Identification

Name
Cephaloglycin
Accession Number
DB00689  (APRD00858)
Type
Small Molecule
Groups
Approved
Description

A cephalorsporin antibiotic that is no longer commonly used.

Structure
Thumb
Synonyms
  • 7-(2-D-alpha-Aminophenylacetamido)cephalosporanic acid
  • 7-(D-2-Amino-2-phenylacetamido)-3-acetoxymethyl-delta(sup3)-cephem-4-carboxylic acid
  • 7-(D-alpha-Aminophenyl-acetamido)cephalosporanic acid
  • Cefaloglicina
  • Cefaloglycin
  • Cefaloglycine
  • Cefaloglycinum
  • CEG
  • Cephaloglycine
  • Cephaoglycin acid
  • D-(-)-Cephaloglycin
  • D-Cephaloglycine
Product Ingredients
IngredientUNIICASInChI Key
Cefaloglycin dihydrateNE7R11LA9522202-75-1KURFSUDYQUKEJZ-SBMYYUOMSA-N
Cefaloglycin monohydrateKR2KCF5IBM22202-76-2FFOHOZBDRVVZIM-PFBPGKLMSA-N
International/Other Brands
Kafocin (Lilly)
Categories
UNII
HD2D469W6U
CAS number
3577-01-3
Weight
Average: 405.425
Monoisotopic: 405.099456045
Chemical Formula
C18H19N3O6S
InChI Key
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
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][[email protected]]12SCC(COC(C)=O)=C(N1C(=O)[[email protected]]2NC(=O)[[email protected]](N)C1=CC=CC=C1)C(O)=O

Pharmacology

Indication

For treatment of severe infections caused by susceptible bacteria.

Structured Indications
Not Available
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).

TargetActionsOrganism
APenicillin-binding protein 1 (PBP1)
antagonist
Bacillus licheniformis
Absorption

Well absorbed following oral administration.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AcenocoumarolCephaloglycin may increase the anticoagulant activities of Acenocoumarol.Approved
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Cephaloglycin.Investigational
ClorindioneCephaloglycin may increase the anticoagulant activities of Clorindione.Experimental
DicoumarolCephaloglycin may increase the anticoagulant activities of Dicoumarol.Approved
DiphenadioneCephaloglycin may increase the anticoagulant activities of Diphenadione.Experimental
Ethyl biscoumacetateCephaloglycin may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
FluindioneCephaloglycin may increase the anticoagulant activities of Fluindione.Investigational
PhenindioneCephaloglycin may increase the anticoagulant activities of Phenindione.Approved
PhenprocoumonCephaloglycin may increase the anticoagulant activities of Phenprocoumon.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cephaloglycin.Approved
ProbenecidThe serum concentration of Cephaloglycin can be increased when it is combined with Probenecid.Approved
TioclomarolCephaloglycin may increase the anticoagulant activities of Tioclomarol.Experimental
WarfarinCephaloglycin may increase the anticoagulant activities of Warfarin.Approved
Food Interactions
Not 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 References
  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:2133431]
  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:2930580]
External Links
Human Metabolome Database
HMDB14827
KEGG Drug
D01949
KEGG Compound
C13440
PubChem Compound
19150
PubChem Substance
46506850
ChemSpider
18069
ChEBI
34613
ChEMBL
CHEMBL1200971
Therapeutic Targets Database
DAP001158
PharmGKB
PA164781027
Wikipedia
Cephaloglycin

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
  • Eli lilly and co
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)237 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
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 inhibitorNon-inhibitor0.8683
CYP450 2D6 inhibitorNon-inhibitor0.9071
CYP450 2C19 inhibitorNon-inhibitor0.8687
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as cephalosporin 3'-esters. These are cephalosporins that are esterified at the 3'-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporin 3'-esters
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / Aralkylamines / 1,3-thiazines / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids / Azetidines
show 10 more
Substituents
Cephalosporin 3'-ester / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Alpha-amino acid or derivatives / Phenylacetamide / Aralkylamine / Meta-thiazine / Dicarboxylic acid or derivatives / Monocyclic benzene moiety / Benzenoid
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin (CHEBI:34613)

Targets

Kind
Protein
Organism
Bacillus licheniformis
Pharmacological action
Yes
Actions
Antagonist
General Function
Not Available
Specific Function
Penicillin binding
Gene Name
Not Available
Uniprot ID
A0A1Q8GFY7
Uniprot Name
Multimodular transpeptidase-transglycosylase / Penicillin-binding protein 1A/1B (PBP1)
Molecular Weight
97811.3 Da
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:7565098]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
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 cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
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:10525100]

Drug created on June 13, 2005 07:24 / Updated on October 21, 2017 19:16