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Vancomycin information


Vancomycin
Clinical data
Pronunciation/væŋkəˈmsɪn/[1][2]
Trade namesVancocin, others[3]
AHFS/Drugs.comMonograph
MedlinePlusa604038
License data
  • EU EMA: by INN
  • US DailyMed: Vancomycin
  • US FDA: Vancomycin
Pregnancy
category
  • AU: B2[4]
Routes of
administration
Intravenous, oral
Drug classGlycopeptide antibiotic
ATC code
  • A07AA09 (WHO) J01XA01 (WHO) S01AA28 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: WARNING[5]Rx-only
  • EU: Rx-only[6]
Pharmacokinetic data
BioavailabilityNegligible (oral)
MetabolismExcreted unchanged
Elimination half-life4 h to 11 h (adults, normal renal function)
6 d to 10 d (adults, impaired renal function)
Excretionurine (IV), feces (oral)
Identifiers
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)- 5,15- 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[26.14.2.23,6.214,17.18,12.129,33.010,25.034,39]pentaconta- 3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49- pentadecaene- 40- carboxylic acid
CAS Number
  • 1404-90-6 checkY
PubChem CID
  • 14969
PubChem SID
  • 46505261
DrugBank
  • DB00512 checkY
ChemSpider
  • 14253 checkY
UNII
  • 6Q205EH1VU
KEGG
  • D00212 checkY
  • as HCl: D00926 ☒N
ChEBI
  • CHEBI:28001 checkY
ChEMBL
  • ChEMBL262777 checkY
CompTox Dashboard (EPA)
  • DTXSID0042664 Edit this at Wikidata
ECHA InfoCard100.014.338 Edit this at Wikidata
Chemical and physical data
FormulaC66H75Cl2N9O24
Molar mass1449.27 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2Oc3c4cc5cc3Oc6ccc(cc6Cl)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7c8ccc(c(c8)-c9c(cc(cc9O)O)[C@H](NC(=O)[C@H]([C@@H](c1ccc(c(c1)Cl)O4)O)NC7=O)C(=O)O)O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)CO)O)O)(C)N)O
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 checkY
  • Key:MYPYJXKWCTUITO-LYRMYLQWSA-N checkY
  (verify)

Vancomycin is a glycopeptide antibiotic medication used to treat a number of bacterial infections.[7] It is used intravenously (injection into a vein) as a treatment for complicated skin infections, bloodstream infections, endocarditis, bone and joint infections, and meningitis caused by methicillin-resistant Staphylococcus aureus.[8] Blood levels may be measured to determine the correct dose.[9] Vancomycin is also taken orally (by mouth) as a treatment for severe Clostridium difficile colitis.[7] When taken orally it is poorly absorbed.[7]

Common side effects include pain in the area of injection and allergic reactions.[7] Occasionally, hearing loss, low blood pressure, or bone marrow suppression occur.[7] Safety in pregnancy is not clear, but no evidence of harm has been found,[7][10] and it is likely safe for use when breastfeeding.[11] It is a type of glycopeptide antibiotic and works by blocking the construction of a cell wall.[7]

Vancomycin was approved for medical use in the United States in 1958.[12] It is on the World Health Organization's List of Essential Medicines.[13][14] The World Health Organization classifies vancomycin as critically important for human medicine.[15] It is available as a generic medication.[9] Vancomycin is made by the soil bacterium Amycolatopsis orientalis.[7]

  1. ^ "vancomycin". Merriam-Webster.com Dictionary.
  2. ^ "vancomycin - definition of vancomycin in English from the Oxford dictionary". OxfordDictionaries.com. Archived from the original on 20 September 2013. Retrieved 20 January 2016.
  3. ^ "Vancomycin". Drugs.com. 2 December 2019. Archived from the original on 24 December 2019. Retrieved 24 December 2019.
  4. ^ "Vancomycin Use During Pregnancy". Drugs.com. 27 March 2019. Archived from the original on 6 June 2019. Retrieved 24 December 2019.
  5. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  6. ^ "List of nationally authorised medicinal products" (PDF). European Medicines Agency. 15 October 2020. Archived (PDF) from the original on 25 September 2023. Retrieved 27 April 2023.
  7. ^ a b c d e f g h "Vancocin". The American Society of Health-System Pharmacists. Archived from the original on 6 September 2015. Retrieved 4 September 2015.
  8. ^ Liu C, Bayer A, Cosgrove SE, Daum RS, Fridkin SK, Gorwitz RJ, et al. (February 2011). "Clinical practice guidelines by the infectious diseases society of america for the treatment of methicillin-resistant Staphylococcus aureus infections in adults and children: executive summary". Clinical Infectious Diseases. 52 (3): 285–92. doi:10.1093/cid/cir034. PMID 21217178.
  9. ^ a b Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 91. ISBN 978-1-284-05756-0.
  10. ^ "Prescribing medicines in pregnancy database". Australian Government. September 2015. Archived from the original on 8 April 2014.
  11. ^ "Vancomycin use while Breastfeeding". Archived from the original on 7 September 2015. Retrieved 5 September 2015.
  12. ^ Levine DP (January 2006). "Vancomycin: a history". Clinical Infectious Diseases. 42 (Suppl 1): S5–12. doi:10.1086/491709. PMID 16323120.
  13. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  14. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  15. ^ World Health Organization (2019). Critically important antimicrobials for human medicine (6th revision ed.). Geneva: World Health Organization. hdl:10665/312266. ISBN 978-92-4-151552-8.

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Vancomycin

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Vancomycin is a glycopeptide antibiotic medication used to treat a number of bacterial infections. It is used intravenously (injection into a vein) as...

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Enterococcus faecium

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pathogenic, causing diseases such as neonatal meningitis or endocarditis. Vancomycin-resistant E. faecium is often referred to as VRE. This bacterium has developed...

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Glycopeptide antibiotic

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antibiotics vancomycin, teicoplanin, telavancin, ramoplanin and decaplanin, corbomycin, complestatin and the antitumor antibiotic bleomycin. Vancomycin is used...

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Enterococcus

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ampicillin, penicillin and vancomycin. Urinary tract infections can be treated specifically with nitrofurantoin, even in cases of vancomycin resistance. Enterococcal...

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List of antibiotics

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Antibiotics that cover methicillin-resistant Staphylococcus aureus (MRSA): Vancomycin Teicoplanin Linezolid Daptomycin Trimethoprim/sulfamethoxazole Doxycycline...

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Enterococcus faecalis

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chromosome or plasmid. Resistance to vancomycin in E. faecalis is becoming more common. Treatment options for vancomycin-resistant E. faecalis include nitrofurantoin...

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Linezolid

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most Gram-positive bacteria that cause disease, including streptococci, vancomycin-resistant enterococci (VRE), and methicillin-resistant Staphylococcus...

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Lactobacillus

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Homofermentative with strain-specific ability to ferment pentoses, thermophilic, vancomycin-sensitive, adapted to vertebrate or insect hosts. Holzapfelia Wilhelm...

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Intravenous therapy

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are commonly administered intravenously. In some cases, such as with vancomycin, a loading or bolus dose of medicine is given before beginning a dosing...

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Visa

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village, Jucu Commune, Cluj County, Romania Vancomycin intermediate-resistant Staphylococcus aureus or vancomycin-intermediate Staphylococcus aureus, a bacterium...

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Clostridioides difficile infection

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three days in about 20% of those infected. The antibiotics metronidazole, vancomycin, or fidaxomicin, will cure the infection. Retesting after treatment, as...

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Fidaxomicin

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24.0% with oral vancomycin. The study also met its exploratory endpoint of global cure (77.7% for fidaxomicin vs. 67.1% for vancomycin). Clinical cure...

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Staphylococcus aureus

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β-lactam antibiotics. For this reason, vancomycin, a glycopeptide antibiotic, is commonly used to combat MRSA. Vancomycin inhibits the synthesis of peptidoglycan...

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ESKAPE

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rise in vancomycin resistant enterococci (VRE) strains, including an increase in E. faecium resistance to vancomycin, particularly vancomycin-A. These...

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Metronidazole

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first episode of mild-to-moderate Clostridioides difficile colitis if vancomycin or fidaxomicin is unavailable. Metronidazole is available orally (by mouth)...

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Dalbavancin

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lipoglycopeptide antibiotic medication. It belongs to the same class as vancomycin, the most widely used and one of the treatments available to people infected...

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Treatment of infections after exposure to ionizing radiation

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where infections due to these organisms are prevalent. ( amoxicillin, vancomycin, or linezolid). These are the antimicrobial agents that can be used for...

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Enterococcus avium

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it is also a cause of infection in humans, and in such cases, may be vancomycin-resistant, and is referred to as VREA. VREA cases in humans have been...

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Amycolatopsis orientalis

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substances with antimicrobial properties, including the antibiotic drug vancomycin. A. orientalis was originally discovered by Edmund Kornfeld, an organic...

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Aryl halide

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Vancomycin, an important antibiotic, is an aryl chloride isolated from soil fungi....

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Staphylococcus haemolyticus

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of vancomycin heteroresistant Staphylococcus haemolyticus and vancomycin intermediate resistant Staphylococcus epidermidis by means of vancomycin screening...

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Granulicatella adiacens

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still often susceptible to clindamycin, erythromycin, rifampicin and vancomycin. Granulicatella spp. have been associated with malodorous breath (halitosis)...

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Clostridioides difficile

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of oral vancomycin will not work. In these cases, a vancomycin taper is the preferred treatment. Patients take decreasing doses of vancomycin over a period...

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Penicillin

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smaller ampicillin and amoxicillin diffuse much faster. In contrast, large vancomycin can not pass through porins and is thus ineffective for Gram-negative...

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Septic arthritis

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and timely. Initial treatment typically includes antibiotics such as vancomycin, ceftriaxone or ceftazidime. Surgery in the form of joint drainage is...

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Teicoplanin

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semisynthetic glycopeptide antibiotic with a spectrum of activity similar to vancomycin. Its mechanism of action is to inhibit bacterial cell wall peptidoglycan...

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Vancosamine

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are a part of vancomycin and other molecules within the vancomycin family of antibiotics. Vancosamine synthesis is encoded by the vancomycin (vps) biosynthetic...

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