Cefalexin
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Basic Info
| Common Name | Cefalexin(F05832) |
| 2D Structure | |
| FRCD ID | F05832 |
| CAS Number | |
| PubChem CID | 27447 |
| Formula | C16H17N3O4S |
| IUPAC Name | (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 acid |
| InChI Key | ZAIPMKNFIOOWCQ-UEKVPHQBSA-N |
| 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 |
| Canonical SMILES | CC1=C(N2C(C(C2=O)NC(=O)C(C3=CC=CC=C3)N)SC1)C(=O)O |
| Isomeric SMILES | CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)SC1)C(=O)O |
| Synonyms |
cephalexin
Cefalexin
Cephacillin
Keflex
Ceporexin
Cepexin
Cephalexinum
Cefalexina
Cefalexine
Cefalexinum
|
| Classifies |
Predicted: Veterinary Drug
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Organoheterocyclic compounds |
| Class | Lactams |
| Subclass | Beta lactams |
| Intermediate Tree Nodes | Cephems |
| Direct Parent | Cephalosporins |
| Alternative Parents |
|
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Cephalosporin - N-acyl-alpha amino acid or derivatives - Alpha-amino acid amide - Alpha-amino acid or derivatives - Phenylacetamide - Aralkylamine - Meta-thiazine - Monocyclic benzene moiety - Benzenoid - Tertiary carboxylic acid amide - Amino acid or derivatives - Amino acid - Carboxamide group - Azetidine - Secondary carboxylic acid amide - Carboxylic acid - Monocarboxylic acid or derivatives - Carboxylic acid derivative - Azacycle - Thioether - Hemithioaminal - Dialkylthioether - Organic nitrogen compound - Primary aliphatic amine - Organonitrogen compound - Organooxygen compound - Carbonyl group - Primary amine - Hydrocarbon derivative - Organic oxide - Amine - Organopnictogen compound - Organic oxygen compound - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 347.389 |
| Hydrogen Bond Donor Count | 3 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 4 |
| Complexity | 600 |
| Monoisotopic Mass | 347.094 |
| Exact Mass | 347.094 |
| XLogP | 0.6 |
| Formal Charge | 0 |
| Heavy Atom Count | 24 |
| Defined Atom Stereocenter Count | 3 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB- | 0.9960 |
| Human Intestinal Absorption | HIA- | 0.7537 |
| Caco-2 Permeability | Caco2- | 0.8956 |
| P-glycoprotein Substrate | Substrate | 0.7860 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9033 |
| Non-inhibitor | 0.9921 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.9485 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.4732 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.8011 |
| CYP450 2D6 Substrate | Non-substrate | 0.8308 |
| CYP450 3A4 Substrate | Non-substrate | 0.5289 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.9242 |
| CYP450 2C9 Inhibitor | Non-inhibitor | 0.9251 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.9359 |
| CYP450 2C19 Inhibitor | Non-inhibitor | 0.9220 |
| CYP450 3A4 Inhibitor | Non-inhibitor | 0.8310 |
| CYP Inhibitory Promiscuity | Low CYP Inhibitory Promiscuity | 0.9303 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9971 |
| Non-inhibitor | 0.8686 | |
| AMES Toxicity | Non AMES toxic | 0.6834 |
| Carcinogens | Non-carcinogens | 0.8861 |
| Fish Toxicity | High FHMT | 0.9745 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.8781 |
| Honey Bee Toxicity | Low HBT | 0.6975 |
| Biodegradation | Not ready biodegradable | 0.9812 |
| Acute Oral Toxicity | IV | 0.6641 |
| Carcinogenicity (Three-class) | Non-required | 0.5826 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -2.8356 | LogS |
| Caco-2 Permeability | 0.5431 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.2715 | LD50, mol/kg |
| Fish Toxicity | 1.3608 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.4142 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Milk | Japan | 0.1ppm | |||
| Cattle,Edible Offal | Japan | 0.2ppm | |||
| Cattle,Kidney | Japan | 1ppm | |||
| Cattle,Liver | Japan | 0.2ppm | |||
| Cattle,Fat | Japan | 0.2ppm | |||
| Cattle,Muscle | Japan | 0.2ppm |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Stability study of veterinary drugs in standard solutions for LC-MS/MS screening in food. | Food Addit Contam Part A Chem Anal Control Expo Risk Assess | 2018Apr | 29377759 |
| Antibiotic susceptibilities of livestock isolates of leptospira. | Int J Antimicrob Agents | 2018 May | 29305960 |
| Whole-Genome Sequencing and Genetic Analysis Reveal Novel Stress Responses toIndividual Constituents of Essential Oils in Escherichia coli. | Appl Environ Microbiol | 2018 Mar 19 | 29374037 |
| Tomatidine and analog FC04-100 possess bactericidal activities against Listeria, Bacillus and Staphylococcus spp. | BMC Pharmacol Toxicol | 2018 Feb 13 | 29439722 |
| Occurrence and fate of most prescribed antibiotics in different waterenvironments of Tehran, Iran. | Sci Total Environ | 2018 Apr 1 | 29156265 |
| Detection of food-borne bacteria in ready to eat betel leaf sold at local marketsin Mymensingh. | Vet World | 2017 Sep | 29062191 |
| Plant Growth, Antibiotic Uptake, and Prevalence of Antibiotic Resistance in anEndophytic System of Pakchoi under Antibiotic Exposure. | Int J Environ Res Public Health | 2017 Nov 3 | 29099753 |
| Development and validation of a quantitative confirmatory method for 30 β-lactam antibiotics in bovine muscle using liquid chromatography coupled to tandem massspectrometry. | J Chromatogr A | 2017 Jun 2 | 28449875 |
| Urinary Excretion of Tetrodotoxin Modeled in a Porcine Renal Proximal Tubule Epithelial Cell Line, LLC-PK₁. | Mar Drugs | 2017 Jul 17 | 28714912 |
| Sub-inhibitory concentration of essential oils induces antibiotic resistance inStaphylococcus aureus. | Nat Prod Res | 2017 Dec 22:1-5 | 29272983 |
| Simulated microgravity affects some biological characteristics of Lactobacillusacidophilus. | Appl Microbiol Biotechnol | 2017 Apr | 28013406 |
| Occurrence and characteristics of extended-spectrum β-lactamases producingEscherichia coli in foods of animal origin and human clinical samples inChhattisgarh, India. | Vet World | 2016 Sep | 27733802 |
| Virulence of Trypanosoma cruzi in Açai ( Euterpe oleraceae Martius) Pulpfollowing Mild Heat Treatment. | J Food Prot | 2016 Oct | 28221851 |
| Multiresidue analysis of cephalosporin antibiotics in bovine milk based onmolecularly imprinted polymer extraction followed by liquid chromatography-tandemmass spectrometry. | J Chromatogr A | 2016 Nov 25 | 27816225 |
| Analysis of Six β-Lactam Residues in Milk and Egg by Micellar ElectrokineticChromatography with Large-Volume Sample Stacking and Polarity Switching. | J Agric Food Chem | 2016 May 4 | 27088652 |
| Addition of meloxicam to the treatment of clinical mastitis improves subsequentreproductive performance. | J Dairy Sci | 2016 Mar | 26778316 |
| Interaction of Peptide Transporter 1 With D-Glucose and L-Glutamic Acid; PossibleInvolvement of Taste Receptors. | J Pharm Sci | 2016 Jan | 26852864 |
| Integration of nickel doping with loading on graphene for enhanced adsorptive andcatalytic properties of CdS nanoparticles towards visible light degradation ofsome antibiotics. | J Hazard Mater | 2016 Dec 15 | 27565855 |
| Molecular characterization of Salmonella enterica serotype Enteritidis isolatesfrom food and human samples by serotyping, antimicrobial resistance, plasmidprofiling, (GTG)5-PCR and ERIC-PCR. | New Microbes New Infect | 2016 Aug 4 | 27656286 |
| Synthesis and application of cephalexin imprinted polymer for solid phaseextraction in milk. | Food Chem | 2015 Oct 1 | 25872441 |