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Nitrocefin

CAT: 0804-HY-108913-06Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-108913-06Size:50 mg
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Description
Nitrocefin is a highly activated, chromogenic cephalosporin derivative. Nitrocefin is a chromogenic β-lactamase substrate. Nitrocefin undergoes a distinctive color change from yellow to red as the amide bond in the β-lactam ring is hydrolyzed by β-lactamase. Nitrocefin is used in competitive inhibition studies in developmental work on β-lactamase-resistant antibiotics[1][2][3][4].
CAS Number
41906-86-9
UNSPSC
12352005
Hazard Statement
H302, H315, H319, H335
Target
Antibiotic; Bacterial; Beta-lactamase
Type
Reference compound
Related Pathways
Anti-infection
Applications
COVID-19-immunoregulation
Field of Research
Infection
Assay Protocol
https://www.medchemexpress.com/nitrocefin.html
Purity
98.11
Solubility
DMSO : 100 mg/mL (ultrasonic)
Smiles
O=C(C(N12)=C(/C=C/C3=CC=C([N+]([O-])=O)C=C3[N+]([O-])=O)CS[C@]2([H])[C@H](NC(CC4=CC=CS4)=O)C1=O)O
Molecular Formula
C21H16N4O8S2
Molecular Weight
516.50
Precautions
H302, H315, H319, H335
References & Citations
[1]Lee M, et al. A practical synthesis of nitrocefin. J Org Chem. 2005 Jan 7;70 (1) :367-9.|[2]Worthington RJ, et al. Overcoming resistance to β-lactam antibiotics. J Org Chem. 2013 May 3;78 (9) :4207-13.|[3]O'Callaghan CH, et al. Novel method for detection of beta-lactamases by using a chromogenic cephalosporin substrate. Antimicrob Agents Chemother. 1972 Apr;1 (4) :283-8.|[4]Chow C, et al. Blanchard JS. Kinetic characterization of hydrolysis of nitrocefin, cefoxitin, and meropenem by β-lactamase from Mycobacterium tuberculosis. Biochemistry. 2013 Jun 11;52 (23) :4097-104.
Shipping Conditions
Room Temperature
Storage Conditions
-20°C, 3 years; 4°C, 2 years (Powder)
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Isoform
β-lactam

Chemical Information

Nitrocefin

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.

CAS Number41906-86-9
PubChem CID6436140
IUPAC Name(6R,7R)-3-[(E)-2-(2,4-dinitrophenyl)ethenyl]-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Molecular FormulaC21H16N4O8S2
Molecular Weight516.5
XLogP2.2
Topological Polar Surface Area232
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count10
Rotatable Bond Count6
Heavy Atom Count35
Formal Charge0
Complexity991
SMILES
C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CS3)C(=O)O)/C=C/C4=C(C=C(C=C4)[N+](=O)[O-])[N+](=O)[O-]
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
InChIKey
LHNIIDJCEODSHA-OQRUQETBSA-N
Chemical Structure
2D Structure
2D structure of Nitrocefin
CAS: 41906-86-9
CID: 6436140
Formula: C21H16N4O8S2
MW: 516.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight516.5
XLogP32.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count10
Rotatable Bond Count6
Exact Mass516.04095583
Monoisotopic Mass516.04095583
Topological Polar Surface Area232 Ų
Heavy Atom Count35
Formal Charge0
Complexity991
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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