perfluorooctanesulfonamide

Synonyms: "perfluorooctanesulfonamide", "1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide", "perfluorooctane sulfonamide", "perfluoroctylsulfonamide", "PFOSA", "heptadecafluorooctanesulphonamide", "perfluorooctanesulfonic acid amide", "1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluoro-1-octanesulfonamide".

Source: perfluorooctanesulfonamide is a precursor of PFOS (perfluorooctane sulfonate%29, an anthropogenic fluorosurfactant and global pollutant.

Identifiers:

IUPAC Name: 1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecafluorooctane-1-sulfonamide
CAS Number: 754-91-6
PubChem ID: 69785
InChiKey: RRRXPPIDPYTNJG-UHFFFAOYSA-N
Canonical SMILES: C(C(C(C(C(F)(F)S(=O)(=O)N)(F)F)(F)F)(F)F)(C(C(C(F)(F)F)(F)F)(F)F)(F)F

Structural Properties:

Molecular Formula: C₈H₂F₁₇NO₂S
Molecular Weight: 499.142

Pharmacophore Features:

Number of bond donors: 1
Number of bond acceptors: 20
Number of atoms different from hydrogen: 29

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3D structure (.sdf)
3D structure (.mol2)
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Evidence Supporting This Chemical as an Endocrine Disruptor
TEDX List of Potential Endocrine Disruptors

Louis GMB, Chen Z, Schisterman EF, Kim S, Sweeney AM, Sundaram R, Lynch CD, Gore-Langton RE and Barr DB. 2015. Perfluorochemicals and human semen quality: the LIFE study. Environ Health Perspect 123(1):57-63. DOI: 10.1289/ehp.1307621. URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4286271/.
Louis GMB, Sundaram R, Schisterman EF, Sweeney AM, Lynch CD, Gore-Langton RE, Maisog J, Kim S, Chen Z and Barr DB. 2013. Persistent environmental pollutants and couple fecundity: the LIFE study. Environ Health Perspect 121(2):231-6. DOI: 10.1289/ehp.1205301. URL: https://www.ncbi.nlm.nih.gov/pubmed/23151773.
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Shipley, J.M., Hurst, C.H., Tanaka, S.S., DeRoos, F.L., Butenhoff, J.L., Seacat, A.M. and Waxman, D.J., 2004. Trans-activation of PPAR? and induction of PPAR? target genes by perfluorooctane-based chemicals. Toxicological Sciences, 80(1), pp.151-160. DOI: 10.1093/toxsci/kfh130. URL: https://doi.org/10.1093/toxsci/kfh130.
Whitworth KW, Haug LS, Sabaredzovic A, Eggesbo M and Longnecker MP. 2016. Brief Report: Plasma Concentrations of Perfluorooctane Sulfonamide and Time-to-pregnancy Among Primiparous Women. Epidemiology, 27(5), pp.712-715. DOI: 10.1097/EDE.0000000000000524. URL: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5387409/.