Description Indications Mechanism of Action Brand Name(s) in US Pharmacodynamics Interactions Uses Dosing Information Elimination Side effects Safety Precautions
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Cephalexin

Description Indications Mechanism of Action Brand Name(s) in US Pharmacodynamics Interactions Uses Dosing Information Elimination Side effects Safety Precautions
Product Name
Cephalexin
CAS No.
15686-71-2
Chemical Name
Cephalexin
Synonyms
cex;s6437;syncl;oracef;oroxin;keforal;larixin;CEPOREX;Cefadal;Cefadin
CBNumber
CB1210543
Molecular Formula
C16H17N3O4S
Formula Weight
347.39
MOL File
15686-71-2.mol
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Cephalexin Property

Melting point:
196-198°C
alpha 
[α]D20 +144~+158° (c=0.5, H2O) (Calculated on dehydrous basis)
Boiling point:
727.4±60.0 °C(Predicted)
Density 
1.3040 (rough estimate)
refractive index 
1.6320 (estimate)
storage temp. 
Keep in dark place,Inert atmosphere,2-8°C
solubility 
NH4OH 1 M: 50 mg/mL, clear, yellow
pka
5.2, 7.3(at 25℃)
form 
neat
PH
pH (5g/l, 25℃) 3.5~5.5
Water Solubility 
12.5g/L(25 ºC)
Merck 
13,1986
InChIKey
AVGYWQBCYZHHPN-CYJZLJNKSA-N
CAS DataBase Reference
15686-71-2(CAS DataBase Reference)
EPA Substance Registry System
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-, (6R,7R)- (15686-71-2)
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Safety

Hazard Codes 
Xn
Risk Statements 
42/43
Safety Statements 
22-36/37-45
WGK Germany 
3
RTECS 
XI0350000
HS Code 
29419000
Hazardous Substances Data
15686-71-2(Hazardous Substances Data)
Toxicity
TDLo orl-hmn: 14 mg/kg/D:GIT AACHAX -,361,68
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H318Causes serious eye damage

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

H401Toxic to aquatic life

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
33989
Product name
Cefalexin
Purity
VETRANAL
Packaging
100mg-r
Price
$92.1
Updated
2020/08/18
Sigma-Aldrich
Product number
C4895
Product name
Cephalexin hydrate
Purity
first-generation cephalosporin antibiotic
Packaging
5g
Price
$121
Updated
2018/11/20
Sigma-Aldrich
Product number
1099008
Product name
Cephalexin
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
400 mg
Price
$366
Updated
2021/03/22
Alfa Aesar
Product number
J63172
Product name
Cephalexin hydrate, 97+%
Packaging
25g
Price
$240
Updated
2020/06/24
Alfa Aesar
Product number
J63172
Product name
Cephalexin hydrate, 97+%
Packaging
5g
Price
$64.2
Updated
2020/06/24
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Cephalexin Chemical Properties,Usage,Production

Description

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.

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

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.

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

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.

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.

Description

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.

Chemical Properties

White cryst. powder

Originator

Ceporex,Glaxo,UK,1970

Uses

Antibacterial.

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

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.

Clinical Use

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.

Side effects

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 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

Chemical 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.

Cephalexin Preparation Products And Raw materials

Raw materials

Preparation Products

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Cephalexin Suppliers

HARBIN PHARMACEUTICAL GROUP CO., LTD.GENERAL Pharm.Factory
Tel
--
Fax
--
Email
webadmin@hayaozong.com
Country
China
ProdList
40
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60
Shanghai Boyle Chemical Co., Ltd.
Tel
Mr Qiu:021-50182298(Demestic market) Miss Xu:021-50180596(Abroad market)
Fax
+86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2213
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J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
Email
jkinfo@jkchemical.com;market6@jkchemical.com
Country
China
ProdList
96815
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76
future industrial shanghai co., ltd
Tel
400-0066-400;021-60496031
Fax
021-55660885
Email
sales@jonln.com;sales@jonln.com
Country
China
ProdList
1999
Advantage
65
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
1938
Advantage
70
Nanjing Chemlin Chemical Co., Ltd
Tel
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
20007
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64
Shanghai Hanhong Scientific Co.,Ltd.
Tel
;021-54306202- ;
Email
jerry.ma@hanhonggroup.com;jerry.ma@hanhonggroup.com;jerry.ma@hanhonggroup.com
Country
China
ProdList
43251
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Chemsky (shanghai) International Co.,Ltd
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
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15424
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Nanjing MeiBo Biological Technology Co., Ltd.
Tel
025-58619198
Fax
025-58619197
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sales@mbbio.com
Country
China
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XiaoGan ShenYuan ChemPharm co,ltd
Tel
0712-2580635- ;0712-2580635
Email
1791901229@qq.com;1791901229@qq.com;
Country
China
ProdList
8933
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View Lastest Price from Cephalexin manufacturers

Handan Tongyi New Material Technology Co., Ltd
Product
edical Grade Cephalexin 15686-71-2
Price
US $10.00/Kg
Min. Order
1KG
Purity
99
Supply Ability
500KG/MONTH
Release date
2021-03-16
Baoji Guokang Healthchem co.,ltd
Product
Cephalexin 15686-71-2
Price
US $157.00/KG
Min. Order
1KG
Purity
USP
Supply Ability
20tons
Release date
2021-06-03
WUHAN FORTUNA CHEMICAL CO., LTD
Product
Cephalexin 15686-71-2
Price
US $0.00-0.00/Kg/Drum
Min. Order
1KG
Purity
95%-102%;BP
Supply Ability
1000 KG
Release date
2021-06-03

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