Cefaloridine
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Identification
- Generic Name
- Cefaloridine
- DrugBank Accession Number
- DB09008
- Background
Cephaloridine or cefaloridine is a first generation semisynthetic cephalosporin. It is derived from cephalosporin C and is a zwitterion at physiological pH.
- Type
- Small Molecule
- Groups
- Experimental, Withdrawn
- Structure
- Weight
- Average: 415.486
Monoisotopic: 415.066047427 - Chemical Formula
- C19H17N3O4S2
- Synonyms
- (6R,7R)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)- 7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1- azabicyclo[4.2.0]oct-2-ene-2-carboxylate
- Cefaloridin
- Cefaloridina
- Cefaloridine
- Céfaloridine
- Cefaloridinum
- Cephalomycine
- Cephaloridine
- External IDs
- 40602
- Ceph 87/4
- Lilly 40602
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Renal.
- 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. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- 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 Cefaloridine 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 Cefaloridine. Acamprosate The excretion of Acamprosate can be decreased when combined with Cefaloridine. Aceclofenac The risk or severity of nephrotoxicity can be increased when Aceclofenac is combined with Cefaloridine. Acemetacin The risk or severity of nephrotoxicity can be increased when Cefaloridine is combined with Acemetacin. - 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.
- International/Other Brands
- Cephalin (CCPC) / Ceporan (GlaxoSmithKline) / Kefloridin / Loridine
Categories
- ATC Codes
- J01DB02 — Cefaloridine
- Drug Categories
- Amides
- Anti-Bacterial Agents
- Anti-Infective Agents
- Antibacterials for Systemic Use
- Antiinfectives for Systemic Use
- beta-Lactams
- Cephalosporins
- First-Generation Cephalosporins
- Heterocyclic Compounds, Fused-Ring
- Lactams
- Nephrotoxic agents
- OAT1/SLC22A6 Substrates
- OAT3/SLC22A8 Inhibitors
- OAT3/SLC22A8 Substrates
- Sulfur Compounds
- Thiazines
- Chemical TaxonomyProvided by Classyfire
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Organoheterocyclic compounds
- Class
- Lactams
- Sub Class
- Beta lactams
- Direct Parent
- Cephalosporins
- Alternative Parents
- N-acyl-alpha amino acids and derivatives / 1,3-thiazines / Pyridinium derivatives / Thiophenes / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Azetidines / Carboxylic acid salts / Thiohemiaminal derivatives show 11 more
- Substituents
- Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Carbonyl group / Carboxamide group / Carboxylic acid / Carboxylic acid derivative / Carboxylic acid salt / Cephalosporin show 21 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- cephalosporin (CHEBI:3537)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- LVZ1VC61HB
- CAS number
- 50-59-9
- InChI Key
- CZTQZXZIADLWOZ-CRAIPNDOSA-N
- InChI
- InChI=1S/C19H17N3O4S2/c23-14(9-13-5-4-8-27-13)20-15-17(24)22-16(19(25)26)12(11-28-18(15)22)10-21-6-2-1-3-7-21/h1-8,15,18H,9-11H2,(H-,20,23,25,26)/t15-,18-/m1/s1
- IUPAC Name
- 1-{[(6R,7R)-2-carboxylato-7-{[1-hydroxy-2-(thiophen-2-yl)ethylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl]methyl}pyridin-1-ium
- SMILES
- [H][C@]12SCC(C[N+]3=CC=CC=C3)=C(N1C(=O)[C@H]2NC(=O)CC1=CC=CS1)C([O-])=O
References
- Synthesis Reference
U.S. Patent 3,270,012.
- General References
- Not Available
- External Links
- KEGG Drug
- D01075
- KEGG Compound
- C11754
- PubChem Compound
- 5773
- PubChem Substance
- 310264967
- ChemSpider
- 5569
- BindingDB
- 50103624
- 2233
- ChEBI
- 3537
- ChEMBL
- CHEMBL316157
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cephaloridine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00383 mg/mL ALOGPS logP -1 ALOGPS logP -2.3 Chemaxon logS -5.1 ALOGPS pKa (Strongest Acidic) 3.06 Chemaxon pKa (Strongest Basic) -0.017 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 96.91 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 117.8 m3·mol-1 Chemaxon Polarizability 41.49 Å3 Chemaxon Number of Rings 4 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
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 187.26431 predictedDeepCCS 1.0 (2019) [M+H]+ 189.65987 predictedDeepCCS 1.0 (2019) [M+Na]+ 195.5724 predictedDeepCCS 1.0 (2019)
Transporters
1. DetailsSolute carrier family 22 member 6
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- Curator comments
- Substrate profile was investigated during in vitro studies using HEK293 cells.
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
2. DetailsSolute carrier family 22 member 8
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- Substrate and inhibitor activity were demonstrated in vitro using human OAT3 expressed on HEK293 cells and rat OAT3 expressed on S2 cells.
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
Drug created at June 20, 2014 17:02 / Updated at February 21, 2021 18:52