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Details

Stereochemistry ACHIRAL
Molecular Formula C5H8BrNO4
Molecular Weight 226.025
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIBROXANE

SMILES

CC1OCC(Br)(CO1)[N+]([O-])=O

InChI

InChIKey=VFBSFSGHILWWIJ-UHFFFAOYSA-N
InChI=1S/C5H8BrNO4/c1-4-10-2-5(6,3-11-4)7(8)9/h4H,2-3H2,1H3

HIDE SMILES / InChI

Molecular Formula C5H8BrNO4
Molecular Weight 226.025
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Nibroxane, 5-bromo-2-methyl-5-nitro-m-dioxane, is a topically effective antimicrobial agent with a broad spectrum of activity. Nibroxane is unusual in that it not only possesses high microbiocidal activity against Gram positive (Staphylococcus uureus) and Gram negative (Pseudomonas aeruginosa) bacteria but also against yeasts (Candida albicans) and moulds (Aspergillus niger). In addition, the 5-bromo-5-nitro-m-dioxanes have, as a class of compounds, the distinct advantage of being chemically stable over a wide pH range. This inherent stability, coupled with its broad spectrum of microbiocidal activity, makes nibroxane an excellent candidate as a preservative for cosmetic and pharmaceutical formulations.

Approval Year

PubMed

PubMed

TitleDatePubMed
Metabolism of the antimicrobial agent nibroxane, 5-bromo-2-methyl-5-nitro-m-dioxane, in the rat.
1978 Aug

Sample Use Guides

In Vivo Use Guide
In study in vivo, nibroxane (200 mg/kg, approx. the LD50) was administered orally to rats
Route of Administration: Oral
In Vitro Use Guide
The study of plasma concentrations by the g.l.c. method revealed a rapid debromination of nibroxane in vitro to 2-methyl-5-nitro-m-dioxane. To determine the rate of this conversion, nibroxane (500 ng/ml) in rat plasma was incubated, samples removed and analysed by g.l.c. at times from 1 to 60 min.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:56:57 GMT 2023
Edited
by admin
on Fri Dec 15 18:56:57 GMT 2023
Record UNII
U611CGM1FW
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NIBROXANE
INN   USAN  
INN   USAN  
Official Name English
nibroxane [INN]
Common Name English
NIBROXANE [USAN]
Common Name English
COMPOUND 85287
Code English
5-BROMO-2-METHYL-5-NITRO-M-DIOXANE
Systematic Name English
1,3-DIOXANE, 5-BROMO-2-METHYL-5-NITRO-
Systematic Name English
NSC-290304
Code English
COMPOUND-85287
Code English
Classification Tree Code System Code
EPA PESTICIDE CODE 116101
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
Code System Code Type Description
NSC
290304
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
NCI_THESAURUS
C84005
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
EVMPD
SUB09219MIG
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
MESH
C017556
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105156
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
CAS
53983-00-9
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
INN
3951
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
FDA UNII
U611CGM1FW
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
ECHA (EC/EINECS)
258-898-7
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
PUBCHEM
40955
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
EPA CompTox
DTXSID4042202
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
SMS_ID
100000084164
Created by admin on Fri Dec 15 18:56:57 GMT 2023 , Edited by admin on Fri Dec 15 18:56:57 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY