Methicillin

380.415

380.42

200-505-8

Q91FH1328A

DTXSID6023284

C61842

J - Antiinfectives for systemic use

131

1.22

Solid

1.44±0.1 g/cm3(Predicted)

3.10e-01 g/L

Commercially available methicillin sodium powder for injection should be stored at 15-30 deg C. /Methicillin sodium/

2.77None

2.77

3

Xn

Penicillinase-resistant penicillins are generally stable in the dry state @ room temp for several yr; however, the drugs are stable only for short periods of time in soln unless frozen. Stability of the drugs is pH and temp dependent. Methicillin, nafcillin, and oxacillin are generally stable @ pH 5-8.

P264, P270, P301+P312, P330, P501

H302

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|Aggregated GHS information provided by 39 companies from 1 notifications to the ECHA C&L Inventory.

Three forms of liver injury have been attributed to the penicillinase-resistant and other penicillins. The first is a transient and usually asymptomatic elevation in serum aminotransferase levels that occurs with high dose intravenous therapy with oxacillin (Case 1, Oxacillin) and rarely with standard penicillins (Case 1, Penicillin G). This reaction has not been described with nafcillin or dicloxacillin and patients can be safety switched to these or other forms of penicillin in the face of oxacillin injury. This form of penicillin-induced liver injury occurs only with high dose therapy that is likely due to direct hepatotoxicity.

Methicillin sodium is potentially physically and/or chemically incompatible with some drugs, including aminoglycosides and tetracyclines, but the compatibility depends on several factors (e.g., concentrations of the drugs, specific diluents used, resulting pH, temperature). /Methicillin sodium/|Mixing penicillins with aminoglycosides in vitro has resulted in substantial mutual inactivation; if these groups of antibacterials are to be administered concurrently, they should be administered at separate sites at least 1 hour apart. /Penicillins/|Concurrent of /methotrexate/ with penicillins has resulted in decreased clearance of methotrexate and in methotrexate toxicity; this is thought to be due to competition for renal tubular secretion; patients should be closely monitored; leucovorin doses may need to be increased and administered for longer periods of time. /Penicillins/|Since bacteriostatic drugs /Chloramphenicol, erythromycins, sulfonamides, or tetracyclines/ may interfere with the bactericidal effect of penicillins in the treatment of meningitis or in other situations in which a rapid bactericidal effect is necessary, it is best to avoid concurrent therapy; however, chloramphenicol and ampicillin are sometimes administered concurrently to pediatric patients. /Penicillins/|For more Interactions (Complete) data for METHICILLIN (7 total), please visit the HSDB record page.

Used to treat infections caused by susceptible Gram-positive bacteria, particularly beta-lactamase-producing organisms such as Staphylococcus aureus that would otherwise be resistant to most penicillins.

Penicillins|Methicillin /is/ indicated in the treatment of bone and joint infections caused by susceptible organisms. /Included in US product labeling; Not included in Canadian product labeling/|Methicillin /is/ indicated in the treatment of bacterial endocarditis caused by susceptible organisms. /Included in US product labeling; Not included in Canadian product labeling/|Methicillin /is/ indicated in the treatment of bacterial septicemia caused by susceptible organisms. /Included in US product labeling/|For more Therapeutic Uses (Complete) data for METHICILLIN (7 total), please visit the HSDB record page.

METHICILLIN MUST NOT BE USED IN PREFERENCE TO PENICILLIN G IN INFECTIONS AMENDABLE TO TREATMENT WITH LATTER DRUG.|IMPORTANT BIOLOGICAL EFFECT OF PENICILLIN, UNRELATED TO HYPERSENSITIVITY OR TO "TOXIC" REACTION, IS ALTERATION OF BACTERIAL FLORA IN AREAS OF BODY TO WHICH IT GAINS ACCESS. /PENICILLIN/|IM INJECTION OF METHICILLIN IS MORE PAINFUL THAN IS CASE FOR OTHER PENICILLINS; NEED FOR FREQUENT INJECTIONS (EVERY 2-3 HR) IS DEFINITE DISADVANTAGE WHEN PROLONGED THERAPY BY THIS ROUTE IS REQUIRED.|IN SOME PERSONS...SUPRAINFECTION RESULTS FROM CHANGES IN FLORA. DERMATITIS INVOLVING PRIMARILY SCROTAL & INGUINAL SKIN...HAS BEEN OBSERVED... DRAMATIC EFFECT THAT MAY FOLLOW USE OF PENICILLIN IN SYPHILIS IS JARISCH-HERXHEIMER REACTION... /PENICILLINS/|For more Drug Warnings (Complete) data for METHICILLIN (21 total), please visit the HSDB record page.

Meticillin (INN, BAN) or methicillin (USAN) is a narrow spectrum beta-lactam antibiotic of the penicillin class. It is no longer clinically used. Its role in therapy has been largely replaced by flucloxacillin and dicloxacillin, however the term methicillin-resistant Staphylococcus aureus (MRSA) continues to be used to describe Staphylococcus aureus strains resistant to all penicillins.

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

Not absorbed following oral administration.|METHICILLIN IS NOT EMPLOYED BY ORAL ROUTE BECAUSE IT IS POORLY ABSORBED & READILY DESTROYED BY ACIDIC GASTRIC CONTENTS. WHEN DRUG IS GIVEN IM, PEAK PLASMA CONCN ARE REACHED IN ABOUT 30 MIN-1 HR. AFTER CONVENTIONAL DOSE OF 1 G IN ADULTS, PLASMA CONCN IN EXCESS OF 10 UG/ML ARE DEMONSTRABLE...|...2-G DOSE PROVIDES PEAK CONCN OVER 20 UG/ML, & APPROX 8 UG/ML IS STILL PRESENT AFTER 4 HR. ABOUT 40% OF METHICILLIN IN PLASMA IS BOUND TO PROTEIN. METHICILLIN DOES NOT READILY PENETRATE INTO CSF; HOWEVER, SIGNIFICANT CONCN ARE PRESENT IN PATIENTS WITH MENINGITIS... DRUG...WELL DISTRIBUTED IN VARIOUS BODY FLUIDS & TISSUES.|METHICILLIN IS EXCRETED UNCHANGED IN URINE...ABOUT 2/3 OF IM DOSE IS ELIMINATED BY THIS ROUTE IN 4 HR. ... METHICILLIN PERSISTS FOR LONG PERIOD & @ HIGH CONCN IN PLASMA IN CASES OF RENAL FAILURE. ... PORTION OF INJECTED METHICILLIN THAT CANNOT BE DETECTED IN URINE IS EXCRETED INTO BILE & IS ELIMINATED BY WAY OF FECES.|DRUGS RECENTLY SHOWN TO ACTIVELY CROSS HUMAN PLACENTA INCL...SODIUM METHICILLIN... /METHICILLIN SODIUM/|For more Absorption, Distribution and Excretion (Complete) data for METHICILLIN (21 total), please visit the HSDB record page.

Hepatic (20-40%).|YIELDS 2,6-DIMETHOXYPHENYLPENICILLOIC ACID IN BACILLUS. /FROM TABLE/

25-60 minutes|The serum half-life of methicillin in adults with normal renal function is 0.4-0.5 hours.|Serum concn of methicillin may be higher and the serum half-life prolonged in patients with impaired renal function. The serum half-life of the drug reportedly averages 4-6 hr in anuric patients.|In one study in children 2-16 yr of age, the serum half-life of methicillin averaged 0.8 hr after IV administration and 1.6 hr after IM administration. Serum concn of methicillin are generally higher and the serum half-life is longer in neonates than in older children. The serum half-life of the drug is generally inversely proportional to birthweight, gestational age, and chronologic age. The serum half-life of methicillin reportedly ranges from 2-3.9 hr in low birthweight neonates 2 wk of age or younger and ranges from 0.9-3.3 hr in low birthweight neonates older than 2 wk of age or neonates weighing 2 kg or more who are 6.5 wk of age or younger.

Similar to other beta-lactam antimicrobials, meticillin blocks synthesis of the bacterial cell wall. Meticillin stops cross-linkage between the peptidoglycan polymer chains, which make up a large portion of gram-positive bacterial cell walls. It does this by binding to and competitively inhibiting the transpeptidase enzyme used by bacteria to cross-link the peptide (D-alanyl-alanine) used in peptidogylcan synthesis.|The penicillins and their metabolites are potent immunogens because of their ability to combine with proteins and act as haptens for acute antibody-mediated reactions. The most frequent (about 95 percent) or "major" determinant of penicillin allergy is the penicilloyl determinant produced by opening the beta-lactam ring of the penicillin. This allows linkage of the penicillin to protein at the amide group. "Minor" determinants (less frequent) are the other metabolites formed, including native penicillin and penicilloic acids. /Penicillins/|Bactericidal; inhibit bacterial cell wall synthesis. Action is dependent on the ability of penicillins to reach and bind penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. Penicillin-binding proteins (which include transpeptidases, carboxypeptidases, and endopeptidases) are enzymes that are involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Penicillins bind to, and inactivate, penicillin-binding proteins, resulting in the weakening of the bacterial cell wall and lysis. /Penicillins/

MASSIVE IV DOSES IN MAN...MAY RESULT IN ENCEPHALOPATHY WITH MUSCULAR HYPERIRRITABILITY, MYOCLONUS, VISUAL & AUDITORY HALLUCINATIONS...|HEMATURIA, ALBUMINURIA, PYURIA, RENAL-CELL & OTHER CASTS IN URINE, ELEVATION OF SERUM CREATININE, & EVEN OLIGURIA HAVE BEEN NOTED IN PT RECEIVING METHICILLIN...EOSINOPHILIA & SKIN RASH WERE PRESENT AT SAME TIME.|MOST SERIOUS HYPERSENSITIVITY REACTIONS...ARE ANGIOEDEMA, SERUM SICKNESS, ANAPHYLAXIS, & ARTHUS PHENOMENON. ... ACUTE ANAPHYLACTIC OR ANAPHYLACTOID REACTIONS...CONSTITUTE MOST IMPORTANT IMMEDIATE DANGER CONNECTED WITH THEIR USE. /PENICILLINS/|ANAPHYLAXIS...SUDDEN, SEVERE HYPOTENSION & RAPID DEATH. ...BRONCHOCONSTRICTION WITH SEVERE ASTHMA, OR ABDOMINAL PAIN, NAUSEA, & VOMITING, OR EXTREME WEAKNESS & FALL IN BLOOD PRESSURE, OR DIARRHEA & PURPURIC SKIN ERUPTIONS... /PENICILLINS/|For more Human Toxicity Excerpts (Complete) data for METHICILLIN (50 total), please visit the HSDB record page.

Dimethoxyphenyl Penicillin

...METHICILLIN SODIUM, USP (STAPHICILLIN)). ... PREPN FOR IM OR IV ADMIN IS METHICILLIN SODIUM FOR INJECTION, USP. DRUG IS MARKETED IN AMPULS CONTAINING 1, 4, OR 6 G OF SALT. SOLN SHOULD BE FRESH, & OTHER DRUGS SHOULD NOT BE INCL, SINCE MANY ARE INCOMPATIBLE WITH METHICILLIN IN SOLN. /METHICILLIN SODIUM/|6-(2,6-DIMETHOXYBENZAMIDO-PENICILLANIC ACID SODIUM SALT; SODIUM 2,6-DIMETHOXYPHENYLPENICILLIN; 2,6-DIMETHOXYPHENYLPENICILLIN SODIUM SALT; SODIUM 6-(2,6-DIMETHOXYBENZAMIDO)PENICILLINATE; 2,6-DIMETHOXYBENZOYLPENIN SODIUM SALT; DIMETHOXYPHENECILLIN SODIUM /METHICILLIN SODIUM/|SODIUM METHICILLIN; BRL 1241; X-1497; BELFACILLIN; CELPILLINA; CELBENIN; CINOPENIL; DIMOCILLIN; FLABELLINE; PENISTAPH; STAPHCILLIN /METHICILLIN SODIUM/|DIMOCILLIN-R-2; DIMOCILLIN SODIUM; CELPILLINE; ESTAFCILINA; PENYSOL; LUCOPENIN; STAFICYN; PENAUREUS; SYNTICILLIN; CINOPENIL; METICILLIN SODIUM /METHICILLIN SODIUM/

PREPN STARTING WITH 6-AMINOPENICILLANIC ACID: DOYLE ET AL, J CHEM SOC 1962, 1457; DOYLE ET AL, US PATENT 2,951,839 (1960)... /METHICILLIN SODIUM/|IT IS ABOUT 1/20 AS POTENT AS PENICILLIN G IN INFECTIONS CAUSED BY HEMOLYTIC STREPTOCOCCI, PNEUMOCOCCI, GONOCOCCI, OR PENICILLIN G-RESISTANT STAPHYLOCOCCI. IT IS 10 TIMES AS POTENT AGAINST PENICILLIN G-RESISTANT STAPHYLOCOCCI. /METHICILLIN SODIUM/

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients