Sulfamethoxazole D4 (benzene D4)

Catalog Number	ACM1020719861-1
CAS	1020719-86-1
Structure
Synonyms	Sulfamethoxazole D4 (benzene D4)
IUPAC Name	4-amino-2,3,5,6-tetradeuterio-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
Molecular Weight	257.3
Molecular Formula	C10D4H7N3O3S
Canonical SMILES	[2H]c1c([2H])c(c([2H])c([2H])c1N)S(=O)(=O)Nc2cc(C)on2
InChI	InChI=1S/C10H11N3O3S/c1-7-6-10(12-16-7)13-17(14,15)9-4-2-8(11)3-5-9/h2-6H,11H2,1H3,(H,12,13)/i2D,3D,4D,5D
Storage	+20 °C
Accurate Mass	257.0772
Format	Neat
Shipping Temperature	+20 °C
SIL Type	Deuterium
CAS (Unlabeled)	723-46-6

Case Study

Study on the Reversible Transformation of Transformation Products of Sulfamethoxazole Using Sulfamethoxazole D4

Barbieri, Manuela, et al. Science of the Total Environment, 2012, 426, 256-263.

A series of batch experiments under denitrification conditions examined the reversible transformation of aromatic amines, specifically diclofenac (DCF) and sulfamethoxazole (SMX), in aquifer materials. Deuterated analogs (diclofenac-d4 and sulfamethoxazole-d4) served as surrogate standards for quantifying DCF and SMX during micropollutant analysis. The experiments evaluated two scenarios: one with an initial pollutant concentration of 1 μg/L and another with 1 mg/L. Both compounds, negatively charged at the experimental pH, temporarily declined in concentration mid-test but rebounded by the end, suggesting denitrification reversibly influences aromatic amine dynamics.
Nitro-diclofenac and 4-nitro-sulfamethoxazole transformation products were detected in bioassays alongside nitrite, with their concentrations inversely correlated to parent compounds. This reversible interaction under denitrification may have environmental significance, potentially clarifying inconsistencies in reported subsurface removal efficiencies of DCF and SMX and variations in SMX behavior.

Sulfamethoxazole D4 Was Used to Evaluate the Enhanced Biodegradation Potential of SFX by Ammonia Oxidizing Bacteria

Kassotaki, Elissavet, et al. Water Research, 2016, 94, 111-119.

The common use of sulfamethoxazole (SFX) as an antibiotic has led to its frequent detection in wastewater and surface water. The study focused on how enriched ammonia oxidizing bacteria (AOB) cultures improve SFX biodegradation potential. The existence of SFX and its transformation products as well as their formation and breakdown were continuously observed.
The short-term and long-term analysis experiments received 10 mmL of sulfamethoxazole-d4 at 1 mg/L concentration as an internal standard within 1 mL of extracts before undergoing ultra-performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) evaluation.
The enrichment process resulted in AOB cultures that degraded recalcitrant micropollutants like SFX efficiently without needing an adaptation period. In aerobic short-term experiments (contact time of 6 h) and long-term experiments (contact time of 24 h) in SBR reactors, degradation of SFX was as high as 86% and 98%, respectively.
The degradation rate of SFX showed a strong connection with nitrification levels since increased specific ammonia oxidation rates led to more effective SFX removal.
Both short-term and long-term experiments generated transformation products (TPs) at a rate of approximately 30% of SFX. During both experiments, the primary TPs resulted in 4-nitro-SFX formation while deamination-SFX and N4-acetyl-SFX appeared less frequently. In batch tests, TPs were not degraded.

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Sulfamethoxazole D4 (benzene D4) (1020719-86-1)

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