Penicillinase-Resistant Penicillin

Aka: Penicillinase-Resistant Penicillin, Penicillinase-Resistant Semisynthetic Penicillin, Cloxacillin, Dicloxacillin, Methicillin, Nafcillin, Oxacillin

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II. Indications

  1. Staphylococcus Infection
    1. Staphylococcus aureus
    2. Staphylococcus epidermidis
  2. Specific Infections
    1. Skin Infection
    2. Soft tissue infection
    3. Lymphatic infection
    4. Bone Infection
    5. Joint infection

III. Mechanism

  1. Same action to Natural Penicillins
  2. Prevents Penicillinase hydrolysis of Beta lactam ring

IV. Mechanism: Bacterial Resistance mechanisms

  1. Alteration of Bacterial cell wall

V. Mechanism: Activity Spectrum

  1. Same as for Natural Penicillins

VI. Preparations: Oral

  1. Directions
    1. Take on an empty Stomach
    2. Take more than 1 hour before or two hours after food
  2. Cloxacillin (Cloxapen) 250-500 mg PO qid
  3. Dicloxacillin (Dynapen)
    1. Adult: 125 to 500 mg PO qid
    2. Child: 12.5 to 25 mg/kg/day PO divided qid

VII. Preparations: Parenteral

  1. Methicillin (Staphcillin)
  2. Nafcillin (Nafcil, Unipen)
    1. Adult: 1 to 2 grams IM or IV every 4 hours
    2. Child: 50 to 200 mg/kg/day divided every 4 to 6 hours
  3. Oxacillin (Bactocill)
    1. Adult: 1 to 2 grams IM or IV every 4 to 6 hours

VIII. Adverse effects

  1. Nephritis (Methicillin)
  2. Venous inflammation (Nafcillin)

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Related Studies

Cost: Medications

dicloxacillin (on 5/17/2017 at Medicaid.Gov Survey of pharmacy drug pricing)
DICLOXACILLIN 250 MG CAPSULE Generic $0.50 each
DICLOXACILLIN 500 MG CAPSULE Generic $0.80 each
FPNotebook does not benefit financially from showing this medication data or their pharmacy links. This information is provided only to help medical providers and their patients see relative costs. Insurance plans negotiate lower medication prices with suppliers. Prices shown here are out of pocket, non-negotiated rates. See Needy Meds for financial assistance information.

Ontology: Cloxacillin (C0009077)

Definition (NCI) A semisynthetic beta-lactamase resistant penicillin antibiotic with antibacterial activity. Cloxacillin binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall, thereby preventing the cross-linkage of peptidoglycans, which are critical components of the bacterial cell wall. This leads to an interruption of the bacterial cell wall and causes bacterial cell lysis.
Definition (MSH) A semi-synthetic antibiotic that is a chlorinated derivative of OXACILLIN.
Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH D003023
SnomedCT 373276005, 68422006
LNC LP15442-4, MTHU006903
English Chloroxacillin, Cloxacillin, 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2-chlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-, cloxacillin, Cloxacillin [Chemical/Ingredient], CLOXACILLIN, Cloxacillin (product), Cloxacillin (substance)
Swedish Kloxacillin
Czech kloxacilin
Finnish Kloksasilliini
Russian NATRIIA KLOKSATSILLIN, KLOKSATSILLIN, KHLOROKSATSILLIN, КЛОКСАЦИЛЛИН, НАТРИЯ КЛОКСАЦИЛЛИН, ХЛОРОКСАЦИЛЛИН
Japanese クロキサシリンナトリウム, クロロキサシリン, クロキサシリン, ソジウムクロキサシリン
Italian Cloro oxacillina, Cloxacillina
Croatian KLOKSACILIN
Polish Syntarpen, Kloksacylina
Spanish cloxacilina (producto), cloxacilina (sustancia), cloxacilina, Cloroxacilina, Cloxacilina
French Cloxacilline
German Chloroxacillin, Cloxacillin
Portuguese Cloroxacilina, Cloxacilina
Derived from the NIH UMLS (Unified Medical Language System)

Ontology: Dicloxacillin (C0012093)

Definition (NCI) A broad-spectrum, semi-synthetic, beta-lactam, penicillin antibiotic with bactericidal and beta-lactamase resistant activity. Dicloxacillin binds to penicillin binding proteins (PBP) located on the inner membrane of the bacterial cell wall. It also inhibits the cross-linkage of peptidoglycan, a critical component of bacterial cell walls. This leads to the inhibition of bacterial cell wall synthesis and eventually causes cell lysis.
Definition (MSH) One of the PENICILLINS which is resistant to PENICILLINASE.
Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH D004009
SnomedCT 372873001, 8416000
LNC LP14990-3, MTHU002293
English Dichloroxacillin, Dicloxaciclin, Dicloxacillin, Dicloxacycline, 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2,6-dichlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-, 3-(2,6-Dichlorophenyl)-5-methyl-4-isoxazolylpenicillin, dicloxacillin, Dicloxacillin [Chemical/Ingredient], dicloxacillin (medication), DICLOXACILLIN, Dicloxacillin (product), Dicloxacillin (substance)
Swedish Dikloxacillin
Czech dikloxacilin
Finnish Dikloksasilliini
Russian DIKHLOROKSATSILLIN, DIKLOKSATSILLIN, ДИКЛОКСАЦИЛЛИН, ДИХЛОРОКСАЦИЛЛИН
Japanese ジクロキサシリン, ジクロロキサシリン, ジクロキサシリンナトリウム
Italian Dicloxacilina, Dicloxaciclina, Dicloxacillina
Polish Dikloksacylina
Spanish dicloxacilina (producto), dicloxacilina (sustancia), dicloxacilina, Dicloroxacilina, Dicloxacilina
French Dicloxacilline
German Dichloroxacillin, Dicloxacillin
Portuguese Dicloroxacilina, Dicloxacilina
Derived from the NIH UMLS (Unified Medical Language System)

Ontology: Methicillin (C0025643)

Definition (NCI) A semisynthetic, narrow spectrum beta-lactamase-resistant penicillin antibiotic with bactericidal and beta-lactamase resistant activity. Methicillin binds to specific penicillin-binding proteins (BPBs) on the bacterial cell wall, thereby preventing the cross-linkage of peptidoglycans, which are critical components of the bacterial cell wall. This leads to an interruption of the bacterial cell wall and causes bacterial lysis.
Definition (MSH) One of the PENICILLINS which is resistant to PENICILLINASE but susceptible to a penicillin-binding protein. It is inactivated by gastric acid so administered by injection.
Definition (CSP) semisynthetic penicillin used as an antibacterial in resistant staphylococcal infections.
Concepts Organic Chemical (T109) , Antibiotic (T195)
MSH D008712
SnomedCT 373515001, 61862008
LNC LP15975-3, MTHU008454
English Dimethoxyphenyl Penicillin, Methicillin, Penicillin, Dimethoxyphenyl, methicillin, 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((2,6-dimethoxybenzoyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-, Meticillin, 2,6 dimethoxyphenylpenicillin, Methicillin [Chemical/Ingredient], meticillin, Methicillin (product), Methicillin (substance), METHICILLIN
Swedish Meticillin
Czech methicilin
Finnish Metisilliini
Russian METITSILLIN, PENITSILLIN, DIMETOKSIFENIL, МЕТИЦИЛЛИН, ПЕНИЦИЛЛИН, ДИМЕТОКСИФЕНИЛ
Japanese ジメトキシフェニルペニシリン, メチシリン, メチシリンナトリウム
Italian Dimetossifenil-penicillina, Meticillina
Croatian METICILIN
Polish Penicylina dwumetoksyfenylowa, Metycylina
Spanish meticilina (producto), meticilina (sustancia), meticilina, Dimetoxifenil Penicilina, Meticilina
French Méticilline
German Methicillin, Penicillin, Dimethoxyphenyl-
Portuguese Dimetoxifenil Penicilina, Meticilina
Derived from the NIH UMLS (Unified Medical Language System)

Ontology: Nafcillin (C0027324)

Definition (NCI) A semi-synthetic naphthalene and beta-lactam antibiotic with antibacterial activity. Nafcillin inhibits bacterial wall synthesis by a mechanism of action similar to penicillin. Penicillinase-resistant Nafcillin is used to treat infections caused by penicillin-resistant strains of Staphylococci. (NCI04)
Definition (MSH) A semi-synthetic antibiotic related to penicillin.
Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH D009254
SnomedCT 372898000, 91169009
LNC LP14999-4, MTHU002302
English Nafcillin, Naphthamidopenicillin, 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, (2S-(2alpha,5alpha,6beta))-, Nafcillin [Chemical/Ingredient], nafcillin (medication), nafcillin, NAFCILLIN, Nafcillin (product), Nafcillin (substance)
Swedish Nafcillin
Czech nafcilin
Finnish Nafsilliini
Russian NAFTAMIDOPENITSILLIN, NATRIIA NAFTSILLIN, NAFTSILLIN, НАТРИЯ НАФЦИЛЛИН, НАФТАМИДОПЕНИЦИЛЛИН, НАФЦИЛЛИН
Japanese ナフシリンナトリウム, ナフタミドペニシリン, ソジウムナフシリン, ナフシリン
Polish Nafcylina
Spanish nafcilina (producto), nafcilina (sustancia), nafcilina, Nafcilina, Naftamidopenicilina
French Nafcilline
German Nafcillin, Naphthamidopenicillin
Italian Nafcillina
Portuguese Nafcilina, Naftamidopenicilina
Derived from the NIH UMLS (Unified Medical Language System)

Ontology: Oxacillin (C0029983)

Definition (NCI) A semisynthetic penicillinase-resistant and acid-stable penicillin with an antimicrobial activity. Oxacillin binds to penicillin-binding proteins in the bacterial cell wall, thereby blocking the synthesis of peptidoglycan, a critical component of the bacterial cell wall. This leads to inhibition of cell growth and causes cell lysis.
Definition (MSH) An antibiotic similar to FLUCLOXACILLIN used in resistant staphylococci infections.
Concepts Antibiotic (T195) , Organic Chemical (T109)
MSH D010068
SnomedCT 372868007, 83201006, 85724000
LNC LP16206-2, MTHU008465
English Methylphenylisoxazolyl Penicillin, Oxacillin, Oxazocilline, Penicillin, Methylphenylisoxazolyl, 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 3,3-dimethyl-6-(((5-methyl-3-phenyl-4-isoxazolyl)carbonyl)amino)-7-oxo-, (2S-(2alpha,5alpha,6beta))-, Oxacillin [Chemical/Ingredient], oxacillin (medication), oxacillin, OXACILLIN, Methylphenyl isoxazolyl penicillin, Oxacillin (product), Oxacillin (substance)
Swedish Oxacillin
Czech oxacilin
Finnish Oksasilliini
Russian OKSATSILLIN, NATRIIA OKSATSILLIN, OKSAZOTSILLIN, PENITSILLIN, METILFENILIZOKSAZOLIL, НАТРИЯ ОКСАЦИЛЛИН, ОКСАЗОЦИЛЛИН, ОКСАЦИЛЛИН, ПЕНИЦИЛЛИН, МЕТИЛФЕНИЛИЗОКСАЗОЛИЛ
Japanese オキサゾシリン, メチルフェニルイソキサゾリルペニシリン, オキサシリン, ペニシリン-メチルフェニルイソキサゾリル, ソジウムオキサシリン, オキサシリンナトリウム
Croatian Not Translated[Oxacillin]
Polish Oksacylina, Penicylina metylfenyloksazolowa
Spanish metilfenil isoxazolil penicilina, oxacilina (producto), oxacilina (sustancia), oxacilina, Metilfenilisoxazolil Penicilina, Oxacilina, Oxazocilina
French Oxacilline
German Oxacillin, Oxazocillin, Penicillin, Methylphenylisoxazolyl-
Italian Oxacillina
Portuguese Metilfenilisoxazolil Penicilina, Oxacilina, Oxazocilina
Derived from the NIH UMLS (Unified Medical Language System)

Related Topics in Pharmacology

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