Cephalothin

Cephalothin Properties

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)
FDA UNII	R72LW146E6
EPA Substance Registry System	Cephalothin (153-61-7)

SAFETY

Risk and Safety Statements

Symbol(GHS)	GHS08
Signal word	Warning
Hazard statements	H317-H334
Precautionary statements	P261-P272-P280g-P285-P302+P352-P304+P341-P333+P313-P342+P311-P363-P403-P501c
RTECS	XI0388000
Toxicity	LD50 intracrebral in mouse: 81mg/kg

Cephalothin price More Price(30)

Manufacturer	Product number	Product description	CAS number	Packaging	Price	Updated	Buy
Alfa Aesar	H36175	Cephalothin (acid) 97%	153-61-7	25g	$249.65	2024-03-01	Buy
Alfa Aesar	H36175	Cephalothin (acid) 97%	153-61-7	5g	$92.9	2023-06-20	Buy
TRC	C261150	Cephalothin	153-61-7	1g	$55	2021-12-16	Buy
Biosynth Carbosynth	FA32097	(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	153-61-7	100g	$70	2021-12-16	Buy
Matrix Scientific	076118	(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 95+%	153-61-7	1g	$48	2021-12-16	Buy

Product number	Packaging	Price	Buy
H36175	25g	$249.65	Buy
H36175	5g	$92.9	Buy
C261150	1g	$55	Buy
FA32097	100g	$70	Buy
076118	1g	$48	Buy

Cephalothin Chemical Properties,Uses,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.
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Cephalothin synthesis

Synthesis of Cephalothin from 2-Thiopheneacetic acid, 2,5-dioxo-1-pyrrolidinyl ester and 7-Aminocephalosporanic acid

Cephalothin Preparation Products And Raw materials

Raw materials

Sodium hydroxide Thionyl chloride 7-Aminocephalosporanic acid 2-Thiopheneacetic acid

Preparation Products

Cefoxitin 7α-Methoxycephalotin Monosodium Salt (6R-trans)-3-(hydroxymethyl)-8-oxo-7-(2-thienylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Cephalothin Suppliers

Global( 157)Suppliers

Supplier	Tel	Email	Country	ProdList	Advantage
Shanghai Daken Advanced Materials Co.,Ltd	+86-371-66670886	info@dakenam.com	China	15928	58
career henan chemical co	+86-0371-86658258	sales@coreychem.com	China	29914	58
SHANDONG ZHI SHANG CHEMICAL CO.LTD	+86 18953170293	sales@sdzschem.com	China	2931	58
Alchem Pharmtech,Inc.	8485655694	sales@alchempharmtech.com	United States	63711	58
CONIER CHEM AND PHARMA LIMITED	+8618523575427	sales@conier.com	China	49390	58
Antai Fine Chemical Technology Co.,Limited	18503026267	info@antaichem.com	CHINA	9641	58
Neostar United (Changzhou) Industrial Co., Ltd.	+86-519-519-85557386	marketing1@neostarunited.com	China	8349	58
Zhengzhou Alfa Chemical Co.,Ltd	+8618530059196	sale04@alfachem.cn	China	12468	58
SIMAGCHEM CORP	+86-13806087780	sale@simagchem.com	China	17367	58
Hefei TNJ Chemical Industry Co.,Ltd.	0551-65418671	sales@tnjchem.com	China	34572	58

Supplier	Advantage
Shanghai Daken Advanced Materials Co.,Ltd	58
career henan chemical co	58
SHANDONG ZHI SHANG CHEMICAL CO.LTD	58
Alchem Pharmtech,Inc.	58
CONIER CHEM AND PHARMA LIMITED	58
Antai Fine Chemical Technology Co.,Limited	58
Neostar United (Changzhou) Industrial Co., Ltd.	58
Zhengzhou Alfa Chemical Co.,Ltd	58
SIMAGCHEM CORP	58
Hefei TNJ Chemical Industry Co.,Ltd.	58

View Lastest Price from Cephalothin manufacturers

Image	Update time	Product	Price	Min. Order	Purity	Supply Ability	Manufacturer
	2022-02-25	Cemastin 153-61-7	US $1.22 / KG	300g	99%	3tons	Hong Kong Tiansheng New Material Trading Co., Ltd
	2019-09-02	(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	US $7.00 / KG	1KG	99%	JD 527	Career Henan Chemical Co

Cemastin
153-61-7
US $1.22 / KG
99%
Hong Kong Tiansheng New Material Trading Co., Ltd

(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
US $7.00 / KG
99%
Career Henan Chemical Co

Cephalothin Spectrum

Cephalothin(153-61-7)¹HNMR

153-61-7(Cephalothin)Related 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

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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 5-dihydrophthalide 3-Butylidene-4 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 CEFALOTHIN ACID Cefalonium Impurity 1 Cefalonium Impurity A (Cefalotin) 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 Cephalotinic acid 153-61-7 KEFLIN Amines Chiral Reagents Heterocycles Intermediates & Fine Chemicals Pharmaceuticals