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ChemicalBook--->CAS DataBase List--->91832-40-5

91832-40-5

91832-40-5 Structure

91832-40-5 Structure
IdentificationMore
[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 PropertiesBack 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 DataBack Directory
[WGK Germany ]

3
[RTECS ]

XI0367250
[HS Code ]

2941906000
[Toxicity]

LD50 orl-rat: >5600 mg/kg IYKEDH 23,93,1992
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Ethyl acetate-->Trifluoroacetic acid-->Anisole-->N,N-Dimethylacetamide-->Chloromethane-->Acetyl bromide-->(FORMYLMETHYLENE)TRIPHENYLPHOSPHORANE-->N-(Trimethylsilyl)acetamide-->Sodium nitrite-->S-2-BENZOTHIAZOLYL (Z)-2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2-METHOXYIMINO THIOACETATE-->(Benzothiazol-2-yl)-(Z)-2-trityloxyimino-2-(2-aminothiazole-4-yl)-thioacetate-->7-AVCA
Material Safety Data Sheet(MSDS)Back Directory
[msds information]

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(91832-40-5).msds
Hazard InformationBack Directory
[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 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.
Questions And AnswerBack Directory
[Brand Name(s) in US]

Omnicef
Spectrum DetailBack Directory
[Spectrum Detail]

Cefdinir(91832-40-5)1HNMR
Cefdinir(91832-40-5)IR1
Cefdinir(91832-40-5)IR2
Well-known Reagent Company Product InformationBack Directory
[Sigma Aldrich]

91832-40-5(sigmaaldrich)
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