Cefaloridine

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Experimental, Withdrawn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
Thumb
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

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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
Adverseeffects
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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.
DrugInteraction
AbacavirCefaloridine 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 Cefaloridine.
AcamprosateThe excretion of Acamprosate can be decreased when combined with Cefaloridine.
AceclofenacThe risk or severity of nephrotoxicity can be increased when Aceclofenac is combined with Cefaloridine.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Cefaloridine is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Cefaloridine is combined with Acenocoumarol.
AcetaminophenCefaloridine may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideThe excretion of Cefaloridine can be decreased when combined with Acetazolamide.
Acetylsalicylic acidThe excretion of Cefaloridine can be decreased when combined with Acetylsalicylic acid.
AclidiniumCefaloridine may decrease the excretion rate of Aclidinium which could result in a higher serum level.
Interactions
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Food Interactions
Not Available

Products

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International/Other Brands
Cephalin (CCPC) / Ceporan (GlaxoSmithKline) / Kefloridin / Loridine

Categories

ATC Codes
J01DB02 — Cefaloridine
Drug Categories
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
KEGG Drug
D01075
KEGG Compound
C11754
PubChem Compound
5773
PubChem Substance
310264967
ChemSpider
5569
BindingDB
50103624
RxNav
2233
ChEBI
3537
ChEMBL
CHEMBL316157
Drugs.com
Drugs.com Drug Page
Wikipedia
Cephaloridine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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
PropertyValueSource
Water Solubility0.00383 mg/mLALOGPS
logP-1ALOGPS
logP-2.3ChemAxon
logS-5.1ALOGPS
pKa (Strongest Acidic)3.06ChemAxon
pKa (Strongest Basic)-0.017ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area96.91 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity117.8 m3·mol-1ChemAxon
Polarizability41.49 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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

Transporters

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
  1. 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]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. 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 on June 20, 2014 17:02 / Updated on February 21, 2021 18:52