(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

• ChemBase ID: 449
• Molecular Formular: C16H17N3O4S
• Molecular Mass: 347.38888
• Monoisotopic Mass: 347.09397704
• SMILES: S1[C@H]2N(C(=O)[C@H]2NC(=O)[C@H](N)c2ccccc2)C(=C(C1)C)C(=O)O
• Canonical SMILES: N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C
• 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

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: cephalexin
• Brand Name: Alcephin; Alexin; Alsporin; Biocef; Carnosporin; Cefa-iskia; Cefablan; Cefadal; Cefadin; Cefadina; Cefaleksin; Cefalin; Cefaloto; Cefaseptin; Cefax; Ceforal; Cefovit; Celexin; Cepastar; Cepexin; Cephacillin; Cephanasten; Cephaxin; Cephin; Cepol; Ceporex; Ceporex Forte; Ceporexin; Ceporexin-E; Ceporexine; Check; Cophalexin; Durantel; Durantel DS; Ed A-Ceph; Erocetin; Factagard; Felexin; Fexin; Ibilex; Ibrexin; Inphalex; Kefalospes; Keflet; Keflex; Kefolan; Keforal; Keftab; Kekrinal; Kidolex; L-Keflex; Lafarine; Larixin; Lenocef; Lexibiotico; Lonflex; Lopilexin; Madlexin; Mamalexin; Mamlexin; Medoxine; Neokef; Neolexina; Novolexin; Nufex; Oracef; Oriphex; Oroxin; Ortisporina; Ospexin; Palitrex; Panixine Disperdose; Pectril; Pyassan; Roceph; Sanaxin; Sartosona; Sencephalin; Sepexin; Servispor; Sialexin; Sinthecillin; Sporicef; Sporidex; Syncl; Syncle; Synecl; Tepaxin; Tokiolexin; Uphalexin; Voxxim; Winlex; Zozarine
• Synonyms: Cefalessina [DCIT]; Cefalexin Sodium; Cefalexina [INN-Spanish]; Cefalexine [INN-French]; Cefalexinum [INN-Latin]; Cefalexin; Cephalexin 1-hydrate; Cephalexin hydrate; Cephalexin monohydrate; Cephalexinum; Cephalexine; CEX; Cephalexin; Cefalexin; 7-(D-α-amino-phenylacetamido)-3-methyl-3-cepheme-4-carboxylic acid; Cefalexin; Alcephin; Cefablan; keflex; Cefadin; Tepaxin; 头孢氨苄

Database IDs

• CAS Number: 15686-71-2
• EC Number: 239-773-6
• MDL Number: MFCD00056877
• PubChem SID: 160963912; 24860698; 46506749
• PubChem CID: 27447; 2666
• CHEBI ID: 3534
• ATC CODE: QJ51DB01; J01DB01
• CHEMBL: 1727
• Chemspider ID: 25541
• DrugBank ID: DB00567
• KEGG ID: D00263
• Unique Ingredient Identifier: 5SFF1W6677
• Wikipedia Title: Cefalexin
• Medline Plus: a682733

CALCULATED PROPERTIES

JChem

• Molar Refractivity: 88.9736 cm^3
• Polarizability: 34.625595 Å^3
• Polar Surface Area: 112.73 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true
• Acid pKa: 3.4520106
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.1413963
• LogD (pH = 7.4): -2.3951817
• Log P: -2.145041

ALOGPS 2.1

• Solubility (Water): 2.97e-01 g/l
• Log P: 0.55
• LOG S: -3.07

PROPERTIES

Physical Property

• Solubility: 1789 mg/L
• Hydrophobicity(logP): 0

Safety Information

• Storage Condition: -20°C
• RTECS: XI0350000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 22-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: Well absorbed
• Excretion: Renal
• Half Life: For an adult with normal renal function, the serum half-life is 0.5-1.2 hours
• Metabolism: 80% excreted unchanged in urine within 6 hours of administration
• Protein Bound: 15%
• Legal Status: POM (UK); Rx-only (US); S4 (Australia)
• Pregnancy Category: A (Australia); B (US)
• US Licence: Keflex

Product Information

• Grade: VETRANAL™, analytical standard
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C16H17N3O4S

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]

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

REFERENCES

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