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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H20N2O6S
Molecular Weight 380.415
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHICILLIN

SMILES

[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C3=C(OC)C=CC=C3OC)C(O)=O

InChI

InChIKey=RJQXTJLFIWVMTO-TYNCELHUSA-N
InChI=1S/C17H20N2O6S/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)/t11-,12+,15-/m1/s1

HIDE SMILES / InChI
Molecular Formula C17H20N2O6S
Molecular Weight 380.415
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Originator

Doyle, F.P.
3
Sources: Manufacturing Chemist (1930-1963) Volume32 Pages533-5,548
Curator's Comment: https://www.acs.org/content/acs/en/molecule-of-the-week/archive/m/molecule-of-the-week-methicillin.html

Approval Year

1960
107
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8429
STAPHCILLIN

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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:
https://pubmed.ncbi.nlm.nih.gov/7172968
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:
https://pubmed.ncbi.nlm.nih.gov/7172968
Page: p.119
Disc. AE: Eosinophilia...
AEs leading to
discontinuation/dose reduction:
Eosinophilia (10.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/7172968
Page: p.119
AEs

AEs

AESignificanceDosePopulation
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:
https://pubmed.ncbi.nlm.nih.gov/7172968
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:
https://pubmed.ncbi.nlm.nih.gov/7172968
Page: p.119
Sourcing

Sourcing

Vendor/AggregatorIDURL
ChEBI
CHEBI:6827
https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:6827
ZINC
ZINC000003831070
http://zinc15.docking.org/substances/ZINC000003831070
eMolecules
3716059
https://www.emolecules.com/cgi-bin/more?vid=3716059
PubMed

PubMed

TitleDatePubMed
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
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
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
Comparison of length of hospital stay for patients with known or suspected methicillin-resistant Staphylococcus species infections treated with linezolid or vancomycin: a randomized, multicenter trial.
2001 Mar
Methicillin-resistant Staphylococcus aureus keratitis after laser in situ keratomileusis.
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
Patents

Patents

20010014449
3
GB920177
3
JP2007300817A
3
JP2008074865A
3
JP2010505817A
3
JP4792032B2
112
JPH01199979A
3
JPH05125078A
3
JPH06165681A
3
JPH0753360A
3
JPH0753372A
3
JPH10265488A
3
JPH11221096A
3

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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 Sat Dec 16 16:33:13 UTC 2023
Edited
by admin
on Sat Dec 16 16:33:13 UTC 2023
Record UNII
Q91FH1328A
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHICILLIN
VANDF  
Common Name English
meticillin [INN]
Common Name English
METICILLIN [HSDB]
Common Name English
2,6-DIMETHOXYPHENYL PENICILLIN
Common Name English
CELBENIN
Brand Name English
(2S,5R,6R)-6-(2,6-DIMETHOXYBENZAMIDO)-3,3-DIMETHYL-7-OXO-4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID
Systematic Name English
METICILLIN
HSDB   INN   WHO-DD  
INN  
Official Name English
METHICILLIN [VANDF]
Common Name English
Meticillin [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1500
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
WHO-VATC QJ01CF03
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
WHO-VATC QJ51CF03
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
WHO-ATC J01CF03
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C61842
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
CAS
61-32-5
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
EVMPD
SUB08885MIG
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
HSDB
3121
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
ChEMBL
CHEMBL575
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
LACTMED
Methicillin
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
INN
1103
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
RXCUI
2181306
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
CHEBI
6827
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
WIKIPEDIA
METICILLIN
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-505-8
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
MESH
D008712
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
PUBCHEM
6087
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID6023284
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
FDA UNII
Q91FH1328A
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
DRUG CENTRAL
1744
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
DRUG BANK
DB01603
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
SMS_ID
100000088209
Created by admin on Sat Dec 16 16:33:14 UTC 2023 , Edited by admin on Sat Dec 16 16:33:14 UTC 2023
PRIMARY
Related Record Type Details
Structure of METHICILLIN SODIUM
SALT/SOLVATE -> PARENT
Structure of METHICILLIN SODIUM ANHYDROUS
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of METHICILLIN
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