58-71-9 Usage
Uses
Used in Pharmaceutical Industry:
Cephalothin is used as an antibacterial agent for the treatment of various bacterial infections. It is particularly effective against a range of bacteria, including S. pyogenes, D. pneumoniae, and S. aureus.
Used in Research and Development:
Cephalothin is used as a bacterial transpeptidase inhibitor in the study of the mechanism of liposome encapsulated antibiotics, strategies for co-opting β-lactamases of Gram-negative bacteria for treatment, and for immunology studies in relation to antibiotics.
Used in Bacterial Cell Wall Mucopeptide Synthesis Studies:
Cephalothin is used to study the effect of expression, binding, and inhibition of penicillin-binding proteins, especially PBP6, on bacterial cell wall mucopeptide synthesis.
Chemical Properties:
Cephalothin is a crystalline compound.
Therapeutic Function
Antibacterial
Clinical Use
Cephalothin sodium (Keflin) occurs as a white to off-white,crystalline powder that is practically odorless. It is freelysoluble in water and insoluble in most organic solvents.Although it has been described as a broad-spectrum antibacterialcompound, it is not in the same class as the tetracyclines.Its spectrum of activity is broader than that ofpenicillin G and more similar to that of ampicillin. Unlikeampicillin, cephalothin is resistant to penicillinase producedby S. aureus and provides an alternative to the use ofpenicillinase-resistant penicillins for the treatment of infectionscaused by such strains.Cephalothin is absorbed poorly from the GI tract andmust be administered parenterally for systemic infections. It is relatively nontoxic and acid stable. It is excreted rapidlythrough the kidneys; about 60% is lost within 6 hours of administration.Pain at the site of intramuscular injection andthrombophlebitis following intravenous injection have beenreported. Hypersensitivity reactions have been observed,and there is some evidence of cross-sensitivity in patientsnoted previously to be penicillin sensitive.
Check Digit Verification of cas no
The CAS Registry Mumber 58-71-9 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 8 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 58-71:
(4*5)+(3*8)+(2*7)+(1*1)=59
59 % 10 = 9
So 58-71-9 is a valid CAS Registry Number.
InChI:InChI=1/C16H16N2O6S2.Na/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10;/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23);/q;+1/t12-,15-;/m1./s1
58-71-9Relevant articles and documents
Hydrolysis of 7-Substituted Cephalosporins catalysed by β-Lactamase I and II from Bacillus cereus and by Hydroxide Ion
Buckwell, Stephen C.,Page, Michael I.,Waley, Stephen G.,Longridge, Jethro L.
, p. 1815 - 1822 (2007/10/02)
Kinetic parameters are reported for the Bacillus cereus β-lactamase I- and β-lactamase II-catalysed hydrolysis of a series of thirty-seven cephalosporins substituted in the 7-position.These are compared with the second-order rate constants for the hydroxide ion-catalysed hydrolysis of these derivatives.There is no significant dependence of the rate of the base-catalysed hydrolysis upon the nature of the side-chain substituent.For β-lactamase I, kcat/Km varies over 2x105 but for β-lactamase II the variation with substituents is only 10.For alkyl substituents, kcat/Km increases with chain length and passes through a maximum, for β-lactamase I this is with the undecyl derivative and for β-lactamase II the octylcephalosporin.For β-lactamase I, but not for β-lactamase II, the t-butylcephalosporin is a very poor substrate.There is no evidence for a significant cavity in either enzyme to host aromatic residues.An ionised carboxylate residue on the side-chain significantly reduces reactivity with β-lactamase I but not β-lactamase II.It is suggested that a carboxy group on β-lactamase I acts as a general catalyst facilitating β-lactam C-N bond fission.
Synthesis of 3-functionalised cephalosporins by photoinitiated bromination. Transformations of 2,2,2-trichloroethyl 1S, 6R, 7R)-3-bromomethyl-7-formamidoceph-3-EM-4-carboxylate, 1-oxide
Cowley,Humber,Laundon,et al.
, p. 461 - 467 (2007/10/02)
The 3-bromomethyl derivative 2c, obtained by photoinitiated bromination of the corresponding 3-Me compound 1c, has been converted into the antibiotics cephalothin 18 and cephaloridine 20. Reaction of 2c with lithium dimethyl- and diphenyl-cuprate led to the intermediates 22 and 24 respectively. Further transformation of 24 provided the 3-benzyl derivative 27, an isostere of cephaloridine.
Process for the activation of carboxylic acids
-
, (2008/06/13)
A process for the activation of carboxylic acids which is useful for the subsequent conversion of said carboxylic acids into their corresponding amides or esters, based on reacting a 2-oxazolidinone with phosphorus pentachloride and subsequent addition of a salt of the carboxylic acid to be activated.
