Identification

Name
Vancomycin
Accession Number
DB00512  (APRD01287, EXPT03217)
Type
Small Molecule
Groups
Approved
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.

As of January 29 2018, CutisPharma's Firvanq is the only FDA approved vancomycin oral liquid treatment option available for the the treatment of Clostridium difficile associated diarrhea and enterocolitis caused by Staphylococcus aureus, including methicillin-resistant strains [LP1196]. Such an oral liquid formulation is expected to make Clostridium difficile associated diarrhea therapy more accessible in comparison to previously available specialty compounding products [LP1196].

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-α-L-lyxo-hexopyranosyl)-β-D-glucopyranosyloxy]-5,15-dichloro-2,18,32,35,37-pentahydroxy-19-[(N-methyl-D-leucyl)amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentaazaoctacyclo[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta-3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49-pentadecaene-40-carboxylic acid
  • (2.2Sp,3.5Sa,2.6Sp)-O4.2,C3.4:C5.4,O4.6:C3.5,C2.7-tricyclo[N-methyl-D-leucyl-3-chloro-(R)-β-hydroxy-D-tyrosyl-L-asparaginyl-D-2-(4-{[2-O-(3-amino-2,3,6-trideoxy-3-C-methyl-α-L-lyxo-hexopyranosyl)-β-D-glucopyranosyl]oxy}phenyl)glycyl-D-2-(4-hydroxyphenyl)glycyl-3-chloro-(R)-β-hydroxy-L-tyrosyl-L-2-(3,5-dihydroxyphenyl)glycine]
  • Vancomicina
  • Vancomycine
  • Vancomycinum
Product Ingredients
IngredientUNIICASInChI Key
Vancomycin hydrochloride71WO621TJD1404-93-9LCTORFDMHNKUSG-XTTLPDOESA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
FirvanqKit1 g/1gOralCutisPharma, Inc.2018-01-26Not applicableUs
FirvanqKit1 g/1gOralCutisPharma, Inc.2018-01-26Not applicableUs
FirvanqKit1 g/1gOralCutisPharma, Inc.2018-01-26Not applicableUs
FirvanqKit1 g/1gOralCutisPharma, Inc.2018-01-26Not applicableUs
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 solution500 mgIntravenousPartners Health Care, Inc.1959-12-312008-02-15Canada
Sterile Vancomycin Hydrochloride, USPPowder, for solution1 gIntravenousPartners Health Care, Inc.1987-12-312008-02-15Canada
VancocinCapsule250 mg/1OralCardinal Health1986-04-152011-01-31Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Jamp-vancomycinPowder, for solution10 gIntravenousJamp Pharma Corporation2014-06-06Not applicableCanada
Jamp-vancomycinCapsule125 mgOralJamp Pharma Corporation2014-03-26Not 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-vancomycinPowder, for solution5 gIntravenousJamp Pharma Corporation2014-09-22Not applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPPowder, for solution500 mgIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPPowder, for solution5 gIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPPowder, for solution1 gIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Mylan-vancomycin Hydrochloride for Injection, USPPowder, for solution10 gIntravenousMylan PharmaceuticalsNot applicableNot applicableCanada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Vancomycin HClVancomycin hydrochloride (6 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2012-05-25Not applicableUs
Vancomycin HClVancomycin hydrochloride (5 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2013-08-30Not applicableUs
Vancomycin HClVancomycin hydrochloride (4.2 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2013-05-01Not applicableUs
International/Other Brands
COVANC (Nucleus) / Vancocin / Vancoled
Categories
UNII
6Q205EH1VU
CAS number
1404-90-6
Weight
Average: 1449.254
Monoisotopic: 1447.430199787
Chemical Formula
C66H75Cl2N9O24
InChI Key
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[C@H](CC(C)C)C(=O)N[C@@H]1[C@H](O)C2=CC=C(OC3=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O[C@H]4C[C@](C)(N)[C@H](O)[C@H](C)O4)C4=CC(=C3)[C@@H](NC(=O)[C@H](CC(N)=O)NC1=O)C(=O)N[C@@H]1C3=CC(=C(O)C=C3)C3=C(O)C=C(O)C=C3[C@H](NC(=O)[C@@H](NC1=O)[C@H](O)C1=CC(Cl)=C(O4)C=C1)C(O)=O)C(Cl)=C2

Pharmacology

Indication

A variety of dosage forms (for example, oral, injections, etc.) exist for the treatment of serious or severe infections caused by susceptible strains of methicillin-resistant (beta-lactam-resistant) staphylococci [Label].

Additionally, a unique FDA approved oral liquid treatment is also available and indicated for the treatment of Clostridium difficile associated diarrhea and enterocolitis caused by Staphylococcus aureus, including methicillin-resistant strains [9].

Associated Conditions
Pharmacodynamics

Vancomycin is a branched tricyclic glycosylated nonribosomal peptide produced by the fermentation of the Actinobacteria species Amycolatopsis orientalis (formerly Nocardia orientalis) [10]. It is often reserved as the "drug of last resort", used only after treatment with other antibiotics has 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 [Label].

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. [10]

TargetActionsOrganism
AD-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan
ligand
Gram-positive bacteria
Absorption

Poorly absorbed from gastrointestinal tract, however systemic absorption (up to 60%) may occur following intraperitoneal administration [Label].

Volume of distribution

The volume of distribution, as discussed in the literature, varies between 0.4-1 L/kg [6].

Protein binding

Approximately 50% serum protein bound [7].

Metabolism

Since almost 75-80% of the drug is excreted unchanged in the urine after the first 24 hours following administration, there is seemingly no apparent metabolism of the drug [Label]. The concentration of vancomycin in the liver tissue and bile 24 hours after administration has also been reported at or below detection limits as well [8].

Route of elimination

In the first 24 hours, about 75-80% of an administered dose of vancomycin is excreted in urine by glomerular filtration [Label].

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 [Label].

Clearance

The mean plasma clearance of vancomycin is about 0.058 L/kg/h [Label].

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. [Label]

Conversely, the most common adverse effects associated with vancomycin appear to be nausea, abdominal pain, and hypokalemia [Label]. In particular, incidences of hypokalemia, urinary tracy infection, peripheral edema, insomnia, constipation, anemia, depression, vomiting, and hypotension are higher among subjects >65 years of than in those that are 65 years old or younger [Label].

Additionally, nephrotoxicity involving reports of renal failure, renal impairment, elevated blood creatinine, and others has also occurred with vancomycin therapy during studies, and can occur during or after completion of a course of therapy [Label]. Risk of such nephrotoxicity is increased in patients greater than 65 years of age [Label].

Ototoxicity has also occurred in patients receiving vancomycin treatment, and it can be transient or permanent. This effect has been reported primarily in patients who have been given excessive intravenous doses, who have kidney dysfunction, who have an underlying hearing loss, or who are receiving concomitant therapy with another ototoxic agent like an aminoglycoside [Label]. Potentially related adverse effects like vertigo, dizziness, and tinnitus have also been reported [Label].

Neutropenia, often beginning one week or more after onset of intravenous vancomycin therapy or after a total dose of more than 25 mg has been observed for several dozen patients as well. This neutropenia however, appears to be promptly reversible when the vancomycin treatment is discontinued. Alternatively, thrombocytopenia has also been reported [Label].

Additionally, a condition has been reported that is described as being similar to IV-induced symptoms involving symptoms consistent with anaphylactoid reactions, including hypotension, wheezing, dyspnea, urticaria, pruritus, flushing of the upper body (in what is known as the so-called 'Red Man Syndrome'), pain and muscle spasm of the chest and back. Although on average such reactions usually resolve within 20 minutes, they are just as likely to persist for hours [Label].

In a controlled clinical study, the potential ototoxic and nephrotoxic effects of vancomycin on infants were assessed when the drug was given intravenously to pregnant women for serious staphylococcal infections complicating intravenous drug abuse. The results obtained demonstrated that vancomycin was found in cord blood but that no sensorineural hearing loss or nephrotoxicity attributable to vancomycin was noted. Ultimately however, because the number of subjects treated in this study was limited and vancomycin was administered only in the second and third trimesters, it is not formally known whether vancomycin causes fetal harm. Subsequently, vancomycin should be given to a pregnant woman only if clearly needed [Label].

Although it is known that vancomycin is excreted in human milk based on information obtained from the intravenous administration of the medication, it is not known if vancomycin is excreted into human milk after oral administration. However, because of the overall potential for adverse events, caution must be exercised when vancomycin is given to a nursing woman and a decision must be made whether to discontinue nursing or discontinue the drug, taking into consideration the importance of the drug to the mother [Label].

The safety and effectiveness in pediatric patients have not been formally established [Label].

Patients older than 65 years of age may take longer to respond to therapy compared to patients aged 65 year or younger. Vancomycin treatment in patients aged older than 65 years subsequently should not be discontinued or switched to an alternative treatment prematurely [Label].

Furthermore, clinical studies have demonstrated that geriatric patients are at increased risk of developing nephrotoxicity following treatment with oral vancomycin, which can occur during or after completion of therapy. In patients aged older than 65 years, including those with normal renal function prior to treatment, renal function should be monitored during and following treatment with vancomycin to detect any potential vancomycin induced nephrotoxicity [Label].

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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Vancomycin is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when 3,4-Methylenedioxyamphetamine is combined with Vancomycin.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Vancomycin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Vancomycin.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Vancomycin is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Vancomycin.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Vancomycin.
AceclofenacAceclofenac may decrease the excretion rate of Vancomycin which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Vancomycin which could result in a higher serum level.
AcepromazineThe risk or severity of adverse effects can be increased when Acepromazine is combined with Vancomycin.
Food Interactions
Not Available

References

Synthesis Reference

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]
  6. Rybak MJ: The pharmacokinetic and pharmacodynamic properties of vancomycin. Clin Infect Dis. 2006 Jan 1;42 Suppl 1:S35-9. doi: 10.1086/491712. [PubMed:16323118]
  7. Butterfield JM, Patel N, Pai MP, Rosano TG, Drusano GL, Lodise TP: Refining vancomycin protein binding estimates: identification of clinical factors that influence protein binding. Antimicrob Agents Chemother. 2011 Sep;55(9):4277-82. doi: 10.1128/AAC.01674-10. Epub 2011 Jun 13. [PubMed:21670191]
  8. Matzke GR, Zhanel GG, Guay DR: Clinical pharmacokinetics of vancomycin. Clin Pharmacokinet. 1986 Jul-Aug;11(4):257-82. doi: 10.2165/00003088-198611040-00001. [PubMed:3530582]
  9. CutisPharma Announces FDA Approval of Firvanq (vancomycin) for Treatment of Clostridium Difficile Associated Diarrhea and Staphylococcus Aureus Colitis [Link]
  10. Wikipedia Page on Vancomycin [Link]
External Links
Human Metabolome Database
HMDB0014653
KEGG Drug
D00212
KEGG Compound
C06689
PubChem Compound
14969
PubChem Substance
46505261
ChemSpider
14253
BindingDB
50335519
ChEBI
28001
ChEMBL
CHEMBL262777
Therapeutic Targets Database
DAP001330
PharmGKB
PA451850
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Vancomycin
ATC Codes
A07AA09 — VancomycinJ01XA01 — Vancomycin
AHFS Codes
  • 08:12.28.16 — Glycopeptides
FDA label
Download (57.8 KB)
MSDS
Download (73 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceBMI >30 kg/m2 / Bone destruction / Diabetes Mellitus (DM) / Inflammatory Reaction1
0CompletedTreatmentBacterial Resistance / Respiratory Failure / Respiratory Tract Infections (RTI)1
0Enrolling by InvitationBasic ScienceDietary Modifications / Nutrition1
0RecruitingTreatmentEarly Stage Non-small Cell Lung Cancer1
1CompletedBasic ScienceSimvastatin Pharmacokinetics and Gut Microbiome1
1CompletedSupportive CareCritical Illness / Methicillin-Resistant Staphylococcus Aureus (MRSA) / Sepsis1
1CompletedTreatmentBiliary Atresia / Primary Sclerosing Cholangitis (PSC)1
1CompletedTreatmentCystic Fibrosis (CF) / Healthy Volunteers1
1CompletedTreatmentPrimary Sclerosing Cholangitis (PSC)1
1RecruitingBasic SciencePeritoneal Dialysis-associated Peritonitis1
1RecruitingTreatmentBiliary Atresia / Primary Sclerosing Cholangitis (PSC)1
1RecruitingTreatmentClostridium Difficile Infection (CDI)1
1RecruitingTreatmentDialysis therapy / Pediatric Continuous Renal Replacement Therapy / Renal Failure1
1TerminatedPreventionSurgical Site Infections1
1Unknown StatusTreatmentCystic Fibrosis (CF) / Methicillin-Resistant Staphylococcus Aureus (MRSA)1
1WithdrawnPreventionNeurosurgery1
1, 2CompletedTreatmentAutism Spectrum Conditions/Disorders / Gastrointestinal Problems1
1, 2Not Yet RecruitingPreventionElective Craniotomy-candidated Patients1
2Active Not RecruitingTreatmentChronic Constipation / Slow Transit Constipation1
2CompletedTreatmentBacteremia1
2CompletedTreatmentBacterial Infections1
2CompletedTreatmentBacterial Infections / Infection NOS1
2CompletedTreatmentClostridium Difficile Infection (CDI)2
2CompletedTreatmentClostridium Difficile Infection (CDI) / Diarrhea1
2CompletedTreatmentClostridium Difficile / Pseudomembranous Colitis1
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
2Not Yet RecruitingTreatmentClostridium difficile infection recurrence1
2Not Yet RecruitingTreatmentEnd Stage Renal Disease (ESRD)1
2RecruitingPreventionClostridium Difficile Infection (CDI) / Clostridium difficile infection recurrence1
2RecruitingTreatmentAutism Spectrum Conditions/Disorders / Gastrointestinal Disorders1
2RecruitingTreatmentClostridium Difficile1
2RecruitingTreatmentCrohn's Disease (CD)2
2RecruitingTreatmentLate Onset Neonatal Sepsis1
2RecruitingTreatmentMethicillin-Resistant Staphylococcus Aureus (MRSA) / Pneumonia, Staphylococcal1
2RecruitingTreatmentPre-Diabetic1
2TerminatedTreatmentBacteremia Due to Staphylococcus Aureus1
2TerminatedTreatmentEndocarditis, Bacterial / Infective Endocarditis1
2TerminatedTreatmentHealth-Care-Associated Pneumonia / Pneumonia, Hospital-Acquired / Ventilator-Associated Pneumonia (VAP)1
2TerminatedTreatmentInfected Spacers / Prosthetic Joint Infections of Hip / Prosthetic Joint Infections of Knee1
2TerminatedTreatmentNeoplasms / Neutropenia, Febrile1
2TerminatedTreatmentOsteomyelitis1
2Unknown StatusPreventionWound Infections1
2Unknown StatusTreatmentHip Prosthetic Joint Infection1
2, 3CompletedTreatmentArthropathy of Knee Joint / Revision, Knee Joint1
2, 3Not Yet RecruitingPreventionArthropathy of Knee Joint1
2, 3Not Yet RecruitingTreatmentClostridium Difficile Infection (CDI)1
2, 3RecruitingTreatmentClostridium Difficile1
2, 3TerminatedTreatmentClostridium Difficile Infection (CDI)1
2, 3TerminatedTreatmentClostridium difficile infection recurrence / Laboratory Confirmed Clostridium Difficile Infection1
3CompletedSupportive CareBone Marrow Suppression / Fever, Sweats, and Hot Flashes / Infection NOS / Leukemias / Malignant Lymphomas / 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 / Bacterial Infections / Infections, Gram-Positive Bacterial1
3CompletedTreatmentBacterial Infections1
3CompletedTreatmentClostridium Difficile1
3CompletedTreatmentClostridium Difficile Infection (CDI)4
3CompletedTreatmentClostridium Difficile-Associated Diarrhea (CDAD)1
3CompletedTreatmentClostridium Infections / Diarrhea2
3CompletedTreatmentComplicated Skin and Soft Tissue Infection1
3CompletedTreatmentInfection caused by staphylococci1
3CompletedTreatmentInfection caused by staphylococci / Meningitis / Pneumonia / Sepsis1
3CompletedTreatmentInfectious / Skin Diseases1
3CompletedTreatmentNeutropenia, Febrile1
3CompletedTreatmentNosocomial Neonatal Sepsis1
3CompletedTreatmentPneumonia, Bacterial2
3CompletedTreatmentPrimary Sclerosing Cholangitis (PSC)1
3CompletedTreatmentSkin Diseases, Bacterial / Skin Diseases, Infectious1
3CompletedTreatmentSkin Diseases, Bacterial / Skin Diseases, Infectious / Staphylococcal Skin Infections1
3CompletedTreatmentSkin Structures and Soft Tissue Infections2
3CompletedTreatmentSkin and Subcutaneous Tissue Bacterial Infections / Skin Structures and Soft Tissue Infections1
3CompletedTreatmentSkin and Subcutaneous Tissue Bacterial Infections1
3CompletedTreatmentStaphylococcal Skin Infections2
3Not Yet RecruitingTreatmentCataract operation / Endophthalmitis / Intracameral Antibiotics / Moxifloxacin / Phacoemulsification / Vancomycin1
3Not Yet RecruitingTreatmentChronic Rhinosinusitis (Diagnosis)1
3Not Yet RecruitingTreatmentClostridium Difficile1
3Not Yet RecruitingTreatmentClostridium Difficile Infection (CDI)2
3RecruitingPreventionGeneral Surgery / Infection NOS / Nervous System Diseases1
3RecruitingTreatmentClostridium Difficile1
3RecruitingTreatmentClostridium Difficile Infection (CDI)1
3RecruitingTreatmentConjunctivitis, Bacterial1
3RecruitingTreatmentStaphylococcus Aureus Infections1
3TerminatedTreatmentBacteremia1
3TerminatedTreatmentBacteremia / Infections, Gram-Positive Bacterial1
3TerminatedTreatmentClostridium Infections1
3TerminatedTreatmentComplicated Skin and Soft Tissue Infection1
3TerminatedTreatmentDiabetic Foot1
3TerminatedTreatmentSkin Diseases, Infectious / Soft Tissues Infections1
4Active Not RecruitingBasic ScienceInflammatory Bowel Diseases (IBD) / Primary Sclerosing Cholangitis (PSC)1
4Active Not RecruitingPreventionArrythmias1
4Active Not RecruitingPreventionCalcium Nephrolithiasis / Urinary Tract Infections (UTIs)1
4CompletedNot AvailableComplicated Skin and Structure Infection / Hospital-acquired bacterial pneumonia1
4CompletedNot AvailableStaphylococcus Aureus1
4CompletedBasic ScienceCellulitis1
4CompletedPreventionAortic Valve Disorder / Congenital Heart Disease (CHD)1
4CompletedPreventionClostridium Difficile Infection (CDI) / Prophylaxis / Vancomycin1
4CompletedPreventionMRSA Infections1
4CompletedTreatmentBacteremia1
4CompletedTreatmentCellulitis1
4CompletedTreatmentCellulitis / Skin-structure infections1
4CompletedTreatmentClostridium Difficile1
4CompletedTreatmentCoronary Artery Disease1
4CompletedTreatmentExtracorporeal Membrane Oxygenation1
4CompletedTreatmentInfection NOS / Neutropenia, Febrile1
4CompletedTreatmentInfection NOS / Pneumonia1
4CompletedTreatmentInfective Endocarditis1
4CompletedTreatmentMethicillin Resistant Staphylococcus Aureus (MRSA)1
4CompletedTreatmentMethicillin Resistant Staphylococcus Aureus (MRSA) / Skin/Soft Tissue Infections1
4CompletedTreatmentSkin Diseases, Infectious / Staphylococcal Skin Infections1
4CompletedTreatmentStaphylococcal Skin Infections1
4CompletedTreatmentSurgical Site Infections / Vancomycin1
4CompletedTreatmentVentilator-Associated Pneumonia (VAP)1
4Enrolling by InvitationOtherClostridium Difficile Infection (CDI) / Diarrhea1
4Enrolling by InvitationPreventionClostridium Difficile Infection (CDI)2
4Enrolling by InvitationPreventionFractures, Open / Infection, Postoperative Wound1
4Enrolling by InvitationTreatmentVancomycin1
4Not Yet RecruitingBasic ScienceMicrobial Colonization1
4Not Yet RecruitingPreventionCarpal Tunnel Syndrome (CTS)1
4Not Yet RecruitingTreatmentClostridium Difficile Infection (CDI)1
4Not Yet RecruitingTreatmentFevers / Neutropenia, Febrile1
4RecruitingBasic ScienceNeonatal Infections1
4RecruitingBasic ScienceRabies Human1
4RecruitingPreventionClostridium Difficile Infection (CDI)1
4RecruitingPreventionSpinal Fusion Acquired1
4RecruitingPreventionSurgical Site Infections3
4RecruitingTreatmentAsthma Bronchial1
4RecruitingTreatmentBlood Stream Infections / Endocarditis / MRSA1
4RecruitingTreatmentBone Infection / Joint Infections / Osteomyelitis / Prosthetic Joint Infection / Septic Arthritis1
4RecruitingTreatmentClostridium Difficile Infection (CDI)1
4RecruitingTreatmentClostridium / Difficile / Fidaxomicin / Vancomycin1
4RecruitingTreatmentPrimary Sclerosing Cholangitis (PSC)1
4TerminatedNot AvailableBacteremia / Pneumonia1
4TerminatedHealth Services ResearchComplicated Skin or Skin Structure Infection1
4TerminatedPreventionAcute acute 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
4TerminatedTreatmentImpaired Renal Function / S. Aureus Bacteremia / Skin and Subcutaneous Tissue Bacterial Infections1
4Unknown StatusPreventionClostridium Difficile Infection (CDI)1
4Unknown StatusTreatmentClostridium Difficile Infection (CDI)1
4Unknown StatusTreatmentLiver Cirrhosis1
Not AvailableActive Not RecruitingTreatmentClostridium Difficile Infection (CDI)1
Not AvailableCompletedNot AvailableAcinetobacter Infections1
Not AvailableCompletedNot AvailableAllogenic Blood Stem Cell Transplantation / Neutropenia, Febrile1
Not AvailableCompletedNot AvailableC. Difficile / Diarrhea / Enterocolitis1
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 / Sepsis1
Not AvailableCompletedOtherFlu caused by Influenza1
Not AvailableCompletedPreventionDental Decay1
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 Injury (AKI) / Adverse Effects / Cross-Sectional Study / Infection caused by staphylococci / Vancomycin1
Not AvailableNot Yet RecruitingNot AvailableAcute Kidney Insufficiency / Anti-Infective Agent Toxicity1
Not AvailableNot Yet RecruitingTreatmentInfective Endocarditis1
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 / Sepsis1
Not AvailableTerminatedTreatmentColitis1
Not AvailableTerminatedTreatmentInfection NOS2
Not AvailableUnknown StatusBasic ScienceBMI >30 kg/m2 / Insulin Resistance1
Not AvailableUnknown StatusPreventionInfection NOS1
Not AvailableUnknown StatusPreventionLow Back Pain (LBP)1
Not AvailableUnknown StatusTreatmentAcute Renal Failure (ARF) / Postoperative / Sepsis1
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
  • ACS Dobfar SPA
  • Akorn Inc.
  • Amerisource Health Services Corp.
  • APP Pharmaceuticals
  • Baxter International Inc.
  • Cardinal Health
  • General Injectables and Vaccines Inc.
  • Generamedix Inc.
  • Hospira Inc.
  • Medisca Inc.
  • Mustafa Nevzat Ilac Sanayii AS
  • Neuman Distributors Inc.
  • Norwich Pharmaceuticals Inc.
  • Pharmedium
  • Sandoz
  • Strides Arcolab Limited
  • Viropharma Inc.
Dosage forms
FormRouteStrength
KitOral1 g/1g
CapsuleOral125 mg
CapsuleOral250 mg
Powder, for solutionIntravenous1.0 g
Injection, powder, lyophilized, for solutionIntravenous500 mg/10mL
PowderIntravenous1 g
Injection, solutionIntravenous4.2 mg/1mL
Injection, solutionIntravenous5 mg/1mL
Injection, solutionIntravenous6 mg/1mL
CapsuleOral125 mg/1
CapsuleOral250 mg/1
InjectionIntravenous10 g/100mL
InjectionIntravenous5 g/100mL
Injection, powder, for solutionIntravenous1 g/1
Injection, powder, for solutionIntravenous10 g/1
Injection, powder, lyophilized, for solutionIntravenous1 g/8mL
Injection, powder, lyophilized, for solutionIntravenous1 g/1
Injection, powder, lyophilized, for solutionIntravenous1 g/250mL
Injection, powder, lyophilized, for solutionIntravenous1 g/20mL
Injection, powder, lyophilized, for solutionIntravenous1.25 g/25mL
Injection, powder, lyophilized, for solutionIntravenous1.5 g/30mL
Injection, powder, lyophilized, for solutionIntravenous10 g/1
Injection, powder, lyophilized, for solutionIntravenous10 g/100mL
Injection, powder, lyophilized, for solutionIntravenous100 g/1
Injection, powder, lyophilized, for solutionIntravenous100 mg/1mL
Injection, powder, lyophilized, for solutionIntravenous250 mg/5mL
Injection, powder, lyophilized, for solutionIntravenous5 g/100mL
Injection, powder, lyophilized, for solutionIntravenous5 g/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/4mL
Injection, powder, lyophilized, for solutionIntravenous500 mg/1
Injection, powder, lyophilized, for solutionIntravenous500 mg/100mL
Injection, powder, lyophilized, for solutionIntravenous750 mg/15mL
Injection, powder, lyophilized, for solutionIntravenous750 mg/1
Injection, solutionIntravenous1 g/200mL
Injection, solutionIntravenous1 g/1
Injection, solutionIntravenous500 mg/1
Injection, solutionIntravenous500 mg/100mL
Injection, solutionIntravenous750 mg/150mL
Powder, for solutionIntravenous10 g
Powder, for solutionIntravenous1000 mg
Powder, for solutionIntravenous1 g
Powder, for solutionIntravenous5 g
Powder, for solutionIntravenous500 mg
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.
Patents
Not Available

Properties

State
Solid
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 FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-Ion Trap , PositiveLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-Hybrid FT , PositiveLC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as cyclic peptides. These are compounds containing a cyclic moiety bearing a peptide backbone.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Cyclic peptides
Alternative Parents
Aminoglycosides / Phenolic glycosides / Diarylethers / Disaccharides / O-glycosyl compounds / Alpha amino acids and derivatives / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids / Aryl chlorides / Oxanes
show 19 more
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
show 40 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
glycopeptide (CHEBI:28001)

Targets

1. D-Ala-D-Ala moiety of NAM/NAG peptide subunits of peptidoglycan
Kind
Group
Organism
Gram-positive bacteria
Pharmacological action
Yes
Actions
Ligand
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]

Carriers

Details
1. Serum albumin
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Substrate
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 colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
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 group
Organism
Human
Pharmacological action
No
Actions
Substrate
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
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]
3. Gamma Globulin
Kind
Protein group
Organism
Human
Pharmacological action
No
Actions
Substrate
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]

Drug created on June 13, 2005 07:24 / Updated on October 16, 2018 08:27