Identification

Name
Cephaloridine
Accession Number
DB09008
Type
Small Molecule
Groups
Experimental, Withdrawn
Description

Cephaloridine (or cefaloridine) is a first generation semisynthetic derivative of cephalosporin C. It is unique among cephalosporins in that it exists as a zwitterion.

Structure
Thumb
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
  • Céfaloridine
  • cefaloridine
  • Cefaloridinum
  • Cephalomycine
External IDs
40602 / Ceph 87/4 / Lilly 40602
International/Other Brands
Cephalin (CCPC) / Ceporan (GlaxoSmithKline)
Categories
UNII
LVZ1VC61HB
CAS number
50-59-9
Weight
Average: 415.486
Monoisotopic: 415.066047427
Chemical Formula
C19H17N3O4S2
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@@]2([H])N=C(O)CC1=CC=CS1)C([O-])=O

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding can be increased when Cephaloridine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding can be increased when Cephaloridine is combined with (S)-Warfarin.
4-hydroxycoumarinThe risk or severity of bleeding can be increased when Cephaloridine is combined with 4-hydroxycoumarin.
AbacavirCephaloridine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseCephaloridine may decrease the excretion rate of Acarbose which could result in a higher serum level.
AceclofenacCephaloridine may decrease the excretion rate of Aceclofenac which could result in a higher serum level.
AcemetacinThe risk or severity of nephrotoxicity can be increased when Cephaloridine is combined with Acemetacin.
AcenocoumarolThe risk or severity of bleeding can be increased when Cephaloridine is combined with Acenocoumarol.
AcetaminophenCephaloridine may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
AcetazolamideThe excretion of Cephaloridine can be decreased when combined with Acetazolamide.
Food Interactions
Not Available

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
ChEBI
3537
ChEMBL
CHEMBL316157
Drugs.com
Drugs.com Drug Page
Wikipedia
Cephaloridine
ATC Codes
J01DB02 — Cefaloridine

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.00719 mg/mLALOGPS
logP-0.78ALOGPS
logP-2.3ChemAxon
logS-4.8ALOGPS
pKa (Strongest Acidic)3.27ChemAxon
pKa (Strongest Basic)-0.017ChemAxon
Physiological Charge-1ChemAxon
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

Taxonomy

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
Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / Meta-thiazine / Pyridine / Pyridinium / Heteroaromatic compound / Tertiary carboxylic acid amide / Thiophene / Azetidine
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin (CHEBI:3537)

Transporters

Kind
Protein
Organism
Human
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. [PubMed:19953504]
Kind
Protein
Organism
Human
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. [PubMed:19953504]

Drug created on June 20, 2014 11:02 / Updated on November 02, 2018 06:57