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Showing drug card for Vancomycin (DB00512)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-02-19 16:03:33
Primary Accession Number DB00512
Secondary Accession Number
  • APRD01287
  • EXPT03217
Name Vancomycin
Drug Type
  • Approved
  • Small Molecule
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]
Synonyms
  1. Vancomycin HCL
Brand Names
  1. Vancocin
  2. Vancocin HCL
  3. Vancoled
  4. Vancor
Brand Mixtures Not Available
Chemical IUPAC Name (1S,2R,18R,22S,25R,28R,40R)-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)-5,15-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[26.14.2.2^{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(39),35,37,46,49-pentadecaene-40-carboxylic acid
Chemical Formula C66H75Cl2N9O24
Chemical Structure Structure
CAS Registry Number 1404-90-6
InChI Identifier InChI=1/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/f/h72-77,94H,69H2
InChI Key MYPYJXKWCTUITO-RBHQQIGCDM
KEGG Drug D00212 Link Image
KEGG Compound C06689 Link Image
PubChem Compound 441141 Link Image
PubChem Substance 8914 Link Image
ChEBI ID 28001 Link Image
PharmGKB ID PA451850 Link Image
HET ID DVV Link Image
GenBank ID Not Available
Drug ID Number [DIN] 02241807 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/vancomycin.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Vancomycin Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 1449.2540
Monoisotopic Molecular Weight 1447.4302
State Solid
Melting Point Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 2.25e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity -3.1 Source: PhysProp
Predicted LogP 1.12 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -3.81 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID 1PNV Link Image
Experimental PDB File Show
Experimental PDB Structure
Isomeric SMILES CN[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)C2=CC(Cl)=C(OC3=CC4=CC(OC5=C(Cl)C=C(C=C5)[C@@H](O)[C@@H]5NC(=O)[C@H](NC(=O)[C@@H]4NC(=O)[C@H](CC(N)=O)NC1=O)C1=CC(=C(O)C=C1)C1=C(C=C(O)C=C1O)[C@@H](NC5=O)C(O)=O)=C3O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1)C=C2
Canonical SMILES CNC(CC(C)C)C(=O)NC1C(O)C2=CC(Cl)=C(OC3=CC4=CC(OC5=C(Cl)C=C(C=C5)C(O)C5NC(=O)C(NC(=O)C4NC(=O)C(CC(N)=O)NC1=O)C1=CC(=C(O)C=C1)C1=C(C=C(O)C=C1O)C(NC5=O)C(O)=O)=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1)C=C2
Drug Category
  • Anti-Bacterial Agents
  • Glycopeptide antibacterials
ATC Codes
AHFS Codes
  • 08:12.28.16
Indication For the treatment of serious or severe infections caused by susceptible strains of methicillin-resistant (beta-lactam-resistant) staphylococci.
Pharmacology Vancomycin 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 Action The 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.
Absorption Poorly absorbed from gastrointestinal tract, however systemic absorption (up to 60%) may occur following intraperitoneal administration.
Toxicity The 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.
Protein Binding Approximately 55% serum protein bound.
Biotransformation Not Available
Half Life Half-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.
Dosage Forms
Form Route
Capsule Oral
Powder, for solution Intravenous
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Colistimethate Additive nephrotoxic effects may occur. Consider alternate therapy or monitor for renal function during concomitant therapy.
Gallium nitrate Additive nephrotoxic effects may occur. Avoid concomitant therapy.
Food Interactions Not Available
Pathways Not Available
General References
  1. 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 Link Image]
  2. Sivagnanam S, Deleu D: Red man syndrome. Crit Care. 2003 Apr;7(2):119-20. Epub 2002 Dec 23. [PubMed Link Image]
  3. Levine DP: Vancomycin: a history. Clin Infect Dis. 2006 Jan 1;42 Suppl 1:S5-12. [PubMed Link Image]
  4. Small PM, Chambers HF: Vancomycin for Staphylococcus aureus endocarditis in intravenous drug users. Antimicrob Agents Chemother. 1990 Jun;34(6):1227-31. [PubMed Link Image]
  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 Link Image]
  6. Wikipedia Link Image
  7. RxList Link Image
Organisms Affected
  • Enteric bacteria and other eubacteria
Targets
  1. DNA
  2. Glycosyltransferase GtfA
Drug Target 1 [top]
Target 1 ID 874
Target 1 Name DNA
Target 1 Synonyms
  1. Deoxyribonucleic acid
Target 1 Gene Name Not Available
Target 1 Protein Sequence Not Available
Target 1 Number of Residues 0
Target 1 Molecular Weight 7656 (double strand)
Target 1 Theoretical pI Not Available
Target 1 GO Classification
Function
information storage
information transfer
Process
DNA replication and chromosomal cycle
DNA replication
DNA-dependent DNA replication
DNA replication, synthesis of RNA primer
transcription
transcription, DNA dependent
Component
cell
intracellular
nucleus
mitochondria
Target 1 General Function Biological information storage and information transfer
Target 1 Specific Function DNA is the molecule of heredity, as it is responsible for the genetic propagation of most inherited traits. It is a polynucleic acid that carries genetic information on cell growth, division, and function. DNA consists of two long strands of nucleotides twisted into a double helix and held together by hydrogen bonds. The sequence of nucleotides determines hereditary characteristics. Each strand serves as the template for subsequent DNA replication and as a template for mRNA production, leading to protein synthesis via ribosomes.
Target 1 Pathways
Name SMPDB Link KEGG Link
DNA polymerase map03030 Link Image
RNA polymerase map03020 Link Image
Target 1 Reactions
  • DNA + DNA polymerase + nNTP = 2 DNA + nNDP; DNA + RNA polymerase + NTP = mRNA + nNDP
Target 1 Pfam Domain Function Not Available
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Essential
Target 1 GenBank ID Protein Not Available
Target 1 UniProtKB/Swiss-Prot ID Not Available
Target 1 UniProtKB/Swiss-Prot Entry Name Not Available
Target 1 PDB ID 1BNA Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Nucleus and mitochondria
Target 1 Gene Sequence >Example: Dickerson dodecamer 
CGCGAATTCGCG
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus All loci
Target 1 SNPs Not Available
Target 1 General References
  1. Nadeau D, Marchand C: Change in the kinetics of sulphacetamide tissue distribution in Walker tumor-bearing rats. Drug Metab Dispos. 1975 Nov-Dec;3(6):565-76. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  3. Bernardeau M, Vernoux JP, Henri-Dubernet S, Gueguen M: The Lactobacillus genus. Int J Food Microbiol. 2007 Aug 22;. [PubMed Link Image]
  4. Baddour MM, Abuelkheir MM, Fatani AJ, Bohol MF, Al-Ahdal MN: Molecular epidemiology of methicillin-resistant Staphylococcus aureus (MRSA) isolates from major hospitals in Riyadh, Saudi Arabia. Can J Microbiol. 2007 Aug;53(8):931-6. [PubMed Link Image]
  5. Prere MF, Baron O, Fayet O: Rapid identification of bacteria, mecA and van genes from blood cultures. Pathol Biol (Paris). 2007 Oct 1;. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 4790
Target 2 Name Glycosyltransferase GtfA
Target 2 Synonyms
  1. PCZA361.19
Target 2 Gene Name gtfA
Target 2 Protein Sequence >Glycosyltransferase GtfA 
MRVLITGCGSRGDTEPLVALAARLRELGADARMCLPPDYVERCAEVGVPMVPVGRAVRAG
AREPGELPPGAAEVVTEVVAEWFDKVPAAIEGCDAVVTTGLLPAAVAVRSMAEKLGIPYR
YTVLSPDHLPSEQSQAERDMYNQGADRLFGDAVNSHRASIGLPPVEHLYDYGYTDQPWLA
ADPVLSPLRPTDLGTVQTGAWILPDERPLSAELEAFLAAGSTPVYVGFGSSSRPATADAA
KMAIKAVRASGRRIVLSRGWADLVLPDDGADCFVVGEVNLQELFGRVAAAIHHDSAGTTL
LAMRAGIPQIVVRRVVDNVVEQAYHADRVAELGVGVAVDGPVPTIDSLSAALDTALAPEI
RARATTVADTIRADGTTVAAQLLFDAVSLEKPTVPA
Target 2 Number of Residues 402
Target 2 Molecular Weight 41663
Target 2 Theoretical pI 4.56
Target 2 GO Classification
Function
catalytic activity
transferase activity
transferase activity, transferring glycosyl groups
transferase activity, transferring hexosyl groups
Process
biopolymer metabolism
biopolymer modification
lipid modification
lipid glycosylation
physiological process
metabolism
macromolecule metabolism
carbohydrate metabolism
Component
Not Available
Target 2 General Function Involved in transferase activity, transferring hexosyl groups
Target 2 Specific Function Not Available
Target 2 Pathways Not Available
Target 2 Reactions Not Available
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • None
Target 2 Essentiality Essential
Target 2 GenBank ID Protein Not Available
Target 2 UniProtKB/Swiss-Prot ID P96558 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name P96558_AMYOR Link Image
Target 2 PDB ID 1PNV Link Image
Target 2 PDB File Show
Target 2 3D Structure
Target 2 Cellular Location Not Available
Target 2 Gene Sequence >1191 bp 
ATGCGCGTGTTGATTACGGGGTGTGGATCGCGCGGAGATACCGAACCGTTGGTGGCATTG
GCGGCACGGTTGCGGGAACTCGGTGCGGACGCGCGGATGTGCCTGCCGCCGGACTACGTG
GAGCGGTGCGCCGAGGTCGGTGTGCCGATGGTGCCGGTCGGTCGGGCGGTGCGCGCAGGG
GCACGCGAGCCGGGAGAACTGCCGCCGGGGGCGGCCGAAGTCGTGACCGAGGTGGTCGCC
GAATGGTTCGACAAGGTCCCGGCGGCCATCGAGGGGTGTGACGCGGTGGTGACGACCGGC
TTGCTGCCCGCCGCGGTCGCTGTCCGGTCGATGGCCGAGAAGCTGGGCATCCCGTACCGC
TACACCGTGCTGTCTCCGGACCATCTGCCGTCGGAGCAAAGCCAGGCGGAGCGGGACATG
TACAACCAGGGCGCCGACAGGCTTTTCGGTGACGCGGTCAACAGCCACCGGGCCTCGATC
GGCCTGCCACCGGTGGAGCACCTCTACGACTACGGCTACACCGATCAGCCCTGGCTGGCG
GCGGACCCGGTGCTGTCCCCGCTGCGGCCGACGGACCTCGGCACTGTGCAGACCGGTGCG
TGGATCCTGCCCGACGAACGGCCGCTTTCCGCGGAGCTGGAGGCGTTTCTGGCTGCCGGG
TCGACGCCGGTGTACGTGGGTTTCGGCAGCTCGTCCCGACCGGCAACCGCTGACGCCGCG
AAGATGGCCATCAAGGCGGTCCGTGCCAGTGGCCGCCGGATCGTTCTCTCCCGCGGCTGG
GCCGATTTGGTCCTGCCGGACGACGGGGCCGACTGCTTCGTGGTCGGCGAAGTGAACCTT
CAGGAGCTGTTCGGCCGGGTGGCCGCCGCCATCCACCACGACAGCGCGGGCACGACGCTG
CTGGCCATGCGGGCGGGCATCCCCCAGATCGTGGTGCGCCGCGTAGTGGACAACGTGGTG
GAGCAGGCGTACCACGCCGACCGGGTGGCCGAGCTGGGTGTCGGTGTGGCGGTCGACGGT
CCGGTCCCGACCATCGACTCCTTGTCGGCCGCGCTCGACACGGCTCTGGCCCCGGAGATC
CGTGCGCGAGCGACGACCGTGGCAGACACGATTCGCGCCGATGGGACAACGGTGGCCGCG
CAGCTGCTGTTCGACGCGGTCAGCCTGGAAAAGCCGACTGTTCCCGCCTGA
Target 2 GenBank Gene ID
Target 2 GeneCard ID Not Available
Target 2 GenAtlas ID Not Available
Target 2 HGNC ID Not Available
Target 2 Chromosome Location Not Available
Target 2 Locus Not Available
Target 2 SNPs SNPJam Report Link Image
Target 2 General References Not Available
Target 2 Drug References Not Available

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.