Methicillin Sodium

Methicillin Sodium

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Methicillin Sodium
Category Antibiotics
Catalog number BBF-03820
CAS 132-92-3
Molecular Weight 402.40
Molecular Formula C17H19N2NaO6S
Purity 96%

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Description

The sodium salt of Meticillin, a β-lactam antibiotic, could be obtained through semi-synthetic and used as an antibacterial agent especially against Gram-positive bacteria.

Specification

Related CAS 61-32-5 (free acid) 7246-14-2 (monohydrate)
Synonyms Azapen; BRL 1241; Belfacillin; Celbenin; Sodium 6-(2',6'-dimethoxybenzamido)penicillanate; Penaureus; Sodium Methicillin; Staficyn; Staphcillin; Synticillin; 2-carboxylic acid sodium salt; Belfacillin; Penaureus
Shelf Life As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly
Storage Store at -20°C
IUPAC Name sodium;(2S,5R,6R)-6-[(2,6-dimethoxybenzoyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
Canonical SMILES CC1(C(N2C(S1)C(C2=O)NC(=O)C3=C(C=CC=C3OC)OC)C(=O)[O-])C.[Na+]
InChI 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
InChI Key MGFZNWDWOKASQZ-UMLIZJHQSA-M
Source Semi-synthetic

Properties

Appearance White to Off-white Solid
Antibiotic Activity Spectrum Gram-positive bacteria
Boiling Point 640°C at 760 mmHg
Melting Point >179°C (dec.)
Solubility Soluble in DMSO (Slightly), Methanol (Slightly), Water (Slightly)

Reference Reading

1.The Distribution of 18 Enterotoxin and Enterotoxin-Like Genes in Staphylococcus aureus Strains from Different Sources in East China.
Cheng J1, Wang Y2, Cao Y1, Yan W1, Niu X1, Zhou L2, Chen J1, Sun Y1, Li C1, Zhang X1, Wu Y1. Foodborne Pathog Dis. 2016 Apr;13(4):171-6. doi: 10.1089/fpd.2015.1963.
The distribution of 18 staphylococcal enterotoxin (SE) or SE-like (SEl) genes in Staphylococcus aureus strains from different sources in east China was investigated. Among all 496 S. aureus strains, 291 strains carried one or more SE genes. The more frequently occurred genes were sea, seb, seg, selk, sell, selm, selo, and seq; the less frequent occurred genes were sec, selj, and ser. The classic SE genes and the enterotoxin gene cluster (egc) (seg, sei, selm, seln, selo, and/or selu) accounted for 25.67% and 61.68% of all detected genes, respectively. There were three gene clusters (egc, sea-sek-seq, and sed-sej-ser), of which the egc cluster was the important one that could generate novel complexes, and the sea-sek-seq cluster was a close relative to the hospital-acquired methicillin-resistant S. aureus. The SE gene distributions were different among strains of different sources and formed diverse toxin gene profiles. The human- and foodborne-origin strains harbored classic and novel SE and SEl genes, whereas animal-origin strains harbored egc and other novel SE and SEl genes mainly.
2.Development of ebsulfur analogues as potent antibacterials against methicillin-resistant Staphylococcus aureus.
Ngo HX1, Shrestha SK1, Green KD1, Garneau-Tsodikova S2. Bioorg Med Chem. 2016 Mar 31. pii: S0968-0896(16)30220-6. doi: 10.1016/j.bmc.2016.03.060. [Epub ahead of print]
Antibiotic resistance is a worldwide problem that needs to be addressed. Staphylococcus aureus is one of the dangerous "ESKAPE" pathogens that rapidly evolve and evade many current FDA-approved antibiotics. Thus, there is an urgent need for new anti-MRSA compounds. Ebselen (also known as 2-phenyl-1,2-benzisoselenazol-3(2H)-one) has shown promising activity in clinical trials for cerebral ischemia, bipolar disorder, and noise-induced hearing loss. Recently, there has been a renewed interest in exploring the antibacterial properties of ebselen. In this study, we synthesized an ebselen-inspired library of 33 compounds where the selenium atom has been replaced by sulfur (ebsulfur derivatives) and evaluated them against a panel of drug-sensitive and drug-resistant S. aureus and non-S. aureus strains. Within our library, we identified three outstanding analogues with potent activity against all S. aureus strains tested (MIC values mostly ⩽2μg/mL), and numerous additional ones with overall very good to good antibacterial activity (1-7.
3.Successful Use of High-dose Daptomycin in a Child With Staphylococcus aureus Endocarditis.
Prabhudesai S1, Kanjani A, Nambi PS, Gnanasambandam S, Ramachandran B. Pediatr Infect Dis J. 2016 May;35(5):517-8. doi: 10.1097/INF.0000000000000958.
We report the successful use of daptomycin in a child with methicillin-resistant Staphylococcus aureus endocarditis with persistent bacteremia and clinical deterioration, despite treatment with vancomycin and rifampicin. She had acute kidney injury, requiring daptomycin dosage adjustment.

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