Iferanserin

Iferanserin (INN; VEN-309) is a drug which acts as a selective 5-HT2A receptor antagonist.[1] It is under development as an intra-rectal formulation for the treatment of hemorrhoid disease, and as of February 2012, is in phase IIb clinical trials.[1]

Iferanserin
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • (E)-N-[2-[2-[(2S)-1-methylpiperidin-2-yl]ethyl]phenyl]-3-phenylprop-2-enamide
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC23H28N2O
Molar mass348.490 g·mol−1
3D model (JSmol)
SMILES
  • O=C(\C=C\c1ccccc1)Nc2ccccc2CC[C@H]3N(C)CCCC3
InChI
  • InChI=1S/C23H28N2O/c1-25-18-8-7-12-21(25)16-15-20-11-5-6-13-22(20)24-23(26)17-14-19-9-3-2-4-10-19/h2-6,9-11,13-14,17,21H,7-8,12,15-16,18H2,1H3,(H,24,26)/b17-14+/t21-/m0/s1
  • Key:UXIPFQUBOVWAQW-UEBLJOKOSA-N

Synthesis
Patent:[2]

The condensation between 2-nitrobenzaldehyde [552-89-6] (1) and 2-picoline [109-06-8] (2) gives 2-(o-nitrostyryl)pyridine [50385-24-5] (3). Alkylation with methyliodide gives the quat salt, CID:54050692 (4). Catalytic hydrogenation at elevated pressure gives 2-(2-aminophenethyl)-1-methylpiperidine, CID:11085282 (5). Separation of the enantiomers and amide formation with cinnamoyl chloride [17082-09-6] (6) completed the synthesis of Iferanserin (7).

See also

References
  1. Herold A, Dietrich J, Aitchison R (February 2012). "Intra-anal Iferanserin 10 mg BID for hemorrhoid disease: a prospective, randomized, double-blind, placebo-controlled trial". Clinical Therapeutics. 34 (2): 329–40. doi:10.1016/j.clinthera.2011.12.012. PMID 22244049.
  2. Moh Samir Amer, WO 2012026914 (2012).


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