20Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/20mLintravenousHospira, Inc.1988-08-04Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/20mLintravenousSandoz Inc2010-04-27Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/20mLintravenousGland Pharma Limited2016-02-23Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousMylan Institutional LLC2012-01-10Not applicableUs
Vancomycin Hydrochloridecapsule125 mg/1oralAlvogen, Inc.2012-04-09Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/20mLintravenousMylan Institutional LLC2008-12-31Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousAuro Medics Pharma Llc2016-03-31Not applicableUs
Vancomycin Hydrochloridecapsule250 mg/1oralAkorn, Inc.2012-04-09Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution1 g/20mLintravenousPfizer Laboratories Div Pfizer Inc2011-05-10Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution10 g/100mLintravenousMylan Institutional LLC2011-09-19Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution500 mg/10mLintravenousAPP Pharmaceuticals, LLC2000-09-01Not applicableUs
Vancomycin Hydrochlorideinjection, powder, lyophilized, for solution100 mg/mLintravenousHospira, Inc.2009-04-29Not applicableUs
Vancomycin Hydroclorideinjection, powder, lyophilized, for solution10 g/80mLintravenousHeritage Pharmaceuticals Inc.2011-11-29Not 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, solution6 mg/mLintravenousCantrell Drug Company2012-05-25Not applicableUs
Vancomycin HClinjection, solution5 mg/mLintravenousCantrell Drug Company2012-05-25Not applicableUs
International Brands
NameCompany
COVANCNucleus
VancoledNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Vancomycin Hydrochloride
Thumb
  • InChI Key: LCTORFDMHNKUSG-XTTLPDOESA-N
  • Monoisotopic Mass: 1483.406877526
  • Average Mass: 1485.715
DBSALT000300
Categories
UNII6Q205EH1VU
CAS number1404-90-6
WeightAverage: 1449.254
Monoisotopic: 1447.430199787
Chemical FormulaC66H75Cl2N9O24
InChI KeyInChIKey=MYPYJXKWCTUITO-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentCyclic peptides
Alternative Parents
Substituents
  • Cyclic alpha peptide
  • Phenolic glycoside
  • N-acyl-alpha amino acid or derivatives
  • Amino sugar
  • Alpha-amino acid amide
  • O-glycosyl compound
  • Glycosyl compound
  • Disaccharide
  • Diaryl ether
  • Alpha-amino acid or derivatives
  • N-substituted-alpha-amino acid
  • Resorcinol
  • Amino saccharide
  • Fatty acyl
  • Benzenoid
  • Oxane
  • N-acyl-amine
  • Fatty amide
  • Saccharide
  • Aryl halide
  • Aryl chloride
  • Secondary carboxylic acid amide
  • Secondary alcohol
  • Primary carboxylic acid amide
  • Polyol
  • Lactam
  • Carboxamide group
  • 1,2-diol
  • 1,2-aminoalcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Ether
  • Secondary aliphatic amine
  • Carboxylic acid
  • Carboxylic acid amide
  • Acetal
  • Hydrocarbon derivative
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the treatment of serious or severe infections caused by susceptible strains of methicillin-resistant (beta-lactam-resistant) staphylococci.
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.
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
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
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
Powder for solutionintravenous1 g
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/250mL
Injection, powder, lyophilized, for solutionintravenous1 g/1
Injection, powder, lyophilized, for solutionintravenous1 g/20mL
Injection, powder, lyophilized, for solutionintravenous10 g/100mL
Injection, powder, lyophilized, for solutionintravenous10 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/4mL
Injection, powder, lyophilized, for solutionintravenous500 mg/100mL
Injection, powder, lyophilized, for solutionintravenous500 mg/1
Injection, powder, lyophilized, for solutionintravenous750 mg/250mL
Injection, solutionintravenous1 g/200mL
Injection, solutionintravenous500 mg/100mL
Injection, solutionintravenous750 mg/150mL
Powder for solutionintravenous1000 mg
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
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
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
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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)
Interactions
Drug Interactions
Drug
AmikacinVancomycin may increase the nephrotoxic activities of Amikacin.
ArbekacinVancomycin may increase the nephrotoxic activities of Arbekacin.
Atracurium besylateVancomycin may increase the neuromuscular blocking activities of Atracurium besylate.
CelecoxibThe serum concentration of Vancomycin can be increased when it is combined with Celecoxib.
CholestyramineThe therapeutic efficacy of Vancomycin can be decreased when used in combination with Cholestyramine.
Cisatracurium besylateVancomycin may increase the neuromuscular blocking activities of Cisatracurium besylate.
ColesevelamThe therapeutic efficacy of Vancomycin can be decreased when used in combination with Colesevelam.
ColestipolThe therapeutic efficacy of Vancomycin can be decreased when used in combination with Colestipol.
ColistimethateVancomycin may increase the nephrotoxic activities of Colistimethate.
ColistinVancomycin may increase the nephrotoxic activities of Colistin.
DiclofenacThe serum concentration of Vancomycin can be increased when it is combined with Diclofenac.
DiflunisalThe serum concentration of Vancomycin can be increased when it is combined with Diflunisal.
EtodolacThe serum concentration of Vancomycin can be increased when it is combined with Etodolac.
FenoprofenThe serum concentration of Vancomycin can be increased when it is combined with Fenoprofen.
FloctafenineThe serum concentration of Vancomycin can be increased when it is combined with Floctafenine.
FlurbiprofenThe serum concentration of Vancomycin can be increased when it is combined with Flurbiprofen.
FramycetinVancomycin may increase the nephrotoxic activities of Framycetin.
GentamicinVancomycin may increase the nephrotoxic activities of Gentamicin.
IbuprofenThe serum concentration of Vancomycin can be increased when it is combined with Ibuprofen.
IndomethacinThe serum concentration of Vancomycin can be increased when it is combined with Indomethacin.
InfliximabThe serum concentration of Vancomycin can be increased when it is combined with Infliximab.
KanamycinVancomycin may increase the nephrotoxic activities of Kanamycin.
KetoprofenThe serum concentration of Vancomycin can be increased when it is combined with Ketoprofen.
KetorolacThe serum concentration of Vancomycin can be increased when it is combined with Ketorolac.
Mefenamic acidThe serum concentration of Vancomycin can be increased when it is combined with Mefenamic acid.
MeloxicamThe serum concentration of Vancomycin can be increased when it is combined with Meloxicam.
NabumetoneThe serum concentration of Vancomycin can be increased when it is combined with Nabumetone.
NaproxenThe serum concentration of Vancomycin can be increased when it is combined with Naproxen.
NeomycinVancomycin may increase the nephrotoxic activities of Neomycin.
NetilmicinVancomycin may increase the nephrotoxic activities of Netilmicin.
OxaprozinThe serum concentration of Vancomycin can be increased when it is combined with Oxaprozin.
PancuroniumVancomycin may increase the neuromuscular blocking activities of Pancuronium.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Vancomycin.
PiperacillinPiperacillin may increase the nephrotoxic activities of Vancomycin.
PiroxicamThe serum concentration of Vancomycin can be increased when it is combined with Piroxicam.
RibostamycinVancomycin may increase the nephrotoxic activities of Ribostamycin.
RocuroniumVancomycin may increase the neuromuscular blocking activities of Rocuronium.
SpectinomycinVancomycin may increase the nephrotoxic activities of Spectinomycin.
StreptomycinVancomycin may increase the nephrotoxic activities of Streptomycin.
SuccinylcholineVancomycin may increase the neuromuscular blocking activities of Succinylcholine.
SulindacThe serum concentration of Vancomycin can be increased when it is combined with Sulindac.
Tiaprofenic acidThe serum concentration of Vancomycin can be increased when it is combined with Tiaprofenic acid.
TobramycinVancomycin may increase the nephrotoxic activities of Tobramycin.
TolmetinThe serum concentration of Vancomycin can be increased when it is combined with Tolmetin.
VecuroniumVancomycin may increase the neuromuscular blocking activities of Vecuronium.
Food InteractionsNot Available

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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11