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| 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 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 | | pka | 9.70(at 25℃) | | color | Pale Yellow to Light Yellow | | Water Solubility | Soluble in water | | λmax | 295nm(DMSO)(lit.) | | Merck | 14,1920 | | BCS Class | 4 | | 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) |
| WGK Germany | 3 | | RTECS | XI0367250 | | HS Code | 2941906000 | | Toxicity | LD50 orl-rat: >5600 mg/kg IYKEDH 23,93,1992 |
| | 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 Preparation Products And Raw materials |
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