Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H16N4O8S2 |
Molecular Weight | 516.504 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SCC(\C=C\C3=CC=C(C=C3[N+]([O-])=O)[N+]([O-])=O)=C(N1C(=O)[C@H]2NC(=O)CC4=CC=CS4)C(O)=O
InChI
InChIKey=LHNIIDJCEODSHA-OQRUQETBSA-N
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
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/8345168Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20498317 | https://www.ncbi.nlm.nih.gov/pubmed/19884379 | https://www.ncbi.nlm.nih.gov/pubmed/17438050 | https://www.ncbi.nlm.nih.gov/pubmed/41001
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8345168
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20498317 | https://www.ncbi.nlm.nih.gov/pubmed/19884379 | https://www.ncbi.nlm.nih.gov/pubmed/17438050 | https://www.ncbi.nlm.nih.gov/pubmed/41001
Nitrocefin is a chromogenic cephalosporin substrate routinely used to detect the presence of beta-lactamase enzymes produced by various microbes. Intact beta-lactam antibiotics act as an analog to penicillin-binding proteins (PBPs) involved in peptidoglycan synthesis. Beta-lactamases hydrolyze the amide bond between the carbonyl carbon and the nitrogen in the beta-lactam ring of susceptible beta-lactams and members of beta-lactam subclasses (including certain cephalosporins). After hydrolysis of the amide bond, the antibiotic lacks the ability to mimic bacterial PBPs and is rendered useless. Visual detection of this process is essentially impossible with most cephalosporins because the shift of ultraviolet absorption from the intact versus hydrolyzed product occurs outside of the visible spectrum. Hydrolysis of nitrocefin, however, produces a shift of ultraviolet absorption inside the visible light spectrum from intact (yellow) nitrocefin (~380 nm) to degraded (red) nitrocefin (~500 nm) allowing visual detection of beta-lactamase activity on a macroscopic level.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL5031 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19884379 |
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Target ID: CHEMBL1255147 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20498317 |
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Target ID: CHEMBL5303 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17438050 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/41001
A working solution of Nitrocefin is prepared by adding 0.5 ml of dimethyl sulfoxide to 5 mg of Nitrocefin powder. A 9.5-ml amount of 0.1 M phosphate buffer (pH 7.0) is added to provide a final Nitrocefin concentration of 500mkg/ml. The solution is dispensed in 0.5-ml portions and frozen at -20°C. A loopful of the test organism is removed from colonial growth on the surface of a brucella blood agar plate and emulsified in one drop of the Nitrocefin solution on a clean glass microscope slide. A change in color from yellow to red within 15 min indicates a positive reaction.
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NCI_THESAURUS |
C260
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DB11592
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41906-86-9
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CHEMBL480517
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m7951
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NITROCEFIN
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EWP54G0J8F
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DTXSID401318525
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C76562
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6436140
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SUBSTANCE RECORD