| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
| Targets |
Cephalosporin antibiotic; bacterial cell wall synthesis; penicillin binding proteins (PBPs)
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|---|---|
| ln Vitro |
Cephalexin lysine (10 μg/mL) inactivates an enzyme known as penicillin-binding protein (PBP), which disturbs the synthesis of the polymer peptidoglycan (PG) [1]. Numerous Gram-positive and Gram-negative bacteria are inhibited by cephalexin lysine. Bacillus anthracis, Vibrio cholerae, Edwardsiella spp., Pasteurella multocida, Edwardsiella lentus, and Alcaligenes have MIC values of 2. Proteus rettgeri and 2, 2, 2, 4, 4.4, and 5.7 μg/mL, respectively, were found in [2].
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| ln Vivo |
The antibacterial action of cephalexin lysine (0-50 mg/kg; oral; 3.5 hours) was seen against male Swiss-Webster mice infected with microorganisms [2].
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| Enzyme Assay |
Penicillin and related beta-lactams comprise one of our oldest and most widely used antibiotic therapies. These drugs have long been known to target enzymes called penicillin-binding proteins (PBPs) that build the bacterial cell wall. Investigating the downstream consequences of target inhibition and how they contribute to the lethal action of these important drugs, we demonstrate that beta-lactams do more than just inhibit the PBPs as is commonly believed. Rather, they induce a toxic malfunctioning of their target biosynthetic machinery involving a futile cycle of cell wall synthesis and degradation, thereby depleting cellular resources and bolstering their killing activity. Characterization of this mode of action additionally revealed a quality control function for enzymes that cleave bonds in the cell wall matrix. The results thus provide insight into the mechanism of cell wall assembly and suggest how best to interfere with the process for future antibiotic development.[1]
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| Animal Protocol |
Animal/Disease Models: Bacterially infected male Swiss-Webster mice [2]
Doses: 0-50 mg/kg Route of Administration: po (po (oral gavage)) 3.5 hrs (hrs (hours)) Experimental Results: Against Streptococcus pyogenes, Streptococcus pneumoniae, Staphylococcus aureus and several Antimicrobial activity against Gram-negative bacteria in mice. |
| ADME/Pharmacokinetics |
Absorption
Cefaloridine is well absorbed in the upper gastrointestinal tract, with an oral bioavailability approaching 100%. Cefaloridine is not absorbed by the stomach but rather by the upper small intestine. The peak plasma concentration in patients taking 250 mg of Cefaloridine is 7.7 mcg/mL, and in patients taking 500 mg, the peak plasma concentration is 12.3 mcg/mL. Excretion Cefaloridine is excreted in the urine after 6 hours via glomerular filtration and tubular secretion. Over 90% of Cefaloridine is excreted in the urine, with an average urinary recovery rate of 99.3%. Cefaloridine is excreted unchanged in the urine. Volume of Distribution 5.2–5.8 L. Clearance The clearance rate in one subject was 376 mL/min. Less than 10% to 15% of the drug binds to plasma proteins, leading to a rapid decline in plasma drug concentration…Over 90% of the drug is excreted unchanged in the urine within 6 hours, primarily through renal tubular secretion. …Even in patients with impaired renal function, therapeutically effective concentrations can still be achieved in the urine. Cephalexin…is readily absorbed from the gastrointestinal tract. After oral administration of 250 mg and 500 mg, peak plasma drug concentrations are approximately 9 μg/mL and 18 μg/mL, respectively, reached approximately 1 hour after administration. Food intake may delay absorption. Absorption and excretion of cephalexin are impaired in newborns, with 24-hour urinary recovery rates ranging from 5% to 66% of the daily oral dose. Metabolism/Metabolites Cephalexin is not metabolized in the body. Biological Half-Life The half-life of cephalexin is 49.5 minutes on an empty stomach and 76.5 minutes after eating, but the difference between these two time points was not statistically significant in this study. The half-life of cephalexin in the serum of adults with normal renal function is 0.5–1.2 hours. It has been reported that the half-life of cephalexin in the serum of newborns is approximately 5 hours, and in children aged 3–12 months, it is approximately 2.5 hours. One study showed that the half-life in the serum of adults with a creatinine clearance of 9.2 ml/min is 7.7 hours, and in adults with a creatinine clearance of 4 ml/min, it is 13.9 hours. Protein Binding The binding rate of cephalexin to serum proteins (including serum albumin) is 10–15%. |
| Toxicity/Toxicokinetics |
Use of Cephalexin During Pregnancy and Lactation
◉ Overview of Use During Lactation Limited information suggests that low concentrations of cephalexin in breast milk after maternal administration generally do not adversely affect breastfed infants. Cephalexin is an alternative treatment for mastitis. There are reports that cephalosporins occasionally disrupt the infant's gut microbiota, leading to diarrhea or thrush, but these effects have not been fully assessed. There has been one rare case of a severe allergic reaction in an infant who had previously received intravenous cefazolin, and whose mother began taking cephalexin while breastfeeding. Cephalexin use is acceptable for breastfeeding women. ◉ Effects on Breastfed Infants In a prospective follow-up study, seven breastfeeding mothers reported taking cephalexin (dosage not specified). Two of these mothers reported their infants experiencing diarrhea. No rashes or candidiasis were reported in infants exposed to cephalexin. A prospective controlled study surveyed mothers who called the information service center about adverse reactions in their breastfed infants. One in 11 infants exposed to cephalexin reported diarrhea while their mothers were receiving cephalexin treatment. One woman received intravenous cefotaxime 1 gram every 6 hours for 3 days. Her breastfed infant developed green, loose stools, severe diarrhea, discomfort, and crying. The mother's regimen was subsequently changed to oral cephalexin 500 mg plus oral probenecid 500 mg four times daily for 16 days. During this period, the infant continued to have diarrhea. The authors believe the diarrhea may be related to cephalexin in the breast milk. A 4-month-old infant received intravenous cefazolin for a urinary tract infection. Nine days after discharge and discontinuation of cefazolin, the infant developed a vesicular rash covering most of the body and was diagnosed with toxic epidermal necrolysis (TEN). The infant was breastfed by their mother (degree of breastfeeding unknown), who had started taking cephalexin two days before the onset of symptoms. A lymphocyte transformation test performed 4 weeks after the completion of TEN treatment showed that the infant was allergic to both cefazolin and Cefaloridine. The infant's reaction may have been due to initial sensitization to Cefaloridine followed by cross-reaction with cefazolin, resulting in the presence of Cefaloridine in breast milk. ◉ Effects on breastfeeding and breast milk As of the revision date, no relevant published information was found. View more◈ What is Cefaloridine? |
| References | |
| Additional Infomation |
Cephalexin is a semi-synthetic first-generation cephalosporin antibiotic with a methyl group at position 3 and a β-(2R)-2-amino-2-phenylacetamide group at positions 7 of its cephalosporin skeleton. It is effective against both Gram-negative and Gram-positive bacteria and is used to treat skin, respiratory, and urinary tract infections. It is an antibacterial drug. It belongs to the cephalosporin class, is a semi-synthetic derivative, and is also a β-lactam antibiotic allergen. It is the conjugate acid of cephalexin (1-). Cephalexin is a representative of first-generation cephalosporins. This antibiotic contains a β-lactam and dihydrothiazide structure. Cephalexin treats infections caused by a variety of susceptible bacteria by inhibiting cell wall synthesis. Cephalexin was approved by the U.S. Food and Drug Administration (FDA) on January 4, 1971. Anhydrous cephalexin is a cephalosporin antibacterial drug. Cephalexin has been reported to be present in Streptomyces. Cephalexin is a β-lactam antibiotic, belonging to the first-generation cephalosporin class, and possesses bactericidal activity. Cephalexin binds to and inactivates penicillin-binding protein (PBP) located on the inner membrane of the bacterial cell wall. Inactivation of PBP interferes with the cross-linking of peptidoglycan chains, which is crucial for maintaining the strength and rigidity of the bacterial cell wall. This leads to weakening of the bacterial cell wall, ultimately resulting in cell lysis. Compared to second- and third-generation cephalosporins, cephalexin exhibits stronger activity against Gram-positive bacteria and weaker activity against Gram-negative bacteria. Anhydrous cephalexin is the anhydrous form of cephalexin, a semi-synthetic first-generation cephalosporin with antibacterial activity. Cephalexin binds to and inactivates penicillin-binding protein (PBP) located on the inner membrane of the bacterial cell wall. PBP is an enzyme involved in the final stages of bacterial cell wall assembly and in remodeling the cell wall during growth and division. Inactivation of PBP interferes with the cross-linking of peptidoglycan chains, which is crucial for the strength and rigidity of bacterial cell walls. This leads to weakening of the bacterial cell wall and cell lysis. Cephalexin is a semi-synthetic cephalosporin antibiotic with antibacterial activity similar to cefuroxime or cefotaxime, but slightly less potent. It is effective against both Gram-positive and Gram-negative bacteria.
View MoreIndications for Use Cephalexin is indicated for the treatment of certain infections caused by susceptible bacteria. These infections include respiratory tract infections, otitis media, skin and soft tissue infections, bone infections, and genitourinary tract infections.Pharmacodynamics Cephalexin (also known as cephalexin) is a first-generation cephalosporin antibiotic. It is one of the most prescribed antibiotics, commonly used to treat superficial infections caused by minor wounds or lacerations. It is effective against most Gram-positive bacteria by inhibiting the cross-linking reaction between N-acetylmuramic acid and N-acetylglucosamine in the cell wall, leading to cell lysis. Mechanism of Action Cephalexin is a first-generation cephalosporin antibiotic. Cephalosporins contain β-lactam and dihydrothiazide domains. Unlike penicillin, cephalosporins are more resistant to the action of β-lactamases. Cephalexin inhibits bacterial cell wall synthesis, leading to cell wall rupture and ultimately cell death. Cefothiophene and its homologues inhibit bacterial cell wall synthesis in a manner similar to penicillin. Cephalosporin Drugs Penicillin and its metabolites are potent immunogens because they can bind to proteins and act as haptens to trigger an acute antibody-mediated immune response. The most common (approximately 95%) or "major" determinant of penicillin allergy is the penicillin acyl determinant, which arises from the ring-opening of the penicillin β-lactam ring. This allows penicillin to bind to proteins via the amide group. "Minor" determinants (less common) are other metabolites, including native penicillin and penicillinic acid. Penicillins have bactericidal activity; their mechanism of action depends on reaching and binding to penicillin-binding proteins located on the bacterial cell membrane. Cephalosporins may inhibit bacterial septum and cell wall synthesis by acylating membrane-bound transpeptidases. This prevents the cross-linking of peptidoglycan chains, which is crucial for the strength and rigidity of the bacterial cell wall. Furthermore, cell division and growth are also inhibited, and susceptible bacteria frequently lyse and elongate. Rapidly dividing bacteria are most sensitive to the effects of cephalosporins. |
| Molecular Formula |
C16H17N3O4S.C6H14N2O2
|
|---|---|
| Molecular Weight |
493.57644
|
| Exact Mass |
493.199
|
| CAS # |
53950-14-4
|
| Related CAS # |
Cephalexin;15686-71-2;Cephalexin hydrochloride;59695-59-9;Cephalexin monohydrate;23325-78-2;Cephalexin hydrochloride monohydrate;105879-42-3
|
| PubChem CID |
92135907
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| Appearance |
Typically exists as solid at room temperature
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| Hydrogen Bond Donor Count |
6
|
| Hydrogen Bond Acceptor Count |
10
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| Rotatable Bond Count |
9
|
| Heavy Atom Count |
34
|
| Complexity |
706
|
| Defined Atom Stereocenter Count |
4
|
| SMILES |
CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)SC1)C(=O)O.C(CCN)C[C@@H](C(=O)O)N
|
| InChi Key |
CSXICSKZWGBACI-SSDGIDNNSA-N
|
| InChi Code |
InChI=1S/C16H17N3O4S.C6H14N2O2/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9;7-4-2-1-3-5(8)6(9)10/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23);5H,1-4,7-8H2,(H,9,10)/t10-,11-,15-;5-/m10/s1
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| Chemical Name |
(6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(2S)-2,6-diaminohexanoic acid
|
| Synonyms |
53950-14-4; Cephalexin lysinate; (6R,7R)-7-[(2-amino-2-phenylacetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;(2S)-2,6-diaminohexanoic acid; L-lysine compound with (6R,7R)-7-(2-amino-2-phenylacetamido)-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (1:1); L-lysine mono[[6R-[6alpha,7beta(R*)]]-7-[(aminophenylacetyl)amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate]; DTXSID30968760; CSXICSKZWGBACI-ZMZYGIGZSA-N; DB-230587;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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|---|---|
| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.0260 mL | 10.1301 mL | 20.2601 mL | |
| 5 mM | 0.4052 mL | 2.0260 mL | 4.0520 mL | |
| 10 mM | 0.2026 mL | 1.0130 mL | 2.0260 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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