II. Indications
- Staphylococcus Infection
- Specific Infections
- Skin Infection
- Soft tissue infection
- Lymphatic infection
- Bone Infection
- Joint infection
III. Mechanism
-
Antibiotic activity
- Same action to Natural Penicillins
- Large, bulky side chain
- Blocks Penicillinase hydrolysis of Beta Lactam ring
- Hydrophobic side chain prevents penetration of Gram Negative Bacteria membrane via hydrophilic pores
- Therefore Penicillinase-Resistant Penicillins are inactive against Gram Negative Bacteria
-
Bacterial Resistance mechanisms
- Alteration of Bacterial cell wall
IV. Mechanism: Activity Spectrum
- Same as for Natural Penicillins
V. Preparations: Oral
- Directions
- Take on an empty Stomach
- Take more than 1 hour before or two hours after food
-
Dicloxacillin (Dynapen)
- Adult: 125 to 500 mg PO qid
- Child: 12.5 to 25 mg/kg/day orally divided four times daily
- Cloxacillin (Cloxapen)
- Still used internationally, but no longer available in the U.S.
- Adults: 250-500 mg orally four times daily
VI. Preparations: Parenteral
VII. Adverse effects
- Nephritis (Methicillin)
- Venous inflammation (Nafcillin)
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| 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 |
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 |
