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Cefetamet

Cefetamet structure

CAS No:
65052-63-3
Formula:
C14H15N5O5S2
Chemical Name:
Cefetamet
Synonyms:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-methyl-8-oxo-,(6R,7R)-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-methyl-8-oxo-,[6R-[6α,7β(Z)]]-;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid,7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-3-methyl-8-oxo-,(6R,7R)-;(6R,7R)-7-[[(2Z)-2-(2-Amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;Cefetamet;Deacetoxycefotaxime;LY 97964;Ro 15-8074;FR 13300;Antibiotic Ro 15-8074;Ro 15-8074/005;Altamet;Cepime O;Ultipime O
Categories:
Active Pharmaceutical Ingredients > Antibiotics

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Cefetamet Basic Attributes

Molecular Weight：

548.03

Exact Mass：

397.43

EC Number：

1308068-626-2

ATC Code：

J - Antiinfectives for systemic use

HScode：

2941906000

Characteristics

PSA：

200.75000

XLogP3：

1.18

Density：

1.8±0.1 g/cm3

Refractive Index：

1.821

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

hazard class code：

R36/37/38:Irritating to eyes, respiratory system and skin . R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .

safety instructions：

S26-S36-S37/39

Marks：

Xi,Xn

Drug Information

MeSH：

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

MeSH Entry Terms：

2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido-3-desacetoxyceph-3-em-4-carboxylic acid

Cefetamet Use and Manufacturing

Methods of Manufacturing

Suspend 2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetic acid in tetrahydrofuran, add half the amount of phosphorus oxychloride dropwise at 0℃, keep the temperature not exceeding 5℃, drop After 30 minutes of reaction. Add dimethylformamide and the other half of phosphorus oxychloride, and react at 0°C for 1h to obtain a solution of active ester (I), and cool to -5°C for use. 7-ADCA, bis-trimethylsilylurea and ethyl acetate were refluxed at 75-77°C for 2 hours to obtain a solution of 7-ADCA silicon ester (II), which was cooled to -5°C. Combine it with the active ester solution and stir at -5 to 0°C for 2h. Raise to 15"C, add water and stir for 30min. Separate the water layer, adjust to Ph=2.6~3.0 with sodium hydroxide solution, and place the precipitated crystals. Filter and recrystallize with acetone to obtain ceftazidime in 82% yield.

Uses

Cefetametis a third-generation cephalosporin antibiotic and the active agent of Cefeamet pivoxil (C242780) after hydrolysis.

Computed Properties

Molecular Weight:397.4
XLogP3:-0.7
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:5
Exact Mass:397.05146094
Monoisotopic Mass:397.05146094
Topological Polar Surface Area:201
Heavy Atom Count:26
Complexity:712
Defined Atom Stereocenter Count:2
Undefined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

7-Aminodeacetoxycephalosporanic acid

Dimethylformamide

Drug Function and Efficacy

This product is an oral third-generation broad-spectrum cephalosporin antibiotic. It has strong antibacterial activity against Gram-positive bacteria such as Streptococcus (except faecal Streptococcus) and Streptococcus pneumoniae; Gram-negative bacteria such as Escherichia coli, Haemophilus influenzae, Klebsiella, Salmonella, Shigella, and Neisseria gonorrhoeae, especially against Serratia, indole-positive Proteus, Enterobacter, and Citrobacter, which are less sensitive to cephalosporins. It is stable to beta-lactamase produced by bacteria. This product is ineffective against drug-resistant microorganisms such as Pseudomonas, Mycoplasma, Chlamydia, and Enterococcus.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Cefetamet Pivoxil Hydrochloride Capsules
Ingredients	(6R,7R)3-methyl-7[(Z)2(2-amino-4-thiazolyl)2(methoxyimino)acetylamino]8-oxo-5-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid pivaloyloxymethyl ester hydrochloride
Indication	Antacids and H2 antagonists have no effect on the pharmacokinetics of this product. So far, there have been no reports of this product affecting laboratory test values and/or methods, and no damage to renal function has been observed in patients receiving concomitant diuretic therapy when using this product.
Specifications	90.65 mg (calculated as C14H15N505S2)
Manufacturer	NORTHEAST Pharmaceutical Group Shenyang NO.1 Pharmaceutical Co., Ltd.

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