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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
KafocinLilly
Brand mixturesNot Available
SaltsNot 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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid amide
  • Phenylacetamide
  • Alpha-amino acid or derivatives
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Meta-thiazine
  • Acetate salt
  • Tertiary carboxylic acid amide
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Carboxylic acid ester
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption-0.9628
Blood Brain Barrier-0.9962
Caco-2 permeable-0.8239
P-glycoprotein substrateSubstrate0.8637
P-glycoprotein inhibitor INon-inhibitor0.857
P-glycoprotein inhibitor IINon-inhibitor0.9675
Renal organic cation transporterNon-inhibitor0.9073
CYP450 2C9 substrateNon-substrate0.7983
CYP450 2D6 substrateNon-substrate0.829
CYP450 3A4 substrateNon-substrate0.5498
CYP450 1A2 substrateNon-inhibitor0.8872
CYP450 2C9 substrateNon-inhibitor0.8683
CYP450 2D6 substrateNon-inhibitor0.9071
CYP450 2C19 substrateNon-inhibitor0.8687
CYP450 3A4 substrateNon-inhibitor0.6747
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7799
Ames testNon AMES toxic0.6959
CarcinogenicityNon-carcinogens0.9063
BiodegradationNot ready biodegradable0.9855
Rat acute toxicity1.5769 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9952
hERG inhibition (predictor II)Non-inhibitor0.714
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 Solubility0.148 mg/mLALOGPS
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
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
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