Cefadroxil
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| Category | Antibiotics |
| Catalog number | BBF-00707 |
| CAS | 50370-12-2 |
| Molecular Weight | 363.39 |
| Molecular Formula | C16H17N3O5S |
| Purity | ≥95% |
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Description
It is produced by the strain of Semisynthetic first generation oral cephalosporin. Its antimicrobial spectrum is the same as cefalexin, but its blood concentration is higher and longer than cefalexin. It is used to treat urinary tract infections.
Specification
| Related CAS | 66592-87-8 (hydrate) |
| Synonyms | Cefprozil Monohydrate EP Impurity B; Cephadroxil; D-Cefadroxil; Cefadroxilo; Cefadroxilum; Duricef; BL-S578; (6R,7R)-7-((R)-2-Amino-2-(p-hydroxyphenyl)acetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid |
| Shelf Life | As supplied, 2 years from the QC date provided on the Certificate of Analysis, when stored properly |
| Storage | −20 °C |
| IUPAC Name | (6R,7R)-7-[[(2R)-2-amino-2-(4-hydroxyphenyl)acetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid |
| Canonical SMILES | CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)SC1)C(=O)O |
| InChI | 1S/C16H17N3O5S/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)/t10-,11-,15-/m1/s1 |
| InChI Key | BOEGTKLJZSQCCD-UEKVPHQBSA-N |
Properties
| Appearance | White Crystal |
| Application | A broad-spectrum antibiotic |
| Boiling Point | 789.9 °C at 760 mmHg |
| Melting Point | 197 °C (dec.) |
| Density | 1.59 g/cm3 |
| Solubility | Soluble in Water |
Reference Reading
1.New valid spectrofluorimetric method for determination of selected cephalosporins in different pharmaceutical formulations using safranin as fluorophore.
Derayea SM1, Ahmed HM2, Abdelmageed OH3, Haredy AM1. Spectrochim Acta A Mol Biomol Spectrosc. 2016 Jan 15;153:655-60. doi: 10.1016/j.saa.2015.10.001. Epub 2015 Oct 9.
A new validated spectrofluorimetric method has been developed for the determination of some cephalosporins namely; cefepime, cefaclor, cefadroxil, cefpodoxime and cefexime. The method was based on the reaction of these drugs with safranin in slightly alkaline medium (pH 8.0), to form ion-association complexes. The fluorescent products were extracted into chloroform and their fluorescence intensities were measured at 544-565 nm after excitation at 518-524 nm. The reaction conditions influencing the product formation and stability were investigated and optimized. The relative fluorescence intensity was proportional to the drug concentration in the linear ranges of 0.15-1.35, 0.35-1.25, 0.35-1.25, 0.20-1.44 and 0.20-1.25 μg/mL for cefepime, cefaclor, cefadroxil, cefpodoxime proxetil and cefexime, respectively. The detection limits were 40, 100, 100, 60 and 70 ng/mL, respectively. The performance of the developed method was evaluated in terms of Student's t-test and variance ratio F-test to find out the significance of proposed methods over the reference spectrophotometric method.
2.Species differences in the pharmacokinetics of cefadroxil as determined in wildtype and humanized PepT1 mice.
Hu Y1, Smith DE2. Biochem Pharmacol. 2016 May 1;107:81-90. doi: 10.1016/j.bcp.2016.03.008. Epub 2016 Mar 12.
PepT1 (SLC15A1) is a high-capacity low-affinity transporter that is important in the absorption of digested di/tripeptides from dietary protein in the small intestine. PepT1 is also crucial for the intestinal uptake and absorption of therapeutic agents such as the β-lactam aminocephalosporins and antiviral prodrugs. Species differences, however, have been observed in PepT1-mediated intestinal absorption and pharmacokinetics, thereby, making it more difficult to predict systemic drug exposure. In the present study, we evaluated the in situ intestinal permeability of the PepT1 substrate cefadroxil in wildtype and humanized PepT1 (huPepT1) mice, and the in vivo absorption and disposition of drug after escalating oral doses. The in situ perfusions indicated that cefadroxil had a twofold higher affinity (i.e., twofold lower Km) for jejunal PepT1 in huPepT1 mice, lower but substantial permeability in all regions of the small intestine, and low but measureable permeability in the colon as compared to wildtype animals.
3.Comparison of Extended-Spectrum β-Lactamase (ESBL) CTX-M Genotypes in Franklin Gulls from Canada and Chile.
Bonnedahl J1, Stedt J2, Waldenström J2, Svensson L2, Drobni M3, Olsen B3. PLoS One. 2015 Oct 23;10(10):e0141315. doi: 10.1371/journal.pone.0141315. eCollection 2015.
Migratory birds have been suggested to contribute to long-distance dispersal of antimicrobial resistant bacteria, but tests of this hypothesis are lacking. In this study we determined resistance profiles and genotypes of ESBL-producing bacteria in randomly selected Escherichia coli from Franklin´s gulls (Leucophaeus pipixcan) at breeding sites in Canada and compared with similar data from the gulls' wintering grounds in Chile. Resistant E. coli phenotypes were common, most notably to ampicillin (30.1%) and cefadroxil (15.1%). Furthermore, 17.0% of the gulls in Canada carried ESBL producing bacteria, which is higher than reported from human datasets from the same country. However, compared to gulls sampled in Chile (30.1%) the prevalence of ESBL was much lower. The dominant ESBL variants in Canada were blaCTX-M-14 and blaCTX-M-15 and differed in proportions to the data from Chile. We hypothesize that the observed differences in ESBL variants are more likely linked to recent exposure to bacteria from anthropogenic sources, suggesting high local dissemination of resistant bacteria both at breeding and non-breeding times rather than a significant trans-hemispheric exchange through migrating birds.
4.Study of the Electrophoretic Behavior of Cephalosporins by Capillary Zone Electrophoresis.
Hancu G1, Sasebeşi A1, Rusu A1, Kelemen H1, Ciurba A2. Adv Pharm Bull. 2015 Jun;5(2):223-9. doi: 10.15171/apb.2015.031. Epub 2015 Jun 1.
PURPOSE: The aim of the study was the characterization of the electrophoretic behavior of cephalosporins from different generation having different structural characteristics in order to develop a rapid, simple and efficient capillary electrophoretic method for their identification and simultaneous separation from complex mixtures.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
