Identification

Name
Cephalosporin C
Accession Number
DB03313  (EXPT01031)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
3XIY7HJT5L
CAS number
Not Available
Weight
Average: 415.418
Monoisotopic: 415.104935353
Chemical Formula
C16H21N3O8S
InChI Key
HOKIDJSKDBPKTQ-GLXFQSAKSA-N
InChI
InChI=1S/C16H21N3O8S/c1-7(20)27-5-8-6-28-14-11(13(22)19(14)12(8)16(25)26)18-10(21)4-2-3-9(17)15(23)24/h9,11,14H,2-6,17H2,1H3,(H,18,21)(H,23,24)(H,25,26)/t9-,11-,14-/m1/s1
IUPAC Name
(6R,7R)-3-[(acetyloxy)methyl]-7-{[(5R)-5-amino-5-carboxy-1-hydroxypentylidene]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
CC(=O)OCC1=C(N2[C@H](SC1)[C@H](N=C(O)CCC[C@@H](N)C(O)=O)C2=O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UD-alanyl-D-alanine carboxypeptidaseNot AvailableStreptomyces sp. (strain R61)
APenicillin-binding protein 1b
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 1A
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2B
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 2a
inhibitor
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
APenicillin-binding protein 3
inhibitor
Streptococcus pneumoniae
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
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
7-NitroindazoleThe therapeutic efficacy of 7-Nitroindazole can be decreased when used in combination with Cephalosporin C.
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Cephalosporin C.
AmifampridineThe risk or severity of seizure can be increased when Cephalosporin C is combined with Amifampridine.
AmobarbitalThe therapeutic efficacy of Amobarbital can be decreased when used in combination with Cephalosporin C.
BarbexacloneThe therapeutic efficacy of Barbexaclone can be decreased when used in combination with Cephalosporin C.
BarbitalThe therapeutic efficacy of Barbital can be decreased when used in combination with Cephalosporin C.
BeclamideThe therapeutic efficacy of Beclamide can be decreased when used in combination with Cephalosporin C.
BrivaracetamThe therapeutic efficacy of Brivaracetam can be decreased when used in combination with Cephalosporin C.
ButalbitalThe therapeutic efficacy of Butalbital can be decreased when used in combination with Cephalosporin C.
CannabidivarinThe therapeutic efficacy of Cannabidivarin can be decreased when used in combination with Cephalosporin C.
Food Interactions
Not Available

References

Synthesis Reference

Chun-Lung Hsieh, "Process for preparing alkali salts of cephalosporin C." U.S. Patent US5403929, issued May, 1972.

US5403929
General References
Not Available
External Links
Human Metabolome Database
HMDB0060450
KEGG Compound
C00916
PubChem Compound
65536
PubChem Substance
46505733
ChemSpider
58980
ChEBI
15776
ChEMBL
CHEMBL482858
HET
CSC
Wikipedia
Cephalosporin_C

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 Solubility0.389 mg/mLALOGPS
logP-2.1ALOGPS
logP-3.5ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)1.82ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area179.82 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity95.95 m3·mol-1ChemAxon
Polarizability40.72 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9983
Blood Brain Barrier-0.9961
Caco-2 permeable-0.7586
P-glycoprotein substrateSubstrate0.8668
P-glycoprotein inhibitor INon-inhibitor0.8709
P-glycoprotein inhibitor IINon-inhibitor0.9931
Renal organic cation transporterNon-inhibitor0.9164
CYP450 2C9 substrateNon-substrate0.8183
CYP450 2D6 substrateNon-substrate0.8243
CYP450 3A4 substrateNon-substrate0.5068
CYP450 1A2 substrateNon-inhibitor0.7811
CYP450 2C9 inhibitorNon-inhibitor0.8224
CYP450 2D6 inhibitorNon-inhibitor0.9025
CYP450 2C19 inhibitorNon-inhibitor0.7893
CYP450 3A4 inhibitorNon-inhibitor0.8812
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8764
Ames testNon AMES toxic0.6963
CarcinogenicityNon-carcinogens0.9617
BiodegradationNot ready biodegradable0.5154
Rat acute toxicity1.9527 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.981
hERG inhibition (predictor II)Non-inhibitor0.8359
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids and derivatives
Alternative Parents
D-alpha-amino acids / Tricarboxylic acids and derivatives / Cephems / 1,3-thiazines / Tertiary carboxylic acid amides / Amino acids / Azetidines / Carboxylic acid esters / Thiohemiaminal derivatives / Propargyl-type 1,3-dipolar organic compounds
show 9 more
Substituents
N-acyl-alpha amino acid or derivatives / Alpha-amino acid / D-alpha-amino acid / Cephem / Tricarboxylic acid or derivatives / Meta-thiazine / Beta-lactam / Tertiary carboxylic acid amide / Azetidine / Amino acid
show 25 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
cephalosporin (CHEBI:15776) / Cephems (C00916)

Targets

Kind
Protein
Organism
Streptomyces sp. (strain R61)
Pharmacological action
Unknown
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Catalyzes distinct carboxypeptidation and transpeptidation reactions during the last stages of wall peptidoglycan synthesis. Mistaking a beta-lactam antibiotic molecule for a normal substrate (i.e....
Gene Name
Not Available
Uniprot ID
P15555
Uniprot Name
D-alanyl-D-alanine carboxypeptidase
Molecular Weight
42916.725 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Transferase activity, transferring acyl groups
Specific Function
Not Available
Gene Name
pbp1b
Uniprot ID
Q7CRA4
Uniprot Name
Penicillin-binding protein 1b
Molecular Weight
89479.92 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Cell wall formation.
Gene Name
pbpA
Uniprot ID
Q8DR59
Uniprot Name
Penicillin-binding protein 1A
Molecular Weight
79700.9 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Not Available
Specific Function
Penicillin binding
Gene Name
penA
Uniprot ID
P0A3M6
Uniprot Name
Penicillin-binding protein 2B
Molecular Weight
73872.305 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
Yes
Actions
Inhibitor
General Function
Transferase activity, transferring acyl groups
Specific Function
Not Available
Gene Name
pbp2a
Uniprot ID
Q8DNB6
Uniprot Name
Penicillin-binding protein 2a
Molecular Weight
80797.94 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]
Kind
Protein
Organism
Streptococcus pneumoniae
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serine-type d-ala-d-ala carboxypeptidase activity
Specific Function
Not Available
Gene Name
pbp3
Uniprot ID
Q75Y35
Uniprot Name
Penicillin-binding protein 3
Molecular Weight
45209.84 Da
References
  1. Williamson R, Hakenbeck R, Tomasz A: In vivo interaction of beta-lactam antibiotics with the penicillin-binding proteins of Streptococcus pneumoniae. Antimicrob Agents Chemother. 1980 Oct;18(4):629-37. [PubMed:7447421]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:33