Novel, broad-spectrum anticonvulsants containing a sulfamide group: advancement of N-((benzo[b]thien-3-yl)methyl)sulfamide (JNJ-26990990) into human clinical studies

J Med Chem. 2009 Dec 10;52(23):7528-36. doi: 10.1021/jm801432r.

Abstract

In seeking broad-spectrum anticonvulsants to treat epilepsy and other neurological disorders, we synthesized and tested a group of sulfamide derivatives (4a-k, 5), which led to the clinical development of 4a (JNJ-26990990). This compound exhibited excellent anticonvulsant activity in rodents against audiogenic, electrically induced, and chemically induced seizures, with very weak inhibition of human carbonic anhydrase-II (IC(50) = 110 microM). The pharmacological profile for 4a supports its potential in the treatment of multiple forms of epilepsy, including pharmacoresistant variants. Mechanistically, 4a inhibited voltage-gated Na(+) channels and N-type Ca(2+) channels but was not effective as a K(+) channel opener. The pharmacokinetics and metabolic properties of 4a are discussed.

MeSH terms

  • Amides / chemistry*
  • Amides / metabolism
  • Amides / pharmacokinetics
  • Amides / pharmacology*
  • Animals
  • Anticonvulsants / chemistry*
  • Anticonvulsants / metabolism
  • Anticonvulsants / pharmacokinetics
  • Anticonvulsants / pharmacology*
  • Carbonic Anhydrase II / antagonists & inhibitors
  • Cell Line
  • Clinical Trials as Topic
  • Drug Evaluation, Preclinical
  • Female
  • Humans
  • Male
  • Mice
  • Rats
  • Sulfonamides / chemistry*
  • Sulfonamides / metabolism
  • Sulfonamides / pharmacokinetics
  • Sulfonamides / pharmacology*
  • Thiophenes / chemistry*
  • Thiophenes / metabolism
  • Thiophenes / pharmacokinetics
  • Thiophenes / pharmacology*

Substances

  • Amides
  • Anticonvulsants
  • Sulfonamides
  • Thiophenes
  • Carbonic Anhydrase II
  • N-((benzo(b)thien-3-yl)methyl)sulfamide