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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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Cephalothin Suppliers

J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Liaoning Tianhua Chemical Co., Ltd.
Tel
0418-6530555 2855550
Fax
+86-418-6502885
Country
China
ProdList
338
Advantage
69
Energy Chemical
Tel
021-021-58432009 400-005-6266
Fax
021-58436166
Email
sales8178@energy-chemical.com
Country
China
ProdList
44751
Advantage
61
Jia Xing Isenchem Co.,Ltd
Tel
0573-85285100 18627885956
Fax
0573-85285100
Email
isenchem@163.com
Country
China
ProdList
9555
Advantage
66
Shanghai Hanhong Scientific Co.,Ltd.
Tel
021-54306202 13764082696;
Email
info@hanhongsci.com
Country
China
ProdList
42982
Advantage
64
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32344
Advantage
50
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
14059
Advantage
65
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12338
Advantage
58
TOKYO CHEMICAL INDUSTRY CO., LTD.
Tel
03-36680489
Fax
03-3668-0520
Email
Sales-JP@TCIchemicals.com
Country
Japan
ProdList
28398
Advantage
80
TCI Europe
Tel
320-37350700
Fax
+32 (0)37350701
Email
sales@tcieurope.eu
Country
Europe
ProdList
23680
Advantage
75
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View Lastest Price from Cephalothin manufacturers

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:


  • 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
  • KEFLIN
  • Amines
  • Chiral Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Pharmaceuticals