CAS 15686-71-2|CAS 23325-78-2|Servispor|Alexin|Sartosona|Sanaxin|Cefadal|Erocetin|Medoxine|Keflex|Sencephalin|Alcephin|Alsporin|Zozarine|Keflet|Lenocef|cephalexin|Cepexin|Cephalexin 1-hydrate|Uphale...

General Information

Structure

Molecular Formula

C₁₆H₁₇N₃O₄S

Molecular Mass

347.38888

Exact Mass

347.09397704

Charge

InChI

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

InChIKey

ZAIPMKNFIOOWCQ-UEKVPHQBSA-N

Canonic Smiles

N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C

Isomeric Smiles

S1[C@H]2N(C(=O)[C@H]2NC(=O)[C@H](N)c2ccccc2)C(=C(C1)C)C(=O)O

Calculated Properties

JChem

LogD (pH = 7.4)

-2.50

LogD (pH = 5.5)

-2.14

Log P

-2.14

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

3.26

Polar Surface Area

112.73

Polarizability

34.93

Molar Refractivity

88.97

LOG S

-3.96

Data Source

Names and Identifiers

Brand Name

ServisporAlexinSartosonaSanaxinCefadalErocetinMedoxineKeflexSencephalinAlcephinAlsporinZozarineKefletLenocefCepexinUphalexinKidolexCelexinCefalinCophalexinWinlexNeolexinaCeforalEd A-CephSyneclSialexinSporidexOroxinCefalotoNovolexinL-KeflexOriphexLarixinFactagardCefa-iskiaCephinTokiolexinBiocefKeftabNeokefCefadinVoxximDurantel DSKefolanCeporexineCefablanPyassanSporicefCeporex ForteInphalexOspexinSinthecillinSepexinCepolCephanastenTepaxinNufexFexinLopilexinMamlexinRocephCepastarOrtisporinaKeforalPalitrexCeporexin-ECarnosporinOracefMadlexinIbrexinCefaseptinCephaxinSyncleCefadinaLonflexCefovitLafarineCephacillinDurantelMamalexinIbilexCefaxPanixine DisperdoseKefalospesPectrilCeporexinCheckFelexinLexibioticoCefaleksinSynclKekrinalCeporex

IUPAC Traditional name

cephalexin

Synonyms

Cephalexin 1-hydrateCephalexin hydrateCephalexinCephalexineCefalexinCefalessina [DCIT]Cefalexinum [INN-Latin]Cefalexin SodiumCefalexine [INN-French]Cephalexin monohydrateCEXCefalexina [INN-Spanish]CephalexinumAlcephinCefablanCefadinkeflexTepaxinCefalexinCefalexin7-(D-α-amino-phenylacetamido)-3-methyl-3-cepheme-4-carboxylic acid头孢氨苄Cephacillin(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 acidCeporexinCefalexinCelexinCEXCepexin7-(D-alpha-Aminophenylacetamido)desacetoxycephalosporanic acidcephalexin7-beta-(D-alpha-Amino-alpha-phenylacetylamino)-3-methyl-3-cephem-4-carboxylic acidCepastar

IUPAC name

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

API Name

Cephalexin hydrate

International Nonproprietary Name (INN)

cefalexinacefalexinecefalexinum

Names and Identifiers

Registration numbers

EC Number

239-773-6

CAS Number

15686-71-223325-78-2

PubChem SID

248606981609639124650674987246423

MDL Number

PubChem CID

Chemspider ID

Medline Plus

ATC CODE

DrugBank ID

KEGG ID

Unique Ingredient Identifier

Wikipedia Title

CHEBI ID

CHEMBL

MetaboLights Database

MTBLS2406MTBLS136MTBLS804

LINCS Database

LSM-5957

BRENDA Ligand Database

1597751026

PubMed Citation Links

24268227109306302368827612833570138486823061564290178332083978225599902454809223545436234570801256998723811740

Beilstein Number

965503

BRENDA Database

3.1.1.432.3.2.B141.14.11.261.14.20.13.4.16.43.5.2.63.5.1.11

VSDB Database

1,791

SureChEMBL Database

SCHEMBL2961

UniProt Database

P40603Q8K0H1Q96FL8Q5I0E9A4IIS8A1L1P9P85302Q5RFD2

Patent number

US3507861US3275626

ACToR Database

15686-71-214101-75-8

SABIO-RK Database

8144716797267168716910054

KEGG DRUG Database

BKMS React Database

HMDB Database

Reaxys Registry

CompTox Database

Drug Central Database

571

IEDB Database

117132

Registration numbers

Properties

Physical Property

Solubility

1789 mg/L

Hydrophobicity(logP)

Product Information

Salt Data

Free Base

Grade

VETRANAL™, analytical standard

Empirical Formula (Hill Notation)

C16H17N3O4S

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

DrugBank

DB00567

Drug Groups

approved

Description

A semisynthetic cephalosporin antibiotic with antimicrobial activity similar to that of cephaloridine or cephalothin, but somewhat less potent. It is effective against both gram-positive and gram-negative organisms. [PubChem]

Indication

For the treatment of respiratory tract infections caused by Streptococcus pneumoniae and Streptococcus pyogenes; 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.

Pharmacology

Cephalexin (also called Cefalexin) is a first generation cephalosporin antibiotic. It is one of the most widely prescribed antibiotics, often used for the treatment of superficial infections that result as complications of minor wounds or lacerations. It is effective against most gram-positive bacteria.

Toxicity

Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting. The oral median lethal dose of cephalexin in rats is >5000 mg/kg.

Affected Organisms

Enteric bacteria and other eubacteria

Biotransformation

No appreciable biotransformation in the liver (90% of the drug is excreted unchanged in the urine).

Absorption

Well absorbed from the gastrointestinal tract

Half Life

1 hour

Protein Binding

14%

Elimination

Cephalexin is excreted in the urine by glomerular filtration and tubular secretion. Studies showed that over 90% of the drug was excreted unchanged in the urine within 8 hours.

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1502

Research Area: Infection
Biological Activity:
Cefalexin or cephalexin is a first-generation cephalosporin antibiotic. It is an orally administered agent with a similar antimicrobial spectrum to the intravenous agents cefalotin and cefazolin. Cefalexin is used to treat urinary tract infections, respiratory tract infections, and skin and soft tissue infections. It is also sometimes used to treat acne. [1]

Wikipedia

Cefalexin

Sigma Aldrich

33989

Application
Commission Regulation (EU) No 37/2010 of 22 December 2009 on pharmacologically active substances and their classification regarding maximum residue limits in foodstuffs of animal origin
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

ChEBI

CHEBI:3534

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 Gram-positive organisms, and is used for treatment of infections of the skin, respiratory tract and urinary tract.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Cefalexin

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Brand Name

IUPAC Traditional name

cephalexin

Synonyms

IUPAC name

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

API Name

Cephalexin hydrate

International Nonproprietary Name (INN)

cefalexinacefalexinecefalexinum

Registration numbers

EC Number

239-773-6

CAS Number

15686-71-223325-78-2

PubChem SID

248606981609639124650674987246423

MDL Number

PubChem CID

Chemspider ID

Medline Plus

ATC CODE

DrugBank ID

KEGG ID

Unique Ingredient Identifier

Wikipedia Title

CHEBI ID

CHEMBL

MetaboLights Database

MTBLS2406MTBLS136MTBLS804

LINCS Database

LSM-5957

BRENDA Ligand Database

1597751026

PubMed Citation Links

24268227109306302368827612833570138486823061564290178332083978225599902454809223545436234570801256998723811740

Beilstein Number

965503

BRENDA Database

3.1.1.432.3.2.B141.14.11.261.14.20.13.4.16.43.5.2.63.5.1.11

VSDB Database

1,791

SureChEMBL Database

SCHEMBL2961

UniProt Database

P40603Q8K0H1Q96FL8Q5I0E9A4IIS8A1L1P9P85302Q5RFD2

Patent number

US3507861US3275626

ACToR Database

15686-71-214101-75-8

SABIO-RK Database

8144716797267168716910054

KEGG DRUG Database

BKMS React Database

HMDB Database

Reaxys Registry

CompTox Database

Drug Central Database

571

IEDB Database

117132

Molecule Details

DrugBank

DB00567

Drug Groups

approved

Description

Indication

Pharmacology

Toxicity

Symptoms of overdose include blood in the urine, diarrhea, nausea, upper abdominal pain, and vomiting. The oral median lethal dose of cephalexin in rats is >5000 mg/kg.

Affected Organisms

Enteric bacteria and other eubacteria

Biotransformation

No appreciable biotransformation in the liver (90% of the drug is excreted unchanged in the urine).

Absorption

Well absorbed from the gastrointestinal tract

Half Life

1 hour

Protein Binding

14%

Elimination

Cephalexin is excreted in the urine by glomerular filtration and tubular secretion. Studies showed that over 90% of the drug was excreted unchanged in the urine within 8 hours.

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

S1502

33989