Cephalothin

ChemicalBook > CAS DataBase List > Cephalothin

Product Name: Cephalothin
CAS No.: 153-61-7
Chemical Name: Cephalothin
Synonyms: C07761;CEPHALOTHIN;3-Butylidene-4;CEFALOTHIN ACID;Cephaliotin Acid;Cephalotinic acid;-3-(Acetoxymethyl);5-dihydrophthalide;Cefalonium Impurity A;Cefalonium Impurity 1
CBNumber: CB52130371
Molecular Formula: C16H16N2O6S2
Formula Weight: 396.44
MOL File: 153-61-7.mol

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Cephalothin Property

Melting point:: 160-161 ºC
alpha: D20 +50° (c = 1.03 in acetonitrile)
Boiling point:: 757.2±60.0 °C(Predicted)
Density: 1.4162 (rough estimate)
refractive index: 1.6510 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: DMSO (Sparingly), Dioxane (Slightly), Methanol (Slightly)
form: Solid
pka: pKa 2.5 (Uncertain)
color: White to Off-White
Water Solubility: 158 MG/L
λmax: 263nm(H2O)(lit.)
Merck: 14,1982
CAS DataBase Reference: 153-61-7(CAS DataBase Reference)
EPA Substance Registry System: Cephalothin (153-61-7)

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Safety

RTECS: XI0388000
Hazardous Substances Data: 153-61-7(Hazardous Substances Data)
Toxicity: LD50 intracrebral in mouse: 81mg/kg

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P272Contaminated work clothing should not be allowed out of the workplace.

P285In case of inadequate ventilation wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P341IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

P363Wash contaminated clothing before reuse.

P403Store in a well-ventilated place.

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N-Bromosuccinimide Price

Alfa Aesar

Product number: H36175
Product name: Cephalothin (acid)
Purity: 97%
Packaging: 25g
Price: $249.65
Updated: 2024/03/01

Alfa Aesar

Product number: H36175
Product name: Cephalothin (acid)
Purity: 97%
Packaging: 5g
Price: $92.9
Updated: 2023/06/20

TRC

Product number: C261150
Product name: Cephalothin
Packaging: 1g
Price: $55
Updated: 2021/12/16

Biosynth Carbosynth

Product number: FA32097
Product name: (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Packaging: 100g
Price: $70
Updated: 2021/12/16

Matrix Scientific

Product number: 076118
Product name: (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Purity: 95+%
Packaging: 1g
Price: $48
Updated: 2021/12/16

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Cephalothin Chemical Properties,Usage,Production

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.

Definition

ChEBI: Cefalotin is a semisynthetic, first-generation cephalosporin antibiotic with acetoxymethyl and (2-thienylacetyl)nitrilo moieties at positions 3 and 7, respectively, of the core structure. Administered parenterally during surgery and to treat a wide spectrum of blood infections. It has a role as an antimicrobial agent and an antibacterial drug. It is a semisynthetic derivative, a beta-lactam antibiotic allergen, a cephalosporin, a carboxylic acid, a member of thiophenes and an azabicycloalkene. It is a conjugate acid of a cefalotin(1-).

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

Cephalothin Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Cephalothin manufacturers

Shaanxi Dideu Medichem Co. Ltd

Product: Cephalothin 153-61-7
Price: US $0.00-0.00/KG
Min. Order: 1KG
Purity: 99.0%
Supply Ability: 1000KG
Release date: 2024-07-16

Hong Kong Tiansheng New Material Trading Co., Ltd

Product: Cemastin 153-61-7
Price: US $1.22/KG
Min. Order: 300g
Purity: 99%
Supply Ability: 3tons
Release date: 2021-12-09

Career Henan Chemical Co

Product: (6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 153-61-7
Price: US $7.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: JD 527
Release date: 2019-09-01

153-61-7, CephalothinRelated Search:

Thifensulfuron methyl Thiophene Benzyloxyacetyl chloride Methyltriacetoxysilane Tetrahydrothiophene Acetoxyacetyl chloride Cephalothin sodium Sodium triacetoxyborohydride Thianaphthene Cefotaxime sodium Ceftiofur Ceftiofur sodium Cefotaxime Cephalonium lactone Δ3-Cephalothin-3-isomer POLYTHIOPHENE Hydroxymethyl-7-Aminocephalosporanic acid THIOPHENE-2-ACETAMIDE

CEPHALOTHIN

(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-[2-(2-thienyl)acetylamino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

C07761

(6R,7R)-3-[(acetyloxy)Methyl]-8-oxo-7-[2-(thiophen-2-yl)acetaMido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

(6R,7R)-3-[(Acetyloxy)Methyl]-8-oxo-7-[[2-(2-thienyl)acetyl]aMino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

(6R)-3-acetoxyMethyl-8-oxo-7t-(2-thiophen-2-yl-acetylaMino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylicacid, 3-[(acetyloxy)methyl]-8-oxo-7-[[2-(2-thienyl)acetyl]amino]-, (6R,7R)-

-3-(Acetoxymethyl)

-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

-8-oxo-7-(2-(thiophen-2-yl)

(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2

(6R,7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en

Cefalonium Impurity A

Cephaliotin Acid

sodium 3-(acetyloxymethyl)-8-oxo-7-[(1-oxo-2-thiophen-2-ylethyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

Cefalonium Impurity A (Cefalotin)

Cefalonium Impurity 1

CEFALOTHIN ACID

7R)-3-(Acetoxymethyl)-8-oxo-7-(2-(thiophen-2-yl)acetamido)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

3-Butylidene-4

5-dihydrophthalide

Cephalotinic acid

153-61-7

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