Identification

Generic Name
Deacetoxycephalosporin C
DrugBank Accession Number
DB03938
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 357.382
Monoisotopic: 357.099456045
Chemical Formula
C14H19N3O6S
Synonyms
  • DAOC
  • De(acetyloxy)cephalosporin C
  • Deacetoxycephalosporin C
  • Deacetoxycephalosporin-C

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDeacetoxycephalosporin C synthaseNot AvailableStreptomyces clavuligerus (strain ATCC 27064 / DSM 738 / JCM 4710 / NBRC 13307 / NCIMB 12785 / NRRL 3585 / VKM Ac-602)
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

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
AcetazolamideThe therapeutic efficacy of Acetazolamide can be decreased when used in combination with Deacetoxycephalosporin C.
AmifampridineThe risk or severity of seizure can be increased when Deacetoxycephalosporin C is combined with Amifampridine.
AmobarbitalThe therapeutic efficacy of Amobarbital can be decreased when used in combination with Deacetoxycephalosporin C.
BrexanoloneThe therapeutic efficacy of Brexanolone can be decreased when used in combination with Deacetoxycephalosporin C.
BrivaracetamThe therapeutic efficacy of Brivaracetam can be decreased when used in combination with Deacetoxycephalosporin C.
BupropionThe risk or severity of seizure can be increased when Bupropion is combined with Deacetoxycephalosporin C.
ButalbitalThe therapeutic efficacy of Butalbital can be decreased when used in combination with Deacetoxycephalosporin C.
CannabidiolThe therapeutic efficacy of Cannabidiol can be decreased when used in combination with Deacetoxycephalosporin C.
CarbamazepineThe therapeutic efficacy of Carbamazepine can be decreased when used in combination with Deacetoxycephalosporin C.
CenobamateThe therapeutic efficacy of Cenobamate can be decreased when used in combination with Deacetoxycephalosporin C.
Interactions
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Food Interactions
Not Available

Categories

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 / D-alpha-amino acids / Medium-chain fatty acids / Heterocyclic fatty acids / 1,3-thiazines / N-acyl amines / Dicarboxylic acids and derivatives / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids
show 10 more
Substituents
Aliphatic heteropolycyclic compound / Alpha-amino acid / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Azacycle / Azetidine / Carbonyl group / Carboxamide group
show 26 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
cephalosporin (CHEBI:18229)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
26924-74-3
InChI Key
NNQIJOYQWYKBOW-JWKOBGCHSA-N
InChI
InChI=1S/C14H19N3O6S/c1-6-5-24-12-9(11(19)17(12)10(6)14(22)23)16-8(18)4-2-3-7(15)13(20)21/h7,9,12H,2-5,15H2,1H3,(H,16,18)(H,20,21)(H,22,23)/t7-,9-,12-/m1/s1
IUPAC Name
(6R,7R)-7-[(5R)-5-amino-5-carboxypentanamido]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)CCC[C@@H](N)C(O)=O)C(O)=O

References

General References
Not Available
KEGG Compound
C06565
PubChem Compound
160139
PubChem Substance
46509194
ChemSpider
140762
ChEBI
18229
PDBe Ligand
P1C
PDB Entries
1uog / 1w2o

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 Solubility2.51 mg/mLALOGPS
logP-2.3ALOGPS
logP-3.5ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)1.84ChemAxon
pKa (Strongest Basic)9.23ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area150.03 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity84.5 m3·mol-1ChemAxon
Polarizability34.95 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9045
Blood Brain Barrier-0.9943
Caco-2 permeable-0.8332
P-glycoprotein substrateSubstrate0.7979
P-glycoprotein inhibitor INon-inhibitor0.8976
P-glycoprotein inhibitor IINon-inhibitor0.997
Renal organic cation transporterNon-inhibitor0.9465
CYP450 2C9 substrateNon-substrate0.858
CYP450 2D6 substrateNon-substrate0.8265
CYP450 3A4 substrateNon-substrate0.5057
CYP450 1A2 substrateNon-inhibitor0.8655
CYP450 2C9 inhibitorNon-inhibitor0.8901
CYP450 2D6 inhibitorNon-inhibitor0.9273
CYP450 2C19 inhibitorNon-inhibitor0.8582
CYP450 3A4 inhibitorNon-inhibitor0.8934
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9568
Ames testNon AMES toxic0.7337
CarcinogenicityNon-carcinogens0.9549
BiodegradationNot ready biodegradable0.8972
Rat acute toxicity1.8680 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9907
hERG inhibition (predictor II)Non-inhibitor0.935
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 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

Targets

Drugtargets2
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Kind
Protein
Organism
Streptomyces clavuligerus (strain ATCC 27064 / DSM 738 / JCM 4710 / NBRC 13307 / NCIMB 12785 / NRRL 3585 / VKM Ac-602)
Pharmacological action
Unknown
General Function
L-ascorbic acid binding
Specific Function
Catalyzes the step from penicillin N to deacetoxy-cephalosporin C.
Gene Name
cefE
Uniprot ID
P18548
Uniprot Name
Deacetoxycephalosporin C synthase
Molecular Weight
34555.38 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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52