Nitrocefin

Identification

Generic Name
Nitrocefin
DrugBank Accession Number
DB11592
Background

Nitrocefin is a chromogenic cephalosporin substrate used to detect the presence of beta-lactamase enzymes, an important mediator of bacterial antibiotic resistance. While other detection methods exist, such as PCR, nitrocefin allows for rapid detection using few materials and inexpensive equipment.

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 516.5
Monoisotopic: 516.040955839
Chemical Formula
C21H16N4O8S2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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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.
Not Available
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 / Nitrobenzenes / Styrenes / Nitroaromatic compounds / 1,3-thiazines / Thiophenes / Tertiary carboxylic acid amides / Heteroaromatic compounds / Secondary carboxylic acid amides / Azetidines
show 12 more
Substituents
Allyl-type 1,3-dipolar organic compound / Alpha-amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azetidine / Benzenoid / C-nitro compound / Carbonyl group / Carboxamide group / Carboxylic acid
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
EWP54G0J8F
CAS number
41906-86-9
InChI Key
LHNIIDJCEODSHA-OQRUQETBSA-N
InChI
InChI=1S/C21H16N4O8S2/c26-16(9-14-2-1-7-34-14)22-17-19(27)23-18(21(28)29)12(10-35-20(17)23)4-3-11-5-6-13(24(30)31)8-15(11)25(32)33/h1-8,17,20H,9-10H2,(H,22,26)(H,28,29)/b4-3+/t17-,20-/m1/s1
IUPAC Name
(6R,7R)-3-[(E)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[2-(thiophen-2-yl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][C@]12SCC(\C=C\C3=CC=C(C=C3[N+]([O-])=O)[N+]([O-])=O)=C(N1C(=O)[C@H]2NC(=O)CC1=CC=CS1)C(O)=O

References

General References
Not Available
PubChem Compound
6436140
PubChem Substance
347827999
ChemSpider
4940809
ChEMBL
CHEMBL480517
ZINC
ZINC000039995635
Wikipedia
Nitrocefin

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 Solubility0.0022 mg/mLALOGPS
logP2.52ALOGPS
logP2.48Chemaxon
logS-5.4ALOGPS
pKa (Strongest Acidic)3.07Chemaxon
pKa (Strongest Basic)-3.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area172.99 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity125.92 m3·mol-1Chemaxon
Polarizability46.68 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-207.31015
predicted
DeepCCS 1.0 (2019)
[M+H]+209.13504
predicted
DeepCCS 1.0 (2019)
[M+Na]+214.74086
predicted
DeepCCS 1.0 (2019)

Drug created at May 11, 2016 20:21 / Updated at June 12, 2020 16:53