Stereochemical definitions and nomenclature: Changing signs?

Research output: Contribution to journalArticle


Classification of chirality rests on the elements of asymmetry, a concept theoretically questionable, but useful. In chemistry, the Cahn, Ingold, Prelog (CIP) Convention is well-established, generally accepted, and applied. It introduced the R- and S- prefixes to be applied before the names of compounds involving a single asymmetry element, or the M- and P- prefixes for helical asymmetry. For molecules involving multiple elements of asymmetry, the prefixes were complementary with reference to the exact location and should be distinctively applied to each element. If the same system were applied to international nonproprietary (generic) drug names, awkward notations would result. To this end, the SIGNS nomenclature was proposed. In practice, neither of the stereochemical systems is applied, leading to a high degree of ignorance about the number and quality of the pharmacological entities implied by common drug names.

Original languageEnglish
Pages (from-to)533-540
Number of pages8
JournalTherapeutic Innovation and Regulatory Science
Issue number2
Publication statusPublished - 1994



  • CIP convention
  • SIGNS nomenclature
  • Stereochemical characterization of drug names

ASJC Scopus subject areas

  • Pharmacology (medical)
  • Public Health, Environmental and Occupational Health
  • Pharmacology, Toxicology and Pharmaceutics (miscellaneous)

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