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+].[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C3=C(OC)C=CC=C3OC)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
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: Page: p.119 |
unhealthy, 4.00±4.89 n = 28 Health Status: unhealthy Condition: Infections Age Group: 4.00±4.89 Sex: M+F Population Size: 28 Sources: Page: p.119 |
Disc. AE: Eosinophilia... AEs leading to discontinuation/dose reduction: Eosinophilia (10.7%) Sources: Page: p.119 |
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: Page: p.119 |
unhealthy, 4.00±4.89 n = 28 Health Status: unhealthy Condition: Infections Age Group: 4.00±4.89 Sex: M+F Population Size: 28 Sources: Page: p.119 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Letter: Interstitial nephritis after methicillin. | 1975 May 22 |
|
| Perfusionist-transmitted bacterial mediastinitis in a heart transplant recipient. | 2001 |
|
| Acute gastric dilatation accompanied by diabetes mellitus. | 2001 Apr |
|
| [Glycopeptides]. | 2001 Apr |
|
| [Clinical relevance of hetero-VRSA in surgical infections]. | 2001 Apr |
|
| [Mupirocin resistant MRSA in Japan]. | 2001 Apr |
|
| [Mechanisms of methicillin and vancomycin resistance in Staphylococcus aureus]. | 2001 Apr |
|
| Staphylococcus aureus bacteriuria and surgical site infections by methicillin-resistant Staphylococcus aureus. | 2001 Apr |
|
| Impact of Gram-positive resistance on outcome of nosocomial pneumonia. | 2001 Apr |
|
| Emergence and spread of low-level mupirocin resistance in methicillin-resistant Staphylococcus aureus isolated from a community hospital in Japan. | 2001 Apr |
|
| 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 Apr |
|
| A modified population analysis profile (PAP) method to detect hetero-resistance to vancomycin in Staphylococcus aureus in a UK hospital. | 2001 Apr |
|
| [Combination effect of arbekacin and cefepime on mixed culture of MRSA and P. aeruginosa]. | 2001 Feb |
|
| High frequency of colonization and absence of identifiable risk factors for methicillin-resistant Staphylococcus aureus (MRSA)in intensive care units in Brazil. | 2001 Feb |
|
| [Antibiotic resistance of Staphylococcus aureus in urban experience: 6 month study in Aquitaine]. | 2001 Feb |
|
| [Epidemic of Staphylococcus aureus nosocomial infections resistant to methicillin in a maternity ward]. | 2001 Feb |
|
| [Detection of gram-negative bacteria in patients and hospital environment at a room in geriatric wards under the infection control against MRSA]. | 2001 Feb |
|
| A case of thrombotic thrombocytopenic purpura refractory to plasma exchange. | 2001 Feb |
|
| Guiding hands of our teachers. Hand-hygiene Liaison Group. | 2001 Feb 10 |
|
| [Methicillin-resistant Staphylococcus colonization. Impact on morbidity, mortality, and glycopeptide use]. | 2001 Feb 24 |
|
| [Enterocolitis caused by methicillin-resistant Staphylococcus aureus]. | 2001 Jan |
|
| Aerobic bacterial and fungal infections in peripheral blood stem cell transplants. | 2001 Jan |
|
| Antimicrobial-drug use and methicillin-resistant Staphylococcus aureus. | 2001 Jan-Feb |
|
| Staphylococcal septicaemia in burns. | 2001 Mar |
|
| [A study on the transmission of MRSA among the family members including clients of visiting nurse and related infection control]. | 2001 Mar |
|
| A blinded comparison of three laboratory protocols for the identification of patients colonized with methicillin-resistant Staphylococcus aureus. | 2001 Mar |
|
| Significant reduction of methicillin-resistant Staphylococcus aureus bacteremia in geriatric wards after introduction of infection control measures against nosocomial infections. | 2001 Mar |
|
| Characteristics of a new epidemic MRSA in Germany ancestral to United Kingdom EMRSA 15. | 2001 Mar |
|
| [Diagnostic test approved by Ministry of Health and Welfare (February 2001)]. | 2001 Mar |
|
| Isolation and characterization of methicillin-resistant Staphylococcus aureus strains from nares of nurses and their gowns. | 2001 Mar |
|
| Comparison of two sampling methods for the detection of gram-positive and gram-negative bacteria in the environment: moistened swabs versus Rodac plates. | 2001 Mar |
|
| [Physicians wash their hands too infrequently]. | 2001 Mar 1 |
|
| Anti-MRSA cephems. Part 1: C-3 substituted thiopyridinium derivatives. | 2001 Mar 26 |
|
| Eradication of methicillin-resistant Staphylococcus aureus from a health center ward and associated nursing home. | 2001 Mar 26 |
|
| Infectious complications of cutaneous t-cell lymphoma. | 2001 Mar-Apr |
|
| Molecular epidemiology of methicillin-resistant Staphylococcus aureus. | 2001 Mar-Apr |
|
| The changing epidemiology of Staphylococcus aureus? | 2001 Mar-Apr |
|
| Mupirocin resistance among Malaysian isolates of methicillin-resistant Staphylococcus aureus. | 2001 May |
|
| In vitro anti-methicillin-resistant Staphylococcus aureus activity of 2,4-diacetylphloroglucinol produced by Pseudomonas sp. AMSN isolated from a marine alga. | 2001 May |
|
| In vitro activity of sitafloxacin against Clostridium difficile. | 2001 May |
|
| Carriage of antibiotic-resistant bacteria by healthy children. | 2001 May |
|
| Cadaveric allograft discards as a result of positive skin cultures. | 2001 May |
|
| 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 May 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 May 15 |
|
| Inhibition of methicillin-resistant Staphylococcus aureus colonization of oral cavities in newborns by viridans group streptococci. | 2001 May 15 |
|
| Duration of colonization by methicillin-resistant Staphylococcus aureus after hospital discharge and risk factors for prolonged carriage. | 2001 May 15 |
|
| Nasal carriage of Staphylococcus aureus. | 2001 May 3 |
|
| Improvement of water-soluble cephalosporin derivatives having antibacterial activity against methicillin-resistant Staphylococcus aureus. | 2001 May-Jun |
|
| Molecular epidemiology of methicillin-resistant Staphylococcus aureus in Colombian hospitals: dominance of a single unique multidrug-resistant clone. | 2001 Spring |
|
| Sequence analysis of dru regions from methicillin-resistant Staphylococcus aureus and coagulase-negative staphylococcal isolates. | 2001 Spring |
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
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52065
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CHEMBL575
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SUB03264MIG
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NBQ410S76Y
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132-92-3
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m7311
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100000089081
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205-083-9
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23667627
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ACTIVE MOIETY
SUBSTANCE RECORD
