Nitrocefin

CAT: 0804-HY-108913-01Size: 1 mgDry Ice: NoHazardous: No

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CAT#:0804-HY-108913-01Size:1 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 Number	41906-86-9
PubChem CID	6436140
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 Formula	C21H16N4O8S2
Molecular Weight	516.5
XLogP	2.2
Topological Polar Surface Area	232
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	6
Heavy Atom Count	35
Formal Charge	0
Complexity	991

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

CAS: 41906-86-9

CID: 6436140

Formula: C21H16N4O8S2

MW: 516.5

Interactive 3D Structure

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View on PubChem Raw 3D data

Computed Properties

Property	Value
Molecular Weight	516.5
XLogP3	2.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	6
Exact Mass	516.04095583
Monoisotopic Mass	516.04095583
Topological Polar Surface Area	232 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	991
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently-Bonded Unit Count	1
Compound Is Canonicalized	Yes

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