Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C17H19N2O6S.Na |
| Molecular Weight | 402.397 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].COC1=CC=CC(OC)=C1C(=O)N[C@H]2[C@H]3SC(C)(C)[C@@H](N3C2=O)C([O-])=O
InChI
InChIKey=MGFZNWDWOKASQZ-UMLIZJHQSA-M
InChI=1S/C17H20N2O6S.Na/c1-17(2)12(16(22)23)19-14(21)11(15(19)26-17)18-13(20)10-8(24-3)6-5-7-9(10)25-4;/h5-7,11-12,15H,1-4H3,(H,18,20)(H,22,23);/q;+1/p-1/t11-,12+,15-;/m1./s1
| Molecular Formula | C17H19N2O6S |
| Molecular Weight | 379.408 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/14085254 | https://www.ncbi.nlm.nih.gov/pubmed/6835496 | https://www.drugs.com/cons/methicillin.html | https://www.drugbank.ca/drugs/DB01603
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/14085254 | https://www.ncbi.nlm.nih.gov/pubmed/6835496 | https://www.drugs.com/cons/methicillin.html | https://www.drugbank.ca/drugs/DB01603
Methicillin sodium anhydrous is a sodium salt of methicillin (methicillin). Methicillin is an antibiotic formerly used in the treatment of bacterial infections caused by organisms of the genus Staphylococcus. Methicillin is a semisynthetic derivative of penicillin. It was first produced in the late 1950s and was developed as a type of antibiotic called penicillinase-resistant penicillin—it contained a modification to the original penicillin structure that made it resistant to a bacterial enzyme called penicillinase (beta-lactamase). Compared to other penicillins that face antimicrobial resistance due to β-lactamase, it is less active, can be administered only parenterally, and has a higher frequency of interstitial nephritis, an otherwise-rare adverse effect of penicillins. However, the selection of meticillin depended on the outcome of susceptibility testing of the sampled infection, and since it is no longer produced, it is also not routinely tested for anymore.
CNS Activity
Approval Year
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
25 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/404369/ |
15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHICILLIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
27.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/404369/ |
15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHICILLIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.05 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/404369/ |
15 mg/kg single, intravenous dose: 15 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHICILLIN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
106 mg/kg 1 times / day multiple, intravenous Recommended Dose: 106 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 106 mg/kg, 1 times / day Sources: |
unhealthy, 4.00±4.89 Health Status: unhealthy Age Group: 4.00±4.89 Sex: M+F Sources: |
Disc. AE: Eosinophilia... AEs leading to discontinuation/dose reduction: Eosinophilia (10.7%) Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Eosinophilia | 10.7% Disc. AE |
106 mg/kg 1 times / day multiple, intravenous Recommended Dose: 106 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 106 mg/kg, 1 times / day Sources: |
unhealthy, 4.00±4.89 Health Status: unhealthy Age Group: 4.00±4.89 Sex: M+F Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Survey of infections due to Staphylococcus species: frequency of occurrence and antimicrobial susceptibility of isolates collected in the United States, Canada, Latin America, Europe, and the Western Pacific region for the SENTRY Antimicrobial Surveillance Program, 1997-1999. | 2001-05-15 |
|
| H(2)O(2) produced by viridans group streptococci may contribute to inhibition of methicillin-resistant Staphylococcus aureus colonization of oral cavities in newborns. | 2001-05-15 |
|
| Inhibition of methicillin-resistant Staphylococcus aureus colonization of oral cavities in newborns by viridans group streptococci. | 2001-05-15 |
|
| Duration of colonization by methicillin-resistant Staphylococcus aureus after hospital discharge and risk factors for prolonged carriage. | 2001-05-15 |
|
| Nasal carriage of Staphylococcus aureus. | 2001-05-03 |
|
| Mupirocin resistance among Malaysian isolates of methicillin-resistant Staphylococcus aureus. | 2001-05 |
|
| In vitro anti-methicillin-resistant Staphylococcus aureus activity of 2,4-diacetylphloroglucinol produced by Pseudomonas sp. AMSN isolated from a marine alga. | 2001-05 |
|
| In vitro activity of sitafloxacin against Clostridium difficile. | 2001-05 |
|
| Carriage of antibiotic-resistant bacteria by healthy children. | 2001-05 |
|
| Cadaveric allograft discards as a result of positive skin cultures. | 2001-05 |
|
| Infectious complications of cutaneous t-cell lymphoma. | 2001-04-28 |
|
| Improvement of water-soluble cephalosporin derivatives having antibacterial activity against methicillin-resistant Staphylococcus aureus. | 2001-04-18 |
|
| Molecular epidemiology of methicillin-resistant Staphylococcus aureus. | 2001-04-11 |
|
| The changing epidemiology of Staphylococcus aureus? | 2001-04-11 |
|
| Acute gastric dilatation accompanied by diabetes mellitus. | 2001-04 |
|
| [Glycopeptides]. | 2001-04 |
|
| [Clinical relevance of hetero-VRSA in surgical infections]. | 2001-04 |
|
| [Mupirocin resistant MRSA in Japan]. | 2001-04 |
|
| [Mechanisms of methicillin and vancomycin resistance in Staphylococcus aureus]. | 2001-04 |
|
| Staphylococcus aureus bacteriuria and surgical site infections by methicillin-resistant Staphylococcus aureus. | 2001-04 |
|
| Impact of Gram-positive resistance on outcome of nosocomial pneumonia. | 2001-04 |
|
| Emergence and spread of low-level mupirocin resistance in methicillin-resistant Staphylococcus aureus isolated from a community hospital in Japan. | 2001-04 |
|
| Source and route of methicillin-resistant Staphylococcus epidermidis transmitted to the surgical wound during cardio-thoracic surgery. Possibility of preventing wound contamination by use of special scrub suits. | 2001-04 |
|
| A modified population analysis profile (PAP) method to detect hetero-resistance to vancomycin in Staphylococcus aureus in a UK hospital. | 2001-04 |
|
| Antimicrobial-drug use and methicillin-resistant Staphylococcus aureus. | 2001-03-27 |
|
| Anti-MRSA cephems. Part 1: C-3 substituted thiopyridinium derivatives. | 2001-03-26 |
|
| Eradication of methicillin-resistant Staphylococcus aureus from a health center ward and associated nursing home. | 2001-03-26 |
|
| [Physicians wash their hands too infrequently]. | 2001-03-01 |
|
| Staphylococcal septicaemia in burns. | 2001-03 |
|
| [A study on the transmission of MRSA among the family members including clients of visiting nurse and related infection control]. | 2001-03 |
|
| A blinded comparison of three laboratory protocols for the identification of patients colonized with methicillin-resistant Staphylococcus aureus. | 2001-03 |
|
| Significant reduction of methicillin-resistant Staphylococcus aureus bacteremia in geriatric wards after introduction of infection control measures against nosocomial infections. | 2001-03 |
|
| Characteristics of a new epidemic MRSA in Germany ancestral to United Kingdom EMRSA 15. | 2001-03 |
|
| [Diagnostic test approved by Ministry of Health and Welfare (February 2001)]. | 2001-03 |
|
| Isolation and characterization of methicillin-resistant Staphylococcus aureus strains from nares of nurses and their gowns. | 2001-03 |
|
| Comparison of two sampling methods for the detection of gram-positive and gram-negative bacteria in the environment: moistened swabs versus Rodac plates. | 2001-03 |
|
| [Methicillin-resistant Staphylococcus colonization. Impact on morbidity, mortality, and glycopeptide use]. | 2001-02-24 |
|
| Guiding hands of our teachers. Hand-hygiene Liaison Group. | 2001-02-10 |
|
| [Combination effect of arbekacin and cefepime on mixed culture of MRSA and P. aeruginosa]. | 2001-02 |
|
| High frequency of colonization and absence of identifiable risk factors for methicillin-resistant Staphylococcus aureus (MRSA)in intensive care units in Brazil. | 2001-02 |
|
| [Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine]. | 2001-02 |
|
| [Epidemic of Staphylococcus aureus nosocomial infections resistant to methicillin in a maternity ward]. | 2001-02 |
|
| [Detection of gram-negative bacteria in patients and hospital environment at a room in geriatric wards under the infection control against MRSA]. | 2001-02 |
|
| A case of thrombotic thrombocytopenic purpura refractory to plasma exchange. | 2001-02 |
|
| [Enterocolitis caused by methicillin-resistant Staphylococcus aureus]. | 2001-01 |
|
| Aerobic bacterial and fungal infections in peripheral blood stem cell transplants. | 2001-01 |
|
| Perfusionist-transmitted bacterial mediastinitis in a heart transplant recipient. | 2001 |
|
| Molecular epidemiology of methicillin-resistant Staphylococcus aureus in Colombian hospitals: dominance of a single unique multidrug-resistant clone. | 2001 |
|
| Sequence analysis of dru regions from methicillin-resistant Staphylococcus aureus and coagulase-negative staphylococcal isolates. | 2001 |
|
| Letter: Interstitial nephritis after methicillin. | 1975-05-22 |
Sample Use Guides
Adults, teenagers, and children weighing more than 40 kilograms (kg) (88 pounds)—1 gram injected into a muscle every four to six hours; or 1 gram injected into a vein every six hours.
Children weighing up to 40 kg (88 pounds)—Dose is based on body weight and must be determined by your doctor. The usual dose is 25 milligrams (mg) per kg (11.4 mg per pound) of body weight, injected into a vein or muscle every six hours.
Route of Administration:
Intramuscular
Determination of Meticillin susceptibility was done by plating diluted overnight cultures of strain COL on petri dishes containing tryptic soy agar (TSA; Difco) and serial (twofold) dilutions of the Meticillin. Colonies were counted after 48 h of incubation at 37 and 42°C. The high-level methicillin resistance at 37°C (MIC = 800 mkg/ml) was reduced to 12 mkg/ml at 42°C
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:27:22 GMT 2025
by
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on
Mon Mar 31 19:27:22 GMT 2025
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| Record UNII |
NBQ410S76Y
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| Record Status |
Validated (UNII)
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| Record Version |
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ACTIVE MOIETY |