CEPHALEXIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H17N3O4S.H2O
Molecular Weight	365.404
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CC=CC=C3)C(O)=O

InChI

InChIKey=AVGYWQBCYZHHPN-CYJZLJNKSA-N

InChI=1S/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

HIDE SMILES / InChI

Molecular Formula	C16H17N3O4S
Molecular Weight	347.389
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050405s097lbl.pdf

Cephalexin is a semisynthetic cephalosporin antibiotic intended for oral administration. In vitro tests demonstrate that the cephalosporins are bactericidal because of their inhibition of cell-wall synthesis. Cephalexin has been shown to be active against most strains of the following microorganisms both in vitro: Staphylococcus aureus (including penicillinase-producing strains), Streptococcus pneumoniae (penicillin-susceptible strains), Streptococcus pyogenes, Escherichia coli, Haemophilus influenzae, Klebsiella pneumoniae, Moraxella (Branhamella) catarrhalis, Proteus mirabilis. Cephalexin is indicated for the treatment of the respiratory tract, skin and skin structure, bone and genitourinary tract infections when caused by susceptible strains of the designated microorganisms.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial Infections 63 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050405s097lbl.pdf	Curative		Approved 8429	KEFLEX Approved Use Cephalexin capsules are indicated for the treatment of the following infections when caused by susceptible strains of the designated microorganisms: Respiratory tract infections caused by Streptococcus pneumoniae and Streptococcus pyogenes (Penicillin is the usual drug of choice in the treatment and prevention of streptococcal infections, including the prophylaxis of rheumatic fever. Cephalexin capsules are generally effective in the eradication of streptococci from the nasopharynx; however, substantial data establishing the efficacy of cephalexin capsules in the subsequent prevention of rheumatic fever are not available at present.) Otitis media due to Streptococcus pneumoniae, Haemophilus influenzae, Staphylococcus aureus, Streptococcus pyogenes , and Moraxella catarrhalis Skin and skin structure infections caused by Staphylococcus aureus and/or Streptococcus pyogenes Bone infections caused by Staphylococcus aureus and/or Proteus mirabilis Genitourinary tract infections, including acute prostatitis, caused by Escherichia coli, Proteus mirabilis, and Klebsiella pneumoniae Note — Culture and susceptibility tests should be initiated prior to and during therapy. Renal function studies should be performed when indicated. To reduce the development of drug-resistant bacteria and maintain the effectiveness of cephalexin and other antibacterial drugs, cephalexin should be used only to treat or prevent infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antibacterial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Launch Date 1971

C_max

Value	Dose	Co-administered	Analyte	Population
18.25 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23688276/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		CEPHALEXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
126 mg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23811740	40 mg/kg 3 times / day multiple, oral dose: 40 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered:		CEPHALEXIN plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
31.22 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23688276/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		CEPHALEXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
245 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23811740	40 mg/kg 3 times / day multiple, oral dose: 40 mg/kg route of administration: Oral experiment type: MULTIPLE co-administered:		CEPHALEXIN plasma	Homo sapiens population: UNHEALTHY age: CHILD sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
1.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23688276/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		CEPHALEXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

F_unbound

Value	Dose	Co-administered	Analyte	Population
85% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/23688276/	500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered:		CEPHALEXIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
40 mg/kg 3 times / day multiple, oral (median) Dose: 40 mg/kg, 3 times / day Route: oral Route: multiple Dose: 40 mg/kg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23811740	unhealthy, 1-16 years n = 12 Health Status: unhealthy Condition: Osteoarticular Infections Age Group: 1-16 years Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/23811740	Disc. AE: Neutropenia... AEs leading to discontinuation/dose reduction: Neutropenia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/23811740
500 mg 2 times / day multiple, oral Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30915263	unhealthy, 90 years n = 1 Health Status: unhealthy Age Group: 90 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/30915263	Disc. AE: Tendonitis... AEs leading to discontinuation/dose reduction: Tendonitis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/30915263

AEs

AE	Significance	Dose	Population
Neutropenia	1 patient Disc. AE	40 mg/kg 3 times / day multiple, oral (median) Dose: 40 mg/kg, 3 times / day Route: oral Route: multiple Dose: 40 mg/kg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/23811740	unhealthy, 1-16 years n = 12 Health Status: unhealthy Condition: Osteoarticular Infections Age Group: 1-16 years Sex: M+F Population Size: 12 Sources: https://pubmed.ncbi.nlm.nih.gov/23811740
Tendonitis	1 patient Disc. AE	500 mg 2 times / day multiple, oral Dose: 500 mg, 2 times / day Route: oral Route: multiple Dose: 500 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30915263	unhealthy, 90 years n = 1 Health Status: unhealthy Age Group: 90 years Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/30915263

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 270 PEPT1 49 PEPT2 32

Drug as victim

Target	Modality	Activity
CYP 270	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/antibiotics1968/22/5/22_5_195/_article/-char/en	no
PEPT1 49	substrate 3367 Sources: https://www.jstage.jst.go.jp/article/bpb/29/1/29_1_90/_article/-char/ja/	yes
PEPT2 32	substrate 3367 Sources: https://link.springer.com/article/10.1007/s00228-008-0488-4	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-0058	http://www.3bsc.com/index/pro_info.php?id=19414
3B Scientific (Wuhan) Corp	3B1-01401	http://www.3bsc.com/index/pro_info.php?id=21613
AA Blocks	AA0037NO	https://www.aablocks.com/goods/Goods/detail?id=AA0037NO
AHH Chemical co.,ltd	API-1053	http://www.ahhchemical.com/product/API-1053.html
AK Scientific, Inc. (AKSCI)	2312AH	http://www.aksci.com/item_detail.php?cat=2312AH
Aaron Chemicals	AR0038FG	http://www.aaronchem.com/15686-71-2
AbMole Bioscience	M4900	http://www.abmole.com/products/cephalexin.html
Achemtek	0104-058165	http://www.achemtek.com/15686-71-2
Alfa Chemistry	AP15686712	https://reagents.alfa-chemistry.com/product/cefalexin-cas-15686-71-2-5788.html
ApexBio Technology	B1692	http://www.apexbt.com/cephalexin.html
Aurora Fine Chemicals LLC	A17.908.211	http://online.aurorafinechemicals.com/info?ID=A17.908.211
Aurora Fine Chemicals LLC	K14.726.335	http://online.aurorafinechemicals.com/info?ID=K14.726.335
BLD Pharm	BD120242	http://www.bldpharm.com/products/15686-71-2.html
BioCrick	BCC4646	http://www.biocrick.com/Cephalexin-BCC4646.html
BioSynth	Q-200819	https://www.biosynth.com/en/products/life-science/culture-media-additives/products/Q-200819.html
BioSynth	C-2660	https://www.biosynth.com/products/biochemistry/culture-media-additives/products/C-2660.html
CSNpharm	CSN10562	https://www.csnpharm.com/products/cephalexin.html
Chem Scene	CS-2137	http://www.chemscene.com/15686-71-2.html
ChemMol	49411600	http://www.chemmol.com/chemmol/49411600.html
Chemspace	CSSB00020617717	https://chem-space.com/CSSB00020617717
Clearsynth	CS-O-30876	https://www.clearsynth.com/en/CSO30876.html
Glentham Life Sciences	GA1648	http://www.glentham.com/products/product/GA1648/
Lab Network	LN00003630	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00003630
MedChem Express	HY-B0200	https://www.medchemexpress.com/Cephalexin.html
MuseChem	A001152	https://www.musechem.com/product/A001152.html
Selleck Chemicals	S1502	http://www.selleckchem.com/products/Cephalexin-(Cefalexin).html
Sigma-Aldrich	33989_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/33989?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	BP061_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/bp061?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	PHR1848_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/phr1848?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S061061	http://www.sinfoobiotech.com/product/1064464
eNovation Chemicals	D673807	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673807
iChemical	EBD56457	http://www.ichemical.com/products/15686-71-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs

PubMed

Title	Date	PubMed
Cephalexin-related nephropathy.	1975 Nov 10	1242194
Drug inhibition of Gly-Sar uptake and hPepT1 localization using hPepT1-GFP fusion protein.	2001	11741253
Encouraging good antimicrobial prescribing practice: a review of antibiotic prescribing policies used in the South East Region of England.	2001	11388888
Bioaugmentation and treatment of cephalexin drug-based pharmaceutical effluent in an upflow anaerobic fluidized bed system.	2001 Feb	11198183
Paediatric antibiotic prescribing by general dental practitioners in England.	2001 Jul	11570439
Factors associated with antibiotic resistance in coliform organisms from community urinary tract infection in Wales.	2001 Mar	11222563
Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase.	2001 May	11437242
[The use of veterinary drugs during pregnancy of the dog].	2001 Nov 15	11758478
Equal allergenic potency of beta-lactam antibiotics produced by chemical or enzymatic manufacturing--mouse IgE test.	2001 Oct	11729356
Fine structural recognition specificities of IgE antibodies distinguishing amoxicilloyl and amoxicillanyl determinants in allergic subjects.	2001 Sep-Oct	11746950
The effect of tablet formulation and hardness on in vitro release of cephalexin from Eudragit L100 based extended release tablets.	2002 Apr	11995942
The role of hydrophobic active-site residues in substrate specificity and acyl transfer activity of penicillin acylase.	2002 Apr	11985586
Effect of UV-B radiation on some common antibiotics.	2002 Apr	11869874
Prophylactic antibiotics in cirrhotics with upper gastrointestinal hemorrhage: a prospective, controlled trial.	2002 Aug	12455806
Localized lymphatic sporotrichosis after fish-induced injury (Tilapia sp.).	2002 Aug	12230224
Solid state 'adsorption' of fine antibiotic powders onto sorbitol: effects of particle size, state of sorbed water and surface free energy characteristics.	2002 Dec	12453612
A comparison of the efficacy and safety of mupirocin cream and cephalexin in the treatment of secondarily infected eczema.	2002 Jan	11952661
Sensitivity and resistance of antibiotics in common infection of male and female.	2002 Jan-Mar	12043324
Outcome of percutaneous nephrostomy for the management of pyonephrosis.	2002 Jul	12376218
Pharmacokinetics of cephalexin in the horse after intravenous and intramuscular administration of two formulations.	2002 Jul	12359489
Antibacterial activity of oral antibiotics against community-acquired respiratory pathogens from three European countries.	2002 Jul	12077154
Comparison of several methods used for the determination of cephalosporins. Analysis of cephalexin in pharmaceutical samples.	2002 Jul 1	12062642
Typhoidal focal suppurative lymphatic abscess.	2002 Jun	12070955
In vitro and in situ evidence for the contribution of Labrasol and Gelucire 44/14 on transport of cephalexin and cefoperazone by rat intestine.	2002 Nov	12445561
Influence of a new prophylactic antibiotic therapy on the incidence of liver abscesses after chemoembolization treatment of liver tumors.	2002 Nov	12427817
Risk of serious skin disorders among users of oral antifungals: a population-based study.	2002 Nov 28	12456265
Modelling of the enzymatic kinetically controlled synthesis of cephalexin: influence of diffusion limitation.	2002 Nov 5	12226866
In vitro permeation of beta-lactam antibiotics across rat jejunum and its correlation with oral bioavailability in humans.	2002 Oct	12392595
Uptake of cyclic dipeptide by PEPT1 in Caco-2 cells: phenolic hydroxyl group of substrate enhances affinity for PEPT1.	2002 Sep	12356285
Private pharmacies in Hanoi, Vietnam: a randomized trial of a 2-year multi-component intervention on knowledge and stated practice regarding ARI, STD and antibiotic/steroid requests.	2002 Sep	12225513
Quantitative characterization of the nucleophile reactivity in penicillin acylase-catalyzed acyl transfer reactions.	2002 Sep 23	12479414

Patents

Sample Use Guides

In Vivo Use Guide

Adults — The adult dosage ranges from 1 to 4 g daily in divided doses. The usual adult dose is 250 mg every 6 hours. For the following infections, a dosage of 500 mg may be administered every 12 hours: streptococcal pharyngitis, skin and skin structure infections, and uncomplicated cystitis in patients over 15 years of age. Cystitis therapy should be continued for 7 to 14 days. For more severe infections or those caused by less susceptible organisms, larger doses may be needed. If daily doses of Keflex greater than 4 g are required, parenteral cephalosporins, in appropriate doses, should be considered. Pediatric Patients — The usual recommended daily dosage for pediatric patients is 25 to 50 mg/kg in divided doses. For streptococcal pharyngitis in patients over 1 year of age and for skin and skin structure infections, the total daily dose may be divided and administered every 12 hours. In severe infections, the dosage may be doubled. In the therapy of otitis media, clinical studies have shown that a dosage of 75 to 100 mg/kg/day in 4 divided doses is required. In the treatment of β-hemolytic streptococcal infections, a therapeutic dosage of Keflex should be administered for at least 10 days.

Route of Administration: Oral

In Vitro Use Guide

All strains of group A beta-hemolytic streptococci and Diplococcus pneumoniae were inhibited by 3.1 mug/ml. Of the Staphylococcus aureus strains, 88% were inhibited by 6.3 mug/ml, and 12.5 mug/ml was inhibitory for all S. aureus, 80% of Escherichia coli, 72% of Klebsiella-Aerobacter, and 56% of Proteus mirabilis strains. About 90 to 96% of E. coli, Klebsiella Aerobacter, and P. mirabilis strains were inhibited by 25 mug of cephalexin per ml. Pseudomonas and indole-positive Proteus strains proved to be quite resistant to cephalexin.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:18:57 GMT 2023` Edited by `admin` on `Fri Dec 15 15:18:57 GMT 2023`
Record UNII	OBN7UDS42Y
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEPHALEXIN

Official Name

English

CEFALEXIN MONOHYDRATE

Common Name

English

66873

Code

English

7-(D-.ALPHA.-AMINO-.ALPHA.-PHENYLACETAMIDO)-3-METHYL-3-CEPHEM-4-CARBOXYLIC ACID MONOHYDRATE

Common Name

English

KEFLEX

Brand Name

English

CEPHALEXIN MONOHYDRATE [MI]

Common Name

English

CEFANEX

Brand Name

English

CEPHALEXIN MONOHYDRATE

Common Name

English

CEPHALEXIN [USP-RS]

Common Name

English

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

Systematic Name

English

CEPHALEXIN [USAN]

Common Name

English

CEFALEXIN MONOHYDRATE [EP IMPURITY]

Common Name

English

CEPHALEXIN [VANDF]

Common Name

English

NovoLexin

Brand Name

English

Cefalexin monohydrate [WHO-DD]

Common Name

English

CEFALEXIN MONOHYDRATE [EP MONOGRAPH]

Common Name

English

Biocef

Brand Name

English

CEPHALEXIN MONOHYDRATE [VANDF]

Common Name

English

KEFLET

Brand Name

English

CEPHALEXIN [USP MONOGRAPH]

Common Name

English

CEPHALEXIN [ORANGE BOOK]

Common Name

English

PANIXINE DISPERDOSE

Brand Name

English

LY-66873

Code

English

Classification Tree Code System Code

LIVERTOX

NBK548358