CEPHALEXIN ANHYDROUS

First approved in 1971

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H17N3O4S
Molecular Weight	347.389
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=C(N2[C@H](SC1)[C@H](NC(=O)[C@H](N)C3=CC=CC=C3)C2=O)C(O)=O

InChI

InChIKey=ZAIPMKNFIOOWCQ-UEKVPHQBSA-N

InChI=1S/C16H17N3O4S/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)/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

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 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial Infections 63 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2006/050405s097lbl.pdf	Curative		Approved 8583	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 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 Health Status: unhealthy Age Group: 1-16 years Sex: M+F 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 Health Status: unhealthy Age Group: 90 years Sex: F 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 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 Health Status: unhealthy Age Group: 1-16 years Sex: M+F 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 Health Status: unhealthy Age Group: 90 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/30915263

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP 303 PEPT1 60 PEPT2 37

Drug as victim

Target	Modality	Activity
CYP 303	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/antibiotics1968/22/5/22_5_195/_article/-char/en	no
PEPT1 60	substrate 4014 Sources: https://www.jstage.jst.go.jp/article/bpb/29/1/29_1_90/_article/-char/ja/	yes
PEPT2 37	substrate 4014 Sources: https://link.springer.com/article/10.1007/s00228-008-0488-4	yes

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B1-01401	http://www.3bsc.com/index/pro_info.php?id=21613
3B Scientific (Wuhan) Corp	3B2-0058	http://www.3bsc.com/index/pro_info.php?id=19414
AA Blocks	AA0037NO	https://www.aablocks.com/goods/Goods/detail?id=AA0037NO
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
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
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
BioCrick	BCC4646	http://www.biocrick.com/Cephalexin-BCC4646.html
BioSynth	C-2660	https://www.biosynth.com/products/biochemistry/culture-media-additives/products/C-2660.html
BioSynth	Q-200819	https://www.biosynth.com/en/products/life-science/culture-media-additives/products/Q-200819.html
BLD Pharm	BD120242	http://www.bldpharm.com/products/15686-71-2.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
CSNpharm	CSN10562	https://www.csnpharm.com/products/cephalexin.html
eNovation Chemicals	D673807	https://www.enovationchem.com/ProductDetails.asp?ProductID=D673807
Glentham Life Sciences	GA1648	http://www.glentham.com/products/product/GA1648/
iChemical	EBD56457	http://www.ichemical.com/products/15686-71-2.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
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

PubMed

Title	Date	PubMed
Current issues in antimicrobial therapy for the treatment of acne.	2001	11843235
Synthesis and antibacterial activity of 5-nitrofuryl and 3-methoxy-2-nitrophenyl derivatives of 6 beta-aminopenicillanic, 7 beta-aminocephalosporanic and 7 beta-aminodesacetoxy-cephalosporanic acids.	2001	11799847
Drug inhibition of Gly-Sar uptake and hPepT1 localization using hPepT1-GFP fusion protein.	2001	11741253
Treatment of mycobacterial exit-site infections in patients on continuous ambulatory peritoneal dialysis.	2001	11510269
Upper respiratory tract infections.	2001 Dec	11838568
Skin and soft tissue infection.	2001 Jul	11980459
Paediatric antibiotic prescribing by general dental practitioners in England.	2001 Jul	11570439
Introduction of recirculatory analysis into portal and systemic concentration difference method.	2001 Nov	11725968
Consensus statement on management of antenatally detected hydronephrosis.	2001 Nov	11721064
PepT1-mediated epithelial transport of dipeptides and cephalexin is enhanced by luminal leptin in the small intestine.	2001 Nov	11714740
ED management of cellulitis: a review of five urban centers.	2001 Nov	11698996
Correlation between epithelial cell permeability of cephalexin and expression of intestinal oligopeptide transporter.	2001 Nov	11602669
[The use of veterinary drugs during pregnancy of the dog].	2001 Nov 15	11758478
Ocular pharmacokinetics of cephalosporins using microdialysis.	2001 Oct	11765153
Equal allergenic potency of beta-lactam antibiotics produced by chemical or enzymatic manufacturing--mouse IgE test.	2001 Oct	11729356
Outpatient management of low-velocity gunshot-induced fractures.	2001 Oct	11688773
CF and antistaphylococcal prophylaxis.	2001 Oct	11596571
Invasive group A streptococcus in two siblings: a case for antibiotic prophylaxis of close contacts.	2001 Sep 1	11550623
Effect of cephalexin on the pharmacokinetics of metformin in healthy human volunteers.	2002	12222753
Moxifloxacin in uncomplicated skin and skin structure infections.	2002	11929342
Cefdinir: an advanced-generation, broad-spectrum oral cephalosporin.	2002 Apr	12017394
Salmonella mastitis in a child.	2002 Apr	11999687
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
A two-step, one-pot enzymatic synthesis of cephalexin from D-phenylglycine nitrile.	2002 Aug 5	12115424
Advantages of using non-isothermal bioreactors for the enzymatic synthesis of antibiotics: the penicillin G acylase as enzyme model.	2002 Aug 5	12115422
[Improvement of efficacy of the bacteriological diagnosis in whooping cough].	2002 Feb	11899534
Clinical significance and epidemiology of NO-1, an unusual bacterium associated with dog and cat bites.	2002 Feb	11897069
A comparison of the efficacy and safety of mupirocin cream and cephalexin in the treatment of secondarily infected eczema.	2002 Jan	11952661
[Streptococcus salivarius meningitis after oral trauma by a skewer: a case report].	2002 Jan	11852478
Comparison of bidirectional cephalexin transport across MDCK and caco-2 cell monolayers: interactions with peptide transporters.	2002 Jan	11837697
Antimicrobial sensitivity in enterobacteria from AIDS patients, Zambia.	2002 Jan	11749759
Enrofloxacin resistance in Escherichia coli isolated from dogs with urinary tract infections.	2002 Jan 15	12126128
[Pharmacokinetics of cephalexin from two oral formulations in dogs].	2002 Jan-Feb	11852685
Sensitivity and resistance of antibiotics in common infection of male and female.	2002 Jan-Mar	12043324
Pharmacokinetics of cephalexin in the horse after intravenous and intramuscular administration of two formulations.	2002 Jul	12359489
Staphylococcus aureus: colonizing features and influence of an antibacterial treatment in adults with atopic dermatitis.	2002 Jul	12100185
Comparison of several methods used for the determination of cephalosporins. Analysis of cephalexin in pharmaceutical samples.	2002 Jul 1	12062642
Susceptibility change to antibiotics of Staphylococcus aureus strains isolated from skin infections between July 1994 and November 2000.	2002 Jun	12111576
Community-acquired methicillin-resistant Staphylococcus aureus, Finland.	2002 Jun	12023917
Febrile urinary tract infection: Escherichia coli susceptibility to oral antimicrobials.	2002 Mar	11956854
Antibiotic prophylaxis in infants and young children with cystic fibrosis: a randomized controlled trial.	2002 Mar	11953726
Emergence of new pathogens in CF: the devil we know or the devil we don't know?	2002 Mar	11953721
Evaluation of UV-radiation induced singlet oxygen generation potential of selected drugs.	2002 May	12024804
Bacterial colonization of intravenous catheters in young dogs suspected to have parvoviral enteritis.	2002 May 1	11991409
Risk of serious skin disorders among users of oral antifungals: a population-based study.	2002 Nov 28	12456265
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
Frequency of isolation and antimicrobial susceptibility patterns of Staphylococcus intermedius and Pseudomonas aeruginosa isolates from canine skin and ear samples over a 6-year period (1992-1997).	2002 Sep-Oct	12220023

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 `Wed Apr 02 06:54:16 GMT 2025` Edited by `admin` on `Wed Apr 02 06:54:16 GMT 2025`
Record UNII	5SFF1W6677
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CEFALEXIN

Preferred Name

English

CEPHALEXIN ANHYDROUS

Common Name

English

CEPHALEXIN [HSDB]

Common Name

English

NSC-758162

Code

English

DURANTEL

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((AMINOPHENYLACETYL)AMINO)-3-METHYL-8-OXO-,(6R-(6.ALPHA.,7.BETA.(R*)))-

Common Name

English

UPHALEXIN

Common Name

English

FELEXIN

Common Name

English

EFALEXIN

Common Name

English

KEFLORIDINA

Common Name

English

TAICELEXIN

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

Systematic Name

English

CEFALEXIN ANHYDROUS

Common Name

English

ORACOCIN

Common Name

English

Cefalexin [WHO-DD]

Common Name

English

cefalexin [INN]

Common Name

English

PYASSAN

Common Name

English

SINTHECILLIN

Common Name

English

IWALEXIN

Common Name

English

LILLY-66873

Common Name

English

S-6437

Common Name

English

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

Common Name

English

CEFALEKSIN

Common Name

English

CEPHAMASTEN

Common Name

English

ANHYDROUS CEPHALEXIN

Common Name

English

ALSPORIN

Common Name

English

CEPHALEXIN [MI]

Common Name

English

CEFADROS

Common Name

English

CARNOSPORIN

Common Name

English

CEFALEXIN [JAN]

Common Name

English

MAMALEXIN

Common Name

English

GARASIN

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000011161