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| {{Short description|Antibiotic}} | |||
| {{Use dmy dates|date=June 2024}} | |||
| {{cs1 config|name-list-style=vanc|display-authors=6}} | |||
| {{Drugbox | {{Drugbox | ||
| | Verifiedfields = changed | |||
| | verifiedrevid = 406674764 | |||
| | verifiedrevid = 408381992 | |||
| | type = combo | |||
| | type = combo | |||
| | component1 = Benzylpenicillin | |||
| | image = Benzylpenicillin-Benzathin Structural Formula V.1.svg | |||
| | class1 = ] | |||
| | component2 = Benzathine | |||
| <!--Combo data--> | |||
| | class2 = | |||
| | component1 = Benzylpenicillin | |||
| | CAS_number = 54-35-3 | |||
| | class1 = ] | |||
| | ATC_prefix = J01 | |||
| | component2 = Benzathine | |||
| | ATC_suffix = CE08 | |||
| | class2 = stabilizer | |||
| | PubChem = 15232 | |||
| | DrugBank = | |||
| <!--Clinical data--> | |||
| | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | |||
| | tradename = Bicillin L-A,<ref name=Ric2015>{{cite book| vauthors = Hamilton R |title=Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition|date=2015|publisher=Jones & Bartlett Learning|isbn=9781284057560|page=94}}</ref> Permapen, others | |||
| | pregnancy_US = <!-- A / B / C / D / X --> | |||
| | Drugs.com = {{drugs.com|ppa|penicillin-g-benzathine}} | |||
| | pregnancy_category= | |||
| | DailyMedID = Penicillin G benzathine | |||
| | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | |||
| | pregnancy_AU = A | |||
| | legal_CA = <!-- Schedule I, II, III, IV, V, VI, VII, VIII --> | |||
| | pregnancy_AU_comment = | |||
| | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | |||
| | routes_of_administration = ]<ref name=PPA2016/> | |||
| | legal_US = <!-- OTC / Rx-only / Schedule I, II, III, IV, V --> | |||
| | ATC_prefix = J01 | |||
| | legal_status = | |||
| | ATC_suffix = CE08 | |||
| | routes_of_administration = | |||
| | legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled--> | |||
| | legal_CA = Rx-only | |||
| | legal_CA_comment = <ref>{{cite web | title=Product monograph brand safety updates | website=] | date=6 June 2024 | url=https://www.canada.ca/en/health-canada/services/drugs-health-products/drug-products/drug-product-database/label-safety-assessment-update/product-monograph-brand-safety-updates.html | access-date=8 June 2024}}</ref> | |||
| | legal_UK = <!-- GSL, P, POM, CD, or Class A, B, C --> | |||
| | legal_US = Rx-only | |||
| <!--Identifiers--> | |||
| | CAS_number_Ref = {{cascite|changed|??}} | |||
| | CAS_number = 41372-02-5 | |||
| | PubChem = 15232 | |||
| | ChEMBL_Ref = {{ebicite|changed|EBI}} | |||
| | ChEMBL = 3989515 | |||
| | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | |||
| | DrugBank = DB01053 | |||
| | UNII_Ref = {{fdacite|changed|FDA}} | |||
| | UNII = RIT82F58GK | |||
| | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | |||
| | ChemSpiderID = 14498 | |||
| | ChEBI_Ref = {{ebicite|changed|EBI}} | |||
| | ChEBI = 51352 | |||
| | KEGG_Ref = {{keggcite|changed|kegg}} | |||
| | KEGG = D02157 | |||
| | synonyms = penicillin benzathine benzyl, benzathine penicillin, penicillin G benzathine, benzylpenicillin benzathine<ref name=Eng2014/> | |||
| <!--Chemical data--> | |||
| }} | }} | ||
| <!-- Definition and medical uses --> | |||
| '''Benzathine benzylpenicillin''' (]) is a form of ] also known as '''benzathine penicillin'''. It is slowly absorbed into the circulation, after ], and hydrolysed to benzylpenicillin ''in vivo''. It is the drug-of-choice when prolonged low concentrations of benzylpenicillin are required and appropriate, allowing prolonged antibiotic action over 2–4 weeks after a single IM dose. It is marketed by Wyeth under the trade name ''Bicillin L-A''. | |||
| '''Benzathine benzylpenicillin''', also known as '''benzathine penicillin G''' (BPG), is an ] medication useful for the treatment of a number of ].<ref name=PPA2016/> Specifically it is used to treat ], ], ], and ].<ref name=PPA2016/><ref name=WHO2008/> It is also used to prevent ].<ref name=WHO2008/> It is given by ].<ref name=PPA2016/><ref name=WHO2008/> It is known as "Peanut Butter Shot" in US ] due to its appearance.<ref name=Kirkpatrick>{{Cite web| vauthors = Kirkpatrick T |date=11 February 2020|title=Why the Most Dreaded Injection is Called the 'Peanut Butter' Shot|url=https://www.military.com/off-duty/2020/02/10/why-most-dreaded-injection-called-peanut-butter-shot.html|access-date=21 December 2021|website=Military.com|language=en}}</ref> | |||
| <!-- Side effects and mechanism --> | |||
| Specific indications for benzathine penicillin include:<ref name="AMH2006">{{cite book | editor=Rossi S, editor | title=] | year=2006 | location=Adelaide | publisher=Australian Medicines Handbook | isbn=0-9757919-2-3}}</ref> | |||
| Side effects include ]s including ], and pain at the site of injection.<ref name=WHO2008/> When used to treat syphilis a reaction known as ] may occur.<ref name=WHO2008/> It is not recommended in those with a history of ] or those with syphilis involving the ].<ref name=WHO2008/><ref name=PPA2016>{{cite web|title=Penicillin G Benzathine (Professional Patient Advice) - Drugs.com|url=https://www.drugs.com/ppa/penicillin-g-benzathine.html|website=www.drugs.com|access-date=10 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220230843/https://www.drugs.com/ppa/penicillin-g-benzathine.html|archive-date=20 December 2016}}</ref> Use during ] is generally safe.<ref name=PPA2016/> It is in the ] and ] class of medications and works via ].<ref name=PPA2016/><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 | hdl-access=free |pages=98, 104 }}</ref> The ] component slowly releases the penicillin making the combination long acting.<ref>{{cite book| vauthors = Ebadi M | chapter = Penicillin G |title=Desk Reference of Clinical Pharmacology |date=2007 |publisher=CRC Press|isbn=9781420047448|page=555|edition=2nd | chapter-url = https://books.google.com/books?id=ihxyHbnj3qYC&pg=PA555|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220152414/https://books.google.ca/books?id=ihxyHbnj3qYC&pg=PA555|archive-date=20 December 2016}}</ref> | |||
| *Prophylaxis of ] | |||
| *Early or latent ] | |||
| <!-- Society and culture --> | |||
| Benzathine benzylpenicillin was patented in 1950.<ref name=Eng2014>{{cite book| veditors = Engel J, Kleemann A, Kutscher B, Reichert D |title=Pharmaceutical Substances: Syntheses, Patents and Applications of the most relevant APIs | edition = 5th | date = 2009 |publisher=Georg Thieme Verlag|isbn=9783131792754|page=134 |url=https://books.google.com/books?id=4lCGAwAAQBAJ&pg=PA134|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220085328/https://books.google.ca/books?id=4lCGAwAAQBAJ&pg=PA134|archive-date=20 December 2016}}</ref><ref>{{cite patent |country=US |number=2627491 |status=patent |title=Penicillin salts of substituted alkylene diamines |pubdate=1953-02-03 |gdate=1953-02-03 |fdate=1950-07-15 |pridate=1950-07-15 |inventor = Szabo JL, Bruce WF |assign1=Wyeth LLC |assign2=Wyeth Inc |url=https://worldwide.espacenet.com/publicationDetails/biblio?CC=US&NR=2627491&KC=&FT=E&locale=en_EP}}</ref> It is on the ].<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> | |||
| == Medical uses == | |||
| It is used to treat ], ], ], and ].<ref name=PPA2016/><ref name=WHO2008/> | |||
| === Chemopreventive === | |||
| A single large 1.2-million-unit dose of intramuscular BPG is given to US military recruits. The Army in particular has a policy to inject all recruits if not allergic, though supply issues and individual base choices have reduced the coverage. A retrospective analysis shows that it reduces the rate of all-cause acute respiratory disease by 32% among Army recruits.<ref>{{cite journal | vauthors = Ball JD, Prosperi MA, Brown A, Chen X, Kenah E, Yang Y, Cummings DA, Rivers CM | title = The role of benzathine penicillin G in predicting and preventing all-cause acute respiratory disease in military recruits: 1991-2017 | journal = Epidemiology and Infection | volume = 146 | issue = 14 | pages = 1854–1860 | date = October 2018 | pmid = 29974837 | pmc = 9506690 | doi = 10.1017/S0950268818001838 | doi-access = free }}</ref> | |||
| == Adverse effects == | |||
| ] | |||
| {{see|Penicillin drug reaction}} | |||
| The possible adverse effects are generally similar to other forms of penicillin. BPG is overall well-tolerated, but pain from the injection site is a common concern.<ref>{{cite book | vauthors = Gartlan WA, Rahman S, Reti K | chapter = Benzathine Penicillin | chapter-url=https://www.ncbi.nlm.nih.gov/books/NBK507723/ | title = StatPearls |publisher=StatPearls Publishing |date=2023|pmid=29939545 }}</ref> | |||
| ==Society and culture== | |||
| It is marketed by Pfizer (formerly by Wyeth) under the trade name ''Bicillin L-A''.<ref name="FDA">{{cite web|title=Bicillin® L-A|url=https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/050141s237lbl.pdf|access-date=31 July 2023|publisher=US FDA}}</ref> | |||
| == Compendial status == | == Compendial status == | ||
| * ]<ref name=ibp2009>{{cite web |last=British Pharmacopoeia Commission Secretariat |title=Index (BP 2009) |url=http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf |access-date=26 March 2010 |url-status=dead |archive-url=https://web.archive.org/web/20090411071437/http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf |archive-date=11 April 2009 }}</ref> | |||
| * ] <ref name=ibp2009>{{cite web | |||
| | last = British Pharmacopoeia Commission Secretariat | |||
| | first = | |||
| | authorlink = | |||
| | coauthors = | |||
| | title = Index (BP 2009) | |||
| | work = | |||
| | publisher = | |||
| | date = | |||
| | url = http://www.pharmacopoeia.co.uk/pdf/2009_index.pdf | |||
| | doi = | |||
| | accessdate = 26 March 2010 | |||
| }}</ref> | |||
| {{Expand section|date=March 2010}} | |||
| ==References== | == References == | ||
| {{reflist}} | {{reflist}} | ||
| {{Cell wall disruptive antibiotics|state=collapsed}} | |||
| == See also == | |||
| {{Portal bar | Medicine}} | |||
| * ] | |||
| {{PenicillinAntiBiotics}} | |||
| {{Use dmy dates|date=January 2011}} | |||
| {{DEFAULTSORT:Benzathine Benzylpenicillin}} | {{DEFAULTSORT:Benzathine Benzylpenicillin}} | ||
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