66592-87-8

Basic information

• Product Name: Cefadroxil
• Synonyms: (6R,7R)-7-[(R)-2-AMINO-2-(4-HYDROXY-PHENYL)-ACETYLAMINO]-3-METHYL-8-OXO-5-THIA-1-AZA-BICYCLO[4.2.0]OCT-2-ENE-2-CARBOXYLIC ACID;CEFAMOX;CEFADROXIL;CEFADROXIL MONOHYDRATE;P-HYDROXYCEPHALEXINE;monohydrate,(6r-(6-alpha,7-beta(r*)))-l)acetyl)amino)-3-methyl-8-oxo;Cefradroxil;(6R,7R)-7-[[(2R)-Amino-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Monohydrate
• CAS NO: 66592-87-8
• Molecular Formula: C₁₆H₁₇N₃O₅S*H₂O
• Molecular Weight: 381.41
• EINECS: 1308068-626-2
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;DURICEF
• Mol File: 66592-87-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 197 °C
• Boiling Point: 789.9 °C at 760 mmHg
• Flash Point: 431.5 °C
• Appearance: White crystalline solid
• Vapor Pressure: 2.71E-26mmHg at 25°C
• Storage Temp.: -20°C Freezer
• Solubility: Slightly soluble in water, very slightly soluble in ethanol (96 per cen
• PKA: pKa 1.38(H2O t=20±2 N2atmosphere) (Uncertain); 7.35(H2O t=20±2 N2atmosphere) (Uncertain);10.10(H2O t=20±2 N2atmosphere) (Uncertain)
• CAS DataBase Reference: Cefadroxil(CAS DataBase Reference)
• NIST Chemistry Reference: Cefadroxil(66592-87-8)
• EPA Substance Registry System: Cefadroxil(66592-87-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-42/43
• Safety Statements: 26-36-36/37
• WGK Germany: 2
• RTECS: XI0337000
• Hazardous Substances Data: 66592-87-8(Hazardous Substances Data)

Usage

Brand Name(s) in US

Veterinary: Cefa-Tabs, Cefa-Drops? Human dosage form: Duricef and generic

Description

Cefadroxil has an amoxicillin-like side chain at C-7 and is orally active. There are some indications that cefadroxil has some immunostimulant properties mediated through T-cell activation and that this is of material assistance to patients in fighting infections. The prolonged biological half-life of cefadroxil allows once-a-day dosage.

Chemical Properties

White Crystalline Solid

Uses

Different sources of media describe the Uses of 66592-87-8 differently. You can refer to the following data:
1. Semi-synthetic cephalosporin antibiotic. Antibacterial
2. Cefadroxil Monohydrate is a semi-synthetic cephalosporin antibiotic. Antibacterial.

Definition

ChEBI: The hydrate that is the monohydrate of the cephalosporin cefadroxil.

Brand name

Duricef (Bristol-Myers Squibb); Ultracef (Bristol Labs).

Antimicrobial activity

Resembles closely that of cefalexin

Pharmacokinetics

Oral absorption: >90% Cmax 250 mg oral: c. 9 mg/L after 1.2 h 500 mg oral: c. 18 mg/L after 1.2 h Plasma half-life: 1–1.5 h Plasma protein binding : 20% Absorption is little affected by administration with food. Distribution is similar to that of cefalexin. It is eliminated unchanged by glomerular filtration and tubular secretion; 90% of the dose appears in the urine over 24 h, most in the first 6 h, producing concentrations exceeding 500 mg/L.

Pharmacology

Cefadroxil has a broad spectrum of antimicrobial action; it is active with respect to Grampositive and Gram-negative microorganisms. Like all of the other drugs described above, it acts as a bactericide by disrupting the process of restoring the membranes of bacteria. Synonyms of this drug are bidocef, cefadril, duracef, ultracef, and others.

Clinical Use

Different sources of media describe the Clinical Use of 66592-87-8 differently. You can refer to the following data:
1. Cefadroxil (Duricef) is an orally active semisyntheticderivative of 7-ADCA, in which the 7-acyl group is the Dhydroxylphenylglycylmoiety. This compound is absorbedwell after oral administration to give plasma levels that reach75% to 80% of those of an equal dose of its close structuralanalog cephalexin. The main advantage claimed for cefadroxilis its somewhat prolonged duration of action, whichpermits once-a-day dosing. The prolonged duration of actionof this compound is related to relatively slow urinary excretionof the drug compared with other cephalosporins, butthe basis for this remains to be explained completely. Theantibacterial spectrum of action and therapeutic indications ofcefadroxil are very similar to those of cephalexin and cephradine.The D-p-hydroxyphenylglycyl isomer is much moreactive than the L-isomer.
2. It has been used for various community-acquired infections for which oral cephalosporins are appropriate.

Side effects

Side effects described are those common to oral cephalosporins.

Synthesis

Cefadroxil, [6R-[6α,7β(R)]]-3-methyl-8-oxo-7-[[amino(4-hydroxyphenyl) acetyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylic acid (32.1.2.14), is an analog of cephalexin and differs only in the presence of a hydroxyl group in the fourth position of the phenyl ring of phenylglycine, and is synthesized by a scheme analogous to the scheme of cephradin synthesis.

Veterinary Drugs and Treatments

Cefadroxil is approved for oral therapy in treating susceptible infections of the skin, soft tissue, and genitourinary tract in dogs and cats. The veterinary oral tablets have been discontinued (in the USA), but human-labeled oral capsules and tablets are still available.

in vitro

the inhibitory activity of this compound was similar to that of cephalexin and cephradine when tested against 602 clinical isolates on mueller-hinton medium. in the oral treatment of experimental infections of mice, cefadroxil was more effective than cephalexin against streptococcus pyogenes, and comparably effective against streptococcus pneumoniae, staphylococcus aureus, and several gram-negative species [1].

in vivo

in mice, oral administration of cefadroxil at doses ranging from 25 to 100 mg/kg attained peak concentrations in the blood. higher peak levels were noted with cefadroxil than with cephalexin at a dose of 200 mg/kg [1].

Drug interactions

Potentially hazardous interactions with other drugs Anticoagulants: effects of coumarins may be enhanced.

Metabolism

More than 90% of a dose of cefadroxil may be excreted unchanged in the urine within 24 hours by glomerular filtration and tubular secretion.

references

[1] buck r e, price k e. cefadroxil, a new broad-spectrum cephalosporin[j]. antimicrobial agents and chemotherapy, 1977, 11(2): 324-330.[2] gerber m a, randolph m f, chanatry j, et al. once daily therapy for streptococcal pharyngitis with cefadroxil[j]. the journal of pediatrics, 1986, 109(3): 531-537.

InChI:InChI=1/C16H17N3O5S.H2O/c1-7-6-25-15-11(14(22)19(15)12(7)16(23)24)18-13(21)10(17)8-2-4-9(20)5-3-8;/h2-5,10-11,15,20H,6,17H2,1H3,(H,18,21)(H,23,24);1H2/t10?,11-,15-;/m1./s1

Relevant articles and documents

Silylation process

A process for the silylation of 6-aminopenicillanic acid or 7-amino-desacetoxy-cephalosporanic acid by silylation in certain carboxylic acid esters and its use in the production of 6-alpha-aminoacyl-penicillins and 7-alpha-aminoacyl-desacetoxy-cephalosporins.

Substantially anhydrous crystalline cefadroxil and method for producing it

The invention relates to a substantially anhydrous crystalline cefadroxil having a water content between about 0.8% and 3.9%. Such cefadroxil is obtained slurrying a cefadroxil solvate of dimethylacetamide, or of N-methyl-2-pyrrolidone or of monomethylformamide, with isopropyl alcohol with up to 4% of water and preferably in the presence of methanol in an amount lower than 60%, at a temperature of about +45° C. to +55° C. and then filtering the so obtained compound.

Substantially anhydrous crystalline cefadroxil and method for producing it

The invention relates to a substantially anhydrous crystalline ce-fadroxil having a water content between about 0.8% and 3.9%. Such cefadroxil is obtained slurrying a cefadroxil solvate of dimethylacetamide, or of N-methyl-2-pyrrolidone or of monomethyl-formamide, with isopropyl alcohol containing either from about 2% to 4% of water of from about 0.1% to 4% of water and from 0% to about 60% of methanol, at a temperature in the range of about +45°C to +55°C and than filtering the desired cefadroxil so obtained.