| Revision as of 12:08, 5 December 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456998803 of page Phenoxymethylpenicillin for the Chem/Drugbox validation project (updated: ''). |
Latest revision as of 07:17, 17 December 2024 edit Whywhenwhohow (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers49,153 edits rank |
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{{Short description|Antibiotic medication}} |
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{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}} |
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{{Use dmy dates|date=January 2024}} |
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{{Drugbox |
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{{cs1 config |name-list-style=vanc |display-authors=6}} |
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{{Infobox drug |
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| Watchedfields = changed |
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| Watchedfields = changed |
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| verifiedrevid = 408551375 |
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| verifiedrevid = 464200689 |
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| image = Penicillin-V-2D-skeletal.svg |
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| IUPAC_name = 3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicycloheptane-2-carboxylic acid |
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| alt = |
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| image = Penicillin-V-2D-skeletal.png |
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| image2 = Phenoxymethylpenicillin-from-xtal-3D-bs-17.png |
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| drug_name = Penicillin V |
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| alt2 = |
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| caption = |
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<!--Clinical data--> |
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<!-- Clinical data --> |
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| pronounce = |
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| tradename = Veetids |
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| tradename = Veetids, Apocillin,<ref>{{cite web |url=https://www.felleskatalogen.no/medisin/apocillin-actavis-546118 |title=Apocillin |language=no |work=Felleskatalogen |publisher=LMI (Legemiddelindustrien) |access-date=23 June 2018 |quote=fenoksymetylpenicillin }}</ref> others |
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| Drugs.com = {{drugs.com|monograph|penicillin_v}} |
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| Drugs.com = {{drugs.com|monograph|penicillin_v}} |
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| MedlinePlus = a685015 |
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| MedlinePlus = a685015 |
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| DailyMedID = 2658 |
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| DailyMedID = Penicillin V |
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| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> |
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| pregnancy_US = B |
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| pregnancy_AU_comment = |
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| pregnancy_category = |
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| routes_of_administration = ] |
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| class = |
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| ATC_prefix = J01 |
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| ATC_suffix = CE02 |
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| ATC_supplemental = |
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<!-- Legal status --> |
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| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled --> |
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| legal_AU_comment = |
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| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F --> |
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| legal_BR_comment = |
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| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII --> |
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| legal_CA_comment = |
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| legal_DE = <!-- Anlage I, II, III or Unscheduled --> |
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| legal_DE_comment = |
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| legal_NZ = <!-- Class A, B, C --> |
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| legal_NZ_comment = |
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| 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 --> |
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| legal_UK_comment = |
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| legal_US = Rx-only |
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| legal_US_comment = |
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| legal_EU = |
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| legal_EU_comment = |
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| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV --> |
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| legal_UN_comment = |
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| legal_status = Rx-only |
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| legal_status = Rx-only |
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| routes_of_administration = ] |
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<!--Pharmacokinetic data--> |
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<!-- Pharmacokinetic data --> |
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| bioavailability = 60% |
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| bioavailability = 60% |
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| protein_bound = 80% |
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| protein_bound = 80% |
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| metabolism = ] |
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| metabolism = ] |
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| metabolites = |
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| onset = |
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| elimination_half-life = 30–60 min |
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| elimination_half-life = 30–60 min |
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| duration_of_action = |
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| excretion = ] |
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| excretion = ] |
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<!--Identifiers--> |
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<!-- Identifiers --> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 87-08-1 |
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| CAS_number = 87-08-1 |
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| CAS_supplemental = , {{CAS|132-98-9}} (potassium), {{CAS|147-48-8}} (anhydrous calcium), {{CAS|73368-74-8}} (calcium dihydrate) |
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| CAS_supplemental = {{CAS|132-98-9}} (potassium), {{CAS|147-48-8}} (anhydrous calcium), {{CAS|73368-74-8}} (calcium dihydrate) |
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| ATC_supplemental = {{ATC|J01|CE02}} |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 27446 |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChI = 1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = BPLBGHOLXOTWMN-MBNYWOFBSA-N |
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| PubChem = 6869 |
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| PubChem = 6869 |
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| IUPHAR_ligand = |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank = DB00417 |
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| DrugBank = DB00417 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 6607 |
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| ChemSpiderID = 6607 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = Z61I075U2W |
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| UNII = Z61I075U2W |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D05411 |
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| KEGG = D05411 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 27446 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 615 |
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| ChEMBL = 615 |
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| NIAID_ChemDB = |
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| PDB_ligand = |
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| synonyms = penicillin phenoxymethyl, penicillin V, penicillin VK |
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<!--Chemical data--> |
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<!-- Chemical and physical data --> |
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| IUPAC_name = 3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicycloheptane-2-carboxylic acid |
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| C=16 | H=18 | N=2 | O=5 | S=1 |
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| C=16 | H=18 | N=2 | O=5 | S=1 |
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| molecular_weight = 350.39 ]/] |
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| smiles = OC(=O)2N3C(=O)(NC(=O)Cc1ccccc1)3SC2(C)C |
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| SMILES = CC1((N2(S1)(C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C16H18N2O5S/c1-16(2)12(15(21)22)18-13(20)11(14(18)24-16)17-10(19)8-23-9-6-4-3-5-7-9/h3-7,11-12,14H,8H2,1-2H3,(H,17,19)(H,21,22)/t11-,12+,14-/m1/s1 |
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| StdInChI_comment = |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = BPLBGHOLXOTWMN-MBNYWOFBSA-N |
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| density = |
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| density_notes = |
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| melting_point = 120-128 |
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| melting_high = |
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| boiling_point = |
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| solubility = |
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| specific_rotation = |
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}} |
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}} |
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<!-- Definition and medical uses --> |
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'''Phenoxymethylpenicillin''', also known as '''penicillin V''' ('''PcV''') and '''penicillin VK''', is an ] useful for the treatment of a number of ].<ref name="WHO2008" /> Specifically it is used for the treatment of ], ], and ].<ref name="WHO2008" /> It is also used to prevent ] and to prevent infections following ].<ref name="WHO2008" /> It is given by mouth.<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 }}</ref> |
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<!-- Side effects and mechanism --> |
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Side effects include ], ], and ]s including ].<ref name=WHO2008/> It is not recommended in those with a history of ].<ref name=WHO2008/> It is relatively safe for use during ].<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=95}}</ref> It is in the ] and ] family of medications.<ref name=AHFS2016/> It usually results in ].<ref name=AHFS2016/> |
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<!-- History and culture --> |
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Phenoxymethylpenicillin was first made in 1948 by ].<ref name="Greenwood2008">{{cite book| vauthors = Greenwood D | chapter = Wonder Drugs |title=Antimicrobial Drugs: Chronicle of a Twentieth Century Medical Triumph|date=2008|publisher=OUP Oxford|isbn=978-0-19-953484-5| chapter-url = https://books.google.com/books?id=i4_FZHmzjzwC&pg=PA121|language=en|url-status=live|archive-url=https://web.archive.org/web/20161220084325/https://books.google.ca/books?id=i4_FZHmzjzwC&pg=PA121|archive-date=20 December 2016}}</ref>{{rp|121}} 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> It is available as a ].<ref name=AHFS2016>{{cite web|title=Penicillin V|url=https://www.drugs.com/monograph/penicillin-v.html|publisher=The American Society of Health-System Pharmacists|access-date=8 December 2016|url-status=live|archive-url=https://web.archive.org/web/20161220230657/https://www.drugs.com/monograph/penicillin-v.html|archive-date=20 December 2016}}</ref> In 2022, it was the 259th most commonly prescribed medication in the United States, with more than 1{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = PenicillinV Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/PenicillinV | access-date = 30 August 2024 }}</ref> |
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== Medical uses == |
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Specific uses for phenoxymethylpenicillin include:<ref name="Martindale"/><ref name="AMH2006">{{cite book | editor=Rossi S. | title=Australian Medicines Handbook | year=2006 | location=Adelaide | publisher=Australian Medicines Handbook Pty Ltd| isbn=0-9757919-2-3| title-link=Australian Medicines Handbook }}</ref> |
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* Infections caused by '']'' |
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** ] |
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** ] |
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** ] infections |
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* ] (mild uncomplicated infections) |
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* ] (early stage in pregnant women or young children) |
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* ] (primary and secondary prophylaxis) |
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* ] skin infections |
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* ] (pneumococcal infection prophylaxis) |
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* Initial treatment for dental abscesses |
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* Moderate-to-severe ] (with ]) |
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* ] of teeth (as an alternative to tetracycline) |
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* Blood infection prophylaxis in children with ]. |
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Penicillin V is sometimes used in the treatment of ] infections.{{cn|date=March 2023}} |
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It is less active than ] (penicillin G) against ].<ref name="Garrod1960"> |
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{{cite journal | vauthors = Garrod LP | title = Relative antibacterial activity of three penicillins | journal = British Medical Journal | volume = 1 | issue = 5172 | pages = 527–529 | date = February 1960 | pmid = 13826674 | pmc = 1966560 | doi = 10.1136/bmj.1.5172.527 }}</ref><ref name="Garrod1960a"> |
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{{cite journal | vauthors = Garrod LP | title = The relative antibacterial activity of four penicillins | journal = British Medical Journal | volume = 2 | issue = 5214 | pages = 1695–1696 | date = December 1960 | pmid = 13703756 | pmc = 2098302 | doi = 10.1136/bmj.2.5214.1695 }}</ref> Phenoxymethylpenicillin has a range of antimicrobial activity against ] that is similar to that of benzylpenicillin and a similar mode of action, but it is substantially less active than benzylpenicillin against ].<ref name="Garrod1960" /><ref name="Garrod1960a" /> |
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Phenoxymethylpenicillin is more acid-stable than benzylpenicillin, which allows it to be given orally.{{cn|date=March 2023}} |
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Phenoxymethylpenicillin is usually used only for the treatment of mild to moderate infections, and not for severe or deep-seated infections since ] can be unpredictable. Except for the treatment or prevention of infection with '']'' (which is uniformly sensitive to penicillin), therapy should be guided by bacteriological studies (including sensitivity tests) and by clinical response.<ref name="DailyMed"/> People treated initially with ] benzylpenicillin may continue treatment with phenoxymethylpenicillin by mouth once a satisfactory response has been obtained.<ref name="Martindale">{{cite book|editor=Sweetman S.|title=Martindale: The complete drug reference|publisher=Royal Pharmaceutical Society of Great Britain and the Pharmaceutical Press|location=London|year=2002|edition=Electronic version}}</ref> |
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It is not active against ]-producing bacteria, which include many strains of '']''.<ref name="DailyMed">{{cite web|url=http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=645|title=Penicillin V Potassium tablet: Drug Label Sections|date=December 2006|publisher=], ]: Current Medication Information|access-date=2 August 2009|url-status=live|archive-url=https://web.archive.org/web/20090727065618/http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=645|archive-date=27 July 2009}}</ref> |
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== Adverse effects == |
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{{further|Penicillin drug reaction}} |
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Phenoxymethylpenicillin is usually well tolerated but may occasionally cause transient ], vomiting, epigastric distress, ], constipation, acidic smell to urine and ]. A previous ] to ''any'' ] is a ].<ref name="Martindale"/><ref name="DailyMed"/> |
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==Mechanism of action== |
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{{further|Penicillin#Mechanism of action}} |
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The mechanism of phenoxymethylpenicillin is identical to that of all other penicillins. It exerts a ] action against penicillin-sensitive microorganisms during the stage of active multiplication. It acts by ] the ] of cell-wall ].<ref>{{cite journal | vauthors = Yocum RR, Rasmussen JR, Strominger JL | title = The mechanism of action of penicillin. Penicillin acylates the active site of Bacillus stearothermophilus D-alanine carboxypeptidase | journal = The Journal of Biological Chemistry | volume = 255 | issue = 9 | pages = 3977–3986 | date = May 1980 | pmid = 7372662 | doi = 10.1016/S0021-9258(19)85621-1 | doi-access = free }}</ref> |
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== Compendial status == |
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* ]<ref name=ibp2009>{{cite web| work =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> |
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==History== |
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The Austrian pharmaceutical company, Biochemie, was founded in ] in July 1946 at the site of a derelict brewery, at the suggestion of a French officer, Michel Rambaud (a chemist), who was able to obtain a small amount of ''Penicillium'' start culture from France. Contamination of the fermentation tanks was a persistent problem and in 1951, the company biologist, ], attempted to solve this by adding ] to the tanks as an anti-bacterial disinfectant. This resulted unexpectedly in an increase in penicillin production: but, the penicillin produced was not benzylpenicillin, but phenoxymethylpenicillin. Phenoxyethanol was fermented to ]<ref>{{cite web|title=Phenoxyacetic acid |website=PubChem |publisher=National Center for Biotechnology Information, National Library of Medicine |url=https://pubchem.ncbi.nlm.nih.gov/compound/Phenoxyacetic-acid |date=26 December 2020 |access-date=1 January 2021 |location=Bethesda, MD, USA }}</ref> in the tanks, which was then incorporated into penicillin via biosynthesis. Importantly, Brandl realised that phenoxymethylpenicillin is not destroyed by stomach acid and can therefore be given by mouth. Phenoxymethyl penicillin was originally discovered by Eli Lilly in 1948 as part of their efforts to study penicillin precursors, but was not further exploited, and there is no evidence that Lilly understood the significance of their discovery at the time.<ref name="Greenwood2008"/>{{rp|119–121}}<ref>{{cite journal | vauthors = Behrens OK, Corse J | title = Biosynthesis of penicillins; biological precursors for benzylpenicillin (penicillin G) | journal = The Journal of Biological Chemistry | volume = 175 | issue = 2 | pages = 751–764 | date = September 1948 | pmid = 18880772 | doi = 10.1016/S0021-9258(18)57194-5 | doi-access = free }}</ref> |
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Biochemie is part of ].{{cn|date=January 2024}} |
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== Society and culture == |
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=== Names === |
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There were four named penicillins at the time penicillin V was discovered (]), however, Penicillin V was named "V" for ''Vertraulich'' (German for ''confidential'');<ref name="Greenwood2008"/>{{rp|121}} it was not named for the Roman numeral "5". |
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Penicillin VK is the ] salt of penicillin V (K is the chemical symbol for potassium).{{cn|date=March 2023}} |
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== References == |
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{{reflist}} |
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{{PenicillinAntiBiotics}} |
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{{Portal bar | Medicine}} |
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{{Authority control}} |
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] |
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] |
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] |
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] |
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] |