Cefdinir

Cefdinir Basic information
Brand Name(s) in US
Product Name:Cefdinir
Synonyms:(6R,7R)-7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-hydroxyimino-1-oxoethyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(6r-(6-alpha,7-beta(z)))-)(hydroxyiminoacetyl)amino)-3-ethenyl-8-oxo;bmy28488;cefdinyl;8-[2-(2-amino-1,3-thiazol-4-yl)-1-hydroxy-2-nitroso-ethenyl]amino-4-ethenyl-7-oxo-2-thia-6-azabicyclo[4.2.0]oct-4-ene-5-carboxylicacid;7-[2-(2-AMINOTHIAZOL-4-YL)-2-HYDROXYIMINOACETYLAMINO]-8-OXO-3-VINYL-5-THIA-1-AZA-BICYCLO[4.2.0]OCT-2;(6R,7R)-7-[[(2Z)-(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo--5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid;FK-482
CAS:91832-40-5
MF:C14H13N5O5S2
MW:395.41
EINECS:643-088-1
Product Categories:cephalosporins;Chiral Reagents;Miscellaneous Biochemicals;Intermediates & Fine Chemicals;Pharmaceuticals;ACEON;Sulfur & Selenium Compounds
Mol File:91832-40-5.mol
Cefdinir Structure
Cefdinir Chemical Properties
Melting point >180°C dec.
density 1.89±0.1 g/cm3(Predicted)
storage temp. Keep in dark place,Sealed in dry,2-8°C
solubility dilute HCl: slightly soluble
form solid
pka9.70(at 25℃)
color Pale Yellow to Light Yellow
Water Solubility Soluble in water
λmax295nm(DMSO)(lit.)
Merck 14,1920
BCS Class4
InChIKeyRTXOFQZKPXMALH-GHXIOONMSA-N
SMILESN12[C@@]([H])([C@H](NC(/C(/C3=CSC(N)=N3)=N\O)=O)C1=O)SCC(C=C)=C2C(O)=O
CAS DataBase Reference91832-40-5(CAS DataBase Reference)
Safety Information
WGK Germany 3
RTECS XI0367250
HS Code 2941906000
ToxicityLD50 orl-rat: >5600 mg/kg IYKEDH 23,93,1992
Cefdinir Usage And Synthesis
Brand Name(s) in USOmnicef
DescriptionCefdinir is a cephalosporin antibiotic. It is active against numerous Gram-positive and Gram-negative bacteria, including β-lactamase-producing E. coli, K. oxytoca, K. pneumoniae, and P. aeruginosa clinical isolates (MICs = 0.25-16 μg/ml). Cefdinir is protective against sepsis induced by strains of S. aureus or H. influenzae in mice with 50% protective dose (PD50) values of 2.7-35 and 3.1-5.8 mg/kg, respectively. Formulations containing cefdinir have been used in the treatment of Gram-positive and Gram-negative infections.
DescriptionCefdinir is an orally active, beta-lactamase stable cephalosporin with a broad spectrum of activity. Compared to other oral cephalosporins, cefdinir is more potent against Gram-positive bacteria, especially Staphylococci. Its activity against Gram-negative bacteria such as E.coli,K. pneumoniae and P.mirabilis is similar to cefixime, but superior to cefaclor and cephalexin.
Chemical PropertiesPale Yellow Solid
OriginatorFujisawa (Japan)
UsesA Cephalosporin antibiotic structurally similar to Cefixime
Usesantihypertensive, ACE inhibitor
UsesA broad spectrum antibiotic targeting both Gram-positive and Gram-negative pathogens
DefinitionChEBI: A cephalosporin compound having 7beta-2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino- and 3-vinyl side groups.
Manufacturing ProcessBy interaction of 7-amino-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0)oct-2-ene- 2-carboxylic acid 4-methoxyphenyl ester with 4-bromoacetyl bromide was prepared 7-(4-bromo-3-oxo-butyrylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo (4.2.0)oct-2-ene-2-carboxylic acid 4-methoxyphenyl ester. The active methylene group in that product was then nitrosated with sodium nitrite. The initial product spontaneously tautomerizes to afford 7-(4-bromo-2- hydroxyimino-3-oxo-butyrylamino)-8-oxo-3-vinyl-5-thia-1-azabicyclo(4.2.0) oct-2-ene-2-carboxylic acid 4-methoxyphenyl ester. By the reaction of that compound with thiourea and then with trifluoroacetic acid was obtained (6R,7R)-7-(2-(2-amino-4-thiazolyl)glyoxylamido)-8-oxo-3-vinyl-5-thia-1- azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid sodium nitrite, (Z)-oxime (Cefdinir sodium nitrile).
In practice it is usually used as free acid.
Synthesis of 7β-[2-(2-aminothiazol-4-yl)-2-(Z)-(trytiloxyimino)acetamido]-3- vinyl-3-cephem-4-carboxylic acid x p-toluenesulfonic acid x 2 N,N-dimethylacetamide (the precursor of Cefdinir) was described in Patent US 6,093,814.

Brand nameCefzon
Therapeutic FunctionAntibiotic
Antimicrobial activityAn oral cephalosporin similar in structure to cefixime, but with a slightly modified side chain at the 7-amino position. Activity is similar to that of cefixime, but it is more active, especially against staphylococci. It is not hydrolyzed by staphylococcal or the common plasmid-mediated enterobacterial β-lactamases. An enhancing effect on phagocytosis has been demonstrated in vitro.
Oral absorption is about 35%. A 200 mg oral dose achieves a plasma concentration of 1 mg/L after c. 3 h. Absorption is reduced after a fatty meal. Concentrations equal to or higher than corresponding plasma levels were present in blister fluid 6–12 h after administration of an oral dose. The plasma halflife is 1.5 h. Protein binding is 60–70%. A total of 12–20% of the dose was excreted in the urine within 12 h, the renal elimination declining with increasing dose. The elimination half-life and peak plasma concentration are increased in renal failure. About 60% of the drug is removed by hemodialysis.
Side effects and uses are those common to oral cephalosporins.

Safety ProfileModerately toxic by ingestion andintravenous routes. Low toxicity by intraperitoneal andsubcutaneous routes. Experimental reproductive effects.When heated to decomposition it emits toxic vapors ofNOx and SOx.
Betaine Triethoxyvinylsilane Cefditoren N-Vinyl-2-pyrrolidone Cefixime ALTRENOGEST CEFDINIR-15N2,13C1 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE Vinyl ester resin VINYL PROPIONATE Glycine Cefdinir Silicone rubber,methyl-vinyl AMINO ACIDS Vinyl resin CHLOROPHOSPHONAZO III YTTERBIUM(III) IONOPHORE I Ceftiolene

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