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Identification
Name Cephaloglycin
Accession Number DB00689 (APRD00858)
Type small molecule
Groups approved
Description

A cephalorsporin antibiotic. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Cefaloglicina [INN-Spanish]
  • Cefaloglycin
  • Cefaloglycine [INN-French]
  • Cefaloglycinum [INN-Latin]
  • CEG
  • Cephaloglycin anhydrous
  • Cephaloglycine
  • Cephaoglycin acid
  • D-Cephaloglycine
  • Kafocin
  • Kefglycin
Brand name mixtures Not Available
Categories
  • Anti-Bacterial Agents
  • Cephalosporins
CAS number 3577-01-3
Weight Average: 405.425
Monoisotopic: 405.099456045
Chemical Formula C18H19N3O6S
InChI Key InChIKey=FUBBGQLTSCSAON-PBFPGSCMSA-N
InChI
InChI=1S/C18H19N3O6S/c1-9(22)27-7-11-8-28-17-13(16(24)21(17)14(11)18(25)26)20-15(23)12(19)10-5-3-2-4-6-10/h2-6,12-13,17H,7-8,19H2,1H3,(H,20,23)(H,25,26)/t12-,13-,17-/m1/s1
Plain Text
IUPAC Name
(6R,7R)-3-[(acetyloxy)methyl]-7-[(2R)-2-amino-2-phenylacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Cephalosporins
Substructures
  • Carboxylic Acids and Derivatives
  • Hydroxy Compounds
  • Acetates
  • Amino Ketones
  • Aliphatic and Aryl Amines
  • Ethers
  • Benzene and Derivatives
  • Beta Lactams
  • Enamines
  • Phenethylamines
  • Heterocyclic compounds
  • Aromatic compounds
  • Carboxamides and Derivatives
  • Cephalosporins
  • Lactams
  • Azetidines
Pharmacology
Indication For treatment of severe infections caused by susceptible bacteria.
Pharmacodynamics Cephaloglycin is an antibiotic related to cephalosporin but no longer in common use. It is an orally absorbed derivative of cephalosporin C.
Mechanism of action The bactericidal activity of cephaloglycin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
Absorption Well absorbed following oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism
Route of elimination Not Available
Half life Not Available
Clearance Not Available
Toxicity Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
Packagers Not Available
Dosage forms Not Available
Prices Not Available
Patents Not Available
Properties
State solid
Melting point 237 oC
Experimental Properties
Property Value Source
water solubility 154 mg/L PhysProp
logP -0.3 PhysProp
Predicted Properties
Property Value Source
water solubility 1.48e-01 g/l ALOGPS
logP 0.54 ALOGPS
logP -4.43 ChemAxon Molconvert
logS -3.44 ALOGPS
pKa 11.79 ChemAxon Molconvert
hydrogen acceptor count 6 ChemAxon Molconvert
hydrogen donor count 3 ChemAxon Molconvert
polar surface area 139.03 ChemAxon Molconvert
rotatable bond count 7 ChemAxon Molconvert
refractivity 99.90 ChemAxon Molconvert
polarizability 37.64 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Tune BM, Hsu CY: The renal mitochondrial toxicity of beta-lactam antibiotics: in vitro effects of cephaloglycin and imipenem. J Am Soc Nephrol. 1990 Nov;1(5):815-21. Pubmed
  2. Tune BM, Fravert D, Hsu CY: Oxidative and mitochondrial toxic effects of cephalosporin antibiotics in the kidney. A comparative study of cephaloridine and cephaloglycin. Biochem Pharmacol. 1989 Mar 1;38(5):795-802. Pubmed
External Links
Resource Link
KEGG Drug D01949 Link_out
KEGG Compound C13440 Link_out
PubChem Compound 19150 Link_out
PubChem Substance 46506850 Link_out
ChemSpider 18069 Link_out
Therapeutic Targets Database DAP001158 Link_out
Drug Product Database 0 Link_out
Wikipedia http://en.wikipedia.org/wiki/Cephaloglycin Link_out
ATC Codes Not Available
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. PbpA

Pharmacological action: yes
Actions: antagonist
UniProt ID: Q65HB5 Link_out
Gene: pbpA
SNPs: SNPJam Report Link_out

References:
  1. Lepage S, Lakaye B, Galleni M, Thamm I, Crine M, Groslambert S, Frere JM: Saturation of penicillin-binding protein 1 by beta-lactam antibiotics in growing cells of Bacillus licheniformis. Mol Microbiol. 1995 Apr;16(2):365-72. Pubmed
Transporters

1. Organic cation/carnitine transporter 2

Actions: inhibitor

Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cations such as tetraethylammonium (TEA) without the involvement of sodium. Also Relative uptake activity ratio of carnitine to TEA is 11.3

UniProt ID: O76082 Link_out
Gene: SLC22A5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Ohashi R, Tamai I, Yabuuchi H, Nezu JI, Oku A, Sai Y, Shimane M, Tsuji A: Na(+)-dependent carnitine transport by organic cation transporter (OCTN2): its pharmacological and toxicological relevance. J Pharmacol Exp Ther. 1999 Nov;291(2):778-84. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on November 10, 2010 13:41

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.