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Quilostigmine

From Wikipedia, the free encyclopedia
Acetylcholinesterase inhibitor
Quilostigmine
Names
IUPAC name
[(3aR,8bS)-3,4,8b-Trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] 3,4-dihydro-1H-isoquinoline-2-carboxylate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
UNII
  • InChI=1S/C23H27N3O2/c1-23-11-13-24(2)21(23)25(3)20-9-8-18(14-19(20)23)28-22(27)26-12-10-16-6-4-5-7-17(16)15-26/h4-9,14,21H,10-13,15H2,1-3H3/t21-,23+/m1/s1
  • C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)OC(=O)N4CCC5=CC=CC=C5C4)C)C
Properties
C23H27N3O2
Molar mass377.488 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Quilostigmine, also known asNXX-066, is anacetylcholinesterase inhibitor. Its structure is related to that ofphysostigmine,[1] another acetylcholinesterase (AChE) inhibitor.

Biological activity

[edit]

Quilostigmine displays inhibition of the AChE enzyme with anIC50 value of 0.148 µM.[2]

History

[edit]

Quilostigmine was initially studied by AstraZeneca for the treatment ofAlzheimer's disease;[3][4] however, the drug appears to have been discontinued,[5] reaching a maximum trial phase of two.[6]

References

[edit]
  1. ^PubChem."Quilostigmine".pubchem.ncbi.nlm.nih.gov. Retrieved2025-11-20.
  2. ^"AID 511766 - Inhibition of human AChE by Ellmans test - PubChem".pubchem.ncbi.nlm.nih.gov. Retrieved2025-11-20.
  3. ^Sramek, J. J.; Hourani, J.; Jhee, S. S.; Cutler, N. R. (1999). "NXX-066 in patients with Alzheimer's disease: a bridging study".Life Sciences.64 (14):1215–1221.doi:10.1016/s0024-3205(99)00053-3.ISSN 0024-3205.PMID 10210264.
  4. ^"Case No COMP/M.1878 - PFIZER / WARNER- LAMBERT"(PDF).
  5. ^"Quilostigmine - AdisInsight".adisinsight.springer.com. Retrieved2025-11-20.
  6. ^"Delving into the Latest Updates on Quilostigmine with Synapse".synapse.patsnap.com. Retrieved2025-11-20.
Enzyme
(modulators)
ChATTooltip Choline acetyltransferase
AChETooltip Acetylcholinesterase
BChETooltip Butyrylcholinesterase
Transporter
(modulators)
CHTTooltip Choline transporter
VAChTTooltip Vesicular acetylcholine transporter
Release
(modulators)
Inhibitors
Enhancers
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