Cephalothin - CAS 153-61-7

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Category
APIs
Product Name
Cephalothin
Catalog Number
153-61-7
CAS Number
153-61-7
Molecular Weight
396.44
Molecular Formula
C16H16N2O6S2
COA
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MSDS
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Structure
CAS 153-61-7 Cephalothin
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  • CAS 58-71-9 Cephalothin sodium

    Cephalothin sodium
    (CAS: 58-71-9)

    A first generation cephalosporin antibiotic; freely soluble in aqueous solution (50 mg/ml)

Reference Reading
1. Square-wave Voltammetric Behaviour and Automated Determination of Cephalothin by a Novel Sample Handling Approach
Dorit Peled, Chaim Yarnitzky, W. Franklin Smyth*. ANALYST, JULY 1987, VOL. 112
These antibiotics, commonly used for the treatment of infections caused by Gram-positive cocci and Gram-negative bacilli, were each found to exhibit one reduction wave and were used for qualitative and quantitative analysis. Hall et a1.2 have carried out a more exhaustive electrochemical study on cephalosporin C derivatives which included cephalothin. They found a d.c. current at 10-4 M concentrations which was constant in height over the pH range 0-4 and decreased to zero by pH 7-8. They reported that there was no observable reduction wave for the cephalothin anion in buffered solutions up to pH 8 but that a wave at -1.80 V existed in 0.1 M Et4NC1O4 supporting electrolyte
2. Boronic acids in medicinal chemistry: anticancer, antibacterial and antiviral applications
Paul C. Trippier*, Christopher McGuigan. Med. Chem. Commun., 2010, 1, 183–198
The group of Shoichet has published extensively in the field of boronic acid based b-lactamase inhibitors and based upon this previous experience, set out to identify a new, more potent inhibitor. Cephalothin, a widely used Cephalosporin antibiotic, possess a Ki of 320 nM versus AmpC type b-lacta-mases. Shoichet et al. illustrated that the closer the boronic acid resembles the natural substrate, the better the potency. The more the structure mimics the b-lactam of cephalothin, the greater the inhibition, with boronic acid 32 (Ki = 0.32 μM) the weakest. Addition of a stereogenic phenyl group 33, mimicking the dihydrothiazine of cephalothin, provides a 10-fold increase in potency (Ki = 0.035 μM). The insertion of a meta-carboxyphenyl moiety further improved the affinity for AmpC type b-lactamase to provide the most potent inhibitor yet described, boronic acid 34 (Ki = 0.001 μM).
3. β-Lactam-host defence peptide conjugates as antibiotic prodrug candidates targeting resistant bacteria
Stephane Desgranges, Carol C. Ruddle, Marc Devocelle*. RSC Adv., 2012, 2, 2480–2492
The cephalosporin and peptide candidates selected for the synthesis of a prototypical conjugate were cephalothin and Bac8c, respectively. Cephalothin 1, containing a 39-acetate substituent and a thienyl side-chain, is a first generation cephalosporin with a broad spectrum of activity. Bac8c is a peptide amide of sequence RIWVIWRR-NH2, obtained by optimisation of the bovine dodecapeptide bactenecin. The asset of this short 8-mer candidate is an activity against both Gram-negative and Gram-positive bacteria in the low micromolar range. Also, its number of residues, which remains close to the minimal length of a continuous epitope for an antigen, should prevent its immunogenicity and limit its production cost.
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