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Identification
NamePhenoxymethylpenicillin
Accession NumberDB00417  (APRD00423, DB08415)
TypeSmall Molecule
GroupsApproved, Vet Approved
DescriptionPhenoxymethylpenicillin (Penicillin V) is narrow spectrum antibiotic used to treat mild to moderate infections caused by susceptible bacteria. It is a natural penicillin antibiotic that is administered orally. Penicillin V may also be used in some cases as prophylaxis against susceptible organisms. Natural penicillins are considered the drugs of choice for several infections caused by susceptible gram positive aerobic organisms, such as Streptococcus pneumoniae, groups A, B, C and G streptococci, nonenterococcal group D streptococci, viridans group streptococci, and non-penicillinase producing staphylococcus. Aminoglycosides may be added for synergy against group B streptococcus (S. agalactiae), S. viridans, and Enterococcus faecalis. The natural penicillins may also be used as first or second line agents against susceptible gram positive aerobic bacilli such as Bacillus anthracis, Corynebacterium diphtheriae, and Erysipelothrix rhusiopathiae. Natural penicillins have limited activity against gram negative organisms; however, they may be used in some cases to treat infections caused by Neisseria meningitidis and Pasteurella. They are not generally used to treat anaerobic infections. Resistance patterns, susceptibility and treatment guidelines vary across regions.
Structure
Thumb
Synonyms
(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
6-phenoxyacetamidopenicillanic acid
Fenoximetilpenicilina
Oracillin
Penicillin Phenoxymethyl
Penicillin V
Phenoxomethylpenicillin
Phenoxymethyl Penicillin
Phenoxymethylenepenicillinic acid
Phénoxyméthylpénicilline
Phenoxymethylpenicillinum
PV
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ledercillin Vk - Tab 400000 UnitTablet400000 unitOralWyeth Ayerst Canada Inc.1997-06-132000-08-02Canada
Ledercillin Vk - Tab 800000unitsTablet800000 unitOralWyeth Ayerst Canada Inc.1996-12-272001-04-23Canada
Ledercillin Vk Tab 400000unitTablet250 mgOralLederle Cyanamid Canada Inc.1969-12-311997-08-14Canada
Ledercillin Vk Tab 800000unitTablet500 mgOralLederle Cyanamid Canada Inc.1969-12-311997-08-14Canada
Nadopen V 200Powder, for solution40000 unitOralLioh Inc.1969-12-312006-08-25Canada
Nadopen V 400Powder, for solution80000 unitOralLioh Inc.1972-12-312006-08-25Canada
Nadopen V Tab 500000iuTablet500000 unitOralLioh Inc.1960-12-312006-08-25Canada
Novo-pen Vk Syr 500000/5mlPowder, for solution500000 unitOralNovopharm Limited1977-12-31Not applicableCanada
Novo-pen-VK 500 TabTablet500000 unitOralNovopharm Limited1966-12-312015-10-26Canada
Nu-pen-VK Tablets 300mgTablet300 mgOralNu Pharm Inc1990-12-312012-09-04Canada
Pen Vee Sus 180mgLiquid180 mgOralWyeth Ltd.1956-12-311996-09-10Canada
Pen Vk-125 Sus 200000unit/5mlSuspension200000 unitOralPro Doc Limitee1986-12-312000-07-31Canada
Pen Vk-300 Sus 500000unit/5mlSuspension500000 unitOralPro Doc Limitee1987-12-312000-07-31Canada
Pen-vee Oral Tablets 300 mgTablet300 mgOralLioh Inc.1996-11-202006-08-25Canada
Pen-vee Suspension 180 mgSuspension180 mgOralPendopharm Division Of De Pharmascience Inc1996-11-152010-09-22Canada
Pen-vee Suspension 180mg/5mlSuspension180 mgOralWyeth Ayerst Canada Inc.1994-12-311996-09-10Canada
Pen-vee Suspension 300 mgSuspension300 mgOralPendopharm Division Of De Pharmascience Inc1996-11-152010-09-22Canada
Pen-vee Suspension 300mg/5mlSuspension300 mgOralWyeth Ayerst Canada Inc.1994-12-311996-09-10Canada
Pen-vee-oral Tablets 300mgTablet300 mgOralWyeth Ayerst Canada Inc.1994-12-311996-09-10Canada
Pen-VKTablet480000 unitOralAa Pharma Inc1985-12-31Not applicableCanada
Penicilline V 300 TabTablet500000 unitOralPro Doc Limitee1979-12-312014-11-10Canada
Pvf 250susSuspension250000 unitOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1972-12-311998-04-21Canada
Pvf 500susSuspension500000 unitOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1972-12-311998-04-21Canada
Pvf K500tabTablet500000 unitOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1972-12-311998-04-21Canada
Pvf-K 500 TabletsTablet500000 unitOralLioh Inc.1998-06-182006-08-25Canada
V Cillin K 1831 Tablet 250mgTablet250 mgOralEli Lilly Canada Inc1957-12-311999-09-13Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Pen VkPowder, for solution200000 unitOralApotex Inc1985-12-31Not applicableCanada
Apo Pen VkPowder, for solution480000 unitOralApotex Inc1985-12-31Not applicableCanada
Penicillin V PotasiumTablet250 mg/1OralSandoz Inc1995-11-30Not applicableUs
Penicillin V PotasiumTablet500 mg/1OralPhysicians Total Care, Inc.1995-02-22Not applicableUs
Penicillin V PotasiumTablet500 mg/1OralSandoz Inc1995-11-30Not applicableUs
Penicillin V PotasiumTablet500 mg/1OralRed Pharm Drug, Inc.2001-01-01Not applicableUs
Penicillin V PotasiumTablet500 mg/1OralLake Erie Medical DBA Quality Care Products LLC1995-11-30Not applicableUs
Penicillin V PotasiumTablet250 mg/1OralA S Medication Solutions1995-11-30Not applicableUs
Penicillin V PotasiumTablet250 mg/1OralPhysicians Total Care, Inc.2003-09-30Not applicableUs
Penicillin V PotasiumTablet500 mg/1OralBlenheim Pharmacal, Inc.2016-04-12Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2008-04-29Not applicableUs
Penicillin V PotassiumPowder, for solution125 mg/5mLOralPreferred Pharmaceuticals, Inc2012-03-14Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralPd Rx Pharmaceuticals, Inc.1995-11-30Not applicableUs
Penicillin V PotassiumFor solution25 mg/mLOralDAVA Pharmaceuticals, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralA S Medication Solutions2004-02-01Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralRebel Distributors Corp1988-11-23Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralHikma Pharmaceutical2016-01-10Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralA S Medication Solutions Llc2008-04-29Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralREMEDYREPACK INC.2015-10-26Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralWest Ward Pharmaceuticals Corp2013-10-11Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralTeva Pharmaceuticals USA Inc1990-09-30Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralA S Medication Solutions2008-04-29Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralBlenheim Pharmacal, Inc.2009-12-29Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralLake Erie Medical DBA Quality Care Products LLC2008-04-29Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralRed Pharm Drug, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralCitron Pharma LLC2008-04-29Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralAurobindo Pharma Limited2008-04-29Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2008-04-29Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralLiberty Pharmaceuticals, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralAidarex Pharmaceuticals LLC2004-02-01Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralPreferred Pharmaceuticals Inc.2015-05-13Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2008-04-29Not applicableUs
Penicillin V PotassiumTablet, film coated250 mg/1OralLake Erie Medical DBA Quality Care Products LLC2008-04-29Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralPd Rx Pharmaceuticals, Inc.1995-11-30Not applicableUs
Penicillin V PotassiumFor solution50 mg/mLOralDAVA Pharmaceuticals, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumPowder, for solution250 mg/5mLOralA S Medication Solutions1990-09-30Not applicableUs
Penicillin V PotassiumPowder, for solution250 mg/5mLOralRebel Distributors Corp1968-07-31Not applicableUs
Penicillin V PotassiumTablet, film coated250 mg/1OralProficient Rx LP2008-04-29Not applicableUs
Penicillin V PotassiumPowder, for solution250 mg/5mLOralA S Medication Solutions Llc1990-09-30Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralREMEDYREPACK INC.2015-11-12Not applicableUs
Penicillin V PotassiumTablet, film coated250 mg/1OralWest Ward Pharmaceuticals Corp2013-10-11Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralTeva Pharmaceuticals USA Inc1990-09-30Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralProficient Rx LP2008-04-29Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralGolden State Medical Supply, Inc.1996-07-09Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralLake Erie Medical DBA Quality Care Products LLC2008-04-29Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralBlenheim Pharmacal, Inc.2010-09-08Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralUnit Dose Services2004-02-01Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralPd Rx Pharmaceuticals, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralPreferred Pharmaceuticals, Inc.2015-02-02Not applicableUs
Penicillin V PotassiumPowder, for solution250 mg/5mLOralPhysicians Total Care, Inc.2003-11-10Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralDAVA Pharmaceuticals, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumTablet, film coated250 mg/1OralPd Rx Pharmaceuticals, Inc.2008-04-29Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralLiberty Pharmaceuticals, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumTablet, film coated250 mg/1OralPd Rx Pharmaceuticals, Inc.2008-04-29Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralLake Erie Medical DBA Quality Care Products LLC2004-02-01Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralPreferred Pharmaceuticals, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumPowder, for solution250 mg/5mLOralA S Medication Solutions1990-09-30Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralBlenheim Pharmacal, Inc.2012-05-24Not applicableUs
Penicillin V PotassiumPowder, for solution125 mg/5mLOralTeva Pharmaceuticals USA Inc1990-09-30Not applicableUs
Penicillin V PotassiumPowder, for solution125 mg/5mLOralRebel Distributors Corp1968-07-31Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralNu Care Pharmaceuticals, Inc.2008-04-29Not applicableUs
Penicillin V PotassiumPowder, for solution250 mg/5mLOralA S Medication Solutions Llc1990-09-30Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralProficient Rx LP2004-02-01Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralPd Rx Pharmaceuticals, Inc.2008-04-29Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralNorthwind Pharmaceuticals2014-06-01Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralGolden State Medical Supply, Inc.1996-07-09Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralPreferred Pharmaceuticals Inc.2016-02-16Not applicableUs
Penicillin V PotassiumTablet, film coated250 mg/1OralNorth Star Rx Llc2008-04-29Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralPd Rx Pharmaceuticals, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumPowder, for solution250 mg/5mLOralPreferred Pharmaceuticals, Inc2012-03-14Not applicableUs
Penicillin V PotassiumPowder, for solution125 mg/5mLOralPhysicians Total Care, Inc.1992-04-19Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralDAVA Pharmaceuticals, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralA S Medication Solutions2004-02-01Not applicableUs
Penicillin V PotassiumTablet500 mg/1OralLiberty Pharmaceuticals, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralBlenheim Pharmacal, Inc.2010-09-09Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralLake Erie Medical DBA Quality Care Products LLC2004-02-01Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralRed Pharm Drug, Inc.2004-02-01Not applicableUs
Penicillin V PotassiumTablet, film coated250 mg/1OralCitron Pharma LLC2008-04-29Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralPreferred Pharmaceuticals, Inc2012-03-292016-10-29Us
Penicillin V PotassiumPowder, for solution250 mg/5mLOralTeva Pharmaceuticals USA Inc1990-09-30Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralAidarex Pharmaceuticals LLC2004-02-01Not applicableUs
Penicillin V PotassiumTablet, film coated250 mg/1OralA S Medication Solutions2008-04-29Not applicableUs
Penicillin V PotassiumTablet, film coated250 mg/1OralAurobindo Pharma Limited2008-04-29Not applicableUs
Penicillin V PotassiumPowder, for solution250 mg/5mLOralProficient Rx LP1990-09-30Not applicableUs
Penicillin V PotassiumTablet, film coated250 mg/1OralA S Medication Solutions Llc2008-04-29Not applicableUs
Penicillin V PotassiumTablet250 mg/1OralREMEDYREPACK INC.2015-03-07Not applicableUs
Penicillin V PotassiumTablet, film coated250 mg/1OralHikma Pharmaceutical2016-01-10Not applicableUs
Penicillin V PotassiumTablet, film coated500 mg/1OralNorth Star Rx Llc2008-04-29Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Apo-Pen-VKNot Available
Beepen-VKNot Available
Betapen-VKNot Available
Crystapen VNot Available
Distaquaine VNot Available
FenospenNot Available
FenoxypenNot Available
Ledercillin VKNot Available
OratrenNot Available
OspenNot Available
Pen-OralNot Available
Pen-VNot Available
Pen-VeeNot Available
Pen-Vee KNot Available
Penicillin VKNot Available
Pfizerpen VKNot Available
PhenocillinNot Available
Robicillin VKNot Available
RocilinNot Available
Uticillin VKNot Available
V-CillinNot Available
VeetidsNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Phenoxymethylpenicillin benzathine
5928-84-7
Thumb
  • InChI Key: BBTOYUUSUQNIIY-ANPZCEIESA-N
  • Monoisotopic Mass: 940.349934375
  • Average Mass: 941.13
DBSALT001952
Phenoxymethylpenicillin potassium
132-98-9
Thumb
  • InChI Key: HCTVWSOKIJULET-LQDWTQKMSA-M
  • Monoisotopic Mass: 388.04952432
  • Average Mass: 388.48
DBSALT000299
Categories
UNIIZ61I075U2W
CAS number87-08-1
WeightAverage: 350.39
Monoisotopic: 350.093642386
Chemical FormulaC16H18N2O5S
InChI KeyBPLBGHOLXOTWMN-MBNYWOFBSA-N
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
IUPAC Name
(2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[[email protected]]2NC(=O)COC1=CC=CC=C1)C(O)=O
Pharmacology
IndicationFor the treatment of mild to moderately severe infections (e.g. dental infection, infections in the heart, middle ear infections, rheumatic fever, scarlet fever, skin infections, upper and lower respiratory tract infections) due to microorganisms.
Structured Indications
PharmacodynamicsPenicillin V exerts a bactericidal action against penicillin-sensitive microorganisms during the stage of active multiplication. It acts through the inhibition of biosynthesis of cell-wall mucopeptide. It is not active against the penicillinase-producing bacteria, which include many strains of staphylococci. The drug exerts high in vitro activity against staphylococci (except penicillinase-producing strains), streptococci (groups A, C, G, H, L and M), and pneumococci. Other organisms sensitive in vitro to penicillin V are Corynebacteriumdiphtheriae, Bacillus anthracis, Clostridia, Actinomycesbovis, Streptobacillusmoniliformis, Listeria monocytogenes, Leptospira, and Neisseria gonorrhoeae. Treponemapallidum is extremely sensitive.
Mechanism of actionBy binding to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, Penicillin V inhibits the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that Penicillin V interferes with an autolysin inhibitor.
TargetKindPharmacological actionActionsOrganismUniProt ID
Penicillin-binding protein 1AProteinyesNot AvailableClostridium perfringens (strain 13 / Type A)Q8XJ01 details
MecA PBP2' (penicillin binding protein 2')Proteinyes
inhibitor
Staphylococcus aureusQ53707 details
D-alanyl-D-alanine carboxypeptidase DacBProteinunknownNot AvailableEscherichia coli (strain K12)P24228 details
Penicillin acylaseProteinunknownNot AvailableLysinibacillus sphaericusP12256 details
Solute carrier family 15 member 1ProteinunknownNot AvailableHumanP46059 details
Related Articles
Absorption25% of the dose given is absorbed, 50-60% bioavailable
Volume of distributionNot Available
Protein binding80%
Metabolism

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.

SubstrateEnzymesProduct
Phenoxymethylpenicillin
Not Available
6-aminopenicillanic acidDetails
Phenoxymethylpenicillin
Not Available
Penicilloic acidDetails
Route of eliminationMostly renal. A small percentage is eliminated by feces and the biliary route.
Half life30 to 40 minutes
ClearanceNot Available
ToxicityLD50 >1040 mg/kg (Orally in rats with Sodium salt); Nausea, vomiting, stomach pain, diarrhea, and, in rare cases, major motor seizures
Affected organisms
  • Bacteria
  • Gram-negative Bacteria
  • Bacillus anthracis
  • Streptococcus pyogenes
  • Borrelia burgdorferi
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
Interactions
Drug Interactions
DrugInteractionDrug group
AcenocoumarolPhenoxymethylpenicillin may increase the anticoagulant activities of Acenocoumarol.Approved
AclarubicinThe serum concentration of Aclarubicin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
AmrubicinThe serum concentration of Amrubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational
annamycinThe serum concentration of annamycin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
ApramycinThe serum concentration of Apramycin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental, Vet Approved
ArbekacinThe serum concentration of Arbekacin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
BcgThe therapeutic efficacy of Bcg can be decreased when used in combination with Phenoxymethylpenicillin.Investigational
ChlortetracyclineThe therapeutic efficacy of Phenoxymethylpenicillin can be decreased when used in combination with Chlortetracycline.Approved, Vet Approved
DaunorubicinThe serum concentration of Daunorubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
DemeclocyclineThe therapeutic efficacy of Phenoxymethylpenicillin can be decreased when used in combination with Demeclocycline.Approved
DicoumarolPhenoxymethylpenicillin may increase the anticoagulant activities of Dicoumarol.Approved
DihydrostreptomycinThe serum concentration of Dihydrostreptomycin can be decreased when it is combined with Phenoxymethylpenicillin.Vet Approved
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational
DoxycyclineThe therapeutic efficacy of Phenoxymethylpenicillin can be decreased when used in combination with Doxycycline.Approved, Investigational, Vet Approved
EpirubicinThe serum concentration of Epirubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
Ethyl biscoumacetatePhenoxymethylpenicillin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindionePhenoxymethylpenicillin may increase the anticoagulant activities of Fluindione.Investigational
FramycetinThe serum concentration of Framycetin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
GeneticinThe serum concentration of Geneticin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
GentamicinThe serum concentration of Gentamicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
GENTAMICIN C1AThe serum concentration of GENTAMICIN C1A can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
Hygromycin BThe serum concentration of Hygromycin B can be decreased when it is combined with Phenoxymethylpenicillin.Vet Approved
IdarubicinThe serum concentration of Idarubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
INNO-206The serum concentration of INNO-206 can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
KanamycinThe serum concentration of Kanamycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Phenoxymethylpenicillin.Approved
MetrizamideThe serum concentration of Metrizamide can be decreased when it is combined with Phenoxymethylpenicillin.Approved
MinocyclineThe therapeutic efficacy of Phenoxymethylpenicillin can be decreased when used in combination with Minocycline.Approved, Investigational
Mycophenolic acidThe serum concentration of the active metabolites of Mycophenolic acid can be reduced when Mycophenolic acid is used in combination with Phenoxymethylpenicillin resulting in a loss in efficacy.Approved
NeamineThe serum concentration of Neamine can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
NeomycinThe serum concentration of Neomycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
NetilmicinThe serum concentration of Netilmicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
OxytetracyclineThe therapeutic efficacy of Phenoxymethylpenicillin can be decreased when used in combination with Oxytetracycline.Approved, Vet Approved
ParomomycinThe serum concentration of Paromomycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational
PhenindionePhenoxymethylpenicillin may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonPhenoxymethylpenicillin may increase the anticoagulant activities of Phenprocoumon.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Phenoxymethylpenicillin.Approved
PirarubicinThe serum concentration of Pirarubicin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
PlicamycinThe serum concentration of Plicamycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Withdrawn
ProbenecidThe serum concentration of Phenoxymethylpenicillin can be increased when it is combined with Probenecid.Approved
PuromycinThe serum concentration of Puromycin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
RibostamycinThe serum concentration of Ribostamycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
SisomicinThe serum concentration of Sisomicin can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
SP1049CThe serum concentration of SP1049C can be decreased when it is combined with Phenoxymethylpenicillin.Investigational
SpectinomycinThe serum concentration of Spectinomycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
StreptomycinThe serum concentration of Streptomycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Vet Approved
StreptozocinThe serum concentration of Streptozocin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
TetracyclineThe therapeutic efficacy of Phenoxymethylpenicillin can be decreased when used in combination with Tetracycline.Approved, Vet Approved
TobramycinThe serum concentration of Tobramycin can be decreased when it is combined with Phenoxymethylpenicillin.Approved, Investigational
ValrubicinThe serum concentration of Valrubicin can be decreased when it is combined with Phenoxymethylpenicillin.Approved
WarfarinPhenoxymethylpenicillin may increase the anticoagulant activities of Warfarin.Approved
ZorubicinThe serum concentration of Zorubicin can be decreased when it is combined with Phenoxymethylpenicillin.Experimental
Food Interactions
  • Absorption is increased when taken on an empty stomach (one hour before or two hours after meals).
References
Synthesis Reference

Hephzibah Sivaraman, Archana Pundle, Cheravakkattu Suresh, George Dodson, James Brannigan, “Process for production of large amount of penicillin V acylase.” U.S. Patent US20050142652, issued June 30, 2005.

US20050142652
General References
  1. Authors unspecified: Inadvertent use of Bicillin C-R to treat syphilis infection--Los Angeles, California, 1999-2004. MMWR Morb Mortal Wkly Rep. 2005 Mar 11;54(9):217-9. [PubMed:15758893 ]
  2. Gruchalla RS, Pirmohamed M: Clinical practice. Antibiotic allergy. N Engl J Med. 2006 Feb 9;354(6):601-9. [PubMed:16467547 ]
External Links
ATC CodesJ01CE02J01CE10
AHFS Codes
  • 08:12.16.04
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (37.1 KB)
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9071
Blood Brain Barrier-1.0
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.6858
P-glycoprotein inhibitor INon-inhibitor0.9131
P-glycoprotein inhibitor IINon-inhibitor0.9726
Renal organic cation transporterNon-inhibitor0.9219
CYP450 2C9 substrateNon-substrate0.8176
CYP450 2D6 substrateNon-substrate0.847
CYP450 3A4 substrateSubstrate0.5576
CYP450 1A2 substrateNon-inhibitor0.8802
CYP450 2C9 inhibitorNon-inhibitor0.8501
CYP450 2D6 inhibitorNon-inhibitor0.8725
CYP450 2C19 inhibitorNon-inhibitor0.8361
CYP450 3A4 inhibitorNon-inhibitor0.8257
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8785
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.7079
BiodegradationNot ready biodegradable0.9747
Rat acute toxicity1.8953 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9995
hERG inhibition (predictor II)Non-inhibitor0.8344
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
  • Glaxosmithkline
  • Apothecon inc div bristol myers squibb
  • Lederle laboratories div american cyanamid co
  • Parke davis div warner lambert co
  • American antibiotics llc
  • Dava pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Purepac pharmaceutical co
  • Teva pharmaceuticals usa inc
  • Wyeth ayerst laboratories
  • Pfizer laboratories div pfizer inc
  • Apothecon sub bristol myers squibb co
  • Bristol laboratories inc div bristol myers co
  • Aurobindo pharma ltd
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Sandoz inc
  • Pharmacia and upjohn co
Packagers
Dosage forms
FormRouteStrength
Powder, for solutionOral200000 unit
Powder, for solutionOral480000 unit
TabletOral400000 unit
TabletOral800000 unit
TabletOral500 mg
Powder, for solutionOral40000 unit
Powder, for solutionOral80000 unit
Powder, for solutionOral500000 unit
TabletOral300 mg
LiquidOral180 mg
SuspensionOral200000 unit
SuspensionOral180 mg
SuspensionOral300 mg
TabletOral480000 unit
For solutionOral25 mg/mL
For solutionOral50 mg/mL
Powder, for solutionOral125 mg/5mL
Powder, for solutionOral250 mg/5mL
TabletOral250 mg/1
TabletOral500 mg/1
Tablet, film coatedOral250 mg/1
Tablet, film coatedOral500 mg/1
SuspensionOral250000 unit
SuspensionOral500000 unit
TabletOral500000 unit
TabletOral250 mg
Prices
Unit descriptionCostUnit
Penicillin V Potassium 250 mg/5ml Solution 100ml Bottle12.99USD bottle
Penicillin V Potassium 500 mg tablet0.77USD tablet
Penicillin V Potassium 250 mg tablet0.47USD tablet
Veetids 500 mg tablet0.43USD tablet
Penicillin vk 500 mg tablet0.4USD tablet
Veetids 250 mg tablet0.24USD tablet
Penicillin vk 250 mg tablet0.23USD tablet
Apo-Pen-Vk 300 mg Tablet0.07USD tablet
Novo-Pen-Vk 300 mg Tablet0.07USD tablet
Nu-Pen-Vk 300 mg Tablet0.07USD tablet
Apo-Pen-Vk 25 mg/ml Liquid0.06USD ml
Apo-Pen-Vk 60 mg/ml Liquid0.06USD ml
Novo-Pen-Vk 60 mg/ml Liquid0.06USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point120-128 °CNot Available
water solubility<0.1 g/100mLNot Available
logP2.09HANSCH,C ET AL. (1995)
pKa2.79SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.454 mg/mLALOGPS
logP1.78ALOGPS
logP0.76ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area95.94 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity85.77 m3·mol-1ChemAxon
Polarizability34.37 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentPenicillins
Alternative Parents
Substituents
  • Penicillin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Phenol ether
  • Alkyl aryl ether
  • Thiazolidine
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors

Targets

Kind
Protein
Organism
Clostridium perfringens (strain 13 / Type A)
Pharmacological action
yes
General Function:
Transferase activity, transferring glycosyl groups
Specific Function:
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan strands) and a penicillin-sensitive transpeptidase C-terminal domain (cross-linking of the peptide subunits) (By similarity).
Gene Name:
pbpA
Uniprot ID:
Q8XJ01
Molecular Weight:
75176.35 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Kind
Protein
Organism
Staphylococcus aureus
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
mecA
Uniprot ID:
Q53707
Molecular Weight:
76265.485 Da
References
  1. Lemaire S, Glupczynski Y, Duval V, Joris B, Tulkens PM, Van Bambeke F: Activities of ceftobiprole and other cephalosporins against extracellular and intracellular (THP-1 macrophages and keratinocytes) forms of methicillin-susceptible and methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2009 Jun;53(6):2289-97. doi: 10.1128/AAC.01135-08. Epub 2009 Mar 16. [PubMed:19289525 ]
Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
unknown
General Function:
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function:
Not involved in transpeptidation but exclusively catalyzes a DD-carboxypeptidase and DD-endopeptidase reaction.
Gene Name:
dacB
Uniprot ID:
P24228
Molecular Weight:
51797.85 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Lysinibacillus sphaericus
Pharmacological action
unknown
General Function:
Penicillin amidase activity
Specific Function:
The enzyme catalyzes the conversion of penicillin to 6-aminopenicillanate The precursor, furthermore, acts as a self-processing peptidase that cleaves off the propeptide. All peptidase activity is lost on conversion to the mature peptidase.
Gene Name:
Not Available
Uniprot ID:
P12256
Molecular Weight:
37457.375 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Biegel A, Gebauer S, Hartrodt B, Brandsch M, Neubert K, Thondorf I: Three-dimensional quantitative structure-activity relationship analyses of beta-lactam antibiotics and tripeptides as substrates of the mammalian H+/peptide cotransporter PEPT1. J Med Chem. 2005 Jun 30;48(13):4410-9. [PubMed:15974593 ]
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Drug created on June 13, 2005 07:24 / Updated on November 18, 2016 16:20