| Identification | More | [Name]
Cefdinir | [CAS]
91832-40-5 | [Synonyms]
7-[2-(2-AMINOTHIAZOL-4-YL)-2-HYDROXYIMINOACETYLAMINO]-8-OXO-3-VINYL-5-THIA-1-AZA-BICYCLO[4.2.0]OCT-2
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
(6r-(6-alpha,7-beta(z)))-)(hydroxyiminoacetyl)amino)-3-ethenyl-8-oxo
bmy28488
cefdinyl
(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
Omnice
CEFDIRNIR
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2-amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-, [6R-[6a,7b(Z)]]-
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2Z)-(2-amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-, (6R,7R)-
Cefzon
CFDN
CI 983
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
Omnicef
BMY-28488, FK-482, syn-7-[2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetamido]-3-vinyl-3-cephem-4-carboxylic acid, [6R-[6α-7beta(Z)]]-7-[[(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
[6R-[6α，7β(Z)]]_7-[[(2-Amino-4-thiazolyl)(hydroxyimino)acetyl]amino]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Novacef | [EINECS(EC#)]
643-088-1 | [Molecular Formula]
C14H13N5O5S2 | [MDL Number]
MFCD00865030 | [Molecular Weight]
395.41 | [MOL File]
91832-40-5.mol |
| Chemical Properties | Back Directory | [Appearance]
Pale Yellow Solid | [Melting point ]
>180°C dec. | [density ]
1.89±0.1 g/cm3(Predicted) | [storage temp. ]
Room temp | [solubility ]
dilute HCl: slightly soluble | [form ]
solid | [pka]
9.70(at 25℃) | [color ]
Pale Yellow to Light Yellow | [Water Solubility ]
Soluble in water | [Usage]
A Cephalosporin antibiotic structurally similar to Cefixime | [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) |
| Safety Data | Back Directory | [WGK Germany ]
3 | [RTECS ]
XI0367250 | [HS Code ]
2941906000 | [Toxicity]
LD50 orl-rat: >5600 mg/kg IYKEDH 23,93,1992 |
| Hazard Information | Back Directory | [Description]
Cefdinir is a cephalosporin antibiotic.1 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.2 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 broad spectrum antibiotic targeting both Gram-positive and Gram-negative pathogens | [Uses]
A Cephalosporin antibiotic structurally similar to Cefixime | [Uses]
antihypertensive, ACE inhibitor | [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. |
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