Cefadroxil anhydrous, L- | CAS#144790-28-3 | antibiotic

MedKoo Cat#: 596957 | Name: Cefadroxil anhydrous, L-

Featured

Description:

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

Cefadroxil anhydrous, L- is a broad-spectrum antibiotic of the cephalosporin type, effective in Gram-positive and Gram-negative bacterial infections. It is a bactericidal antibiotic.

Chemical Structure

Cefadroxil anhydrous, L-

CAS#144790-28-3

Theoretical Analysis

MedKoo Cat#: 596957

Name: Cefadroxil anhydrous, L-

CAS#: 144790-28-3

Chemical Formula: C16H17N3O5S

Exact Mass: 363.0889

Molecular Weight: 363.38

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

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 1,850.00	2 Weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

No Data

Synonym

Cefadroxil anhydrous, L-; Cefadroxil, L-; Cefadroxil; L-Cefadroxil

IUPAC/Chemical Name

(6R,7R)-7-[(S)-2-Amino-2-(4-hydroxyphenyl)acetamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

InChi Key

BOEGTKLJZSQCCD-FIXISWKDSA-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+/m0/s1

SMILES Code

O=C(C(N12)=C(C)CS[C@]2([H])[C@H](NC([C@@H](N)C3=CC=C(O)C=C3)=O)C1=O)O

Appearance

Solid powder

Purity

>98% (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

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 363.38 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.

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 B, Ji K, Kho Y, Kim PG, Park K, Kim K, Kim Y, Kim KT, Choi K. Effects of chronic exposure to cefadroxil and cefradine on Daphnia magna and Oryzias latipes. Chemosphere. 2017 Oct;185:844-851. doi: 10.1016/j.chemosphere.2017.07.085. Epub 2017 Jul 17. PubMed PMID: 28735237. 2: Stelzl T, Baranov T, Geillinger KE, Kottra G, Daniel H. Effect of N-glycosylation on the transport activity of the peptide transporter PEPT1. Am J Physiol Gastrointest Liver Physiol. 2016 Jan 15;310(2):G128-41. doi: 10.1152/ajpgi.00350.2015. Epub 2015 Nov 19. PubMed PMID: 26585416. 3: Zhou CM, Hu BJ, Gao XD, Bao R, Xie HM, Huang SL, Tao LL, He LX. [Antimicrobial susceptibility of community-acquired respiratory tract pathogens isolated from patients in primary hospitals in Shanghai from 2007 to 2010]. Zhonghua Jie He He Hu Xi Za Zhi. 2013 May;36(5):346-50. Chinese. PubMed PMID: 24047808. 4: Pan J, Wang L, Li D, Ye L. [Synthesis of cefatrizine by recombinant alpha-amino acid ester hydrolase]. Sheng Wu Gong Cheng Xue Bao. 2013 Apr;29(4):501-9. Chinese. PubMed PMID: 23894823. 5: Yang B, Smith DE. Significance of peptide transporter 1 in the intestinal permeability of valacyclovir in wild-type and PepT1 knockout mice. Drug Metab Dispos. 2013 Mar;41(3):608-14. doi: 10.1124/dmd.112.049239. Epub 2012 Dec 21. PubMed PMID: 23264448; PubMed Central PMCID: PMC3583488. 6: Posada MM, Smith DE. Relevance of PepT1 in the intestinal permeability and oral absorption of cefadroxil. Pharm Res. 2013 Apr;30(4):1017-25. doi: 10.1007/s11095-012-0937-8. Epub 2012 Dec 7. PubMed PMID: 23224978; PubMed Central PMCID: PMC3596500. 7: Jang SE, Jung IH, Joh EH, Han MJ, Kim DH. Antibiotics attenuate anti-scratching behavioral effect of ginsenoside Re in mice. J Ethnopharmacol. 2012 Jun 26;142(1):105-112. PubMed PMID: 22855946. 8: Hu Y, Chen X, Smith DE. Species-dependent uptake of glycylsarcosine but not oseltamivir in Pichia pastoris expressing the rat, mouse, and human intestinal peptide transporter PEPT1. Drug Metab Dispos. 2012 Jul;40(7):1328-35. doi: 10.1124/dmd.111.044263. Epub 2012 Apr 9. PubMed PMID: 22490229; PubMed Central PMCID: PMC3382839. 9: Wang Z, Song Z, Chen D. Study on the binding behavior of bovine serum albumin with cephalosporin analogues by chemiluminescence method. Talanta. 2010 Dec 15;83(2):312-9. doi: 10.1016/j.talanta.2010.09.029. Epub 2010 Sep 24. PubMed PMID: 21111139. 10: Xiang J, Jiang H, Hu Y, Smith DE, Keep RF. Kyotorphin transport and metabolism in rat and mouse neonatal astrocytes. Brain Res. 2010 Aug 6;1347:11-8. doi: 10.1016/j.brainres.2010.05.094. Epub 2010 Jun 9. PubMed PMID: 20537989; PubMed Central PMCID: PMC2913889. 11: Liu YM, Xuan CS, Li WY, Feng J. [Study of cefadroxil and cephradine charge transfer process by fluorescence quenching method]. Guang Pu Xue Yu Guang Pu Fen Xi. 2009 Feb;29(2):441-5. Chinese. PubMed PMID: 19445223. 12: Auda SH, Mrestani Y, Ahmed AM, Neubert RH. Characterization of the interaction of cefadroxil with different metal ions using CE. Electrophoresis. 2009 Mar;30(6):1066-70. doi: 10.1002/elps.200800436. PubMed PMID: 19229848. 13: Shoukry MM, Hosny WM, Razik AA, Mohamed RA. Coordination properties of cefadroxil antibiotic: synthesis and equilibrium studies of the binary and ternary complexes involving amino acids and DNA units. Talanta. 1997 Nov;44(11):2109-19. PubMed PMID: 18966960. 14: Knütter I, Hartrodt B, Tóth G, Keresztes A, Kottra G, Mrestani-Klaus C, Born I, Daniel H, Neubert K, Brandsch M. Synthesis and characterization of a new and radiolabeled high-affinity substrate for H+/peptide cotransporters. FEBS J. 2007 Nov;274(22):5905-14. Epub 2007 Oct 18. PubMed PMID: 17944948. 15: Lin H, King N. Demonstration of functional dipeptide transport with expression of PEPT2 in guinea pig cardiomyocytes. Pflugers Arch. 2007 Mar;453(6):915-22. Epub 2006 Nov 21. PubMed PMID: 17120020. 16: Li Y, Lu J. Chemiluminescence flow-injection analysis of beta-lactam antibiotics using the luminol-permanganate reaction. Luminescence. 2006 Jul-Aug;21(4):251-5. PubMed PMID: 16791833. 17: Thongpoon C, Liawruangrath B, Liawruangrath S, Wheatley RA, Townshend A. Flow injection chemiluminescence determination of cefadroxil using potassium permanganate and formaldehyde system. J Pharm Biomed Anal. 2006 Sep 18;42(2):277-82. PubMed PMID: 16766156. 18: Makchit J, Upalee S, Thongpoon C, Liawruangrath B, Liawruangrath S. Determination of cefadroxil by sequential injection with spectrophotometric detector. Anal Sci. 2006 Apr;22(4):591-7. PubMed PMID: 16760604. 19: Liu H, Yu A, Liu F, Shi Y, Han L, Chen Y. Chiral separation of cefadroxil by capillary electrochromatography. J Pharm Biomed Anal. 2006 Jun 16;41(4):1376-9. Epub 2006 Apr 4. PubMed PMID: 16600557. 20: Rühl A, Hoppe S, Frey I, Daniel H, Schemann M. Functional expression of the peptide transporter PEPT2 in the mammalian enteric nervous system. J Comp Neurol. 2005 Sep 12;490(1):1-11. PubMed PMID: 16041713.