153-61-7 Usage
Description
Cephalothin is a semisynthetic, beta-lactam, first-generation cephalosporin antibiotic with bactericidal activity. Cephalothin binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. PBPs participate in the terminal stages of assembling the bacterial cell wall, and in reshaping the cell wall during cell division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.
Chemical Properties
White Solid
Originator
Keflin,Lilly,US,1964
Uses
A first generation cephalosporin antibiotic with a wide range antibacterial activity. It is effective against gram-positive and gram-negative bacteria, and has been tested in respiratory disease and neuromuscular junction studies.Cephalothin is most effective against Gram-positive cocci and is also effective against several Gram-negative organisms. First generation cephalosporins are used primarily to treat skin and soft tissue infections caused by Staphylococcus and Streptococcus species. Cephalothin is ineffective against enterococci and evidence of in vitro sensitivity should be discounted.
Manufacturing Process
7-(2'-Thienylacetamido)cephalosporanic acid sodium salt may be produced
from 2-thienylacetyl chloride, obtainable by treatment of 2-thienylacetic acid
[Ernst, Berichte, 19 (1886) 3281] with thionyl chloride in a conventional
manner. The 2-thienylacetyl chloride is then reacted with 7-
aminocephalosporanic acid and then converted to the sodium salt using
sodium hydroxide.
Brand name
Keflin
(Lilly); Seffin (GlaxoSmithKline).
Therapeutic Function
Antibacterial
Acquired resistance
Cephalothin is relatively susceptible to β-lactamases. Enterobacter, Klebsiella and Citrobacter species have acquired resistance by chromosomal constitutively produced βlactamases that are not inhibited by clavulanic acid. Bacteroides species develop resistance to β-lactams both by plasmids and chromasomally; however Bacteroides resistance remains susceptible to clavulanic acid. P aeruginosa is resistant to first and second generation cephalosporins because of problems with cell permeability/uptake, porin channels and drug efflux. Stenotrophomonas maltophila and Aeromonas species can be resistant through effects on porin channels and drug efflux, while S aureus can also be resistant due to drug efflux.
Mechanism of action
Inhibits bacterial cell wall synthesis by binding to one or more of the penicillin-binding proteins (PBPs) which in turn inhibits the final transpeptidation step of peptidoglycan synthesis in bacterial cell walls, thus inhibiting cell wall biosynthesis. Bacteria eventually lyse due to ongoing activity of cell wall autolytic enzymes (autolysins and murein hydrolases) while cell wall assembly is arrested.
Clinical Use
Cephalothin is a relatively short acting first generation cephalosporin that is administered injectably. Although cephalothin is not approved for use in any animal species in the United States, the drug is used clinically in veterinary medicine. Cephalothin can cause nephrotoxicity.
Side effects
Manifestations may include urticarial or maculopapular rash, bronchospasm, and drug fever. Anaphylaxis, including severe hypotension and cardiac arrest, is reported. Rare cases of renal insufficiency associated with cephalothin may be hypersensitivity-mediated since fever, eosinophilia, and rash are often also present.https://www.drugs.com
Check Digit Verification of cas no
The CAS Registry Mumber 153-61-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 3 respectively; the second part has 2 digits, 6 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 153-61:
(5*1)+(4*5)+(3*3)+(2*6)+(1*1)=47
47 % 10 = 7
So 153-61-7 is a valid CAS Registry Number.
InChI:InChI=1/C16H16N2O6S2/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)/t12-,15-/m0/s1
153-61-7Relevant articles and documents
Synthesis method of cefoxitin sodium key intermediate
-
Paragraph 0010; 0036-0086, (2021/11/03)
The invention provides a synthesis method of a cefoxitin sodium key intermediate, and belongs to the technical field of heterocyclic compounds. The method comprises the following steps: by taking a cephalotin solution as a treatment object, adding organic alkali, adding a halogenating agent, carrying out halogenating methoxyl reaction, adding acetic acid and saline water, regulating acid and layering, drying an organic layer, concentrating, adding cyclohexylamine to form salt, filtering and drying to obtain a key intermediate 7-alpha methoxyl cephalothin cyclohexylamine salt According to the method, one-step synthesis of the 7-alpha methoxyl cephalothin cyclohexylamine salt is realized, subsequent main impurities of cefoxitin sodium are effectively reduced from the source, the quality and purity of the product are improved, the competitiveness of the cefoxitin product is improved, the product is stable and reliable, the yield is high, the synthesis process is greatly simplified, and the method has an industrial prospect.
Progress towards a stable cephalosporin-halogenated phenazine conjugate for antibacterial prodrug applications
Xiao, Tao,Liu, Ke,Huigens, Robert W.
, (2020/10/27)
Resistant bacteria successfully evade the action of conventional antibiotic therapies during infection, often leading to significant illness and death. Our lab has discovered halogenated phenazine (HP) analogues which demonstrate potent antibacterial activities through a unique iron-starving mechanism. Herein, we describe synthetic efforts towards a stable cephalosporin-HP conjugate prodrug with the aim of translating HPs into useful clinical agents. Cephalosporin-antibiotic conjugates offer multiple advantages for antibacterial design, including the release of active agents through the targeting of intracellular cephalosporinase following selective ring-opening of the beta-lactam warhead. During these studies, carbonate-linked cephalosporin-HP conjugate 16 was synthesized; however, we were unable to successfully remove the ester group required for cephalosporinase processing. Cephalosporin-HP 16 was then utilized as a probe to investigate the stability of the carbonate linker in antibacterial assays and, as predicted, this compound proved to be inactive against Staphylococcus aureus (MIC > 100 μM). The lack of 16’s antibacterial activity can be attributed to the carbonate linker remaining intact throughout the MIC assay, thus not liberating the active HP moiety. These efforts have led to a more stable cephalosporin-HP conjugate joined through a carbonate linker compared to a highly unstable ether linked analogue we previously reported.
Preparation method of cephalotin acid
-
Paragraph 0012; 0013; 0014; 0015; 0016; 0017; 0018; 0019, (2018/03/25)
The invention relates to a preparation method of cephalotin acid and belongs to the technical field of pharmaceutical synthesis. In order to solve existing problems of serious environment pollution and high reaction temperature, the invention provides the preparation method of the cephalotin acid; the method comprises the following steps: in the presence of organic alkali, mixing 2-thiopheneaceticacid and EDC (1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride); after activating carboxyl, adding 7-ACA and carrying out one-pot boiling under the condition that the temperature is 25 DEG C to 35 DEG C to obtain the cephalotin acid. The method provided by the invention has the advantages that reaction conditions are moderate, a beta-lactam compound is not degraded and the method is environmentally friendly; the technology operation is simplified and the cost is reduced.
