Identification
- Generic Name
- Cephaloglycin
- DrugBank Accession Number
- DB00689
- Background
A cephalorsporin antibiotic that is no longer commonly used.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Cephaloglycin (DB00689)
- 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.
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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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).
Target Actions Organism APenicillin-binding protein 1B antagonistEscherichia 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Cephaloglycin may decrease the excretion rate of Abacavir which could result in a higher serum level. Abciximab The therapeutic efficacy of Abciximab can be decreased when used in combination with Cephaloglycin. Aceclofenac The risk or severity of nephrotoxicity can be increased when Cephaloglycin is combined with Aceclofenac. Acemetacin The risk or severity of nephrotoxicity can be increased when Cephaloglycin is combined with Acemetacin. Acenocoumarol The risk or severity of bleeding can be increased when Cephaloglycin is combined with Acenocoumarol. Acetaminophen Cephaloglycin may decrease the excretion rate of Acetaminophen which could result in a higher serum level. Acetylsalicylic acid The risk or severity of nephrotoxicity can be increased when Cephaloglycin is combined with Acetylsalicylic acid. Aclidinium Cephaloglycin may decrease the excretion rate of Aclidinium which could result in a higher serum level. Acrivastine Cephaloglycin may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir The risk or severity of nephrotoxicity can be increased when Cephaloglycin is combined with Acyclovir. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cefaloglycin dihydrate NE7R11LA95 22202-75-1 KURFSUDYQUKEJZ-SBMYYUOMSA-N Cefaloglycin monohydrate KR2KCF5IBM 22202-76-2 FFOHOZBDRVVZIM-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
- 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]
- 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]
- External Links
- 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
Pharmacoeconomics
- Manufacturers
- Eli lilly and co
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 237 dec °C PhysProp water solubility 154 mg/L Not Available logP -0.3 Not Available - Predicted Properties
Property Value Source Water Solubility 0.148 mg/mL ALOGPS logP 0.54 ALOGPS logP -3 Chemaxon logS -3.4 ALOGPS pKa (Strongest Acidic) 3.15 Chemaxon pKa (Strongest Basic) 7.23 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 139.03 Å2 Chemaxon Rotatable Bond Count 7 Chemaxon Refractivity 99.9 m3·mol-1 Chemaxon Polarizability 37.64 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - 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 inhibitor Non-inhibitor 0.8683 CYP450 2D6 inhibitor Non-inhibitor 0.9071 CYP450 2C19 inhibitor Non-inhibitor 0.8687 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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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
- 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
- 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 at June 13, 2005 13:24 / Updated at March 19, 2023 22:24