Trecadrine

Trecadrine
Clinical data
Routes of
administration		Oral[1]
Drug classSympathomimetic; β3-Adrenergic receptor agonist
Identifiers
  • 2-[methyl-[2-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)ethyl]amino]-1-phenylpropan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC27H29NO
Molar mass383.535 g·mol−1
3D model (JSmol)
  • CC(C(C1=CC=CC=C1)O)N(C)CC=C2C3=CC=CC=C3CCC4=CC=CC=C42
  • InChI=1S/C27H29NO/c1-20(27(29)23-12-4-3-5-13-23)28(2)19-18-26-24-14-8-6-10-21(24)16-17-22-11-7-9-15-25(22)26/h3-15,18,20,27,29H,16-17,19H2,1-2H3
  • Key:BHVGOYREXHCFOE-UHFFFAOYSA-N

Trecadrine (INNTooltip International Nonproprietary Name) is a drug that was originally developed as an anti-ulcer agent but was found to act as a β3-adrenergic receptor agonist with potential anti-obesity and anti-diabetic properties.[2][3][1][4] It is selective for the β3-adrenergic receptor, lacking activity at the β1- and β2-adrenergic receptors.[1] The drug is orally active.[1] Structurally, trecadrine is a substituted β-hydroxyamphetamine and derivative of β-hydroxy-N-methylamphetamine (ephedrine, pseudoephedrine) with a tricyclic moiety attached at the amine.[2][5]

References

  1. ^ a b c d Hu B, Jennings LL (2003). "Orally bioavailable beta 3-adrenergic receptor agonists as potential therapeutic agents for obesity and type-II diabetes". Progress in Medicinal Chemistry. 41: 167–194. doi:10.1016/s0079-6468(02)41005-3. ISBN 978-0-444-51142-3. PMID 12774694.
  2. ^ a b Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. pp. 411, 571. ISBN 978-1-4757-2085-3. Retrieved 17 October 2024.
  3. ^ Milne GW (2002). Drugs: Synonyms and Properties. Wiley. p. 514. ISBN 978-0-566-08491-1. Retrieved 17 October 2024.
  4. ^ "-drine sympathomimetics" (PDF). The use of stems in the selection of International Nonproprietary Names (INN) for pharmaceutical substances 2018 (Stem Book 2018). World Health Organization.
  5. ^ "CID 65823". PubChem. U.S. National Library of Medicine. Retrieved 17 October 2024.