Stereo-Sloppy
Definition: An informal but precise descriptor for scientific, educational, or regulatory practice in which stereochemical distinctions are ignored, misused, oversimplified, or treated as inconsequential.
Context: Stereo-sloppy behavior manifests when chirality, configuration, or isomerism is inadequately specified or misunderstood. In chemistry and pharmacology, stereo-sloppiness can lead to incorrect structures, flawed SAR conclusions, irreproducible synthesis, analytical errors, or unsafe clinical assumptions. The term is particularly relevant in discussions of poor stereochemical literacy, inadequate reporting, and historical drug development failures.
Example: Describing a compound as "the active drug" without specifying whether it is a racemate, eutomer, or enantiopure form; or using D/L, d/l, and R/S interchangeably as if they were equivalent.
Related Terms: Chiral Literacy; Chiral Intelligence; Stereochemistry; Isomerism; Stereo-pharmacology; Misassignment of Configuration.
Reference: Ariens, E. J. Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology. Medical Research Reviews, 4, 197-236 (1984). - Classic paper criticizing careless stereochemical thinking.
Eliel, E. L., Wilen, S. H., & Mander, L. N. Stereochemistry of Organic Compounds. Wiley (1994).
Smith, S. W. Chiral toxicology: it's the same thing...only different. Toxicological Sciences, 110(1), 4-30, (2009).
Nguyen, L. A., He, H., & Pham-Huy, C. Chiral drugs: an overview. International Journal of Biomedical Science, 2(2), 85-100, (2006).