Fipronil-desulfinyl

• CAS: 205650-65-3
• Catalog Number: ACM205650653
• Category: Main Products
• Molecular Weight: 389.08
• Molecular Formula: C₁₂H₄Cl₂F₆N₄
• Synonyms: desulfinyl fipronil; 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-trifluoromethyl-1H-pyrazole-3-carbonitrile; Fipronil Desulfinyl; desthiofipronil; Fipronil-desulfinyl
• IUPAC Name: 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethyl)pyrazole-3-carbonitrile
• Canonical SMILES: C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)C(F)(F)F)N)Cl)C(F)(F)F
• InChI Key: JWKXVHLIRTVXLD-UHFFFAOYSA-N
• Exact Mass: 387.97200

Case Study

Fipronil Desulfinyl and Its Impact on Growth and Endocrine Function in Decapod Crustaceans

Goff A. D, et al. Aquatic Toxicology, 2017, 186, 96-104.

Fipronil desulfinyl has been implicated in endocrine disruption in aquatic invertebrates, particularly in decapod crustaceans like Callinectes sapidus (blue crab). Exposure studies on juvenile crabs revealed significant physiological and molecular effects at environmentally relevant concentrations (0.01-0.5 μg/L) under varying salinity conditions.
Fipronil desulfinyl exposure notably altered growth metrics, including weight and carapace width, with exposed crabs showing increased size compared to controls. At the molecular level, a dose-dependent reduction in the expression of vitellogenin (Vtg) and the ecdysone receptor (EcR) genes was observed, which are critical for reproduction and molting processes. These findings indicate that fipronil desulfinyl disrupts hormonal pathways essential for normal development and reproduction.
The product's bioavailability was shown to vary with salinity, with higher salinity conditions promoting greater tissue partitioning. This salinity-dependent solubility highlights the ecological risk of fipronil desulfinyl in estuarine environments where salinity fluctuates.

Fipronil Desulfinyl and Its Role in Mitochondrial Dysfunction and Bioenergetic Disruption

Tavares M. A, Environmental Toxicology and Pharmacology, 2015, 40(1), 206-214.

Fipronil desulfinyl, a key metabolite of the widely used insecticide fipronil, has been shown to exert significant effects on liver mitochondria, revealing its role in bioenergetic disruption and calcium homeostasis alteration. In vitro studies on isolated rat liver mitochondria demonstrated that fipronil desulfinyl inhibits state-3 respiration by targeting complex I substrates, such as glutamate and malate, within the mitochondrial respiratory chain. This inhibition decreases mitochondrial membrane potential, leading to suppressed ATP synthesis.
Additionally, fipronil desulfinyl uncouples mitochondria energized with succinate, disrupting the efficient coupling of electron transport and ATP generation. It also promotes calcium efflux, a critical factor in mitochondrial calcium homeostasis, further implicating its role in mitochondrial dysfunction. These effects, along with the generation of reactive oxygen species (ROS), suggest a direct connection between fipronil desulfinyl exposure and liver toxicity.

Custom Q&A

What is the molecular formula of Fipronil-desulfinyl?

The molecular formula of Fipronil-desulfinyl is C12H4Cl2F6N4.

What are some synonyms of Fipronil-desulfinyl?

Some synonyms of Fipronil-desulfinyl include Fipronil Desulfinyl, Desulfinylfipronil, FIPRONIL-DESULFINYL, and Fipronil metabolite 46513.

What is the IUPAC name of Fipronil-desulfinyl?

The IUPAC name of Fipronil-desulfinyl is 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(trifluoromethyl)pyrazole-3-carbonitrile.

What is the InChIKey of Fipronil-desulfinyl?

The InChIKey of Fipronil-desulfinyl is JWKXVHLIRTVXLD-UHFFFAOYSA-N.

What is the canonical SMILES of Fipronil-desulfinyl?

The canonical SMILES of Fipronil-desulfinyl is C1=C(C=C(C(=C1Cl)N2C(=C(C(=N2)C#N)C(F)(F)F)N)Cl)C(F)(F)F.

What is the CAS number of Fipronil-desulfinyl?

The CAS number of Fipronil-desulfinyl is 205650-65-3.

What is the molecular weight of Fipronil-desulfinyl?

The molecular weight of Fipronil-desulfinyl is 389.08g/mol.

How many hydrogen bond donor counts does Fipronil-desulfinyl have?

Fipronil-desulfinyl has 1 hydrogen bond donor count.

How many hydrogen bond acceptor counts does Fipronil-desulfinyl have?

Fipronil-desulfinyl has 9 hydrogen bond acceptor counts.

How many rotatable bond counts does Fipronil-desulfinyl have?

Fipronil-desulfinyl has 1 rotatable bond count.