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Cefazedone

Cefazedone structure

CAS No:
56187-47-4
Formula:
C18H15Cl2N5O5S3
Chemical Name:
Cefazedone
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[2-(3,5-dichloro-4-oxo-1(4H)-pyridinyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(3,5-dichloro-4-oxo-1(4H)-pyridinyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-,(6R-trans)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(3,5-dichloro-4-oxo-1(4H)-pyridinyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-,(6R,7R)-;(6R,7R)-7-[[2-(3,5-Dichloro-4-oxo-1(4H)-pyridinyl)acetyl]amino]-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefazedone;Refosporen
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Cefazedone (Refosporen) is a first-generation cephalosporin with activity against Gram-positive and Gram-negative bacteria, and it is effective in the treatment of infections caused by sensitive bacteria. Cefazedone is a time-dependent antibiotic, the time of concentration exceeds the minimum inhibitory concentration (MIC) is the key pharmacokinetic-pharmacodynamic (PK-PD) variable associated with the killing of pathogens[1].

Cefazedone is a first-generation cephalosporin antibiotic having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and [(3,5-dichloro-4-oxopyridin-1(4H)-yl)acetamido side-groups located at positions 3 and 7 respectively. It has a role as an antibacterial drug. It is a cephalosporin, a semisynthetic derivative, a member of thiadiazoles, a carboxylic acid and a member of 4-pyridones.|Cefazedone is a semisynthetic first-generation cephalosporin with antibacterial activity. Cefazedone binds to and inactivates penicillin-binding proteins (PBPs) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and 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.

Cefazedone Basic Attributes

Molecular Weight：

548.45

Exact Mass：

548.44

EC Number：

1308068-626-2

UNII：

7Y86X0D799

DSSTox ID：

DTXSID50204733

NCI Thesaurus Code：

C76157

ATC Code：

J - Antiinfectives for systemic use

Characteristics

PSA：

212

XLogP3：

1.1

Appearance：

White to yellowish white powder

Density：

1.8±0.1 g/cm3

Refractive Index：

1.761

Safety Information

Packing level：

Ⅲ

Transport codes：

2811

hazard class code：

6.1

Precautionary statement(s)：

P201, P202, P260, P264, P270, P273, P281, P301+P312, P308+P313, P314, P330, P405, P501

Hazard Statements：

H302

GHS Classification：

|Danger|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P264, P270, P273, P281, P301+P312, P308+P313, P314, P330, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

MeSH Entry Terms：

7-(2-(3,5-dichloro-4-oxo-1- pyridyl)acetamido)-3-(5-methyl-1,3,4-thiadiazol- 2-ylthiomethyl)-3-cephem-4-carboxylic acid

Cefazedone Use and Manufacturing

Methods of Manufacturing

In a 1 L round bottom flask, Add 800ml absolute ethanol, Triethylamine 1.012g, heated to reflux.Compound V46.39g was dissolved, 2-mercapto-5-methyl-1, 3, 4-thiadiazole 12.30g, Stirring reaction 10h, After the reaction, Remove the solvent, Extraction with chloroform (3 x 250 ml)Then washed with a small amount of water extraction twice, Then dried over anhydrous magnesium sulphate overnight.After removing the solvent, The crude product is recrystallized from petroleum ether, 48.08 g of a solid was obtained, Yield 93.86percentHPLC purity 99.58percent.

Uses

Semi-synthetic cephalosporin antibiotic. Antibacterial.

Computed Properties

Molecular Weight:548.4
XLogP3:1.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:11
Rotatable Bond Count:7
Exact Mass:546.9612375
Monoisotopic Mass:546.9612375
Topological Polar Surface Area:212
Heavy Atom Count:33
Complexity:984
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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Cefazedone sodium

CAS No.: 56187-47-4

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