Editing Amphotericin B (section)

{{Short description|Antifungal and antiparasitaric chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Infobox drug
| image = Amphotericin B new.svg
| image_class = skin-invert-image
| alt =
| caption =
| image2 = Amphotericin-B-based-on-iodoacetyl-xtal-Mercury-3D-bs.png
| image_class2 = bg-transparent

<!--Clinical data-->
| tradename = Fungizone, Mysteclin-F, AmBisome and other
| Drugs.com = {{drugs.com|monograph|amphotericin_b}}
| MedlinePlus = a682643
| DailyMedID = Amphotericin_B
| pregnancy_AU = B2
| pregnancy_AU_comment = <ref>{{cite web | title=Updates to the Prescribing Medicines in Pregnancy database | website=Therapeutic Goods Administration (TGA) | date=12 May 2022 | url=https://www.tga.gov.au/resources/resource/guidance/updates-prescribing-medicines-pregnancy-database | access-date=13 May 2022}}</ref>
| pregnancy_category =
| routes_of_administration = [[Intravenous infusion]]

<!-- Legal status -->
| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->
| 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 = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->
| 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 = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->
| legal_UK_comment =
| legal_US = WARNING Rx-only
| legal_US_comment = <ref name="Ambisome FDA label">{{cite web | title=Ambisome- amphotericin b injection, powder, lyophilized, for solution | website=DailyMed | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f7be6506-4d20-401e-a0ff-02ad7c33158a | access-date=11 August 2021}}</ref>
| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->
| legal_UN_comment =
| legal_status = Rx-only

<!-- Pharmacokinetic data -->
| bioavailability = 100% (IV)
| metabolism = kidney
| elimination_half-life = {{ubl|Initial phase: 24 hours|Second phase: approximately 15 days}}
| excretion = {{ubl|40% found in urine after single cumulated over several days|Biliary excretion is also important}}

<!--Identifiers-->
| CAS_number = 12633-72-6
| CAS_number_Ref = {{cascite|correct|??}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 7XU7A7DROE
| ATC_prefix = A01
| ATC_suffix = AB04
| ATC_supplemental =  {{ATC|A07|AA07}}, {{ATC|G01|AA03}}, {{ATC|J02|AA01}}
| PubChem = 14956
| DrugBank = DB00681
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | ChemSpiderID = 10237579
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| KEGG = D00203
| KEGG_Ref = {{keggcite|correct|kegg}}
| ChEBI = 2682
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 267345
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| NIAID_ChemDB = 000096

<!--Chemical data-->
| IUPAC_name = (1''R'',3''S'',5''R'',6''R'',9''R'', 11''R'',15''S'',16''R'',17''R'',18''S'',19''E'',21''E'', 23''E'',25''E'',27''E'',29''E'',31''E'',33''R'',35''S'',36''R'',37''S'')- 33-[(3-amino- 3,6-dideoxy- β-{{small|D}}-mannopyranosyl)oxy]- 1,3,5,6,9,11,17,37-octahydroxy- 15,16,18-trimethyl- 13-oxo- 14,39-dioxabicyclo [33.3.1] nonatriaconta- 19,21,23,25,27,29,31-heptaene- 36-carboxylic acid
| C=47
| H=73
| N=1
| O=17
| StdInChI = 1S/C47H73NO17/c1-27-17-15-13-11-9-7-5-6-8-10-12-14-16-18-34(64-46-44(58)41(48)43(57)30(4)63-46)24-38-40(45(59)60)37(54)26-47(61,65-38)25-33(51)22-36(53)35(52)20-19-31(49)21-32(50)23-39(55)62-29(3)28(2)42(27)56/h5-18,27-38,40-44,46,49-54,56-58,61H,19-26,48H2,1-4H3,(H,59,60)/b6-5+,9-7+,10-8+,13-11+,14-12+,17-15+,18-16+/t27-,28-,29-,30+,31+,32+,33-,34-,35+,36+,37-,38-,40+,41-,42+,43+,44-,46-,47+/m0/s1
| StdInChIKey = APKFDSVGJQXUKY-INPOYWNPSA-N
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| melting_point = 170
| verifiedrevid = 477002307
| Watchedfields = changed
| smiles = O=C(O)[C@@H]3[C@@H](O)C[C@@]2(O)C[C@@H](O)C[C@@H](O)[C@H](O)CC[C@@H](O)C[C@@H](O)CC(=O)O[C@@H](C)[C@H](C)[C@H](O)[C@@H](C)C=CC=CC=CC=CC=CC=CC=C[C@H](O[C@@H]1O[C@H](C)[C@@H](O)[C@H](N)[C@@H]1O)C[C@@H]3O2
}}
<!-- Definition and medical uses -->
'''Amphotericin B''' is an [[antifungal]] medication used for serious [[mycosis|fungal infection]]s and [[leishmaniasis]].<ref name=WHO2010>{{cite book | vauthors = ((World Health Organization)) |title=Control of the leishmaniasis: report of a meeting of the WHO Expert Committee on the Control of Leishmaniases|date=March 2010|publisher=World Health Organization|isbn=9789241209496|pages=55, 88, 186 | author-link = World Health Organization | location = Geneva | hdl=10665/44412 | hdl-access=free }}</ref> The fungal infections it is used to treat include [[mucormycosis]], [[aspergillosis]], [[blastomycosis]], [[candida infections|candidiasis]], [[coccidioidomycosis]], and [[cryptococcosis]].<ref name=AHFS2015/> For certain infections it is given with [[flucytosine]].<ref name=WHO2008>{{cite book | title = WHO Model Formulary 2008 | year = 2009 | isbn = 9789241547659 | vauthors = ((World Health Organization)) | veditors = Stuart MC, Kouimtzi M, Hill SR | hdl = 10665/44053 | author-link = World Health Organization | publisher = World Health Organization |page=145 | hdl-access=free }}</ref> It is typically given [[intravenously]].<ref name=AHFS2015>{{cite web|title = Amphotericin B|url = https://www.drugs.com/monograph/amphotericin-b.html|publisher = The American Society of Health-System Pharmacists|access-date = January 1, 2015|url-status = live|archive-url = https://web.archive.org/web/20150101143314/http://www.drugs.com/monograph/amphotericin-b.html|archive-date = 2015-01-01}}</ref>

<!-- Side effects -->
Common side effects include a reaction with [[fever]], chills, and [[headaches]] soon after the medication is given, as well as [[kidney problems]].<ref name=AHFS2015/> Allergic symptoms including [[anaphylaxis]] may occur.<ref name=AHFS2015/> Other serious side effects include [[hypokalemia|low blood potassium]] and [[myocarditis]] (inflammation of the heart).<ref name=WHO2010/> It appears to be relatively safe in [[pregnancy]].<ref name=AHFS2015/> There is a lipid formulation that has a lower risk of side effects.<ref name=AHFS2015/> It is in the [[polyene antimycotic|polyene]] class of medications and works in part by interfering with the [[cell membrane]] of the fungus.<ref name=WHO2010/><ref name=AHFS2015/>

<!-- History and culture -->
Amphotericin B was isolated from ''[[Streptomyces nodosus]]'' in 1955 at the Squibb Institute for Medical Research from cultures isolated from the ''streptomycete'' obtained from the river bed of [[Orinoco]] in that region of [[Venezuela]]<ref name=Book2021>{{cite book| vauthors = Velázquez L |title=Farmacología y su proyección a la clínica 13a ed.|date=1976|publisher=Oteo.|isbn=8485152050|page=966|language=es }}</ref> and came into medical use in 1958.<ref name=Wal2012>{{cite book| vauthors = Walker SR |title=Trends and Changes in Drug Research and Development |date=2012 |publisher=Springer Science & Business Media|isbn=9789400926592|page=109|url=https://books.google.com/books?id=FB_2CAAAQBAJ&pg=PA109|language=en|url-status=live|archive-url=https://web.archive.org/web/20170910151826/https://books.google.com/books?id=FB_2CAAAQBAJ&pg=PA109|archive-date=2017-09-10}}</ref><ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=477 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA477 |language=en}}</ref> It is on the [[WHO Model List of Essential Medicines|World Health Organization's List of Essential Medicines]].<ref name="WHO21st">{{cite book | vauthors = ((World Health Organization)) | title = World Health Organization model list of essential medicines: 21st list 2019 | year = 2019 | hdl = 10665/325771 | author-link = World Health Organization | publisher = World Health Organization | location = Geneva | id = WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO | hdl-access=free }}</ref> It is available as a [[generic medication]].<ref name=AHFS2015/><ref>{{cite web | title=Competitive Generic Therapy Approvals | website=U.S. [[Food and Drug Administration]] (FDA) | date=29 June 2023 | url=https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | access-date=29 June 2023 | archive-date=29 June 2023 | archive-url=https://web.archive.org/web/20230629233651/https://www.fda.gov/drugs/generic-drugs/competitive-generic-therapy-approvals | url-status=dead }}</ref>

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