15686-71-2 Usage
Description
Different sources of media describe the Description of 15686-71-2 differently. You can refer to the following data:
1. Cephalexin is a cephalosporin antibiotic that is used to examine the impact of binding, expression, and inhibition of PBP3 as well as additional penicillin-binding proteins (PBPs) on the cell wall during bacterial mucopeptide synthesis. Cephalexin is used for the treatment of infection-causing bacteria that may induce ear, respiratory, urinary tract, and skin infections. Bacteria that are defenseless against Cephalexin may include Streptococcus pneumonia, Staphylococcus aureus, E. coli, and Haemophilus influenza. Cephalexin is also referred to as Keflex (brand name), and it does not relieve viral infections such as flu or colds.
2. Use of the ampicillin-type side chain conveys oral activity to cephalexin. Whereas it no longer has an
activating side chain at C-3 and, as a consequence, is somewhat less potent, it does not undergo metabolic
deactivation and, thus, maintains potency. It is rapidly and completely absorbed from the GI tract and has
become quite popular. Somewhat puzzling is the fact that the use of the ampicillin side chain in the
cephalosporins does not result in a comparable shift in antimicrobial spectrum. Cephalexin, like the other
first-generation cephalosporins is active against many Gram-positive aerobic cocci but is limited against
Gram-negative bacteria. It is a widely used drug, particularly against Gram-negative bacteria causing urinary
tract infections, Gram-positive infections (Staphyl ococcus aureus, Streptococcus pneumoni ae and
Streptococcus pyogenes) of soft tissues, pharyngitis, and minor wounds.
Indications
Cephalexin is prescribed for the treatment of otitis media, genitourinary, bone, respiratory, and skin structure infections.
Mechanism of Action
The mechanism of action of Cephalexin resembles that of penicillin where it inhibits synthesis of the bacterial cell wall, its absence influences death as a result of bacterial lysis. Cell lysis is further mediated by autolytic enzymes particular to the bacterial cell wall, which includes autolysis. Research indicates that there is a probability that Cephalexin impedes the functionality of an autolysin inhibitor.
Brand Name(s) in US
Keflex and generic forms
Pharmacodynamics
Cephalexin is a 1st generation cephalosporin antibiotic that is widely prescribed for the treatment of external infections that may arise from complications associated with lacerations or minor wounds. The drug is effective in fighting a majority of gram-positive bacteria.
Cephalexin illustrates vitro activity that opposes methicillin-susceptible Staphylococcus aureus, a notable pathogen in osteoarticular infections. However, pharmacodynamics and pharmacokinetics are inadequately defined in children.
Interactions
Cephalexin may minimize the impact of typhoid and BCG vaccines. Notably, these three drugs should not be administered at the same time. Patients are also advised to take the drug on an empty stomach at least 1-2 hours after meals.
Uses
Different sources of media describe the Uses of 15686-71-2 differently. You can refer to the following data:
1. Cephalexin is administered to minimize the development of bacteria that are resistant to drugs. To maintain the overall effectiveness of Cephalexin, the drug should be prescribed as a treatment for infections that can be attributed to bacteria. The availability of susceptibility and culture information should be put into consideration while making modifications to antibacterial therapy. The absence of such information may be backed by susceptibility and epidemiology patterns to influence verifiable adoption of treatment.
In some cases, Cephalexin is used for the treatment of patients who are allergic to penicillin and may have a heart condition at the time when they are undergoing a procedure on their respiratory tract, to inhibit the development of infection on their heart valves.
2. Antibacterial.
Dosing Information
A standard dose of Cephalexin should be administered orally in 250mg every 6 hours. Alternatively, in 12 hours, a dose of 500mg should be administered to the patient during the 7-14days treatment period. In instances where the infections are severe, higher doses up to 4g should be administered in 2-4 equal does every day.
For pediatric patients, the appropriate daily dose of Cephalexin is 25-40mg/kg administered in equal doses for a period of 7-14days. Severe infections may necessitate 50-100mg/kg administered in equal doses.
The treatment of Otitis media necessitates 75-100mg/kg in equal doses of Cephalexin. For patients with renal impairments, the dosage requirements may be adjusted accordingly for both pediatric and adult patients.
Elimination
Cephalexin undergoes tubular secretion and glomerular filtration before it is eliminated in urine. Studies indicate that about 90% of Cephalexin is eliminated in its unaltered form in urine within 8 hours.
Side effects
Different sources of media describe the Side effects of 15686-71-2 differently. You can refer to the following data:
1. Allergic reactions to Cephalexin may result in respiratory issues, swelling of the tongue, lips, face, or the throat, and hives. Nonetheless, one may need to consult a doctor if they experience watery diarrhea or intense stomach pains, unusual bleeding or easy bruising, minimal or no urination, hallucinations, confusion or agitation, and severe skin reaction.
Common side effects associated with Cephalexin include vaginal discharge or itching, skin rash, fever, nausea, vomiting, joint pain, headache, feeling of exhaustion, dizziness, or diarrhea.
2. Nausea, vomiting and abdominal discomfort are relatively
common. Pseudomembranous colitis has been described and
overgrowth of Candida with vaginitis may be troublesome.
Otherwise, mild hypersensitivity reactions and biochemical
changes common to cephalosporins occur. Very rare neurological
disturbances have been described, particularly in patients
in whom very high plasma levels have been achieved. There
are rare reports of Stevens–Johnson syndrome and toxic epidermal
necrolysis.
Safety Precautions
A patient should inform the pharmacist or doctor of any allergic reactions to Cephalexin, associated cephalosporin antibiotics, and additional ingredients or medications. The patient should also indicate any nutritional supplements, vitamins, herbal products or medications they are taking or they are planning to take. It is important to notify the doctor of a preexisting liver, kidney or gastrointestinal disease, especially colitis, if one is either pregnant or planning on getting pregnant, and if they conceive while taking Cephalexin.
If Cephalexin is prescribed to a patient with no clear indications of a bacterial infection, there are minimal chances that the drug will benefit the patient. Instead, it will increase the patient’s chances of developing drug-resistant bacteria.
Using Cephalexin over extended periods of time may induce the overgrowth of non-susceptible organisms. Doctors should examine their patients for superinfections during therapy for the implementation of appropriate treatment measures.
Chemical Properties
White cryst. powder
Originator
Ceporex,Glaxo,UK,1970
Definition
ChEBI: A semisynthetic first-generation cephalosporin antibiotic having methyl and beta-(2R)-2-amino-2-phenylacetamido groups at the 3- and 7- of the cephem skeleton, respectively. It is effective against both Gram-negative and G
am-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract.
Manufacturing Process
To a 1 liter flask containing dimethylformamide at 0°C, was added 24.8 g
sodium N-(2-methoxycarbonyl-1-methylvinyl)-D-α-phenylglycine (prepared
from sodium D-α-phenylglycine and methyl acetoacetate). The mixture was
cooled to -40°C and methyl chloroformate (7.5 ml) and dimethylbenzylamine
(0.26 ml) added. After stirring for 25 minutes, p-nitrobenzyl 7-
aminodesacetoxycephalosporanate (32.8 g) in the form of its hydrochloride
salt was added, followed by triethylamine (12.1 ml) and dimethylformamide
(140 ml) over a period of 20 minutes. The reaction mixture was stirred for 2
hours at -25°C to -35°C, then warmed to 0°C and water (32 ml) added. To
the resultant solution, hydrochloric acid (54 ml) was added followed by zinc
(21.8 g) in portions over a period of 5 minutes, the temperature being
maintained at 5°C to 10°C. Further hydrochloric acid (35 ml) was added and
the solution stirred at 15°C to 20°C for 7 hours.
The pH was adjusted to 3.3 with triethylamine and
semicarbazidehydrochloride (9.5 g) added. The mixture was brought back to
pH 3 with further triethylamine, then stirred for 30 minutes at pH 3. The
resultant mixture was adjusted slowly over 4 hours to pH 6.8 by addition of
triethylamine, seeding being carried out when pH 4.5 was reached. The precipitated cephalexin was filtered off, washed with dimethylformamide (200
ml) and the cephalexin recovered, yield 75%.
Brand name
Keflex (Panixine (Ranbaxy).
Therapeutic Function
Antibiotic
Antimicrobial activity
It is resistant to staphylococcal β-lactamase. Gram-positive
rods and fastidious Gram-negative bacilli, such as Bordetella
spp. and H. influenzae, are relatively resistant. It is active
against a range of enterobacteria, but it is degraded by
many enterobacterial β-lactamases. Citrobacter, Edwardsiella,
Enterobacter, Hafnia, Providencia and Serratia spp. are all
resistant. Gram-negative anaerobes other than B. fragilis are
susceptible. Because of its mode of action it is only
slowly bactericidal to Gram-negative bacilli.
Pharmacokinetics
Oral absorption: >90%
Cmax 500 mg oral: c. 10–20 mg/L after 1 h
Plasma half-life: 0.5–1 h
Volume of distribution: 15 L
Plasma protein binding: 10–15%
Absorption and distribution
It is almost completely absorbed when given by mouth, the
peak concentration being delayed by food. Intramuscular
preparations are not available: injection is painful and produces
delayed peak plasma concentrations considerably lower
than those obtained by oral administration.
In synovial fluid, levels of 6–38 mg/L have been described
after a 4 g oral dose, but penetration into the CSF is poor.
Useful levels are achieved in bone (9–44 mg/kg after 1 g orally)
and in purulent sputum. Concentrations of 10–20 mg/L have
been found in breast milk. Concentrations in cord blood
following a maternal oral dose of 0.25 g were minimal.
Metabolism and excretion
It is not metabolized. Almost all the dose is recoverable from
the urine within the first 6 h, producing urinary concentrations
exceeding 1 g/L. The involvement of tubular secretion
is indicated by the increased plasma peak concentration and
reduced urinary excretion produced by probenecid. Renal
clearance is around 200 mL/min and is depressed in renal
failure, although a therapeutic concentration is still obtained
in the urine. It is removed by peritoneal and hemodialysis.
Some is excreted in the bile, in which therapeutic concentrations
may be achieved.
Clinical Use
Different sources of media describe the Clinical Use of 15686-71-2 differently. You can refer to the following data:
1. Cephalexin, 7α-(D-amino-α-phenylacetamido)-3-methylcephemcarboxylicacid (Keflex, Keforal), was designed purposelyas an orally active, semisynthetic cephalosporin. Theoral inactivation of cephalosporins has been attributed to twocauses: instability of the β-lactam ring to acid hydrolysis(cephalothin and cephaloridine) and solvolysis or microbialtransformation of the 3-methylacetoxy group (cephalothin,cephaloglycin). The α-amino group of cephalexin renders itacid stable, and reduction of the 3-acetoxymethyl to a methylgroup circumvents reaction at that site.Cephalexin occurs as a white crystalline monohydrate. Itis freely soluble in water, resistant to acid, and absorbed wellorally. Food does not interfere with its absorption. Becauseof minimal protein binding and nearly exclusive renal excretion,cephalexin is recommended particularly for the treatmentof urinary tract infections. It is also sometimes used forupper respiratory tract infections. Its spectrum of activity isvery similar to those of cephalothin and cephaloridine.Cephalexin is somewhat less potent than these two agentsafter parenteral administration and, therefore, is inferior tothem for the treatment of serious systemic infections.
2. As for group 2 cephalosporins . It should not be used
in infections in which H. influenzae is, or is likely to be, implicated.
It should not be used as an alternative to penicillin in
syphilis.
Safety Profile
Poison by intraperitoneal route.Moderately toxic by ingestion and other routes. An experimental teratogen. Other experimental reproductiveeffects. Human systemic effects by ingestion: nausea,vomiting, and diarrhea. When heated to decomposition itemits
Synthesis
Cephalexin is synthesized from cephalophenylglycine (32.1.2.9),
which is synthesized by reacting 7-aminocephalosporanic acid with a mixed anhydride synthesized by reacting N-carbobenzoxyphenylglycine and isobutyl chloroformate in the presence of triethylamine. Removing the N-carbobenzoxy protective group from the resulting
product (32.1.2.8) using hydrogen and a palladium on carbon catalyst gives cephalophenylglycine (32.1.2.9) in the form of an internal salt. Reducing this product with hydrogen using
a palladium on barium sulfate catalyst results in the deacetoxylation at the third position of
7-aminocephalosporanic acid, making the desired cephalexin (32.1.2.10).
Veterinary Drugs and Treatments
There are no approved cephalexin products for veterinary use in the
USA. However, it has been used clinically in dogs, cats, horses, rabbits,
ferrets, and birds, particularly for susceptible Staphylococcal
infections.
Drug interactions
Potentially hazardous interactions with other drugs
Anticoagulants: effects of coumarins may be
enhanced.
Metabolism
Cefalexin is not metabolised. About 80% or more of a
dose is excreted unchanged in the urine in the first 6
hours by glomerular filtration and tubular secretion.
Probenecid delays urinary excretion. Therapeutically
effective concentrations may be found in the bile and
some may be excreted by this route.
Check Digit Verification of cas no
The CAS Registry Mumber 15686-71-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,5,6,8 and 6 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 15686-71:
(7*1)+(6*5)+(5*6)+(4*8)+(3*6)+(2*7)+(1*1)=132
132 % 10 = 2
So 15686-71-2 is a valid CAS Registry Number.
InChI:InChI=1/C16H17N3O4S.H2O/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;/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23);1H2/t10-,11-,15-;/m1./s1
15686-71-2Relevant articles and documents
Preparation method of cefalexin
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Paragraph 0048-0051, (2020/05/05)
The invention belongs to the field of medicine synthesis, in particular to an improved method of a beta-lactam antibiotic cefalexin synthesis process. According to the method, 7-ADCA is used as a rawmaterial and is protected by carboxyl silane; after activation with alpha-aminophenylacetic acid hydrochloride and trifluoroacetic acid succinimide, condensation reaction is carried out; cefalexin isobtained through hydrolysis after-treatment, the proper pH value is controlled through hydrochloric acid after organic solvent and alkali adjustment treatment, and cefalexin crystals with extremely high purity are obtained. The method has the advantages of being easy and convenient to operate, mild in reaction condition, not prone to causing side reaction and capable of effectively removing impurities and preparing high-purity cefalexin.
MANUFACTURING METHOD AND APPARATUS OF ULTRAFINE PARTICLES HAVING UNIFORM PARTICLE SIZE DISTRIBUTION
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, (2011/09/14)
The present invention relates to a novel technology for forming fine particles with a size of 0.02?3 microns from a solid that can be dissolved in a liquid solvent and is not decomposed by heat. The particle preparation technology according to the present invention may be applicable to the fields of food, cosmetics, biopolymer, polymer compositions, and pharmaceuticals.
Synthesis of cephalosporin-type antibiotics by coupling of their β-lactam nucleus and racemic amino acid side chains using a clathration-induced asymmetric transformation
Kemperman, Gerardus J.,Zhu, Jie,Klunder, Antonius J. H.,Zwanenburg, Binne
, p. 1817 - 1820 (2007/10/03)
The cephalosporin-type antibiotics Cephalexin, Cephradine and Cefadroxil have been prepared by coupling of their β-lactam nucleus and racemic amino acid side chain precursors. The initially obtained mixture of cephalosporin epimers is subjected to a clathration-induced asymmetric transformation which results in the epimerization of the epi-cephalosporin into the cephalosporin with the correct diastereomeric configuration.
