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Identification
NameCephaloglycin
Accession NumberDB00689  (APRD00858)
TypeSmall Molecule
GroupsApproved
Description

A cephalorsporin antibiotic that is no longer commonly used.

Structure
Thumb
Synonyms
SynonymLanguageCode
7-(2-D-alpha-Aminophenylacetamido)cephalosporanic acidNot AvailableNot Available
7-(D-2-Amino-2-phenylacetamido)-3-acetoxymethyl-delta(sup3)-cephem-4-carboxylic acidNot AvailableNot Available
7-(D-alpha-Aminophenyl-acetamido)cephalosporanic acidNot AvailableNot Available
CefaloglicinaSpanishINN
CefaloglycineFrenchINN
CefaloglycinumLatinINN
CEGNot AvailableNot Available
CephaloglycineNot AvailableNot Available
Cephaoglycin acidNot AvailableNot Available
D-(-)-CephaloglycinNot AvailableNot Available
D-CephaloglycineNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
KafocinLilly
Brand mixturesNot Available
Categories
CAS number3577-01-3
WeightAverage: 405.425
Monoisotopic: 405.099456045
Chemical FormulaC18H19N3O6S
InChI KeyFUBBGQLTSCSAON-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
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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassLactams
SubclassBeta Lactams
Direct parentCephalosporins
Alternative parentsN-acyl-alpha Amino Acids and Derivatives; Alpha Amino Acid Amides; 1,3-Thiazines; Benzene and Substituted Derivatives; Tertiary Carboxylic Acid Amides; Azetidines; Tertiary Amines; Hemiaminals; Secondary Carboxylic Acid Amides; Carboxylic Acid Esters; Ethers; Carboxylic Acids; Enolates; Enamines; Polyamines; Aminals; Thioethers; Monoalkylamines
Substituentsn-acyl-alpha amino acid or derivative; alpha-amino acid amide; alpha-amino acid or derivative; benzene; meta-thiazine; tertiary carboxylic acid amide; secondary carboxylic acid amide; carboxylic acid ester; carboxamide group; azetidine; tertiary amine; hemiaminal; aminal; polyamine; enolate; thioether; enamine; carboxylic acid; ether; carboxylic acid derivative; primary amine; primary aliphatic amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the 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 moeity or a derivative thereof.
Pharmacology
IndicationFor treatment of severe infections caused by susceptible bacteria.
PharmacodynamicsCephaloglycin is an antibiotic related to cephalosporin but no longer in common use. It is an orally absorbed derivative of cephalosporin C.
Mechanism of actionThe bactericidal activity of cephaloglycin results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs).
AbsorptionWell absorbed following oral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityAdverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.
Affected organisms
  • Enteric bacteria and other eubacteria
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption - 0.9628
Blood Brain Barrier - 0.9962
Caco-2 permeable - 0.8239
P-glycoprotein substrate Substrate 0.8637
P-glycoprotein inhibitor I Non-inhibitor 0.857
P-glycoprotein inhibitor II Non-inhibitor 0.9675
Renal organic cation transporter Non-inhibitor 0.9073
CYP450 2C9 substrate Non-substrate 0.7983
CYP450 2D6 substrate Non-substrate 0.829
CYP450 3A4 substrate Non-substrate 0.5498
CYP450 1A2 substrate Non-inhibitor 0.8872
CYP450 2C9 substrate Non-inhibitor 0.8683
CYP450 2D6 substrate Non-inhibitor 0.9071
CYP450 2C19 substrate Non-inhibitor 0.8687
CYP450 3A4 substrate Non-inhibitor 0.6747
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7799
Ames test Non AMES toxic 0.6959
Carcinogenicity Non-carcinogens 0.9063
Biodegradation Not ready biodegradable 0.9855
Rat acute toxicity 1.5769 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9952
hERG inhibition (predictor II) Non-inhibitor 0.714
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point237 dec °CPhysProp
water solubility154 mg/LNot Available
logP-0.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.148ALOGPS
logP0.54ALOGPS
logP-3ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.34ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area139.03 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity99.9 m3·mol-1ChemAxon
Polarizability37.64 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Wall, W.F., Fatherey, M. and Boothroyd, 6.; U.S. Patent 3,422,103; January 14,1969; assigned to Glaxo Laboratories, Ltd.
Pfeiffer, R.R. and Bottorff, E.M.; US. Patent 3,497,505; February 24,1970; assigned to Eli
Lilly & Co.
Jackson, B.G.; U.S. Patent 3,671,449; June 20,1972; assigned to Eli Lilly & Co.

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
ResourceLink
KEGG DrugD01949
KEGG CompoundC13440
PubChem Compound19150
PubChem Substance46506850
ChemSpider18069
Therapeutic Targets DatabaseDAP001158
PharmGKBPA164781027
WikipediaCephaloglycin
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
ProbenecidProbenecid may increase the serum level of cephaloglycin.
Food InteractionsNot Available

Targets

1. Penicillin-binding protein 2A

Kind: protein

Organism: Bacillus licheniformis (strain DSM 13 / ATCC 14580)

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Penicillin-binding protein 2A Q65HB5 Details

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. Solute carrier family 22 member 5

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Solute carrier family 22 member 5 O76082 Details

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

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Drug created on June 13, 2005 07:24 / Updated on April 03, 2014 11:33