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

pka

9.70(at 25℃)

form 

solid

color 

Pale Yellow to Light Yellow

Water Solubility 

Soluble in water

λmax

295nm(DMSO)(lit.)

Merck 

14,1920

BCS Class

4

InChI

InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1

InChIKey

RTXOFQZKPXMALH-GHXIOONMSA-N

SMILES

N12[C@@]([H])([C@H](NC(/C(/C3=CSC(N)=N3)=N\O)=O)C1=O)SCC(C=C)=C2C(O)=O

CAS DataBase Reference

91832-40-5(CAS DataBase Reference)

Safety Information

WGK Germany 

3

RTECS 

XI0367250

HS Code 

2941906000

Toxicity

LD50 orl-rat: >5600 mg/kg IYKEDH 23,93,1992

MSDS

• Language:English Provider: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

Cefdinir Usage And Synthesis

Brand Name(s) in US

Omnicef

Description

Cefdinir 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.

Description

Cefdinir 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 Properties

Pale Yellow Solid

Originator

Fujisawa (Japan)

Uses

A Cephalosporin antibiotic structurally similar to Cefixime

Uses

antihypertensive, ACE inhibitor

Uses

A broad spectrum antibiotic targeting both Gram-positive and Gram-negative pathogens

Definition

ChEBI: A cephalosporin compound having 7beta-2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino- and 3-vinyl side groups.

Manufacturing Process

By 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 name

Cefzon

Therapeutic Function

Antibiotic

Antimicrobial activity

An 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 Profile

Moderately 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.

Cefdinir(91832-40-5)Related Product Information

• Glycine
• 4-(4-CHLORO-BENZYLOXY)-PHENYLAMINE
• N-Vinyl-2-pyrrolidone
• VINYL PROPIONATE
• ALTRENOGEST
• Triethoxyvinylsilane
• CHLOROPHOSPHONAZO III
• Betaine
• Silicone rubber,methyl-vinyl
• Vinyl ester resin
• Vinyl resin
• Cefixime
• Ceftiolene
• Cefditoren
• Cefditoren pivoxil
• (Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO ACETIC ACID
• (Benzothiazol-2-yl)-(Z)-2-trityloxyimino-2-(2-aminothiazole-4-yl)-thioacetate
• YTTERBIUM(III) IONOPHORE I