methicillin
Synonym(s):2,6-Dimethoxyphenyl-penicillin;Methicillin;Methicillin Selective Supplement;Staphcillin
- CAS NO.:61-32-5
- Empirical Formula: C17H20N2O6S
- Molecular Weight: 380.42
- MDL number: MFCD00242880
- EINECS: 200-505-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2023-05-04 15:10:44
What is methicillin ?
Absorption
Not absorbed following oral administration.
Description
Methicillin is a member of the penicillin family of antibiotics. Its synthesis from 6-aminopnicillanic acid was patented by F. P. Doyle and co-inventors in 1960. Methicillin is a narrow-spectrum drug that has been replaced by more stable and efficacious penicillin derivatives. Now it is best known as the M in MRSA (methicillin-resistant?Staphylococcus aureus), a term for?S. Aureus?strains that resist all penicillins. In 2005, the International Pharmacopoeia guidelines changed the name of the drug to meticillin, but the original name is still widely used in the United States.
The Uses of methicillin
Antibacterial.
Indications
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.
Background
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
ChEBI: A penicillin that is 6-aminopenicillanic acid in which one of the amino hydrogens is replaced by a 2,6-dimethoxybenzoyl group.
brand name
Staphcillin (Apothecon).
Antimicrobial activity
2,6-Dimethoxyphenylpenicillin; methicillin (international
non-proprietary name). The first β-lactamase-resistant semisynthetic
penicillin. It was initially used widely but has been
superseded by other group 3 members and is no longer commercially
available.
It is less active than benzylpenicillin or other group 3
penicillins. It is very stable to staphylococcal
β-lactamase and is active against β-lactamaseproducing
strains of Staph. aureus that do not produce a
functional PBP 2a. Resistance is common among
staphylococci, with the incidence geographically diverse.
Most methicillin-resistant staphylococcal isolates display
multiresistance.
It is not acid resistant, and must therefore be administered
parenterally. About 10% is metabolized, with 60–80% of the
dose excreted in the urine. Toxicity is similar to that of other
group 3 penicillins. Nephritis appears to be more common
than with other penicillins.
Pharmacokinetics
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.
Pharmacology
Like other semisynthetic penicillins, methicillin exhibits an antibacterial effect similar to that of benzylpenicillin. The main difference between methicillin and benzylpenicillin is that it is not inactivated by the enzyme penicillinase, and therefore it is effective with respect to agents producing this enzyme (staphylococci). It is used for infections caused by benzylpenicillinresistant staphylococci (septicemia, pneumonia, empyemia, osteomyelitis, abscesses, infected wounds, and others). Synonyms of this drug are cinopenil, celbenin, staphcillin, and others.
Synthesis
Methicillin, [2S-(2|á,5|á,6|?)]-3,3-dimethyl-7-oxo-6-(2,6-dimethoxybenzamido)- 4-thia-1-azabicyclo[3.2.0]-heptan-2-carboxylic acid (32.1.1.3), is synthesized by acylating 6- APA with 2,6-dimethoxybenzoic acid chloride in the presence of triethylamine.
Metabolism
Hepatic (20-40%).
Properties of methicillin
Boiling point: | 640.0±55.0 °C(Predicted) |
Density | 1.44±0.1 g/cm3(Predicted) |
pka | pKa 2.77± 0.04(H2O,t = 25,c=0.0097) (Uncertain) |
Safety information for methicillin
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H302:Acute toxicity,oral |
Computed Descriptors for methicillin
New Products
Tert-butyl bis(2-chloroethyl)carbamate 4-Methylphenylacetic acid N-Boc-D-alaninol N-BOC-D/L-ALANINOL 3-Morpholino-1-(4-nitrophenyl)-5,6-dihydropyridin- 2(1H)-one Furan-2,5-Dicarboxylic Acid Tropic acid 1,1’-CARBONYLDIIMIDAZOLE DIETHYL AMINOMALONATE HYDROCHLORIDE R-2-BENZYLOXY PROPIONIC ACID 1,1’-CARBONYLDI (1,2-4 TRIAZOLE) N-METHYL INDAZOLE-3-CARBOXYLIC ACID (2-Hydroxyphenyl)acetonitrile 4-Bromopyrazole 5-BROMO-2CYANO PYRIDINE 5,6-Dimethoxyindanone 5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine 2-(Cyanocyclohexyl)acetic acid 4-methoxy-3,5-dinitropyridine 2-aminopropyl benzoate hydrochloride 1-(4-(aminomethyl)benzyl)urea hydrochloride diethyl 2-(2-((tertbutoxycarbonyl)amino) ethyl)malonate tert-butyl 4- (ureidomethyl)benzylcarbamate Ethyl-2-chloro((4-methoxyphenyl)hydrazono)acetateRelated products of tetrahydrofuran
You may like
-
MRSA Selective Supplement CAS 61-32-5View Details
61-32-5 -
1975-50-4 98%View Details
1975-50-4 -
2-HYDROXY BENZYL ALCOHOL 98%View Details
90-01-7 -
2-Chloro-1,3-Bis(Dimethylamino)Trimethinium Hexafluorophosphate 221615-75-4 98%View Details
221615-75-4 -
61397-56-6 CIS BROMO BENZOATE 98%View Details
61397-56-6 -
14714-50-2 (2-Hydroxyphenyl)acetonitrile 98+View Details
14714-50-2 -
118753-70-1 98+View Details
118753-70-1 -
733039-20-8 5-broMo-2-chloro-N-cyclopentylpyriMidin-4-aMine 98+View Details
733039-20-8