Quilostigmine

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)	Interactive image
ChEBI	CHEBI:188879
ChEMBL	ChEMBL1243298
ChemSpider	116784
KEGG	D03823
PubChem CID	132228
UNII	2L1YNO4SQJ
CompTox Dashboard (EPA)	DTXSID801350915
InChI 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
SMILES C[C@@]12CCN([C@@H]1N(C3=C2C=C(C=C3)OC(=O)N4CCC5=CC=CC=C5C4)C)C
Properties
Chemical formula	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). Infobox references

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

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

History

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

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.