{"ATC Code":["J01CE02","J - Antiinfectives for systemic use","J01 - Antibacterials for systemic use","J01C - Beta-lactam antibacterials, penicillins","J01CE - Beta-lactamase sensitive penicillins","J01CE02 - Phenoxymethylpenicillin","QJ - Antiinfectives for systemic use","QJ01 - Antibacterials for systemic use","QJ01C - Beta-lactam antibacterials, penicillins","QJ01CE - Beta-lactamase sensitive penicillins","QJ01CE02 - Phenoxymethylpenicillin","J01CE02"],"Absorption, Distribution and Excretion":"Upon oral administration, phenoxymethylpenicillin is rapidly but incompletely absorbed. The bioavailability of phenoxymethylpenicillin ranges from 25 to 60%. Compared to the free acid form of the drug, the calcium or potassium salts of phenoxymethylpenicillin displays better absorption profiles. It is reported that fasting state enhances the drug absorption. The peak plasma concentrations of 200 to 700 ng/mL are achieved in 2 hours following an oral dose of 125 mg. Following an oral dose of 500 mg, the peak plasma concentrations of 3 to 5 μg/mL are reached in 30 to 60 minutes post-dose.","Aliases":["Penicillin V","Phenoxymethylpenicillin","Oracillin","Vebecillin","Penicillin phenoxymethyl","Phenopenicillin","Distaquaine V","Meropenin","Phenomycilline","V-Cillin","Fenospen","Beromycin","Fenacilin","Stabicillin","Apopen","Oratren","Ospen","Eskacillin V","Phenoxymethyl penicillin","Pen-V","Pen-vee","Pen-Oral","Phenocillin","Phenoxymethylenepenicillinic acid","phenoxymethylpenicillinic acid","Rocilin","Compocillin V","Eskacillian V","Fenoximetilpenicilina","Crystapen V","V-Cil","V-Tablopen","Acipen V","V-Cylina","V-Cyline","Phenoxymethylpenicilline","Phenoxymethylpenicillinum","P-Mega-Tablinen","6-Phenoxyacetamidopenicillanic acid","Fenossimetilpenicillina","phenoxomethylpenicillin","(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid","Chebi:27446","(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid","(2S,5R,6R)-3,3-Dimethyl-7-oxo-6-[(phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid","Dtxsid3023429","4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-","4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, (2S-(2α,5α,6β))-","Phenoxymethylpenicillinum calcium","Fenoxymethylpenicillin","Beromycin, Penicillin","Berromycin, Penicillin","Penicillin, Phenoxymethyl","4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-, (2S,5R,6R)-","(2S,5R,6R)-3,3-dimethyl-7-oxo-6-((2-phenoxyacetyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid","(2S,5R,6R)-3,3-dimethyl-7-oxo-6-((phenoxyacetyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid","Penicillin Beromycin","Penicillin Berromycin","Sodium, Penicillin V","V Sodium, Penicillin","Dtxcid303429","J01CE02","201-722-0","Fenoxypen","Phenoximethylpenicillinum","Calcipen","(2S,5r,6r)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1- azabicyclo(3.2.0)heptane-2-carboxylic acid","PNV","Phenoxymethylpenicillin 100 microg/mL in Acetonitrile","Penicillanic acid, 6-phenoxyacetamido-","CCRIS 752","HSDB 6314","Einecs 201-722-0","Brn 0096259","Unii-z61i075u2w","Fenacillin;","Phenocillin;","Stabicillin;","Fenoxypen;","Meropenin;","Oracillin;","Penicillin-V","Fenospen;","Fenocin;","Oratren;","Apopen;","Ospen;","Pen-Vee;","penicillin-v-potassium","3,3-Dimethyl-7-oxo-6-((phenyloxyacetyl)amino)-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid","PC Pen VK","Spectrum_001007","Spectrum2_000495","Spectrum3_000543","Spectrum4_000472","Spectrum5_001409","Phenoxymethylpenicillin RS","Phenoxymethylpenicillin CRS","CHEMBL615","Epitope ID:115011","Epitope ID:116056","Penicillin v","Schembl49223","BSPBio_002185","KBioGR_000944","KBioSS_001487","4-27-00-05884","Mls001304105","phenoxymethylpenicillanyl group","DivK1c_000779","SPBio_000389","orb1983600","Chebi:53706","GTPL10920","HY-B0975A","KBio1_000779","KBio2_001487","KBio2_004055","KBio2_006623","KBio3_001685","MSK5619","Ninds_000779","GLXC-25717","2,2-dimethyl-6β-[(phenoxyacetyl)amino]penam-3α-carboxylic acid","Bdbm50370584","EBC-26689","3,3-dimethyl-6β-[(phenoxyacetyl)amino]penam-2α-carboxylic acid","Akos015969737","DB00417","Idi1_000779","phenoxymethyl penicillinic acid*free acid","(2S,5R,6R)-3,3-dimethyl-7-oxo-6-{[(phenyloxy)acetyl]amino}-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid","DA-76706","Smr000539431","Sbi-0051477.p003","AB00514745","CS-0013728","NS00078894","Phenoxymethylpenicillin for system suitability","C08126","D05411","G77824","En300-19735891","Phenoxymethylpenicillin for system suitability CRS","Brd-k43966364-237-02-2","Brd-k43966364-237-03-0","Brd-k43966364-237-04-8","6β-Phenoxyacetamido-2,2-dimethylpenam-3α-carboxylic acid","Penicillin V, United States Pharmacopeia (USP) Reference Standard","Phenoxymethylpenicillin, European Pharmacopoeia (EP) Reference Standard"],"Biological Half-Life":"Upon oral administration, the half-life is about 30 minutes. It can last up to 4 hours in patients with renal impairment.","CAS":"87-08-1","Chemical Classes":".Beta.-Lactams","ChemicalClasses":["amino acid"],"Chirality":"absolute","ChiralityAminoAcid":true,"Classes":["Antibiotic"],"Color/Form":"white, crystalline powder","Drug Classes":["Breast Feeding","Lactation","Anti-Infective Agents","Antibacterial Agents","Penicillins"],"Drug Indication":"Indicated for the treatment of mild to moderately severe infections due to penicillin G­-sensitive microorganisms, with the use of bacteriological studies (including sensitivity tests) and clinical response.   Phenoxymethylpenicillin may be used for the treatment of:   - mild to moderate infections of the upper respiratory tract, scarlet fever, and mild erysipelas caused by Streptococcus without bacteremia - mild to moderately severe infections of the respiratory tract caused by Pneumococcus - mild infections of the skin and soft tissues caused by penicillin G-sensitive Staphylococcus - mild to moderately severe infections of the oropharynx caused by Fusospirochetosis, including Vincent’s gingivitis and pharyngitis, usually respond to oral penicillin therapy  **Off-label**  Indicated for use as prophylaxis against bacterial endocarditis in patients with congenital heart disease or rheumatic or other acquired valvular heart disease when they undergo dental procedures and surgical procedures of the upper respiratory tract.","Drug Warnings":"The most important biological effect of penicillin, unrelated to hypersensitivity or to \"toxic\" reaction, is alteration of bacterial flora in areas of the body to which it gains access. Regardless of the route by which the drug is administered, but most strikingly when it is given by mouth, penicillin changes the composition of the microflora by eliminating sensitive microorganisms. ... In some persons ... suprainfection results from the changes in flora. /Penicillin/","DurationOfAction":"","EliminationHalfLife":"30 – 60\u0026nbsp;min","Esters":[],"European Community (EC) Number":"201-722-0","FDA Pharmacological Classification":[{"Name":"FDA UNII","ReferenceNumber":26,"Value":{"StringWithMarkup":[{"String":"Z61I075U2W"}]}},{"Name":"Active Moiety","ReferenceNumber":26,"Value":{"StringWithMarkup":[{"String":"PENICILLIN V"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":26,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-2349","Length":10,"Start":40,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Penicillin"}],"String":"Established Pharmacologic Class [EPC] - Penicillin-class Antibacterial"}]}},{"Name":"Pharmacological Classes","ReferenceNumber":26,"Value":{"StringWithMarkup":[{"String":"Chemical Structure [CS] - Penicillins"}]}},{"Name":"FDA Pharmacology Summary","ReferenceNumber":26,"Value":{"StringWithMarkup":[{"Markup":[{"Extra":"CID-6869","Length":12,"Start":0,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Penicillin%20v"},{"Extra":"CID-2349","Length":10,"Start":18,"Type":"PubChem Internal Link","URL":"https://pubchem.ncbi.nlm.nih.gov/compound/Penicillin"}],"String":"Penicillin v is a Penicillin-class Antibacterial."}]}}],"Formating":[],"HMDB ID":"HMDB0014561","HeavyAtomCount":24,"Human Drugs":"Breast Feeding; Lactation; Anti-Infective Agents; Antibacterial Agents; Penicillins","IUPACName":"(2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid","Impurities":"Commercially available penicillin ... V preparations may contain small amounts of high molecular weight protein impurities that originate from the fermentation process used to produce the drugs.","InChI":"InChI=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","InChIKey":"BPLBGHOLXOTWMN-MBNYWOFBSA-N","Interactions":"Oral neomycin has been shown to decrease the absorption of penicillin V ... .","KEGG Entries":[{"Id":"D05411","Interactions":[],"Synonyms":["Penicillin V","Phenoxymethylpenicillin","V-Cillin"]},{"Id":"D08360","Interactions":[],"Synonyms":["Phenoxymethylpenicillin calcium","Calcipen"]},{"Id":"D05411","Interactions":[],"Synonyms":["Penicillin V","Phenoxymethylpenicillin","V-Cillin"]},{"Id":"D05411","Interactions":[],"Synonyms":["Penicillin V","Phenoxymethylpenicillin","V-Cillin"]},{"Id":"D08360","Interactions":[],"Synonyms":["Phenoxymethylpenicillin calcium","Calcipen"]},{"Id":"D05411","Interactions":[],"Synonyms":["Penicillin V","Phenoxymethylpenicillin","V-Cillin"]},{"Id":"D08360","Interactions":[],"Synonyms":["Phenoxymethylpenicillin calcium","Calcipen"]}],"MeSH Headers":[{"Id":"M0016142","Link":"https://id.nlm.nih.gov/mesh/M0016142.html","Name":"Penicillin V","Ref":59},{"Id":"M0351153","Link":"https://id.nlm.nih.gov/mesh/M0351153.html","Name":"Beromycin","Ref":61},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":62},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":87},{"Id":"M0448397","Link":"https://id.nlm.nih.gov/mesh/M0448397.html","Name":"Anti-Bacterial Agents","Ref":88}],"MeSH Pharmacological Classification":[{"Id":"M0448397","Link":"https://id.nlm.nih.gov/mesh/M0448397.html","Name":"Anti-Bacterial Agent","Ref":88}],"Mechanism of Action":"Phenoxymethylpenicillin inhibits the biosynthesis of cell wall mucopeptide by binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, which are critical in the cell wall synthesis and maintenance, as well as cell division. This disrupts the third and last stage of bacterial cell wall synthesis. This subsequently leads to cell lysis.","Melting Point":"248 to 262 °F (Decomposes) (NTP, 1992)","Metabolism/Metabolites":"About 35-70% of an oral dose is metabolized to penicilloic acid, an inactive metabolite. Small amounts of 6-aminopenicillanic acid have been recovered in the urine of patients on penicillin G. A small percentage of the drug appears to be hydroxylated into one or more active metabolites, which are also excreted via urine.","MolecularFormula":"C\u003csub\u003e16\u003c/sub\u003eH\u003csub\u003e18\u003c/sub\u003eN\u003csub\u003e2\u003c/sub\u003eO\u003csub\u003e5\u003c/sub\u003eS","MolecularWeight":"350.4 g/mol","Odor":"Odorless","Opticalactivity":"UNSPECIFIED","Pharmacodynamics":"Phenoxymethylpenicillin works against penicillin-sensitive microorganisms with bactericidal effects. It targets the bacteria during its active multiplication stage by interfering with bacterial cell wall peptidoglycan synthesis. _In vitro_, phenoxymethylpenicillin was shown to be active against staphylococci (except penicillinase-producing strains), streptococci (groups A, C, G, H, L and M), and pneumococci, as well as _Corynebacterium diphtheriae_, _Bacillus anthracis_, Clostridia, _Actinomyces bovis_, _Streptobacillus moniliformis_, _Listeria monocytogenes_, _Leptospira_, _Neisseria gonorrhoeae_, and _Treponema pallidum_.","Physical Description":"Penicillin v is a white crystalline powder. (NTP, 1992)","PubChemId":6869,"Record Description":["LiverTox|Antimicrobial|Antibacterial|Penicillin, 1st gen"],"Records":{"UNII":{"Impurities":["phenoxyacetic acid","penicillin g","4-hydroxypenicillin v","6-aminopenicillanic acid"]}},"RefChem":"6106","RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Phenoxymethylpenicillin","Name":"Phenoxymethylpenicillin","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q422215","Name":"Phenoxymethylpenicillin","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB00417","Name":"Phenoxymethylpenicillin","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/6869","Name":"Phenoxymethylpenicillin","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=87-08-1","Name":"Phenoxymethylpenicillin","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0014561","Name":"Phenoxymethylpenicillin","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C08126","Name":"Phenoxymethylpenicillin","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/Z61I075U2W","Name":"Phenoxymethylpenicillin","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID3023429","Name":"Phenoxymethylpenicillin","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 6869, Penicillin V. Accessed April 24, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/6869\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/6869\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Phenoxymethylpenicillin. UNII: Z61I075U2W. Global Substance Registration System. Accessed April 24, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/Z61I075U2W\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/Z61I075U2W\u003c/a\u003e"],"SMILES":"CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)COC3=CC=CC=C3)C(=O)O)C","SaltData":[{"AcidCount":1,"Amine":"Phenoxymethylpenicillin","AmineCount":1,"Formula":"[Na+]","Name":"sodium","RName":"sodium","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 106.425 152.079\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h107v153H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m42.834 6.547-7.639 13.188M35.195 19.735l13.877 6.206M49.072 25.941 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