ChemicalBook > CAS DataBase List > Cefadroxil

Cefadroxil

Product Name
Cefadroxil
CAS No.
66592-87-8
Chemical Name
Cefadroxil
Synonyms
AMOXYCILLIN;CEFADROXIL MONOHYDRATE;Cefadroxil hydrate;CEFADROXILE;Baxan;CEFAMOX;Duracef;Cefa-Drops;CEFADROXIL;Cefradroxil
CBNumber
CB4203658
Molecular Formula
C16H17N3O5S.H2O
Formula Weight
381.41
MOL File
66592-87-8.mol
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Cefadroxil Property

Melting point:
197 °C
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
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)
form 
Solid
color 
White to Off-White
BCS Class
3
InChIKey
NBFNMSULHIODTC-CYJZLJNKSA-N
CAS DataBase Reference
66592-87-8(CAS DataBase Reference)
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Safety

Hazard Codes 
Xn,Xi
Risk Statements 
36/37/38-42/43
Safety Statements 
26-36-36/37
WGK Germany 
2
RTECS 
XI0337000
HS Code 
2941906000
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H314Causes severe skin burns and eye damage

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P310Immediately call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
PHR3579
Product name
Cefadroxil
Purity
certified reference material, pharmaceutical secondary standard
Packaging
400MG
Price
$229
Updated
2024/03/01
Sigma-Aldrich
Product number
C0650000
Product name
Cefadroxil
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
c0650000
Price
$153
Updated
2024/03/01
Sigma-Aldrich
Product number
1097104
Product name
Cefadroxil
Packaging
200mg
Price
$436
Updated
2024/03/01
Sigma-Aldrich
Product number
BP784
Product name
Cefadroxil
Purity
British Pharmacopoeia (BP) Reference Standard
Packaging
100MG
Price
$227
Updated
2023/01/07
Cayman Chemical
Product number
20365
Product name
Cefadroxil (hydrate)
Packaging
100mg
Price
$47
Updated
2024/03/01
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Cefadroxil Chemical Properties,Usage,Production

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. Soluble in chloroform, miscible with ethanol and ether, insoluble in water, and will change color when exposed to light or for a long time.

Uses

Cefadroxil Monohydrate is a semi-synthetic cephalosporin antibacterial. It has been used for various community-acquired infections for which oral cephalosporins are appropriate.

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

General Description

Cefadroxil is a semisynthetic first-generation β-lactam cephalosporin antibiotic derived from cefalexin with antibacterial activity. It is used to treat urinary tract infections, skin and skin structure infections, pharyngitis, and tonsillitis caused by susceptible bacteria.

Application

Cefadroxil was found by Bristol-Myers Co. in 1976. A hydroxyl group was attached to the benzene ring of cephalexin. Like amoxicillin and ampicillin, cefadroxil shows almost the same antibacterial activity spectrum as cephalexin and superior oral absorption. Its in vivo activity is four to six times greater than that of cephalexin, and its half-life in serum is twice as long.

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

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.

Side effects

Side effects described are those common to oral cephalosporins.

Synthesis

Cefadroxil, [6R-[6|á,7|?(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.

Cefadroxil Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from Cefadroxil manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cefadroxil 66592-87-8
Price
US $0.00/Kg/Drum
Min. Order
1KG
Purity
950μg/mg-1050μg/mg;USP
Supply Ability
1000KGS
Release date
2021-06-28
BEIJING SJAR TECHNOLOGY DEVELOPMENT CO., LTD.
Product
Cefadroxil 66592-87-8
Price
US $0.00/g
Min. Order
1g
Purity
More Than 99%
Supply Ability
100kg/Month
Release date
2024-11-13
Shaanxi Dideu Medichem Co. Ltd
Product
Cefadroxil 66592-87-8
Price
US $0.00-0.00/KG
Min. Order
1KG
Purity
99.0%
Supply Ability
10 tons
Release date
2024-09-03

66592-87-8, CefadroxilRelated Search:


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