MedKoo Biosciences, Inc.
Tel:   +1-919-636-5577    Fax:   +1-919-980-4831    Email:   sales@medkoo.com
Search
Login Register
Search
MedKoo Cat#: 317380 | Name: Cefadroxil
Featured

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cefadroxil is a broad-spectrum antibiotic of the cephalosporin type, effective in Gram-positive and Gram-negative bacterial infections. It is a bactericidal antibiotic. Cefadroxil is a semi-synthetic, beta-lactam, first-generation cephalosporin antibiotic with bactericidal activity. Cefadroxil binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. PBPs are enzymes involved in the terminal stages of assembling the bacterial cell wall and in reshaping the cell wall during growth and division. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This results in the weakening of the bacterial cell wall and causes cell lysis.

Chemical Structure

Cefadroxil
CAS#50370-12-2 (free acid)

Theoretical Analysis

MedKoo Cat#: 317380

Name: Cefadroxil

CAS#: 50370-12-2 (free acid)

Chemical Formula: C16H17N3O5S

Exact Mass: 363.0889

Molecular Weight: 363.39

Elemental Analysis: C, 52.88; H, 4.72; N, 11.56; O, 22.01; S, 8.82

Price and Availability

Size Price Availability Quantity
1g USD 250.00 2 Weeks
5g USD 550.00 2 Weeks
10g USD 850.00 2 Weeks
Bulk Inquiry
Buy Now
Add to Cart
Related CAS #
50370-12-2 (free acid) 66592-87-8 (hydrate) 42284-83-3 (sodium)
Synonym
Cefadroxil; Cefadroxil anhydrous; Cephadroxil; Cefadroxilo; Cefadroxilum; D-Cefadroxil; Duricef; Monohydrate, Cefadroxil; S 578; S-578; S578; Ultracef; Cefadroxil; Cefadroxil Anhydrous; Cefadroxil Monohydrate; Cephadroxyl;
IUPAC/Chemical 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
InChi Key
BOEGTKLJZSQCCD-UEKVPHQBSA-N
InChi Code
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
SMILES Code
CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)SC1)C(=O)O
Appearance
Solid powder
Purity
>97% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Cefadroxil is a broad-spectrum antibiotic of the cephalosporin type, effective in Gram-positive and Gram-negative bacterial infections.
In vitro activity:
Minimum inhibitory concentrations (MICs) of cefadroxil were determined for 749 defined clinically-significant bacteria isolated in a London teaching hospital and for 63 strains from an international collection of Gram-negative bacilli. Assuming a breakpoint of 16 mg/l, for the hospital isolates 81.8% of Gram-negative bacilli and 83.4% of Gram-positive cocci were sensitive. No significant difference between in-patient, out-patient or community-acquired isolates was found. Ninety-five and a half per cent of Escherichia coli, Klebsiella aerogenes (including gentamicin-resistant strains), Proteus mirabilis, and (with the exception of Streptococcus faecalis and methicillin-resistant Staphylococcus aureus) all Gram-positive cocci were sensitive. Of 41 strains of Enterobacter spp., were resistant. Most indole-positive Proteus, and all Serratia and Acinetobacter spp. were resistant, including 36 additional strains taken from an international collection. Of 30 strains of Haemophilus influenzae, only six had MICs of 16 mg/l or less. For disc susceptibility testing, the standard disc containing 30 micrograms of cefadroxil reliably gave zones of greater than 17 mm for organisms with MICs of less than 16 mg/l. A zone of less than 14 mm corresponded to MICs of greater than 64 mg/l. Despite a lack of controlled clinical trials, the results of this study (taken with favourable pharmacokinetics) suggest that cefadroxil has potential as an oral cephalosporin in hospital practice in the U.K. Reference: J Antimicrob Chemother. 1987 May;19(5):597-603. https://academic.oup.com/jac/article-lookup/doi/10.1093/jac/19.5.597
In vivo activity:
In the present study, 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 was evaluated. 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. The in vivo experiments indicated almost superimposable pharmacokinetic profiles between the two genotypes after intravenous bolus dosing of cefadroxil. In contrast, after oral dose escalation, the systemic exposure of cefadroxil was reduced in huPepT1 mice as compared to wildtype animals. Moreover, the AUC and Cmax versus dose relationships were nonlinear for huPepT1 but not wildtype mice, and similar to that observed from human subjects. In conclusion, our findings indicate that huPepT1 mice may provide a valuable tool in the drug discovery process by better predicting the oral pharmacokinetic profiles of PepT1 substrates in humans. Reference: Biochem Pharmacol. 2016 May 1;107:81-90. https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/26979860/
Solvent mg/mL mM comments
Solubility
Water 9.2 25.23
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 363.39 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
1. Casewell MW, Bragman SG. The in-vitro activity of cefadroxil, and the interpretation of disc-susceptibility testing. J Antimicrob Chemother. 1987 May;19(5):597-603. doi: 10.1093/jac/19.5.597. PMID: 3610900.
In vivo protocol:
1. Hu Y, Smith DE. Species differences in the pharmacokinetics of cefadroxil as determined in wildtype and humanized PepT1 mice. Biochem Pharmacol. 2016 May 1;107:81-90. doi: 10.1016/j.bcp.2016.03.008. Epub 2016 Mar 12. PMID: 26979860; PMCID: PMC4821691. 2. Hu Y, Smith DE. In Silico Prediction of the Absorption and Disposition of Cefadroxil in Humans using an Intestinal Permeability Method Scaled from Humanized PepT1 Mice. Drug Metab Dispos. 2019 Mar;47(3):173-183. doi: 10.1124/dmd.118.084236. Epub 2018 Dec 28. PMID: 30593545; PMCID: PMC6367690.
1: Kim EJ, Kim JE, Ro YS, Ko JY. Cefaclor-Induced Generalized Fixed Drug Eruption. Ann Dermatol. 2015 Aug;27(4):465-6. doi: 10.5021/ad.2015.27.4.465. Epub 2015 Jul 29. PubMed PMID: 26273172; PubMed Central PMCID: PMC4530166. 2: Qian JQ, Correra TC, Li J, Maître P, Song DQ, Hu CQ. Differentiation of cefaclor and its delta-3 isomer by electrospray mass spectrometry, infrared multiple photon dissociation spectroscopy and theoretical calculations. J Mass Spectrom. 2015 Jan;50(1):265-9. doi: 10.1002/jms.3510. PubMed PMID: 25601701. 3: Thomas PW, Cammarata M, Brodbelt JS, Fast W. Covalent inhibition of New Delhi metallo-β-lactamase-1 (NDM-1) by cefaclor. Chembiochem. 2014 Nov 24;15(17):2541-8. doi: 10.1002/cbic.201402268. Epub 2014 Oct 10. PubMed PMID: 25302694. 4: Yoo HS, Kim SH, Kwon HS, Kim TB, Nam YH, Ye YM, Park HS. Immunologic evaluation of immediate hypersensitivity to cefaclor. Yonsei Med J. 2014 Nov;55(6):1473-83. doi: 10.3349/ymj.2014.55.6.1473. PubMed PMID: 25323882; PubMed Central PMCID: PMC4205685. 5: Huang C, Wang W, Miao L. Determination of cefaclor by UPLC-MS-MS for a Chinese pharmacokinetic study. J Chromatogr Sci. 2014 Aug;52(7):636-40. doi: 10.1093/chromsci/bmt092. Epub 2013 Jul 9. PubMed PMID: 23839802. 6: Vetter F, Pohl J, Pohl B, Bracher F. Analysis of cefaclor in novel chocolate-based camouflage capsules. Pharmazie. 2014 Jun;69(6):455-7. PubMed PMID: 24974581. 7: van de Streek J, Rantanen J, Bond AD. Structures of cefradine dihydrate and cefaclor dihydrate from DFT-D calculations. Acta Crystallogr C. 2013 Nov;69(Pt 11):1229-33. doi: 10.1107/S0108270113026863. Epub 2013 Oct 19. PubMed PMID: 24192164. 8: Lutfullah, Khan F, Rahman N. Solid phase extraction and determination of Cr(III) by spectrophotometry using cefaclor as a complexing reagent and FAAS. Environ Monit Assess. 2013 Jun;185(6):4959-67. doi: 10.1007/s10661-012-2917-1. Epub 2012 Oct 7. PubMed PMID: 23054281. 9: Zhang Z, Xiang Y, Wang B, Chen H, Cai X, Wang X, Mei L, Zheng Y. Intestinal mucosal permeability of children with cefaclor-associated serum sickness-like reactions. Eur J Pediatr. 2013 Apr;172(4):537-43. doi: 10.1007/s00431-012-1926-y. Epub 2013 Jan 8. PubMed PMID: 23296953. 10: Rasool BK, Fahmy SA. Development of coated beads for oral controlled delivery of cefaclor: In vitro evaluation. Acta Pharm. 2013 Mar;63(1):31-44. doi: 10.2478/acph-2013-0003. PubMed PMID: 23482311. 11: Bottaro G, Biasci P, Lo Giudice M, Mele G, Montanari G, Napoleone E, Santucci A, Tucci PL, Fano M, Biraghi MG. [5 days Cefaclor vs. 10 days amoxicillin/clavulanate in the treatment of childhood streptococcal pharyngitis. Data from a randomized clinical trial]. Minerva Pediatr. 2012 Jun;64(3):341-6. Italian. PubMed PMID: 22555328. 12: Chen J, Jiang B, Lou H, Yu L, Ruan Z. Bioequivalence studies of 2 oral cefaclor capsule formulations in chinese healthy subjects. Arzneimittelforschung. 2012 Mar;62(3):134-7. doi: 10.1055/s-0031-1298012. Epub 2012 Jan 27. PubMed PMID: 22286978. 13: Tarawneh KA, Halasah ZA, Khleifat AM, Batarseh MI, Khleifat KM, Al-Mustafa AH. Evaluation of cefaclor oral suspensions stability using reversed phase high performance liquid chromatography and antimicrobial diffusion methods. Pak J Pharm Sci. 2011 Jul;24(3):303-13. PubMed PMID: 21715263. 14: Tristram SG, Littlejohn R, Bradbury RS. blaROB-1 presence on pB1000 in Haemophilus influenzae is widespread, and variable cefaclor resistance is associated with altered penicillin-binding proteins. Antimicrob Agents Chemother. 2010 Nov;54(11):4945-7. doi: 10.1128/AAC.00263-10. Epub 2010 Aug 16. PubMed PMID: 20713676; PubMed Central PMCID: PMC2976118. 15: Endo R, Yamane N, Tamayose MH, Uchibori KK, Nakasone I. [A simple disk diffusion test to identify beta-lactamase-negative, ampicillin-resistant Haemophilus influenzae--application of cephalexin, cefsulodin and cefaclor disks]. Rinsho Byori. 2010 Oct;58(10):963-71. Japanese. PubMed PMID: 21077285. 16: Li JM, Li C, Jiang Y, Ren SM. Pretreatment of plasma samples by a novel hollow fiber centrifugal ultrafiltrate device for the determination of cefaclor concentrations in human plasma. J Chromatogr A. 2010 Oct 29;1217(44):6824-8. doi: 10.1016/j.chroma.2010.08.059. Epub 2010 Sep 20. PubMed PMID: 20863507. 17: Cefaclor: serum sickness. Prescrire Int. 2010 Apr;19(106):75. PubMed PMID: 20568494. 18: Ma J, Bellon M, Wishart JM, Young RL, Jones KL, Horowitz M, Rayner CK. Effects of cefaclor on gastric emptying and cholecystokinin release in healthy humans. Regul Pept. 2010 Jan 8;159(1-3):156-9. doi: 10.1016/j.regpep.2009.11.009. Epub . PubMed PMID: 19914303. 19: Medenecka B, Jelińska A, Zajac M, Bałdyka M, Juszkiewicz K, Oszczapowicz I. Stability of the crystalline form of cefaclor monohydrate and its pharmaceutical preparations. Acta Pol Pharm. 2009 Sep-Oct;66(5):563-9. PubMed PMID: 19894653. 20: Novembre E, Mori F, Pucci N, Bernardini R, Romano A. Cefaclor anaphylaxis in children. Allergy. 2009 Aug;64(8):1233-5. doi: 10.1111/j.1398-9995.2009.02043.x. Epub 2009 Apr 6. PubMed PMID: 19385950.