Cephaloglycin

Identification

Generic Name
Cephaloglycin
DrugBank Accession Number
DB00689
Background

A cephalorsporin antibiotic that is no longer commonly used.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 405.425
Monoisotopic: 405.099456045
Chemical Formula
C18H19N3O6S
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
  • Cephaloglycin anhydrous
  • Cephaloglycine
  • Cephaoglycin acid
  • D-(-)-Cephaloglycin
  • D-Cephaloglycine

Pharmacology

Indication

For treatment of severe infections caused by susceptible bacteria.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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 1B
antagonist
Escherichia coli (strain K12)
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

Adverse Effects
Adverseeffects
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Toxicity

Adverse effects following overdosage include nausea, vomiting, epigastric distress, diarrhea, and convulsions.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirCephaloglycin may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbciximabThe therapeutic efficacy of Abciximab can be decreased when used in combination with Cephaloglycin.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Cephaloglycin is combined with Aceclofenac.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Cephaloglycin is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Cephaloglycin is combined with Acenocoumarol.
AcetaminophenCephaloglycin may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Acetylsalicylic acidThe risk or severity of nephrotoxicity can be increased when Cephaloglycin is combined with Acetylsalicylic acid.
AclidiniumCephaloglycin may decrease the excretion rate of Aclidinium which could result in a higher serum level.
AcrivastineCephaloglycin may decrease the excretion rate of Acrivastine which could result in a higher serum level.
AcyclovirThe risk or severity of nephrotoxicity can be increased when Cephaloglycin is combined with Acyclovir.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Cefaloglycin dihydrateNE7R11LA9522202-75-1KURFSUDYQUKEJZ-SBMYYUOMSA-N
Cefaloglycin monohydrateKR2KCF5IBM22202-76-2FFOHOZBDRVVZIM-PFBPGKLMSA-N
International/Other Brands
Kafocin (Lilly)

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Alpha-amino acid amide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin (CHEBI:34613)
Affected organisms
  • Enteric bacteria and other eubacteria

Chemical Identifiers

UNII
HD2D469W6U
CAS number
3577-01-3
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][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(O)=O

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. [Article]
  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. [Article]
Human Metabolome Database
HMDB0014827
KEGG Drug
D01949
KEGG Compound
C13440
PubChem Compound
19150
PubChem Substance
46506850
ChemSpider
18069
ChEBI
34613
ChEMBL
CHEMBL1200971
ZINC
ZINC000003830503
Therapeutic Targets Database
DAP001158
PharmGKB
PA164781027
Wikipedia
Cefaloglycin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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

Targets

Drugtargets2
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Kind
Protein
Organism
Escherichia coli (strain K12)
Pharmacological action
Yes
Actions
Antagonist
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Cell wall formation. Synthesis of cross-linked peptidoglycan from the lipid intermediates. The enzyme has a penicillin-insensitive transglycosylase N-terminal domain (formation of linear glycan str...
Gene Name
mrcB
Uniprot ID
P02919
Uniprot Name
Penicillin-binding protein 1B
Molecular Weight
94291.875 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. [Article]

Transporters

Kind
Protein
Organism
Humans
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. [Article]

Drug created on June 13, 2005 13:24 / Updated on September 25, 2021 14:59