Editing Vancomycin (section)

{{Short description|Antibiotic medication}}
{{Use dmy dates|date=December 2023}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{drugbox
| Watchedfields = changed
| verifiedrevid = 470628926
| image = Vancomycin structure.svg
| image_class = skin-invert-image
| width = 300
| alt =
| image2 = Vancomycin-from-xtal-1996-3D-balls.png
| width2 = 300
| alt2 =
| drug_name =

<!--Clinical data-->
| pronounce = {{IPAc-en|v|æ|ŋ|k|ə|ˈ|m|aɪ|s|ᵻ|n}}{{refn|{{MerriamWebsterDictionary|vancomycin}}}}{{refn|{{cite web |url=https://www.oxforddictionaries.com/definition/english/vancomycin |archive-url=https://web.archive.org/web/20130920070219/http://oxforddictionaries.com/definition/english/vancomycin |url-status=dead |archive-date=20 September 2013 |title=vancomycin - definition of vancomycin in English from the Oxford dictionary |publisher=[[OxfordDictionaries.com]] |access-date=20 January 2016 }} }}
| tradename = Vancocin, others<ref name="Drugs.com-2019">{{cite web | title=Vancomycin | website=Drugs.com | date=2 December 2019 | url=https://www.drugs.com/international/vancomycin.html | access-date=24 December 2019 | archive-date=24 December 2019 | archive-url=https://web.archive.org/web/20191224190540/https://www.drugs.com/international/vancomycin.html | url-status=live }}</ref>
| Drugs.com = {{drugs.com|monograph|vancomycin-hydrochloride}}
| MedlinePlus = a604038
| licence_CA        = Vancomycin
| licence_EU        = yes
| DailyMedID        = Vancomycin
| licence_US        = Vancomycin
| pregnancy_AU = B2
| pregnancy_AU_comment = <ref name="Drugs.com pregnancy">{{cite web | title=Vancomycin Use During Pregnancy | website=Drugs.com | date=27 March 2019 | url=https://www.drugs.com/pregnancy/vancomycin.html | access-date=24 December 2019 | archive-date=6 June 2019 | archive-url=https://web.archive.org/web/20190606160102/https://www.drugs.com/pregnancy/vancomycin.html | url-status=live }}</ref>
| pregnancy_category =
| routes_of_administration = [[Intravenous]], [[Oral administration|oral]]
| class = [[Glycopeptide antibiotic]]
| ATC_prefix = A07
| ATC_suffix = AA09
| ATC_supplemental = {{ATC|J01|XA01}} {{ATC|S01|AA28}}

<!-- Legal status -->
| legal_AU = S4
| legal_AU_comment =
| legal_BR =  <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F-->
| legal_BR_comment =
| legal_CA = Rx-only
| legal_CA_comment =
| legal_DE = <!-- Anlage I, II, III or Unscheduled-->
| legal_DE_comment =
| legal_NZ = <!-- Class A, B, C -->
| legal_NZ_comment =
| legal_UK = POM
| legal_UK_comment =
| legal_US = Rx-only
| legal_US_comment =
| legal_EU = Rx-only
| legal_EU_comment = <ref name="European Medicines Agency-2020">{{cite web |date=15 October 2020 |title=List of nationally authorised medicinal products |url=https://www.ema.europa.eu/en/documents/psusa/vancomycin-list-nationally-authorised-medicinal-products-psusa/00003097/202001_en.pdf |website=[[European Medicines Agency]] |access-date=27 April 2023 |archive-date=25 September 2023 |archive-url=https://web.archive.org/web/20230925070309/https://www.ema.europa.eu/en/documents/psusa/vancomycin-list-nationally-authorised-medicinal-products-psusa/00003097/202001_en.pdf |url-status=live }}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV-->
| legal_UN_comment =
| legal_status      = <!--For countries not listed above-->

<!--Pharmacokinetic data-->
| bioavailability = Negligible (oral)
| metabolism = Excreted unchanged
| elimination_half-life = 4 h to 11 h <small>(adults, normal renal function)</small><br />6 d to 10 d <small>(adults, impaired renal function)</small>
| excretion = urine (IV), feces (oral)

<!--Identifiers-->
| index2_label = as HCl
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 1404-90-6
| CAS_supplemental  =
| PubChem = 14969
| PubChemSubstance  = 46505261
| IUPHAR_ligand     =
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00512
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 14253
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6Q205EH1VU
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00212
| KEGG2_Ref = {{keggcite|changed|kegg}}
| KEGG2 = D00926
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28001
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 262777
| NIAID_ChemDB      =
| PDB_ligand        =
| synonyms          =

<!--Chemical data-->
| IUPAC_name = (1''S'',2''R'',18''R'',19''R'',22''S'',25''R'',28''R'',40''S'')- 48- {[(2''S'',3''R'',4''S'',5''S'',6''R'')- 3- {[(2''S'',4''S'',5''S'',6''S'')- 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- [(2''R'')- 4- methyl- 2- (methylamino)pentanamido]- 20,23,26,42,44- pentaoxo- 7,13- dioxa- 21,24,27,41,43- pentaazaoctacyclo[26.14.2.2<sup>3,6</sup>.2<sup>14,17</sup>.1<sup>8,12</sup>.1<sup>29,33</sup>.0<sup>10,25</sup>.0<sup>34,39</sup>]pentaconta- 3,5,8(48),9,11,14,16,29(45),30,32,34,36,38,46,49- pentadecaene- 40- carboxylic acid
| C=66 | H=75 | Cl=2 | N=9 | O=24
| 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
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChI_comment  =
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MYPYJXKWCTUITO-LYRMYLQWSA-N
| density           =
| density_notes     =
| melting_point     =
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| specific_rotation =
}}

<!-- Definition and medical uses -->
'''Vancomycin''' is a [[glycopeptide antibiotic]] medication used to treat certain [[bacterial infection]]s.<ref name=AHFS2015>{{cite web|title=Vancocin|url=https://www.drugs.com/monograph/vancocin.html|publisher=The American Society of Health-System Pharmacists|access-date=4 September 2015|url-status=live|archive-url=https://web.archive.org/web/20150906002445/http://www.drugs.com/monograph/vancocin.html|archive-date=6 September 2015}}</ref> It is administered [[intravenously]] ([[Injection (medicine)|injection]] into a [[vein]]) to treat complicated [[skin infection]]s, [[sepsis|bloodstream infection]]s, [[endocarditis]], bone and joint infections, and [[meningitis]] caused by [[methicillin-resistant Staphylococcus aureus|methicillin-resistant ''Staphylococcus aureus'']].<ref name="pmid21217178">{{cite journal | vauthors = Liu C, Bayer A, Cosgrove SE, Daum RS, Fridkin SK, Gorwitz RJ, Kaplan SL, Karchmer AW, Levine DP, Murray BE, J Rybak M, Talan DA, Chambers HF | title = 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 | journal = Clinical Infectious Diseases | volume = 52 | issue = 3 | pages = 285–92 | date = February 2011 | pmid = 21217178 | doi = 10.1093/cid/cir034 | doi-access = free }}</ref> Blood levels may be measured to determine the correct dose.<ref name=Ric2015/> Vancomycin is also taken [[Oral administration|orally]] (by mouth) to treat [[Clostridioides difficile infection|''Clostridioides difficile'' infections]].<ref name=AHFS2015/><ref>{{cite journal | vauthors = McDonald LC, Gerding DN, Johnson S, Bakken JS, Carroll KC, Coffin SE, Dubberke ER, Garey KW, Gould CV, Kelly C, Loo V, Shaklee Sammons J, Sandora TJ, Wilcox MH | title = 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) | journal = Clinical Infectious Diseases | volume = 66 | issue = 7 | pages = e1–e48 | date = March 2018 | pmid = 29462280 | pmc = 6018983 | doi = 10.1093/cid/cix1085 }}</ref><ref>{{Cite journal |url=https://academic.oup.com/cid/article/73/5/e1029/6298219 |access-date=2024-10-23 |journal=Clinical Infectious Diseases |doi=10.1093/cid/ciab549 |title=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 |date=2021 |volume=73 |issue=5 |pages=e1029–e1044 |vauthors=Johnson S, Lavergne V, Skinner AM, Gonzales-Luna AJ, Garey KW, Kelly CP, Wilcox MH |pmid=34164674 |archive-date=10 September 2024 |archive-url=https://web.archive.org/web/20240910144248/https://academic.oup.com/cid/article/73/5/e1029/6298219 |url-status=live }}</ref> When taken orally, it is poorly absorbed.<ref name=AHFS2015/>

<!-- Side effects and mechanism -->
Common side effects include pain in the area of injection and [[allergic reaction]]s.<ref name=AHFS2015/> Occasionally, [[hearing loss]], [[low blood pressure]], or [[bone marrow suppression]] occur.<ref name=AHFS2015/> Safety in pregnancy is not clear, but no evidence of harm has been found,<ref name=AHFS2015/><ref name="Australian Government-2015">{{cite web|title=Prescribing medicines in pregnancy database|url=http://www.tga.gov.au/hp/medicines-pregnancy.htm|work=Australian Government|date=September 2015|url-status=live|archive-url=https://web.archive.org/web/20140408040902/http://www.tga.gov.au/hp/medicines-pregnancy.htm#.U1Yw8Bc3tqw|archive-date=8 April 2014}}</ref> and it is likely safe for use when [[breastfeeding]].<ref name="Vancomycin use while Breastfeeding">{{cite web|title=Vancomycin use while Breastfeeding|url=https://www.drugs.com/breastfeeding/vancomycin.html|access-date=5 September 2015|url-status=live|archive-url=https://web.archive.org/web/20150907040510/http://www.drugs.com/breastfeeding/vancomycin.html|archive-date=7 September 2015}}</ref> It is a type of [[glycopeptide antibiotic]] and works by blocking the construction of a [[cell wall]].<ref name=AHFS2015/>

<!-- History, society and culture -->
Vancomycin was approved for medical use in the United States in 1958.<ref name="pmid16323120">{{cite journal |vauthors=Levine DP |title=Vancomycin: a history |journal=Clinical Infectious Diseases |volume=42 |issue= Suppl 1 |pages=S5–12 |date=January 2006 |pmid=16323120 |doi=10.1086/491709 |doi-access=free }}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO23rd">{{cite book | vauthors = ((World Health Organization)) | title = The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023) | year = 2023 | hdl = 10665/371090 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MHP/HPS/EML/2023.02 | hdl-access=free }}</ref> The WHO classifies vancomycin as critically important for human medicine.<ref name="World Health Organization-2019">{{cite book | vauthors=((World Health Organization)) | year=2019 | title=Critically important antimicrobials for human medicine | edition=6th revision |  author-link = World Health Organization | publisher = World Health Organization | location = Geneva | hdl=10665/312266 | isbn=978-92-4-151552-8 | hdl-access=free }}</ref> It is available as a generic medication.<ref name=Ric2015>{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=978-1-284-05756-0|pages = 91}}</ref> Vancomycin is made by the soil bacterium ''[[Amycolatopsis orientalis]]''.<ref name=AHFS2015/>