Quilostigmine

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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 mass 377.488 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Quilostigmine, also known as NXX-066, is an acetylcholinesterase inhibitor. Its structure is related to that of physostigmine,[1] another acetylcholinesterase (AChE) inhibitor.

Biological activity

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Quilostigmine displays inhibition of the AChE enzyme with an IC50 value of 0.148 µM.[2]

History

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

References

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  1. ^ PubChem. "Quilostigmine". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-11-20.
  2. ^ "AID 511766 - Inhibition of human AChE by Ellmans test - PubChem". pubchem.ncbi.nlm.nih.gov. Retrieved 2025-11-20.
  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. Retrieved 2025-11-20.
  6. ^ "Delving into the Latest Updates on Quilostigmine with Synapse". synapse.patsnap.com. Retrieved 2025-11-20.