Vancomycin

Vancomycin
Clinical data
Pronunciation/væŋkəˈmaɪsɪn/[1][2]
Trade namesVancocin, others[3]
AHFS/Drugs.comMonograph
MedlinePlusa604038
License data
Pregnancy
category
Routes of
administration		Intravenous, oral
Drug classGlycopeptide antibiotic
ATC code
Legal status
Legal status
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
  • (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
PubChem CID
PubChem SID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.014.338 Edit this at Wikidata
Chemical and physical data
FormulaC66H75Cl2N9O24
Molar mass1449.27 g·mol−1
3D model (JSmol)
  • 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=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 certain bacterial infections.[7] It is administered intravenously (injection into a vein) to treat 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) to treat Clostridioides difficile infections.[7][10][11] 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][12] and it is likely safe for use when breastfeeding.[13] 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.[14] It is on the World Health Organization's List of Essential Medicines.[15][16] The WHO classifies vancomycin as critically important for human medicine.[17] It is available as a generic medication.[9] Vancomycin is made by the soil bacterium Amycolatopsis orientalis.[7]

  1. ^ "vancomycin". Merriam-Webster.com Dictionary. Merriam-Webster.
  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. ^ McDonald LC, Gerding DN, Johnson S, Bakken JS, Carroll KC, Coffin SE, et al. (March 2018). "Clinical Practice Guidelines for Clostridium difficile Infection in Adults and Children: 2017 Update by the Infectious Diseases Society of America (IDSA) and Society for Healthcare Epidemiology of America (SHEA)". Clinical Infectious Diseases. 66 (7): e1–e48. doi:10.1093/cid/cix1085. PMC 6018983. PMID 29462280.
  11. ^ Johnson S, Lavergne V, Skinner AM, Gonzales-Luna AJ, Garey KW, Kelly CP, et al. (2021). "Clinical Practice Guideline by the Infectious Diseases Society of America (IDSA) and Society for Healthcare Epidemiology of America (SHEA): 2021 Focused Update Guidelines on Management of Clostridioides difficile Infection in Adults". Clinical Infectious Diseases. 73 (5): e1029–e1044. doi:10.1093/cid/ciab549. Archived from the original on 10 September 2024. Retrieved 23 October 2024.
  12. ^ "Prescribing medicines in pregnancy database". Australian Government. September 2015. Archived from the original on 8 April 2014.
  13. ^ "Vancomycin use while Breastfeeding". Archived from the original on 7 September 2015. Retrieved 5 September 2015.
  14. ^ Levine DP (January 2006). "Vancomycin: a history". Clinical Infectious Diseases. 42 (Suppl 1): S5–12. doi:10.1086/491709. PMID 16323120.
  15. ^ 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.
  16. ^ 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.
  17. ^ 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.