Jump to content

Exisulind

From Wikipedia, the free encyclopedia

This is an old revision of this page, as edited by Fswitzer4 (talk | contribs) at 15:37, 19 June 2020 (Added FDA UNII). The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.

Exisulind
Names
IUPAC name
2-[(1Z)-5-fluoro-1-[(4-methanesulfonylphenyl)methylidene]-2-methyl-1H-inden-3-yl]acetic acid
Other names
Sulindac sulfone, Aptosyn, FGN-1, Prevatac
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C20H17FO4S/c1-12-17(9-13-3-6-15(7-4-13)26(2,24)25)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-
    Key: MVGSNCBCUWPVDA-MFOYZWKCSA-N
  • InChI=1/C20H17FO4S/c1-12-17(9-13-3-6-15(7-4-13)26(2,24)25)16-8-5-14(21)10-19(16)18(12)11-20(22)23/h3-10H,11H2,1-2H3,(H,22,23)/b17-9-
    Key: MVGSNCBCUWPVDA-MFOYZWKCBW
  • CC1=C(CC(O)=O)C2=C(C=CC(F)=C2)\C1=C/C1=CC=C(C=C1)S(C)(=O)=O
Properties
C20H17FO4S
Molar mass 372.41 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Exisulind (tentative trade name Aptosyn) is an antineoplastic agent. It acts by inhibiting the enzyme cyclic guanosine monophosphate phosphodiesterase type 5 (EC 3.1.4.17).[1] It is the sulfone derivative of sulindac, an NSAID. Unlike sulindac, it has known effects on prostaglandin synthesis.[2] It was developed as the potential treatment of several conditions including familial adenomatous polyposis (FAP), precancerous sporadic colonic polyps, cervical dysplasia and the prevention of tumor recurrence in prostate and breast cancer.[3] Exisulind inhibits the enzyme cGMP-PDE, overexpressed in precancerous and cancerous colorectal cells, and induces apoptosis in such cells with minimal effects on normal cells. This apoptotic effect is independent of COX-1 or COX-2 inhibition, p53, Bcl-2, or cell cycle arrest. Preclinical evidence suggests that exisulind also inhibits angiogenesis.[4]

See also

References

  1. ^ [No authors listed] (2004). "Exisulind: Aptosyn, FGN 1, Prevatac, sulindac sulfone". Drugs in R&D. 5 (4): 220–6. doi:10.2165/00126839-200405040-00007. PMID 15230629.
  2. ^ van Stolk, R; Stoner, G; Hayton, WL; Chan, K; DeYoung, B; Kresty, L; Kemmenoe, BH; Elson, P; Rybicki, L; Church, J; Provencher, K; McLain, D; Hawk, E; Fryer, B; Kelloff, G; Ganapathi, R; Budd, GT (January 2000). "Phase I trial of Exisulind (Sulindac Sulfone, FGN-1) as a chemopreventive agent in patients with familial adenomatous polyposis". Clinical Cancer Research. 6 (1): 78–89. PMID 10656435.
  3. ^ Griffiths, GJ (November 2000). "Exisulind Cell Pathways". Current Opinion in Investigational Drugs. 1 (3): 386–91. PMID 11249724.
  4. ^ Skopińska-Rózewska, E; Piazza, GA; Sommer, E; Pamukcu, R; Barcz, E; Filewska, M; Kupis, W; Caban, R; Rudziński, P; Bogdan, J; Mlekodaj, S; Sikorska, E (1998). "Inhibition of Angiogenesis by Sulindac and its Sulfone Metabolite (FGN-1): a Potential Mechanism for Their Antineoplastic Properties". International Journal of Tissue Reactions. 20 (3): 85–9. PMID 9894180.